Early Retirement Roadmap

I Retired at 55—5 Problems My 401(k) Couldn’t Solve

Mon, 10 Aug 2026 08:00:00 -0500

I retired at 55, and I learned that a large 401(k) alone doesn’t solve every early retirement problem—especially access, ACA health insurance, taxes, and market downturns.

In this episode, I walk through five problems our 401(k)s alone could not solve and why having money in a taxable brokerage account, cash reserves, Roth accounts, and other accessible sources gave me the flexibility to retire early.

We’ll cover how account location can affect:

• Access to money before age 59½
• ACA health insurance subsidies and reported income
• Sequence-of-returns risk during a market downturn
• Tax flexibility from year to year
• The ability to delay Social Security without feeling pressured to claim early

I also discuss the longer-term challenge of having a large amount of money in pretax retirement accounts, including required minimum distributions, possible IRMAA surcharges, and losing control over when taxable income appears.

A 401(k) is still an excellent wealth-building tool. But early retirement taught me that the location of your money can matter almost as much as the total amount you’ve saved. The 401(k) helped build the wealth. The brokerage account helped build the bridge. Cash provides stability, and Roth accounts create additional tax flexibility.

✅ Free resources available on my Patreon:

All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more.

To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space.

💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy.
👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

DISCLAIMER: This episode is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

I Retired at 55 — Here’s the Risk Nobody Warns You About

Mon, 03 Aug 2026 08:00:00 -0500

The big question that's always asked when it comes to retirement planning is do you have enough money? But the risk nobody warns you about is retiring too late.

After retiring at 55, I’ve learned that money is only one part of the retirement decision. Time, health, energy, and actually being able to enjoy the life you worked for matter just as much.

In this episode, I share 5 lessons that changed how I think about retirement, spending, work, and the danger of waiting too long. We talk about high-energy dreams, the difference between protection dollars and life dollars, why “good enough” planning matters, the true cost of work, and why retirement only works if you’re building a life you actually want to enter.

I’m not saying everyone should retire at 55. I’m saying the risk of retiring too early gets plenty of attention — but the risk of retiring too late is real too.

If you’re planning for early retirement, thinking about retiring in your 50s or 60s, or wondering whether one more year of work is really worth it, this episode may help you think through the decision differently.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55. My Retirement Plan Is Intentionally Dumb.

Mon, 27 Jul 2026 08:00:00 -0500

I retired at 55 with an intentionally dumb retirement plan—simple retirement planning built around low-cost index funds, cash reserves, flexible spending, and fewer moving parts.

In this episode, I share the seven parts of my early retirement plan that I deliberately keep simple. That includes how I invest, why I use a small number of investments with clear jobs, how I avoid trying to predict the market, and why I treat retirement calculators and Monte Carlo simulations as tools—not guarantees.

I also explain why I don’t try to optimize every tax year, how I built flexibility into my retirement spending plan, and why every retirement strategy should pass the “spouse test.” A retirement plan shouldn’t require perfect forecasts, constant monitoring, or dozens of complicated decisions to keep working.

My goal is not to have the smartest-looking retirement plan. It is to have a resilient retirement plan that is easy to understand, hard to break, and flexible enough to handle market downturns, unexpected expenses, changing tax rules, and real life.

In this episode, we’ll cover:
• Why I prefer low-cost index funds and ETFs
• How cash, stocks, bonds, and taxable accounts each have a clear job
• Why I don’t make retirement decisions based on market predictions
• How I use Monte Carlo retirement projections without obsessing over the score
• Why minimizing taxes every single year is not always the best long-term strategy
• How spending guardrails make retirement more adaptable
• Why your spouse or another trusted person should be able to understand your plan

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55—6 Signs Work Was Taking Too Much From Me

Mon, 20 Jul 2026 08:00:00 -0500

Working too much can quietly drain your time, energy, health, and relationships. After retiring at 55, I saw how burnout, work-life balance, and early retirement are more connected than I realized.

In this episode, I share six signs that work may be taking more from your life than you realize—including the most dangerous one, because it can sound completely responsible. I also walk through the five-part off-ramp I would build if I were still working today: defining what “enough” means, reducing the amount your paycheck must support, creating a financial bridge, building a meaningful life outside work, and giving “one more year” a clear purpose and expiration date.

This isn’t about quitting recklessly or pretending money doesn’t matter. It’s about recognizing that working longer is not always the risk-free choice—and that your time, health, and energy are valuable forms of capital too.

If you’re feeling burned out, questioning how much longer you want to work, or trying to build a realistic path toward early retirement, I hope this episode helps you think through what work is costing you—and what you want the rest of your life to look like.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I’m 57. I Retired at 55. Why Am I Still Afraid to Spend Money?

Mon, 13 Jul 2026 08:00:00 -0500

Retirement spending, early retirement, and the fear of spending money can feel strange after decades of saving. I retired at 55, and even with a solid plan, spending from the pile was harder than I expected.

Before I retired, I thought the hard part was saving enough money. But after retiring early, I realized there’s another challenge people don’t talk about enough: learning how to actually use the money you spent decades building.

In my first year of retirement, my fear around spending was probably an 8 out of 10. Now, in my second year, it’s closer to a 4. In this episode, I share the 5 things that helped me lower that fear and feel more comfortable spending in retirement without being reckless.

I talk about:

- Why the fear of spending is often psychological, not mathematical

- Why different buckets of money feel different emotionally

- How a cash runway helps quiet market noise

- Why flexible spending matters in retirement

- How I separate spending into protection, joy, and noise

- Why I don’t want to accidentally live like I’ve already run out of money

The goal isn’t to die with the biggest portfolio possible. The goal is to use your money wisely while you still have the health, time, and freedom to enjoy it.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55: My 7 Budget Rules That Survived Real Life

Mon, 06 Jul 2026 08:00:00 -0500

Retirement budget rules matter even more when you retire early. I retired at 55, and in this episode I’m sharing the 7 budget rules that helped my retirement plan survive real life.

Before I retired, I had a retirement budget, tracked our spending, planned for health insurance, travel, home repairs, and the things we wanted to enjoy in retirement.

But even with good planning, real life still showed up — including a large unexpected A/C repair, changing travel plans, rising healthcare costs before Medicare, and the mental shift from saving money to actually spending from the pile.

In this episode, I share the retirement budgeting lessons that have actually worked for me so far as an early retiree.

These are not generic retirement budget tips from a spreadsheet. These are the rules that helped me stay flexible, adjust when expenses changed, and avoid panicking when one category went over budget.

Topics covered:

• Retirement budgeting after retiring early
• Why retirement spending is not a straight line
• How to plan for healthcare before Medicare
• Why flexibility matters more than perfect predictions
• How a cash runway can help reduce retirement stress
• Why budgeting for joy matters in retirement
• How monthly budget check-ins helped me trust the plan

If you’re planning for early retirement, wondering how much retirement will really cost, or trying to build a retirement budget that can survive real life, I hope this episode helps.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55: Don't Let a Calculator Keep You Working

Mon, 29 Jun 2026 08:00:00 -0500

Retirement calculators, Monte Carlo simulations, and probability of success can be useful—but they can also keep you working one more year. I retired at 55, and here’s what I think calculators often miss.

Retirement calculators can help you think through spending, inflation, taxes, healthcare, Social Security, and sequence-of-returns risk. But they can also make retirement feel like a pass/fail decision, where anything less than a perfect score feels like a reason to keep working.

In this episode, I talk about why I don’t believe a calculator should be the final authority on when you retire. It can test your plan, but it can’t measure your health, energy, stress, flexibility, time with your spouse, or the cost of delaying the life you’ve been working toward.

I’ll cover five ways retirement calculators can get early retirement wrong, especially for people trying to retire in their 50s or early 60s, and how I personally thought about the decision to retire at 55.

This is not about ignoring the math. The numbers matter. But retirement calculators are tools — not permission slips.

If you’ve been running retirement calculators and wondering whether you’ll ever feel like you have “enough,” this episode is for you.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I’m 57 & Retired: What I Actually Do All Day

Mon, 22 Jun 2026 08:00:00 -0500

Wondering when you retire, what you're going to do all day? And is that fear of being bored one of things holding you back from retiring? I’m 57 and retired, and I’ll share what retirement actually feels like after leaving work behind.

One of the biggest fears people have about early retirement indeed is boredom. What do you do all day when you no longer have a job, a boss, meetings, deadlines, or a work schedule telling you where to be?

In this episode, I share what my daily life looks like after retiring at 55 and now on my second year of retirement — but more importantly, I talk about what retirement actually feels like once work no longer organizes your life.

I’ll cover the simple pleasures of retirement, why I haven’t been bored, how my routine changed, how I spend my time, why health and purpose matter, and why retirement planning does not end once you stop working. It simply changes.

We’ll also talk about the emotional side of retirement, including identity, spending from your nest egg, letting go of a career, and avoiding the “one more year” trap if you’re already financially ready.

If you’re thinking about retiring early, planning for retirement, or wondering whether retired life will feel boring or fulfilling, this video may help you think beyond the numbers and start planning the life you actually want to retire to.

Retirement is not just about having enough money. It’s also about having enough health, purpose, freedom, structure, and meaningful things to do with your time.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55: 10 Money Traps I Refuse to Fall For

Mon, 15 Jun 2026 08:00:00 -0500

I retired at 55, and these are 10 things I refuse to waste money on.

Retirement doesn’t mean you stop spending money. It means you get more honest about what the spending is actually for.

In this episode, I’m sharing 10 money traps I avoid in retirement — including convenience spending, boredom shopping, status spending, supporting adult children without boundaries, long-term care insurance, retirement products that become obligations, housing decisions, car payments, and more.

Some of these are things I avoided before retirement, which helped me save more and retire earlier. Others are things I’m even more careful about now that I’m retired and living on the other side of the paycheck.

This isn’t about being cheap or saying no to everything. It’s about refusing to waste money on things that don’t make retirement better — so you can spend more intentionally on the things that actually matter.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

Working Past 55? 6 Hidden Costs Most People Miss

Mon, 08 Jun 2026 08:00:00 -0500

Early retirement at 55 sounds like the dream — but after retiring early myself, I realized there are things I wish I had understood sooner about retirement planning, money, purpose, and life after work.

In this episode, I’m sharing what I got wrong after retiring at 55 — not because early retirement was a mistake, but because the transition is more complicated than most people admit.

We spend so much time planning the financial side of retirement: saving enough, investing wisely, managing healthcare costs, and figuring out withdrawal strategies. But the emotional and lifestyle side of early retirement can matter just as much.

If you’re thinking about retiring early, planning for retirement in your 50s, or wondering whether you’re truly ready to leave work behind, this episode may help you think through a few things before making the leap.

I’ll share the lessons I’ve learned since retiring early, including what surprised me, what I underestimated, and what I would think about differently if I could do it all over again.

✅ Free resources available on my Patreon:

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I Retired at 55: Here’s What I Wish I Did First

Mon, 01 Jun 2026 08:00:00 -0500

In this episode, I talk about the retirement strategy I wish I had seriously considered before leaving my career: easing into retirement instead of making it a hard stop.

For many people, retirement looks simple from the outside. One day you’re working, and the next day you’re done. But once you actually retire, you may realize work was providing more than just a paycheck. It may have also provided structure, routine, identity, social connection, and even the emotional permission to spend money.

That’s why a slower transition into retirement can make sense for some people — especially early retirees who need their money to last longer, may need to bridge the gap to Medicare, and may still be adjusting to life without a regular paycheck.

In this video, I’ll share why I think I could have handled my own retirement transition differently, how part-time work or consulting can soften the landing, why health insurance matters so much before Medicare, and how to think about retirement as more than just a financial decision.

Retirement isn’t just about asking, “Can I retire?”
It’s also about asking, “How should I retire?”

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 To get these free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap then click Join for Free, then click on the Tools collection. You can download any of them there.

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

I'm 57 & Retired: America Feels Too Expensive.

Mon, 25 May 2026 08:00:00 -0500

Early retirement, retirement planning, cost of living, healthcare, insurance, and retiring in America are all starting to feel different than many of us expected.

I’m 57 and retired, and lately I’ve been asking myself a question I never expected to take seriously: Is America becoming too expensive to retire in?

In this episode, I talk about how rising costs feel different once the paycheck stops — groceries, property taxes, home insurance, auto insurance, healthcare, and everything else that can chip away at retirement confidence.

This is not a political episode. It’s a practical and personal look at how retirement in America feels right now, and why more retirees and near-retirees may be thinking about options they never considered before — moving to a lower-cost state, downsizing, renting, spending part of the year somewhere else, or even retiring abroad.

I’m not saying I’m leaving the United States, although I’ve been thinking about it as a future possibility. I’m not saying everyone should move abroad. But I am saying retirement planning is about more than hitting a number. It’s also about flexibility, quality of life, and whether the place you live still supports the retirement you imagined.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

I’m 57 and Retired: 5 Things I Never Tell Anyone

Mon, 18 May 2026 08:00:00 -0500

Early retirement, retirement planning, and financial independence all require more than just money — they also require boundaries. I’m 57 and retired, and these are 5 things I never tell anyone.

Some information is powerful. And once you share it, you don’t always control where it goes, how people repeat it, how they interpret it, or how they use it.

In this episode, I’m sharing five broad categories of things I’m very careful about sharing now that I’m retired — and many of these apply even if you’re still working and planning for retiremen

We’ll talk about why I don’t share exact financial numbers, salary, net worth, retirement income, exit plans, private opinions, personal vulnerabilities, passwords, identity information, social media, politics, religion, and even certain personal goals.

This isn’t about being secretive or trusting no one. It’s about knowing the difference between your inner circle and everyone else.

Because not everything private is secret.

Sometimes, it’s just none of their business.

If you’re planning for early retirement, already retired, or simply trying to protect your peace, this is a conversation worth having.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

I Retired at 55: My 7 Layers to Avoid Running Out of Money

Mon, 11 May 2026 08:00:00 -0500

Running out of money in retirement is one of the biggest fears. I retired at 55, and in this episode, I share the 7 layers I use to protect my retirement plan.

When I was preparing to retire early, I kept asking myself: What if I’m wrong? What if the market crashes, healthcare costs more than expected, inflation stays high, taxes surprise me, or I live much longer than planned?

I’ll cover:

• Knowing your real spending floor

• Building a cash runway

• Stress-testing your retirement plan

• Understanding why retirement spending is not a straight line

• Why the 4% rule is only a starting point

• Planning healthcare and taxes together

• Building backup levers into your retirement plan

• Reviewing the plan without obsessing over it

This episode is especially helpful if you’re planning for early retirement, worried about sequence of returns risk, trying to manage Affordable Care Act health insurance before Medicare, or wondering how to create a retirement plan that can bend without breaking.

🎧 Episode mentioned during this podcast listen to next: The Cash Runway Plan: Build It, Store It, Refill It (Season 3, Episode 9)

📊 Department of Health and Human Services 2025 FPL Levels (2026 ACA uses 2025's FPL levels): https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

📊Michael Kitces' research mentioned in video: https://www.kitces.com/blog/the-ratcheting-safe-withdrawal-rate-a-more-dominant-version-of-the-4-rule/

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📌 New companion tool for this episode: I created The 7 Layers Retirement Confidence Checklist to go with this episode. It’s a worksheet designed to help you review your own retirement plan, score each of the 7 layers, identify weak spots, and turn the vague fear of running out of money into specific planning actions. It’s available in my Patreon Tools Collection for any paid membership tier. Link to my Patreon here and click the Membership button to check out the different membership tiers: https://www.patreon.com/cw/earlyretirementroadmap

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

My Gen X Retirement Doesn’t Look Like a Boomer’s

Mon, 04 May 2026 08:00:00 -0500

Gen X retirement won’t look like Boomer retirement. Here’s why retirement planning is changing for Generation X, from Social Security to health insurance, 401(k)s, and early retirement.

For many Baby Boomers, retirement followed a more familiar path: work until around 65, collect Social Security, go on Medicare, maybe have a pension, and settle into a more traditional retirement lifestyle.

But for Gen X, retirement may look very different.

In this episode, I talk about why Generation X is facing a different retirement puzzle than many Boomers did — fewer pensions, more reliance on 401(k)s and individual retirement accounts, higher health insurance concerns before Medicare, more uncertainty around Social Security, and more pressure to design a retirement that actually fits real life.

We’ll look at why Gen X retirement may require more flexibility, more planning, and a different mindset — especially for anyone hoping to retire before 65.

Topics covered include:

Why Gen X retirement may be less of a template and more of a design project
How 401(k)s changed retirement planning
Why health insurance before Medicare can be a major early retirement issue
Why Social Security uncertainty matters for Gen X
How family obligations can complicate retirement
Why retirement is not just about your account balance
Why flexibility may be one of the most underrated retirement assets

If you’re in your 40s, 50s, or early 60s, this video is about rethinking what retirement could actually look like for you — not just copying the retirement model that worked for someone else.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

I Retired at 55: 10 Things You Need to Know

Mon, 27 Apr 2026 08:00:00 -0500

Early retirement, retirement planning, retired at 55, and what to know before retirement—here are 10 lessons I’ve learned after 17 months of early retirement that could help you plan smarter.

When I retired at 55, I thought the hard part was getting the numbers to work. But after 17 months of actually living early retirement, I’ve learned that the money plan is only part of the story.

In this episode, I share 10 things I’ve learned about early retirement, including how retirement really feels, why time matters more than most people realize, how spending changes, why taxes and health insurance get more strategic, what market downturns feel like when you’re no longer earning a paycheck, and why identity, relationships, and health matter just as much as the financial side.

If you enjoy honest early retirement journeys and real-world retirement planning insights from someone actually living it, this video is for you.

If this video helped you, subscribe for more videos on early retirement, retirement planning, Affordable Care Act health insurance, taxes in retirement, Roth conversions, Social Security, and building a retirement life that actually works.

🎧 Episode mentioned during this podcast listen to next: The Cash Runway Plan: Build It, Store It, Refill It (Season 3, Episode 9)

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

The Hidden Social Security Math That Changes Early Retirement

Mon, 20 Apr 2026 08:00:00 -0500

Social Security is a much bigger part of early retirement planning than most people realize. In this episode, I share early retirement planning tips on claiming age, portfolio pressure, and how Social Security can change when you can retire.

Most people treat Social Security like a separate decision.

It’s not.

The age you claim can affect how much pressure your portfolio has to carry, how long the years between retirement and Social Security have to last, how much government-backed lifetime income shows up later, and even how much you may need saved before you feel comfortable retiring.

In this episode, I walk through:

Why the usual break-even conversation is too narrow
What waiting to claim can cost your portfolio in the meantime
Why this matters especially for early retirees
How survivor benefits and sequence of returns risk fit into the decision
What the projected 2033 Social Security shortfall really means
The 5 questions I think early retirees should ask before deciding when to claim

If you’re planning for early retirement, already retired early, or trying to figure out how Social Security fits into your broader retirement income plan, this episode is for you.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉To get these free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. While you're there, check out my different membership levels too! There is sure to be a level that fits your needs and budget.Join any paid tier level to get access to my entire tools collection, including my Early Retirement 5 Numbers Excel Worksheet, Cash Runway Calculator Worksheet, Treasury Bill and CD Ladder Guides I mentioned in this episode. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

💼 My Favorite Retirement Planning Tool, and that I mentioned in this episode! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy.
👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Your Roth Conversion Window Closes Faster Than You Think

Mon, 13 Apr 2026 08:00:00 -0500

Early retirement planning tips matter a lot when it comes to Roth conversions. In this episode, I explain why your Roth conversion window can close faster than you think — and how ACA subsidies, Social Security, IRMAA, taxes, and timing can all shrink the opportunity.

If you are planning Roth conversions in early retirement, this is one of the biggest mistakes to avoid.

A lot of retirees assume they will have a long stretch of low-income years to gradually move money from pre-tax accounts into Roth accounts at favorable tax rates. But in real life, that window can get squeezed much faster than expected.

In this episode, I walk through 5 reasons why the Roth conversion window is often smaller than most retirees think, including:

ACA health insurance subsidy tradeoffs before Medicare
Social Security starting earlier than expected
IRMAA surcharges later on
Losing your best low-income years
Why market downturns can create Roth conversion opportunities

I also explain why paying Roth conversion taxes from outside cash can be more powerful than withholding taxes from the conversion itself.

If you are trying to plan early retirement withdrawals, reduce future Required Minimum Distributions, lower lifetime taxes, or think more strategically about Roth conversions, this episode will help you understand the tradeoffs.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Retiring Soon? Don’t Make this Mistake

Mon, 06 Apr 2026 08:00:00 -0500

Retiring soon? In this episode, I cover the biggest retirement planning mistake people make before retirement and the 7 things to figure out now, including spending, taxes, health insurance before Medicare, withdrawal strategy, and cash runway.

A lot of people do a good job saving for retirement, but they wait too long to plan the actual transition into retirement.

That’s the mistake.

In this episode, I walk through 7 key areas to get clear on before you retire so you’re not scrambling late in the game:

What retirement will actually cost
Where your retirement income will come from
Your withdrawal strategy
Health insurance before Medicare
Major financial loose ends to clean up
The mental side of retirement
Why a cash runway matters so much

If you’re planning for retirement or early retirement, this episode will help you think through the practical side of retirement planning, including retirement spending, taxes, Modified Adjusted Gross Income (MAGI), Affordable Care Act health insurance, and sequence of returns risk.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📊ACA Cost Estimator Link mentioned in this episode: https://www.healthcare.gov/see-plans/#/

📊2025 FPL Tables - ACA Uses This for 2026: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

🎧Listen next to my recent podcast episode The Cash Runway Plan: Build It, Store It, Refill It mentioned it in this episode & the episode titled ACA MAGI: How to Calculate & Manage It for Big Savings!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Your Net Worth is the Wrong Number

Mon, 30 Mar 2026 08:00:00 -0500

Early retirement planning is not just about net worth. In this episode, I break down the retirement number that matters more, plus ACA health insurance, taxes, spending, and sequence risk.

Most people ask, “How much net worth do I need to retire?” But that question can be misleading.

In this episode, I explain why the more important question is this: How much does your portfolio need to support each year?

Using simple examples, I show why two households with similar net worth can be in very different positions for retirement depending on:

spending
ACA health insurance costs before Medicare
taxes and MAGI
account structure
withdrawal flexibility
sequence of returns risk

If you’re planning for early retirement, trying to figure out how much you need to retire, or wondering whether your portfolio can really support your lifestyle, this episode will help you think about retirement planning the right way.

I also share the 5 key numbers I believe matter most in retirement planning:

Annual spending
Health insurance costs
Taxes
Bridge years before Medicare and Social Security
The amount your portfolio needs to cover each year

🎧Listen next to my recent podcast episode How Much Do I Need to Retire Early? 5 Numbers That Tell You - mentioned it in this episode and is a dedicated episode on the 5 numbers that really matter for retirement

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉To get these free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. While you're there, check out my different membership levels too! There is sure to be a level that fits your needs and budget. Join any paid tier level to get access to my entire tools collection, including my Early Retirement 5 Numbers Excel Worksheet I mentioned in this episode. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

I Retired at 55: 7 Early Retirement Mistakes I Missed

Mon, 23 Mar 2026 08:00:00 -0500

Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can retire early with fewer surprises and avoid costly retirement planning mistakes.

If you’re searching for early retirement planning tips, retirement planning advice, and early retirement mistakes to avoid, this video walks through what caught me off guard after retiring at 55. I cover how a bad day at work can push you toward early retirement before the plan is ready, why you should not assume you can easily go back to work, how a spouse can be on a different retirement timeline, why spending in retirement can feel harder than expected, how big surprise expenses still sting, why you should test-drive retirement before you quit, and why retirement planning does not end once you retire.

I also share my personal experience with retiring at 55, adjusting to life after full-time work, shifting from saving to spending, and dealing with the real-world side of early retirement planning. That includes health insurance planning, withdrawal strategy, modified adjusted gross income management, Roth conversions, and long-term tax planning.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉To get these free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

How Much Do I Need to Retire Early? 5 Numbers That Tell You

Mon, 16 Mar 2026 08:00:00 -0500

How much do I need to retire early? In this episode, I walk through the five numbers that really determine whether early retirement works — including spending, healthcare costs, taxes, your retirement bridge years, and how much your portfolio actually needs to support.

Most people searching “how much do I need to retire” are hoping for one simple number. But the reality is that early retirement is driven by several key numbers working together, not just one big target like $1 million.

In this episode, I break down the 5 numbers that matter most for early retirement planning:

• Your real annual spending
• Your health insurance costs before Medicare
• Your tax-aware withdrawal number
• Your bridge years before Social Security or Medicare
• Your portfolio support number

If you want to retire before age 65, these numbers become even more important. Healthcare, taxes, withdrawal strategy, and managing your Modified Adjusted Gross Income (MAGI) can dramatically change how much you actually need to retire.

I also talk about:
• Affordable Care Act (ACA) health insurance and the 400% Federal Poverty Level cliff
• Why MAGI is not the same as spending power
• How different withdrawal sources affect taxes and ACA subsidies
• Why early retirement planning is different than traditional retirement at 65+ If you're trying to answer the question “How much do I need to retire?”, understanding these five numbers will give you a much clearer and more realistic framework.

👉Resources:

📊 Healthcare.gov Plan Estimator to check ACA plans, prices including potential subsidies and cost share reductions based upon your estimated Modified Adjusted Gross Income (MAGI): https://www.healthcare.gov/see-plans/

👉Listen to my podcasts with these titles next:

🎧 The Cash Runway Plan: Build It, Store It, Refill It (Season 3: Episode 9)

🎧 ACA Premium Shock? Pay Less All Year (Season 3: Episode 6)

🎧 ACA MAGI: How to Calculate & Manage It for Big Savings! (Season 2: Episode 14)

🎧Health Insurance Options for Early Retirement: What You NEED to Know (Season 1: Episode 4)

✅ Want the companion tool for this episode? I created a 5 Numbers to Retire Early Worksheet to help you estimate these numbers for your own situation.
🎯 Get it inside my Patreon Tools Library (I usually make at least one tool for every major video/podcast topic).
⭐ Join my Patreon (3 levels):
• Tools Library access (including this Scorecard)
• Tools + ad-free, early-access podcast episodes
• Top tier: ask me your early retirement questions directly
👉 Patreon link: https://www.patreon.com/cw/earlyretirementroadmap

✅Free Resources available as well on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Retire Now If You Can Answer Yes to These 6 Questions

Wed, 11 Mar 2026 08:00:00 -0500

Early retirement + retirement planning made simple: Can you retire now?

In this episode, I share 6 questions to test your financial independence and retirement readiness—before you make the leap. If you can honestly answer YES to all six, you may be closer to retirement than you think:

The 6-question retirement test:

1. Are you postponing the life you actually want?

2. Is your job taking a real toll on your health?

3. Have you outgrown this stage of your career?

4. Do you want more time with the people you love—while you can still enjoy it?

5. Do you know what you’re retiring to?

6. Have you run the numbers well enough to trust the decision?

✅ Want the companion tool for this video? I created a Retirement Readiness Scorecard (based on these 6 questions) so you can work through them for yourself and see where you stand.

🎯 Get it inside my Patreon Tools Library (I usually make at least one tool for every major video/podcast topic).

⭐ Join my Patreon (3 levels)

• Tools Library access (including this Scorecard)

• Tools + ad-free, early-access podcast episodes

• Top tier: ask me your early retirement questions directly

👉 Patreon link: https://www.patreon.com/cw/earlyretirementroadmap

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

💼 My Favorite Retirement Planning Tool, and that I mentioned in this video! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy.

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

DISCLAIMER: This video is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

Your First 5 Years of Retirement Decide Everything

Mon, 02 Mar 2026 08:00:00 -0600

Your first 5 retirement years decide everything—retirement planning, withdrawal strategy, taxes, health insurance, spending, purpose, relationships, and the mistakes that derail early retirees. Here are the lessons to get it right.

If you retire in your 50s or early 60s, the first five years aren’t a warm-up. The habits you set, the decisions you lock in, and the systems you build early will compound for decades.

In this episode, I cover 9 crucial lessons:

• Treat withdrawals, taxes, and healthcare as one system
• Healthspan matters more than you think (do the “big stuff” early)
• Two sequence risks: markets and lifestyle habits
• Money is freedom, not a scoreboard (avoid comparison spending)
• Your identity will change — plan for it
• Purpose beats “permanent vacation” (avoid boredom/regret)
• Relationships need active investment (spouse, friends, community)
• Test big decisions before locking them in (moves, downsizing, etc.)
• Most long-term regrets come from inaction

And the 3 biggest first-five-year mistakes to avoid:
• No integrated income plan (withdrawals/taxes/healthcare disconnected)
• No spending guardrails (underspend fear or overspend excitement)
• No review system (drift takes over—financially and emotionally)

✅ Want the tools behind my videos? Join me on Patreon.

Members get access to my Tools & Resources library, organized Q&A threads, and ad-free/early podcast episodes.

The Quarterly Review Retirement Dashboard (Excel template) I mentioned in this episode is available there — built to make quarterly check-ins simple so you can track key numbers, spot issues early, and stay on course.

Resources mentioned in this episode:

📊 RAND (spending trajectories/declines as people age in retirement)

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

The Cash Runway Plan: Build It, Store It, Refill It

Mon, 09 Feb 2026 08:00:00 -0600

Build a cash runway for retirement so you’re not forced to sell stocks in a down market. Learn how many years you need, how to build it, where to hold it (HYSA, CDs, T-bills), and simple refill rules.

If you’re retiring early (or already retired), sequence-of-returns risk can wreck an otherwise solid plan. A cash runway is your “seatbelt” — it buys you time during bear markets so your investments can recover without you selling at the worst moment.

In this episode, I break down:

What a cash runway is (and what it is not)
How much runway to target (1–2 years vs 3–4 vs 4–5)
4 realistic ways to build your runway before/into retirement

Redirect cash flow (save on purpose, temporarily reduce 401(k) or 403(b) above match, runway sprint, add income)
Convert assets to cash (taxable brokerage, sell “other” stuff)
Let cash build naturally (dividends/interest to cash)
Use a backstop (HELOC as a bridge — with cautions)

Where to store runway money (from simplest to structured):
Checking/savings, high-yield savings account (HYSA), money market funds, CD ladders, Treasury bill ladders (TreasuryDirect), short-term Treasury/bond funds The 3 refill rules that turn your runway into a system (not a one-time pile of cash)

✅Free Resources (mentioned in this episode):
📊Free MAGI calculator Excel template
📊Free 12-Step Early Retirement Planning Checklist
📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🔨Want to actually build what I covered in this video? I created 3 companion tools for paid Patreon members only:

1. Cash Runway Worksheet Calculator (size your runway + map out your plan)

2. Treasury Bill Ladder Guide (step-by-step setup + pros/cons + how it works)

3. CD Ladder Guide (step-by-step setup + pros/cons + how it works)

Plus, get organized Q&A threads where you can ask me anything about early retirement planning or lifestyle so you can best prepare for and then thrive in early retirement. And... I'll provide companion tools for my podcasts and YouTube videos regularly. Join my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap

👉 If you have a topic you want me to cover next, email me at mike@mikeupland.com.

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

ACA Subsidy Payback: The Tax-Time Trap

Mon, 02 Feb 2026 08:00:00 -0600

ACA subsidy payback at tax time? Form 8962 + 1095-A reconciliation can trigger a surprise bill when your MAGI ends up higher than expected. In this episode, I’ll you'll learn why it happens, how to fix it, and how to prevent it next year.

If you had Marketplace coverage and your tax software suddenly says you owe thousands, you’re not alone. Here’s the real reason: the ACA premium tax credit you received during the year is an *advance* based on your estimated income. At tax time, the IRS “settles up” using Form 8962 and your Form 1095-A.

In this episode, you’ll learn:

✅ Why you can owe money back (even if nothing felt “wrong” during the year)

✅ The exact forms involved (1095-A + Form 8962)

✅ The 3 most common reasons people get hit with a payback

✅ How to check for (and fix) a wrong or corrected 1095-A

✅ The two simple levers to reduce the risk of a nasty surprise next year

✅ A quick “sanity check” that catches expensive mistakes fast

Key topics covered:

ACA premium tax credit reconciliation (PTC/APTC)
Modified Adjusted Gross Income (MAGI) for ACA (and why it’s not always “total income”)
Capital gains, Roth conversions, IRA withdrawals, dividends, interest, side income (yes—these can all move your subsidy)
Why taking the full credit up front can backfire if your income is “lumpy”
What to do if you can’t pay the full amount right now

Helpful official resources:

▶️ How to use / review Form 1095-A (Healthcare.gov): https://www.healthcare.gov/tax-form-1095/

▶️ IRS: About Form 8962 (Premium Tax Credit): https://www.irs.gov/forms-pubs/about-form-8962

▶️ IRS: Corrected / incorrect / voided Form 1095-A guidance: https://www.irs.gov/affordable-care-act/corrected-incorrect-or-voided-form-1095-a

▶️ IRS payment plan options (Online Payment Agreement): https://www.irs.gov/payments/online-payment-agreement-application

▶️ Department of Health and Human Services 2025 FPL Levels (2026 ACA uses 2025's FPL levels): https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

Listen to these episodes next (mentioned in this episode):

▶️ “ACA MAGI: How to Calculate & Manage It for Big Savings!”

▶️ “ACA Premium Shock? Pay Less All Year.”

Free Resources (mentioned in this video):

📊 Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Choppy Markets? Use This Retirement Defense Plan

Mon, 26 Jan 2026 08:00:00 -0600

Market volatility and choppy markets can wreck retirement plans—if you react the wrong way. In this episode, I share a simple framework to stay calm, avoid panic selling, and protect your long-term investing plan.

If you’re investing for retirement (or already retired), the goal isn’t to predict the market. It’s to have a repeatable plan for choppy years—so you don’t make permanent mistakes in temporary fear.

In this episode, you’ll learn how to:

Build the right cash buffer (based on what income doesn’t cover)
Install “panic brakes” so headlines don’t control your decisions
Rebalance with rules (not vibes) to stay on track
Spot hidden portfolio fragility before it hurts you
Use a down-market spending plan to avoid selling stocks at the worst time
Use tax-loss harvesting as a productive move when markets are down

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

✅Free Resources:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

ACA Premium Shock? Pay Less All Year

Mon, 12 Jan 2026 08:00:00 -0600

ACA premium shock for 2026? If your Marketplace/Obamacare health insurance premium jumped, this video shows 10 practical ways to pay less all year by controlling MAGI (modified adjusted gross income) and avoiding costly income mistakes.

Health insurance is the #1 “elephant in the room” for early retirement. With enhanced ACA subsidies ending after 2025, many early retirees are seeing big premium increases — but the ACA is still income-based, not asset-based, which means you may have more control than you think.

In this episode, I break down:
✅ Why many early retirees still choose ACA/Marketplace plans
✅ How the 400% Federal Poverty Level (FPL) line affects premium tax credits
✅ Why 250% FPL matters for cost-sharing reductions (Silver plans)
✅ 10 specific levers you can use to manage MAGI and pay less — including capital gains control, Roth strategy, cash runway, HSAs, dividend/interest “silent MAGI,” Roth conversion timing, and updating your income during the year

Important: Even after you enroll, you can update your Marketplace income estimate during the year — this can help prevent overpaying (or owing money back at tax time).

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📊 Free Resources:
- Click here for 2025 FPL Tables - ACA Uses the 2025 tables for 2026.
- Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.
- Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long
- Free early retirement checklist, 12 Must-Do Steps to Retire Sonner and Smarter

To get these last 3 downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎧 My Podcast episodes mentioned in this episode to listen to next:
- Season 1, Episode 4: Health Insurance Options for Early Retirement: What You NEED to Know - goes over the pros and cons of health insurance options for early retirement, including and beyond the ACA
- Season 2, Episode 14: ACA MAGI: How to Calculate & Manage It for Big Savings! - goes over exactly how to calculate your Modified Adjusted Gross Income (MAGI)

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)

Mon, 05 Jan 2026 08:00:00 -0600

2026 401(k) and IRA contribution limits are rising from 2025—but maxing out can backfire if you’re planning early retirement. In this episode I break down 3 rules to fund the right accounts in the right order.

If you’re aiming to retire before 59½, the “max everything” advice can accidentally:

lock up money when you need flexibility
increase taxes later (required distributions and tax brackets)
make health insurance more expensive by pushing up income (Affordable Care Act subsidies)

In this episode you’ll learn:

When maxing your 401(k) does make sense (and when it doesn’t)
The best “order of operations” for early retirees (401(k), IRA, Roth, Health Savings Account, taxable brokerage)
How to balance tax savings today vs. flexibility and taxes later

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉Additional Info beyond this episode: If you retire before 59½ and don’t have enough in a taxable brokerage “bridge,” there is another tool called IRS Rule 72(t) (also called SEPP — Substantially Equal Periodic Payments). It can be a legit way to access IRA money early without the 10% penalty, but it comes with some important strings attached (it’s rigid, and mistakes can be costly). Fore more information on this, listen to my podcast episode devoted to this, titled How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained, it's Season 2, Episode 9.

👉 Free Resource Mentioned:

✅ 12 Must-Do Steps to Retire Sooner and Smarter (Checklist)
A simple, practical roadmap to help you get retirement-ready faster.
🔗 To get the free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)

Mon, 15 Dec 2025 08:00:00 -0600

Monthly Dividend ETFs for retirement income can look like a paycheck—but it’s often an illusion. In this episode, I share 3 tests to avoid costly mistakes and keep Affordable Care Act (ACA) taxes in mind.

You’ll learn:
• The 4 main types of monthly income ETFs (covered-call, high-dividend stock, preferred stock, bond funds)
• Why yield can mislead if you ignore total return
• Test #1: What the distribution is made of (dividends, interest, option premium, return of capital)
• Test #2: Whether monthly payouts increase your control—or reduce it
• Test #3: How monthly distributions can raise modified adjusted gross income (MAGI) and affect tax planning

Examples include JEPI/JEPQ/QYLD/XYLD/RYLD, SPHD/DIV/SDIV, PFF/PGX/PFFD, and BND/AGG/LQD.

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Free Resources Mentioned:

✅ 12 Must-Do Steps to Retire Sooner and Smarter (Checklist)
A simple, practical roadmap to help you get retirement-ready faster.
✅ Free MAGI & Tax Estimator Spreadsheet (for ACA + taxes)
Estimate your Modified Adjusted Gross Income (MAGI), keep an eye on ACA subsidy eligibility, and get a rough tax estimate as you go through the year.

👉 To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

6 Levels of Retirement Wealth – Which Level Are You?

Mon, 08 Dec 2025 08:00:00 -0600

Wondering if you really have enough to retire? In this early retirement planning episode, I break down 6 levels of retirement wealth—from Survival to Fulfillment—so you can see which level you’re at and what it takes to move up.

Too many people only ask, “Do I have enough to retire?” when the better question is, “Enough for what level of retirement?” In this episode, I walk through my framework of Survival, Stability, Comfort, Security, Freedom, and Fulfillment Wealth so you can stress-test your plan, avoid white-knuckle retirement, and aim for a life that actually feels secure, free, and meaningful. We’ll also look at a real-world example couple who wants about $75,000/year in retirement spending and how different portfolio sizes can land them at very different levels.

You’ll learn:

Why “just covering the bills” can trap you in Survival or Stability Wealth
What Comfort Wealth feels like—and why it can still be fragile
Why I see Security Wealth (Level 4) as a strong target before you retire
How Freedom and Fulfillment Wealth shift your focus from “Can we afford this?” to “Does this fit the life we want?”
How your withdrawal rate, cash buffer, debt, housing, and health insurance all affect your level
How to use this framework as a targeting system, not a report card

I’ll also share why, for many people, retiring a bit earlier at Level 4 with more healthy years can be more valuable than grinding your way to Level 6 but having less time and energy to enjoy it.

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Free Resources Mentioned:

✅ 12 Must-Do Steps to Retire Sooner and Smarter (Checklist)
A simple, practical roadmap to help you get retirement-ready faster.
✅ Free MAGI & Tax Estimator Spreadsheet (for ACA + taxes)
Estimate your Modified Adjusted Gross Income (MAGI), keep an eye on ACA subsidy eligibility, and get a rough tax estimate as you go through the year.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 More from me:
All my videos, podcast episodes, and freebies: https://mikeupland.com

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Future-Proof Your Lazy Retirement: My 9 Habits of Thriving Retirees

Mon, 01 Dec 2025 08:00:00 -0600

Future-proof your retirement with habits of thriving retirees, early retirement planning tips, and simple retirement investing strategies to help you feel confident about the decades ahead. In this episode, I break down 9 practical habits I myself do and see over and over again in retirees who are not just “getting by,” but actually thriving—financially, emotionally, and health-wise.

We’ll talk about how to spend intentionally instead of fearfully, why a 2–4 year “sleep at night” cash buffer can keep you calm during market downturns, and how to treat your health like a core investment, not an afterthought. We’ll also cover purpose, simplicity, and risk management—so your retirement isn’t wiped out by one bad market, one bad policy change, or one bad life event.

What you’ll learn:
• How to future-proof your retirement with flexible spending “guardrails”
• Why thriving retirees protect their sleep-at-night money
• The key health habits that support a long, active retirement
• How to retire to something, not just from your job
• Why you don’t need a complex portfolio—just a simple, understandable system
• Overlooked risks (insurance, documents, fraud) that can derail retirement
• How to set up regular financial check-ins without obsessing over the market

If you’re planning to retire early—or you’re already retired and want a calmer, more confident path forward—this episode will help you put simple habits in place so you can enjoy your money and your life.

Lazy retirement investing made simple: early retirement, index funds (VTI, VOO, VUG, VIG, VYM), withdrawal rate guardrails, 2–4 year cash liquidity runway, Roth conversions, MAGI/ACA & IRMAA tax strategy.

Ready for a “do less, retire better” portfolio? In this episode, I walk through my lazy retirement investing plan—built for early retirees and anyone who wants a low-maintenance, rules-based retirement approach that’s diversified, tax-smart, and actually livable. We’ll set up a 3-category index portfolio, place assets for taxes, build a 2–4 year cash runway for bear markets, and use flexible withdrawal guardrails so you can sleep at night and still enjoy life.

What you’ll learn:

The “lazy” portfolio (Foundational, Growth, Income) and why boring wins long-term
Examples to research: VTI/VOO (core), VUG (growth), VIG/VYM (dividends)
How to set your mix and rebalance (±5% bands / annual check-in)
Smart tax placement: ETFs in taxable, bonds/REITs in tax-advantaged, avoid surprise cap gains from index mutual funds in taxable
Building a 2–4 year liquidity runway (cash, CDs, short-duration TIPS)
Choosing a starting withdrawal rate (e.g., ~3% for longer retirements) + ±20% guardrails
Practical withdrawal order (taxable → traditional → Roth)
Roth conversions: when they can make sense and how to manage MAGI for ACA subsidies pre-65 and IRMAA after 65
The annual tune-up: rebalance, refill runway, run a tax/MAGI check, adjust withdrawals, and basic account hygiene

Free resources mentioned in this episode:

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎧Listen to these episode titles I mentioned in this podcast:

- My Lazy Retirement Investing Plan (Season 3, Episode 1)

- ACA MAGI: How to Calculate & Manage It for Big Savings! (Season 2, Episode 14)

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

My Lazy Retirement Investing Plan

Mon, 10 Nov 2025 15:00:00 -0600

What you’ll learn:

The “lazy” portfolio (Foundational, Growth, Income) and why boring wins long-term
Examples to research: VTI/VOO (core), VUG (growth), VIG/VYM (dividends)
How to set your mix and rebalance (±5% bands / annual check-in)
Smart tax placement: ETFs in taxable, bonds/REITs in tax-advantaged, avoid surprise cap gains from index mutual funds in taxable
Building a 2–4 year liquidity runway (cash, CDs, short-duration TIPS)
Choosing a starting withdrawal rate (e.g., ~3% for longer retirements) + ±20% guardrails
Practical withdrawal order (taxable → traditional → Roth)
Roth conversions: when they can make sense and how to manage MAGI for ACA subsidies pre-65 and IRMAA after 65
The annual tune-up: rebalance, refill runway, run a tax/MAGI check, adjust withdrawals, and basic account hygiene

Free resources mentioned in this episode:

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎧Listen to this episode titles I mentioned in this podcast and some others that are related/may be of interest:

How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)
🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)
How I Retired at 55: Do These 5 Things
ACA MAGI: How to Calculate & Manage It for Big Savings!
Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About
Will ACA Subsidies Disappear After 2025? What You NEED to Know!
How Early Retirees Can Pay WAY Less for Health Insurance!
The $12,900 Health Insurance Loophole for Early Retirees!
Health Insurance Options for Early Retirement: What You NEED to Know

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Does Retiring Early Reduce Social Security? The Truth.

Mon, 03 Nov 2025 15:00:00 -0600

Does retiring early reduce Social Security? The truth—how benefits are really calculated: the 35-year rule, Average Indexed Monthly Earnings (AIME), bend points, indexing only through age 59, and why “zeros” hurt.

In this episode, I break down:

Why Social Security is based on your highest 35 indexed years—not your last job.
How indexing stops after age 59, so skipping some early-60s work years often matters less than headlines suggest.
Why zeros are the enemy—and simple ways part-time income can replace them.
A clear Path A vs. Path B example (keep working vs. hang it up) to show how the impact often lands in the couple-hundred-per-month ballpark in my scenario.
The crucial difference between retiring and claiming (FRA reductions vs. delayed credits).

Quick checklist to get clarity:

Download your earnings record at SSA.gov and fix any errors.
Count your credited years—if you’re under 35, plan to replace zeros (even modest earnings help).
Compare two scenarios: keep working a bit vs. retire earlier; check benefits at Full Retirement Age and at your actual claim age.
Decide based on dollars and lifestyle, not fear headlines.

Free resources mentioned in this episode:

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎧Listen to these episode titles next that I mentioned in this podcast:

How to Tap Your IRA or 401(k) Early —NO IRS PENALTY!
ACA MAGI: How to Calculate & Manage It for Big Savings!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

7 Signs You Should Retire Earlier Than You Think

Mon, 27 Oct 2025 15:00:00 -0500

Retirement planning, early retirement, 7 signs you’re ready to retire, retire earlier than you think, retire in your 50s, how to retire early—here’s how to know if the numbers and lifestyle say YES.

If you’re wondering “Am I actually ready to retire sooner?”, this episode walks through 7 clear signs—financial, lifestyle, and mindset—that indicate you can retire earlier than you think. We’ll cover bridging to age 59½, penalty-free access options (Rule of 55 and Substantially Equal Periodic Payments under IRS Rule 72(t)), income diversification, healthcare planning, Monte Carlo stress tests, and a low-risk way to “test-drive” retirement before you leap.

What you’ll learn:
• Why 59½ is a key milestone—and smart ways to bridge those years
• Penalty-free access paths: Rule of 55 and 72(t) SEPPs (complex, not for everyone)
• How diversified income (cash, taxable brokerage, dividends/cap gains, Roth basis) boosts flexibility
• Stress-testing your plan with Monte Carlo simulations to validate your withdrawal rate
• Housing decisions (right-sizing or staying put) and their impact on cash flow
• Healthcare budgeting before Medicare and how to plan for premiums/out-of-pocket costs
• A simple “retirement test-drive” to build confidence before you quit

Free resources mentioned in this episode:

🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎧Listen to these episode titles next that I mentioned in this podcast:

How to Tap Your IRA or 401(k) Early —NO IRS PENALTY!
ACA MAGI: How to Calculate & Manage It for Big Savings!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)

Mon, 27 Oct 2025 11:41:54 -0500

2026 health insurance: If Affordable Care Act (ACA) subsidies end, Plan A vs Plan B. Open Enrollment Nov 1; enroll by Dec 15 for Jan 1. MAGI targets, 400% FPL, on-exchange vs off-exchange.

In this video,“No Subsidies in 2026? Plan A vs Plan B (Do This)”— I provide two pathways so you’re ready to enroll by Dec 15 for a Jan 1 health insurance start, and why I’m building both plans now given the uncertainty around enhanced ACA subsidies.

Plan A (assume no enhanced subsidies):

A1: On-exchange, ACA-compliant coverage even without credits (keeps ACA protections).
A2: Off-exchange, ACA-compliant quotes (compare carefully; note that off-exchange doesn’t receive credits if they return mid-year).
A3: “Alternatives” with caution (e.g., short-term, cost-sharing, memberships/DPC): understand pre-existing condition limits, exclusions, and red flags. Only as a time-boxed fallback.

Plan B (if enhanced subsidies continue):

Manage MAGI like a pro: right-size year-end Roth conversions, time capital gains, and use taxable brokerage for spending to avoid accidental income spikes.
If working: lean on pre-tax payroll options and an HSA (with an eligible HDHP) to help control MAGI.
If retired: be deliberate with pre-tax withdrawals—they raise MAGI and can shrink credits, also contribute to an HSA.

📊Free resources mentioned in this episode:

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

To get this free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🔗ACA Cost Estimator

🔗2025 Federal Poverty Level Guidelines

🔗Goto healthcare.gov or your state exchange to enroll in a 2026 ACA plan - open enrollment begins Nov 1.

🎧Listen to these podcasts of mine next for more info on the topics covered in this episode:

ACA MAGI: How to Calculate & Manage It for Big Savings!
Will ACA Subsidies Disappear After 2025? What You NEED to Know!
The $12,900 Health Insurance Loophole for Early Retirees!
Health Insurance Options for Early Retirement: What You NEED to Know
How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)

🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.

💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅ FREE Early Retirement Planning Checklist
Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy.

👉To get the free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources.

5 Things to Sell BEFORE You Retire

Mon, 20 Oct 2025 15:00:00 -0500

Retirement planning: 5 things to sell before you retire—downsize the house, cut support for adult children, ditch RV/boat “toys,” drop the second car, and release your work identity with my Keep-Sell-Swap test.

If you want a calmer, freer retirement, subtraction beats addition. In this video I walk through five high-impact things to sell (or stop funding) to lower ongoing costs, reduce stress, and buy back time for what matters most—travel, family, health, and fun.

What you’ll learn:
• How to decide if your house is sized for your next chapter
• A smart boundary for funding independent adult children without hurting your plan
• Cheaper alternatives to ownership (boat clubs, rentals, peer-to-peer)
• A simple test to see if you still need a second car
• Why letting go of your old work identity creates real freedom

My 3-step Keep, Sell, or Swap framework:

Does this serve my next chapter—or my last one?
What’s the real all-in cost (cash, time, stress, space, opportunity)?
What becomes possible if I release it?

Try the 60-Day Swap: live exactly as if the item is gone (park the RV, ignore the second car, use rentals). Track real inconveniences vs. habit itches. Decide with data, not guilt.

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy.

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

7 “Assets” Rich Retirees Avoid

Mon, 13 Oct 2025 15:00:00 -0500

Retirement planning, early retirement, money traps: timeshares, vacation homes, high-fee annuities, whole life insurance, long-term care insurance, high-yield bonds, high-fee active funds, cash flow, withdrawal rate.

In this episode, we break down 7 “assets” rich retirees avoid—and why skipping them protects your cash flow and flexibility before and after you retire. You’ll learn how these purchases can raise ongoing costs, lock up money, or add risk at the worst time—and what simpler choices to use instead.

What you’ll learn:

Timeshares & vacation homes: exchange fees, rising dues/carrying costs, weak resale; why renting keeps flexibility
High-fee annuities: layers of fees, surrender schedules, complex crediting; why simple, low-cost portfolios + a cash buffer win
Whole life insurance (late start): high premiums, slow cash value; why separating insurance from investing helps cash flow
Long-term care insurance: premium hikes, ADL triggers, fine print; when a dedicated LTC bucket (cash/short-term bonds/TIPS) can be a cleaner path
High-yield corporate bonds: higher default risk right when stability matters; use high-quality bonds for ballast instead
High-fee active funds: expense ratios and taxes drag; low-cost index funds tend to outperform over time

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

How I Retired at 55: Do These 5 Things

Mon, 29 Sep 2025 15:00:00 -0500

I retired early at 55. In this episode I show exactly how to retire early with 5 proven keys to early retirement: the mindset that powers compounding, how to raise your savings rate, the income multiplier, simple investing with low-cost index funds, and retirement planning that avoids sequence-of-returns risk.

If you want to retire early—or just build a larger retirement nest egg—this step-by-step guide covers the Rule of 72, defense vs. offense budgeting, lifestyle-creep control, rental real estate and REITs, cash reserves, and the 4% rule vs. updated safe withdrawal rates and more! These early retirement strategies, investing basics, and financial independence tactics will help you retire early, invest smarter, and create reliable retirement income.

What you’ll learn:

• Key #1: Mindset and the power of compounding (Rule of 72)
• Key #2: Defense + offense budgeting to boost your savings rate
• Key #3: The income multiplier—raises, promotions, and skill stacking
• Key #4: How to invest for retirement (index funds, value funds, real estate, REITs. etc)
• Key #5: Know your number (4% rule, Bengen update, guardrails, cash buffer)

🔗Free checklist 12 Must – Do Steps to Retire Sooner and Smarter.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

ACA MAGI: How to Calculate & Manage It for Big Savings!

Mon, 22 Sep 2025 15:00:00 -0500

ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize premium tax credits/subsidies.

In this episode, we calculate ACA MAGI step-by-step using a real early-retiree scenario and show you how to keep ACA premiums low by hitting your MAGI “sweet spot.”

You’ll learn:
• What counts in MAGI vs. what doesn’t.
• How to add back non-taxable Social Security benefits, tax-exempt interest, and excluded foreign income.
• How Roth conversions, IRA withdrawals, dividends, interest, and capital gains flow into AGI and then ACA MAGI.
• Form 8962 (reconciling with 1095-A) essentials.
• How to plan for the 2026 subsidy cliff as the 400% FPL cap returns.

🔗 Free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

📊 Resources mentioned in this episode:

More information on Traditional IRA contribution limits and the ability to deduct them: Traditional IRA Contribution Limits for 2025 - NerdWallet
IRS Publication 501: 2024 Publication 501
2025 FPL Levels based on household size: detailed-guidelines-2025.pdf
Click here for the ACA Cost Estimator

🎧 Podcast episodes mentioned:

This podcast episode where I talk about about using the ACA cost estimator and saw amazing results, including cost sharing reductions by controlling MAGI, titled: How Early Retirees Can Pay WAY Less for Health Insurance!

This podcast episode on how a taxable brokerage account can be a superhero in reducing MAGI for ACA, titled: The $12,900 Health Insurance Loophole for Early Retirees!

This podcast episode that goes into detail about the enhanced ACA subsidies likely expiring at the end of 2025, and the 400%FPL cliff returning in 2026, titled: Will ACA Subsidies Disappear After 2025? What You NEED to Know!

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About

Mon, 08 Sep 2025 15:00:00 -0500

Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost you ACA health insurance subsidies before Medicare. In this episode, I’ll break down the trade-off, show you real examples, and share strategies to balance Roth conversions and Affordable Care Act subsidies.

Retiring before 65 means health insurance is one of your biggest expenses. Should you save thousands on ACA subsidies today, or avoid massive RMD taxes later with Roth conversions? I’ll cover how subsidies work, how Roth accounts impact your Modified Adjusted Gross Income (MAGI), and what happens if enhanced subsidies expire after 2025.

What you’ll learn:
• Why Roth conversions are so popular in retirement planning
• How ACA subsidies are calculated and why MAGI matters
• Real-world examples of couples facing this Roth vs. ACA trade-off
• Strategies like partial Roth conversions to protect subsidies
• What changes when enhanced ACA subsidies end in 2026

This is one of the most important — and overlooked — retirement planning dilemmas. Listen to see if protecting ACA subsidies or prioritizing Roth conversions is smarter for your retirement strategy.

🎧 Listen to the following episodes mentioned in this podcast for more info that you'll find as show episodes:

- Health Insurance Options for Early Retirement: What You NEED to Know

- How Early Retirees Can Pay WAY Less for Health Insurance!

🎧 And listen to these other episodes about health insurance in early retirement that are full of great information you can't miss!:

- The $12,900 Health Insurance Loophole for Early Retirees!

- Will ACA Subsidies Disappear After 2025? What You NEED to Know!

📊 Here is the link to the ACA cost estimator tool mentioned : https://www.healthcare.gov/see-plans/#/

📊2025 Federal Poverty Level Guidelines: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

✅ FREE MAGI Estimator. This was made after this episode, so was not mentioned, but I've created an ACA MAGI estimator (Excel) that is free to download that you can use to estimate your MAGI.
✅ FREE Early Retirement Planning Checklist. Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy.
👉To get the free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

5 Things I Wish I Knew BEFORE Retiring Early at 55

Mon, 25 Aug 2025 15:00:00 -0500

Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement planning, healthcare costs, spending habits, and mindset shifts that can make or break your retirement years.

Retiring early isn’t just about saving enough money — it’s about knowing how to spend wisely, manage healthcare, and protect your peace of mind. If you’re planning for early retirement (or thinking about retiring at 55 like I did), these insights will help you avoid regrets and set realistic expectations for the journey ahead.

What you’ll learn in this video:
• Why retiring early feels different than expected
• The financial and emotional lessons I wish I knew before retiring
• How healthcare, spending habits, and mindset can shape your retirement
• Tips for avoiding common regrets in early retirement

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

✅Get these Free Resources available too on my Patreon!:
📊Free MAGI calculator Excel template
📊Free 12-Step Early Retirement Planning Checklist
📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long
👉To get these free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

The Biggest Retirement Mistake? Working Past 60

Mon, 18 Aug 2025 15:00:00 -0500

Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing.

You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Medicare premiums eat into those extra earnings, and why your healthiest years may be slipping away. Plus, I’ll share real-life examples, surprising data, and a practical framework for deciding when it’s truly time to retire.

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

Resources Mentioned:

📊 New York Life Study: https://time.com/3821757/this-is-the-retirement-regret-nobody-talks-about/

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

#WorkingPast60 #RetirementPlanning #EarlyRetirement

One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees

Sun, 03 Aug 2025 16:15:00 -0500

Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE implications for retirees, early retirees, and anyone planning for financial independence.

📌 Here’s what you’ll learn:

🏦 2025 retirement tax changes that lock in the 2017 Tax Cuts and Jobs Act (TCJA) permanently
💰 Extended income tax brackets, standard deduction increases, and the brand-new senior tax deduction
🧾 Detailed breakdown of Child Tax Credit enhancements, AMT exemption, SALT cap increase, and capital gains tax stability
🚗 New 2025-2028 deductions for auto loan interest, tip income, and overtime pay
🏥 What the bill didn’t do: the ACA subsidy cliff and how it could affect early retirees in 2026
💼 How to optimize Roth conversions, HSA contributions, and long-term retirement planning

This is the 2025 retirement tax update you can’t afford to miss — I did all the research so you don’t have to! If you’re nearing retirement or in early retirement, these tax changes for retirees in 2025 could seriously impact your strategy. Make smarter money moves with clarity and confidence. ✅

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

✅Get these Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

#RetirementTaxChanges #2025TaxUpdate #EarlyRetirementPlanning, #SeniorTaxDeduction #OneBigBeautifulBill

How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained

Sun, 27 Jul 2025 15:00:00 -0500

Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty?

In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retirement plans—but beware, the rules are strict and the risks are serious.

✅ We’ll cover:

How IRS Rule 72(t) works with IRAs and 401(k)s
Eligibility requirements and account types
How long you must commit to fixed withdrawals
Major risks including sequence-of-returns and tax traps
When Rule 72(t) makes sense—and when it absolutely doesn’t

If you're aiming for early retirement and don’t qualify for the Rule of 55 or have limited brokerage/Roth options, Rule 72(t) could be your lifeline. But it can also backfire if you’re not careful.

⚠️ Don’t attempt this without consulting a tax pro or retirement planner—this is one of the most complex strategies out there.

🎁 Download my free guide: 12 Must-Do Steps to Retire Sooner and Smarter. Whether you're just getting started or refining your plan, this free guide will help you take the next step! It's a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy.

While you're on my Patreon, you may want to download these other free tools too:

📊Free MAGI calculator Excel template

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

#EarlyRetirement #401kWithdrawal #IRSRule72t #RetirementPlanning #FinancialFreedom

Countdown to Retirement: Are You Really Ready to Take the Leap?

Sun, 20 Jul 2025 14:15:00 -0500

Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning.

In this retirement planning video, you’ll discover:

How to pick the ideal retirement age (55, 59½, or 62) to maximize your retirement savings and avoid penalties.
Essential budgeting strategies for retirement, including accurately planning for healthcare expenses before Medicare.
Proven methods to calculate your FIRE number, going beyond the standard 4% rule for early retirement success.
Powerful risk-management techniques to protect your nest egg from sequence of returns risk and market volatility.
Crucial insights about when to claim Social Security, and how avoiding a common trap could save you thousands.

👉 Get started with my free checklist, "12 Must-Do Steps to Retire Sooner and Smarter," to ensure you don't miss a thing as you prepare to retire. To get the free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

While you're on my Patreon, you may want to download these other free tools too:

📊Free MAGI calculator Excel template

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

Stress-test your retirement plan using the highly recommended retirement planning software (Boldin) mentioned in the video: Try Boldin here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com

#CountdownToRetirement #RetirementPlanning #EarlyRetirement #RetirementChecklist #SocialSecurityTips

6 Reasons to Retire AS SOON AS YOU CAN!

Mon, 14 Jul 2025 17:00:00 -0500

Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money.

Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 reasons to retire early,” this episode takes it further—showing why waiting even one more year could cost you more than just money.

We’ll explore the opportunity cost of continued work, how your health and freedom are affected, and why arbitrary retirement goals may be holding you back from the financial independence you’ve already earned. I retired early at 55, and in this episode, I’ll share the reasons that finally made me take the leap—and how it’s changed my life, and that you should consider too.

👉 If you’re ready to rethink your retirement timeline, this video is for you.

❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

#earlyretirement #retireearly #financialfreedom #retirementplanning #retirement

The Top 10 Retirement Myths That Could Cost YOU Thousands!

Mon, 07 Jul 2025 13:15:00 -0500

Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working?

In this episode of the Early Retirement Roadmap Podcast, I bust the top 10 retirement myths—with real data and practical advice. These are the beliefs that could seriously derail your plans and cost you thousands if you fall for them.

We’ll cover myths about:

Retirement savings goals
Taxes in retirement
Social Security and Medicare
Downsizing and expenses
Longevity and lifestyle in retirement
...and much more.

I retired at 55 and have seen firsthand how common these myths are—and how dangerous they can be. Listen now to plan smarter and retire with confidence.

Resources Mentioned:

📊 Myth #10: Federal Reserve Study reports 5% of households have $1 Million Saved and under 2% have 2 million saved, and median savings: https://www.retirementliving.com/do-you-really-need-1-million-to-retire

📊Myth #9 SmartAssett.com – Is Social Security Income Taxable?: https://smartasset.com/retirement/is-social-security-income-taxable

📊Myth #8: Schroder’s Retirement Study: https://www.schroders.com/en-us/us/institutional/media-center/schroders-retirement-study-finds-inflation-taking-toll-on-retirees/

📊Myth #8 Retirement Researcher, Retirement Spending Smile: https://retirementresearcher.com/retirement-spending-smile/

📊Myth #7: National Council on Aging (NCOA), Social Security Only Replaces 37% of earnings, on average, see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/ 📊Myth #7: Kiplinger, Average Social Security Benefits in 2025, see: https://www.kiplinger.com/retirement/social-security/how-to-get-the-maximum-social-security-check

📊Myth #7: The Center On Budget and Policy Priorities, average social security income: https://www.cbpp.org/research/social-security/top-ten-facts-about-social-security

📊Myth #6: Kiplinger, regarding social security running out of money: https://www.kiplinger.com/retirement/social-security/when-will-social-security-and-medicare-trust-funds-run-out-of-money

📊 Myth #5: Fidelity, 2023 Estimates of Healthcare Costs Medicare Parts A & B Don’t Cover: https://newsroom.fidelity.com/pressreleases/fidelity--releases-2023-retiree-health-care-cost-estimate--for-the-first-time-in-nearly-a-decade--re/s/b826bf3a-29dc-477c-ad65-3ede88606d1c

📊Myth #4: National Council on Aging – 64 percent of retiree retired sooner than expected, see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/

📊Myth #3: Merrill Lynch and Age Wave Study – Many retirees don’t downsize as reported by CNBC: https://www.cnbc.com/2021/04/13/op-ed-more-boomers-are-choosing-to-upsize-their-homes-in-retirement.html

📊Myth #2: 1 out of 3 65-year-olds will live until at least age 90 – see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/

📊Myth #1, People are Happier in Retirement, and not bored, see: https://www.massmutual.com/global/media/shared/doc/2024_massmutual_retirement_happiness_study.pdf

❤️ Like, Subscribe, Follow, Share and leave a review if this helped!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com

#retirementmyths #earlyretirement #retirementplanning #personalfinance #financialfreedom

🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!

Tue, 01 Jul 2025 16:15:00 -0500

🚨 Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER! In this episode, I break down why Roth conversions in 2025 are more important than ever—and how early retirees, those already retired, or those thinking about retirement could face massive tax regret if they don’t act soon.

Whether you're already in early retirement or planning to retire soon, you'll learn:

✅ Why the 2025 Roth conversion deadline is a critical tax planning window

✅ How losing ACA subsidies in 2026 could spike your health insurance costs

✅ What triggers Medicare IRMAA penalties—and how to avoid them

✅ How to run your Roth conversion numbers the smart way - all the things you need to be aware of to avoid potential pitfalls

✅ Estate planning, tax brackets, and how strategic Roth conversions can save you six figures

🔥 Don’t miss this Roth conversion opportunity—use it before it disappears.

Resources mentioned or for more information:

📊 Department of Treasury, U.S. National Debt: https://fiscaldata.treasury.gov/americas-finance-guide/national-debt/

📊 Charles Scwaab Conversion Calculator: https://www.schwab.com/ira/ira-calculators/roth-ira-conversion

📊Boldin Conversion Calculator: https://www.boldin.com/retirement/roth-conversion-calculator/

📊Bloomberg Government: 2025 Tax Policy Crossroads—What Will Happen When the TCJA Expires?: https://about.bgov.com/insights/elections/2025-tax-policy-crossroads-what-will-happen-when-the-tcja-expires/

📊Thomson Reuters: What to know about TCJA expiration: https://tax.thomsonreuters.com/blog/what-to-know-about-tcja-expiration/

📊Mariner Wealth Advisors: Early Retirement and Roth Conversions: https://www.marinerwealthadvisors.com/insights/early-retirement-should-you-consider-a-roth-conversion/

📊Kiplinger: Benefits of Roth IRA Conversions Early in Retirement: https://www.kiplinger.com/retirement/benefits-of-roth-ira-conversions-early-in-retirement

📊Investopedia: How Much Tax Do You Pay on a Roth IRA Conversion?: https://www.investopedia.com/articles/retirement/08/roth-conversion-2010.asp

📊Wells Fargo: Roth IRA Conversion Rules and FAQ: https://www.wellsfargo.com/investing/retirement/ira/roth-ira-conversion/

📊Money With Katie: The Roth Conversion Ladder: https://moneywithkatie.com/blog/how-to-use-your-401k-in-early-retirement-without-a-10-penalty

❤️ Like, Subscribe, Follow, Share and leave a review if this helped!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com

#rothconversion #retireearly #retirementplanning #taxplanning #taxesinretirement #earlyretirement

STOP Worrying About Running Out of Money in Retirement!

Tue, 24 Jun 2025 16:15:00 -0500

Are you constantly worried about running out of money in retirement? You’re not alone—and the good news is, the truth might surprise you!

In this podcast, I reveal what most people get wrong about retirement spending, how rare it actually is to run out of money, and the real strategies that work—especially if you're retiring early. We’ll break down the 4% rule, portfolio withdrawal strategies, the guardrails approach, and real-world data that shows how most retirees end up with more money than they started with.

Whether you're planning for early retirement or already living it, this episode will help you stop worrying and start living! Learn how to make your money last, without the stress.

🔍 Topics covered:

✅ How to stop worrying about running out of money in retirement

✅What the 4% rule really means (and its limitations)

✅The truth about retirement portfolio longevity

✅How guardrails can give you more flexibility and confidence

✅Common mistakes retirees make with money

Resources Mentioned:

📊 Michael Kitces article on why most retirees will never spend their entire retirement portfolio: https://www.kitces.com/blog/consumption-gap-in-retirement-why-most-retirees-will-never-spend-down-their-portfolio/

📊Michael Kitches article regarding implementing retirement income guardrails: https://www.kitces.com/blog/implementing-retirement-income-guardrails-to-facilitate-the-right-spending-raises-and-spending-cuts/

📊Retirment Planning Tool I Use, Boldin.com: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

❤️ Like, Subscribe, Follow, Share and leave a review if this helped!

📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

How Much Do You REALLY Need to Retire on $10K a Month?

Tue, 17 Jun 2025 16:15:00 -0500

Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk.

We’ll break down what it really takes to sustain $10,000 in monthly retirement income spending —whether you're aiming for early retirement, following the 4% rule (and why the 4% rule should really be used only as a very rough ballpark estimate), or just want a comfortable, worry-free lifestyle. You’ll also learn how to reduce your savings target without sacrificing your standard of living.

You’ll learn:

✅ How much you need to retire with $10K/month in spending

✅ Why withdrawal rate and account types can make or break your plan

✅ How Social Security and other income reduce your savings target

✅ What risks like sequence of returns and inflation really mean

✅ Strategies to optimize taxes and healthcare before Medicare

🔧 Tools Mentioned: Boldin.com: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!

Resources:

📊 Morningstar, 3.7% Starting Withdrawal Rate: https://www.morningstar.com/business/insights/research/the-state-of-retirement-income

📊 Morningstar: Re-evaluating the 4% Withdrawal Rule: https://www.morningstar.com/retirement/morningstars-retirement-income-research-reevaluating-4-withdrawal-rule 📊Charles Scwaab – How Many Years of Cash Reserve: https://www.schwab.com/learn/story/market-volatility-retirement-what-if-you-havent-prepared

📊 More about bond tents: https://www.thegoodlifejourney.com/home/bond-tent-early-retirement-strategy? & https://www.kitces.com/blog/managing-portfolio-size-effect-with-bond-tent-in-retirement-red-zone/

❤️ Like, Subscribe, Follow, Leave a Review, and Share if this helped!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺When you're not on the go, watch the Early Retirement Roadmap channel on YouTube: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

Tue, 10 Jun 2025 16:15:00 -0500

⚠️ Are ACA subsidies really going away after 2025? If you're planning to retire early or already living off your investments, this could impact your healthcare costs in a big way. In this episode, I explain exactly what's happening with ACA subsidies in 2026—what's expiring, what's staying, and how you can still qualify for financial help through smart retirement planning and income strategies.

You’ll learn:

✅ What the “subsidy cliff” is and how to avoid it

✅ How to use MAGI planning to stay eligible for ACA tax credits

✅ What changes after the Inflation Reduction Act ends

✅ Why taxable brokerage accounts and Roth strategies are your secret weapons.

Even if the enhanced subsidies go away, you can still protect your early retirement plan—if you know how to plan ahead. 📉 Don’t get surprised by skyrocketing ACA healthcare premiums in 2026. This episode breaks it all down.

🎯 If you’re aiming to retire before Medicare kicks in, this is a must-watch.

Episodes to listen to next:

🎧 This episode about health insurance options for early retirement, title of: Health Insurance Options for Early Retirement: What You NEED to Know -- Click here to listen on YouTube: https://youtu.be/3lxFC-ob2E4

🎧 This episode about slashing ACA premiums by strategically funding your retirement income to reduce MAGI, where a taxable brokerage account in particular is the big hero, title of: The $12,900 Health Insurance Loophole for Early Retirees! Click here to listen on YouTube: https://youtu.be/rvbxNVaW3iM

🎧This episode where I talk thru the results I achieved on the actual ACA Estimator Tool on heatlhcare.gov, using the strategy, with 3 case scenarios, from the episode directly above!, title of: How Early Retirees Can Pay WAY Less for Health Insurance! Click here to listen on YouTube: https://youtu.be/2QqresmHRCg

Resources Mentioned/Further Reading:

📊 Commonwealth Fund Article: https://www.commonwealthfund.org/publications/explainer/2025/feb/enhanced-premium-tax-credits-aca-health-plans

📊 Kaiser Family Foundation Articles - lots of current articles/happenings pertaining to the ACA: https://www.kff.org/tag/marketplaces/

📊Medicare Rights Center Article: https://www.medicarerights.org/medicare-watch/2025/04/17/congress-must-act-to-continue-affordable-care-acts-enhanced-premium-tax-credits

❤️ Like, Follow, Comment, Subscribe, and Share if this episode helped you!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺 When you're not on the go, watch the Early Retirement Roadmap Channel on YouTube and subscribe: https://www.youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

DISCLAIMER:

This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

#earlyretirement #retireearly #healthinsurance #financialplanning #retirementplanning

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

Thu, 05 Jun 2025 17:19:46 -0500

If you're in your 40s, 50s, or 60s, listen to this! In this podcast, I share 25 life lessons from people over 70 — timeless wisdom for navigating midlife, retirement planning, relationships, purpose, and happiness.

These life lessons are based on the powerful research of Dr. Karl Pillemer, author of 30 Lessons for Living, who interviewed over 1,000 older adults to uncover the most important advice they would pass on. I’ve distilled those insights into 25 practical lessons tailored especially for those of us between ages 45 and 65.

Whether you’re thinking about retirement, already retired, or simply looking to make the most of your next chapter, this episode is packed with real-world advice from those who’ve been there.

👉 Watch now to learn how to:

Worry less and enjoy more
Nurture relationships before it’s too late
Prioritize time over things
Age with purpose, clarity, and peace
And much, much more!

🧠 Don’t miss these life-changing insights from 70+ year-olds — especially if you’re in your 40s, 50s, or 60s!

📊See more about Dr. Karl Pillemer's book, read reviews and purchase here: https://amzn.to/45g8ziF

Disclosure: The link above is an affiliate link, which means I may earn a small commission if you make a purchase — at no extra cost to you. Thank you for supporting the channel!

❤️ Like, Subscribe, Follow and Share if you found this episode meaningful.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

📺When you're not on the go, watch the Early Retirement Roadmap channel on YouTube: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

#lifelessons #advicefromoldpeople #midlifewisdom #retireearly #retirementplanning

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

Wed, 04 Jun 2025 15:15:00 -0500

Many early retirees forget to factor in their adult children when planning retirement. From weddings and tuition to ongoing support, the financial impact can be substantial—especially when you no longer have a paycheck coming in. In this episode, I’ll walk you through how to plan for potential financial support, set healthy boundaries, and protect your own future—without guilt. Learn why planning ahead can be the difference between peace and pressure in retirement.

👇 Comment Below: Have you had to set boundaries with adult kids or struggled with it? I’d love to hear how you handled it!

📊 Resources Mentioned:

• CNBC 50% of parents support adult children: https://www.cnbc.com/2025/03/25/half-of-parents-financially-support-adult-children-report-finds.html

• 2025 Zola average wedding cost: https://www.zola.com/expert-advice/whats-the-average-cost-of-a-wedding

❤️ Like, Subscribe, Follow and Share if this helped!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit: [mikeupland.com](https://mikeupland.com/)

DISCLAIMER: The information presented is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals.

#retireearly #earlyretirement #retirementplanning #adultchildren #financialboundaries

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

Tue, 27 May 2025 18:15:00 -0500

Should you claim Social Security early, wait until full retirement age, or delay until 70?

In this podcast, we walk through a real retirement case study and run the numbers to show how your claiming age affects your investments, taxes, and even your health insurance premiums.

📊 See why delaying may not always be the best choice—and how opportunity cost could erode your nest egg more than you realize.

💡 You’ll learn:

✅The real math behind claiming at 62, 67, or 70

✅Why investment returns matter more than you think

✅How taxes and ACA premiums are impacted

✅What most people overlook in Social Security planning

👉 Don’t make a decision until you understand these trade-offs!

📊 Resources: • Social Security Benefit Reduction Chart by Claiming Age: https://smartasset.com/retirement/social-security-early-retirement-penalty-chart

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

❤️ Like, Follow, Subscribe, and Share if this helped! 🎧

🌐 Visit: [mikeupland.com](https://mikeupland.com/)

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

DISCLAIMER: This podcast is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals.

#socialsecurity #socialsecuritybenefit #retirementplanning #retireearly #financialfreedom

How Early Retirees Can Pay WAY Less for Health Insurance!

Tue, 20 May 2025 17:15:00 -0500

Want to pay WAY less for health insurance in early retirement? This follow-up to my previous very popular video (link below in watch next) shows how smart retirees legally slash ACA premiums by strategically managing their income. You'll learn how MAGI impacts subsidies, and see real scenarios using Healthcare.gov. Don’t overpay for healthcare—plan smarter and keep more of your money!

Here is a link to the YouTube version of this podcast so you can see the actual demos using the ACA estimator tool on healthcare.gov: https://youtu.be/NXEaYYjQKdI

And here is the link to the youtube video this episode was a follow up to (or listen to my podcast titled "The $12,900 Health Insurance Loophole for Early Retirees!" : https://youtu.be/lxdNnUpdZ-Y

📊 Resources:

ACA Cost Estimator to run it for yourself: https://www.healthcare.gov/see-plans/#/ 2025
Federal Poverty Level Guidelines: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

❤️ Like, Subscribe, Follow, Leave a Review or Comment and Share if this episode helped you!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast.

DISCLAIMER: This content is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals.

#earlyretirement #retireearly #healthinsurance #retirementplanning #financialplanning

Retirement Stats That’ll Make You Rethink Working Another Year

Wed, 14 May 2025 15:15:00 -0500

Is working longer really worth it?

In this episode, I break down 3 retirement stats and insights that could completely change the way you think about work, wealth, and health in retirement. If you're planning for early retirement, these numbers might just shift your whole retirement strategy.

Here's what you'll learn:

• Why 63.9 years is a critical number for your retirement health

• How the average person works 90,000 hours in their lifetime and reclaiming some of that time

• What research says about retirees who never spend their savings

If you're in your 40s, 50s, or early 60s, and you're serious about retirement planning, this video is for you.

👇 Comment Below: What would you do if work became optional tomorrow?

📊 Resources Mentioned:

• [World Health Organization (WHO) – Healthy Life Expectancy (HALE) at Birth] (https://data.who.int/countries/840)

• [• National Bureau Of Economic Research - Consumption and Saving After Retirement](https://www.nber.org/system/files/working_papers/w29826/w29826.pdf)

• [Institute for Fiscal Studies Report](https://ifs.org.uk/sites/default/files/output_url_files/BN236.pdf)

❤️ Like, Subscribe, and Share if this helped!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit: [mikeupland.com](https://mikeupland.com/)

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Why You’re Closer to Early Retirement Than You Think

Mon, 05 May 2025 13:15:00 -0500

Are you wondering why it feels like everyone else is retiring early — and you're not? In this episode of Early Retirement Roadmap, we uncover the real reasons people delay early retirement, even when they have enough saved. Learn how to avoid the "one more year syndrome," stop chasing unrealistic retirement numbers, and discover 5 proven strategies to retire sooner than you think.

If you want to know how much you really need to retire, how to build financial confidence, and how to create a realistic retirement plan, this episode is for you.

We cover the average 401(k) balance by age, how much guaranteed income like Social Security can help, why stress-testing your retirement plan matters, and how redefining retirement could be your key to freedom.

🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.

Episodes to listen to mentioned in this episode:

🎙️Episode 3, How Much Do You REALLY Need to Retire

🎙️Episode 6, The One Retirement Mistake that Could RUIN YOU

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out my Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit mikeupland.com – Connect with me & explore retirement resources including all my videos and blog articles.

The $12,900 Health Insurance Loophole for Early Retirees!

Mon, 28 Apr 2025 04:00:00 -0500

What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break down the smartest way to structure your income before age 65 to maximize your ACA subsidy. You’ll learn why your taxable brokerage account might be your biggest retirement superpower, how MAGI works, and how to avoid the dreaded “coverage gap” in non-Medicaid expansion states. Perfect for anyone eyeing early retirement with a sharp eye on healthcare costs.

🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out my Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit mikeupland.com – Connect with me & explore retirement resources including all my videos and blog articles.

5 Retirement Regrets You’ll Want to Avoid

Tue, 22 Apr 2025 11:00:00 -0500

If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experience, hard-earned lessons, and recent data.

From not saving early enough to underestimating healthcare costs, I break down how you can sidestep these pitfalls and build a retirement that’s not just financially sound, but fulfilling.

Stick around for the final regret — it's one even savvy retirees often miss.

🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

What Vanishes When You Retire (And How to Get it Back!)

Mon, 14 Apr 2025 01:00:00 -0500

You’ve worked hard, saved diligently, and now retirement is here! But nobody warns you about the six major things that disappear the moment you leave the workforce. If you’re not prepared, these changes can hit harder than expected—but the good news? You can replace them with something even better!

In this episode of Early Retirement Roadmap, I’ll break down:
✅ The six things that vanish when you retire—and why they matter 🏆
✅ How to rediscover purpose and avoid feeling lost 💡
✅ Why having structure & routine in retirement is crucial 📅
✅ How to replace career achievements with new personal goals 🏅
✅ The surprising impact of losing your work identity—and how to rebuild it 🎭
✅ How to maintain social connections when your work network disappears 👥

I’ll also share my personal experience transitioning from my 30-year career to early retirement and the lessons I learned along the way!

🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration. And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

🚀 Retirement isn’t the end—it’s a new beginning. Let’s make it amazing!

Thinking About Retiring Early in 2025? Think Again.

Mon, 07 Apr 2025 01:00:00 -0500

Planning for early retirement in 2025? Before you hand in your notice, this episode of Early Retirement Roadmap is your essential guide to navigating the biggest risks facing early retirees this year.

In it, I break down three critical threats — sequence of returns risk, rising inflation, and high market valuations, yes, even with the market downturn due to the Trump tariffs — and I share practical strategies to protect your retirement portfolio. From building cash reserves to using TIPS bonds and dividend-paying ETFs, you'll learn how to retire with confidence even during market volatility.

Whether you're part of the FIRE movement or just ready to leave your 9–5, this episode will help you build a plan to retire early AND STAY retired.

What You’ll Learn:

How a market downturn at the wrong time can destroy your retirement plans
Why inflation silently eats away at your wealth over time
Key investing metrics like the CAPE ratio and Buffett Indicator
How to create a resilient early retirement strategy that lasts decades

🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

The Retirement Wake-Up Call: What the Study AND My Story--Reveals!

Tue, 01 Apr 2025 01:00:00 -0500

Thinking about early retirement or already living it? This episode is your wake-up call — and your roadmap.

In this powerful and personal episode of The Early Retirement Roadmap, I talk about the retirement truths no one warns you about. Discover the real challenges behind the dream — from unexpected loneliness and identity loss to the surprising truth about pre-retirees' expectations vs. reality per a recent study by MassMutual (Mass Mutual).

You’ll learn:

Why retirement feels unstructured or even empty for many
The #1 activity most retirees do daily (hint: it's not what they planned)
How to prepare emotionally, socially, and mentally — not just financially
The 3 characteristics of thriving retirees
Mike’s candid and honest sharing of his own retirement experiences

If you’re searching for early retirement advice, wondering how to build purpose after leaving work, or asking what makes a meaningful retirement, this episode is for you.

🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources.

How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)

Mon, 24 Mar 2025 16:00:00 -0500

Investing in index mutual funds sounds like a safe bet, right? Well, I thought so—until I got hit with an unexpected $17,000 tax bill.

In this episode of Early Retirement Roadmap, I break down the hidden tax trap in taxable mutual funds and why an ETF might be the smarter choice. Plus, I’ll share how tax-loss harvesting helped me fix my mistake and avoid future surprises. If you’re serious about early retirement, financial independence, and smart investing, you won’t want to miss this!

🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources.

The Perfect Retirement Announcement: A Step-by-Step Guide

Mon, 17 Mar 2025 12:00:00 -0500

Planning to retire? Announcing your retirement isn’t as simple as picking a date and telling your boss—it’s about strategy, timing, and setting yourself up for success. In this episode of Early Retirement Roadmap, I’ll guide you through the complete retirement announcement process, so you can make a smooth, professional transition.

🌟 Here’s what we’ll cover:
✅ Choosing a date keeping tax benefits, health insurance, and bonuses 📅💰 in mind
✅ How to maximize PTO payouts and avoid leaving money on the table 🏖️
✅ How much notice to give (and why too much can backfire) 🚨
✅ How to handle your boss’s reaction and preparation 🤯
✅ What to expect from co-workers’ reactions and how to respond—from excitement to skepticism 🤔
✅ The importance of planning ahead for a stress-free, rewarding exit 🚀

I’ll also share some of my personal experiences announcing my early retirement at 55.

🔔 If you found this helpful, please subscribe & leave a review!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

☕ Enjoyed this show? Support me! Buy me a cup of coffee here!

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

🚀 Make your retirement announcement with confidence!

Scared to Retire? Overcome Your RETIREMENT FEARS!

Mon, 17 Mar 2025 12:00:00 -0500

You’ve run the numbers, planned your finances, and dreamed of early retirement—but fear is still holding you back. You’re not alone! What if I run out of money? What about healthcare costs? Will I be bored? These fears are completely normal, and in this episode of Early Retirement Roadmap, I’ll help you tackle them head-on.

🌟 Here’s what you’ll learn:
✅ The #1 financial fear of early retirees—and how to overcome it 💸
✅ How Monte Carlo simulations can give you confidence in your retirement plan 🔢
✅ Why healthcare costs don’t have to be a dealbreaker 🏥
✅ Eliminate debt for a stress-free retirement ✅
✅ The secret to avoiding boredom and creating a fulfilling post-career life 🎨🌍
✅ How to handle criticism from family & friends who don’t "get" early retirement 🤔

I’ll also share my personal experience retiring at 55 years old and how I knew for sure that I was ready.

👉 Links to Resources mentioned:

✅Boldin.com: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

✅Empower

✅Article: Best Retirement Calculators

✅ Watch my video on all your healthcare options prior to Medicare or listen to the podcast

🔔 If you found this helpful, please subscribe & leave a review!

Support me by buying a cup of coffee here! ☕
🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

🚀 Your dream retirement is possible—don’t let fear hold you back!

The ONE Retirement Mistake That Could RUIN You!

Tue, 11 Mar 2025 04:00:00 -0500

You’ve saved up, planned carefully, and are ready to enjoy your retirement—so what could possibly go wrong? In this episode of Early Retirement Roadmap, host Mike Upland reveals a critical mistake that could drain your retirement savings faster than you expect: Sequence of Returns Risk.

With today’s economic uncertainty—rising inflation, stock market volatility, and new tariffs shaking the financial landscape—understanding when you withdraw from your investments is just as important as how much you withdraw.

Tune in as Mike breaks down:
✅ Why withdrawing money during a market downturn can derail your retirement
✅ The shocking impact of the 2008 crash on retirees—and why history may repeat itself
✅ 5 powerful strategies to safeguard your nest egg, including the cash buffer strategy, flexible withdrawals, and the bucket method

Don’t let one mistake ruin your financial future! Whether you're planning for retirement or already there, this episode will help you make smart decisions to keep your money lasting as long as you do.

🎧 Listen now and take control of your retirement future!

🔔 Subscribe/Follow for more financial insights & leave a review if you found this episode helpful.

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

#RetirementPlanning #FinancialFreedom #EarlyRetirement #Investing #WealthManagement
#SequenceOfReturns #SafeWithdrawalRate #StockMarketRisk #RetirementWithdrawals #EconomicUncertainty

Health Insurance Options for Early Retirement: What You NEED to Know

Tue, 04 Mar 2025 10:34:45 -0600

Thinking about early retirement but worried about health insurance? You’re not alone! Healthcare costs are one of the biggest reasons people delay retirement. But don’t let that stop you!

In this episode of Early Retirement Roadmap, I break down all your options for staying covered before Medicare, including:
✅ COBRA – Keep your employer’s plan (but at what cost?) 💼
✅ ACA Marketplace Plans – Subsidies that can make coverage more affordable 💵
✅ Private Insurance – Is it worth the higher cost? 🤔
✅ Short-Term Plans – A risky but potentially viable bridge to Medicare ⏳
✅ Part-Time Work with Benefits – Companies that offer insurance for fewer hours 🏢
✅ Creative Solutions – Health sharing plans, expat insurance, and HSAs ✈️

Plus, I’ll explain how taking care of your physical health can also protect your financial health in retirement!

👉 Resources & Links mentioned:

1. COBRA Information - Click here to learn more about COBRA continuation coverage and eligibility requirements

2. Affordable Care Act (ACA) Marketplace: Click here to find out about ACA plans and check your eligibility for subsidies

3. Private Health Insurance - Compare private insurance options via ehealthinsurance.com or healthcare.com

4. Also, can go to ehealthinsurance.com to view short-term health insurance options too

5. Health sharing programs, Medishare, Zion Health & Christian Health Ministries

6. International health insurance options, Cigna Global & internationalinsurance.com

7. Click here for IRS Info about Health Savings Accounts

8. Click here for a list of employers that offer part-time jobs with health benefits

🎙️ If you found this podcast helpful, please subscribe & leave a review or support this new podcast show by buying me a cup of coffee here!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 Prefer a visual breakdown? Click here to watch this episode on my YouTube Channel: Early Retirement Roadmap .

🌐 MikeUpland.com – Connect with Mike & explore retirement resources

🚀 Don’t let healthcare costs keep you from the retirement you deserve!

Retirement Tax Mistakes that Could Cost You Thousands!

Tue, 04 Mar 2025 10:02:21 -0600

💰 Are you unknowingly making tax mistakes that could drain your retirement savings? In this episode of Early Retirement Roadmap, host Mike Upland breaks down the biggest retirement tax traps and how to avoid them.

📉 Learn how improper IRA and 401(k) withdrawals can push you into a higher tax bracket, trigger unexpected Social Security taxes, and even increase your Medicare premiums. We’ll also cover:

✅ The mistakes retirees make when withdrawing from their retirement accounts
✅ How strategic withdrawals can lower your lifetime tax bill
✅ What you MUST know about Required Minimum Distributions (RMDs)
✅ How to use Roth Conversions and Qualified Charitable Distributions (QCDs) to reduce taxes
✅ Case study: How Bob & Linda lost thousands—and what they should have done instead

Whether you're already retired or planning for the future, these tax-smart retirement strategies can help you keep more of your hard-earned money.

🎧 Listen now to avoid costly mistakes and make your retirement savings last longer!

🔗 Don’t forget to subscribe or follow, rate, and review so more people can benefit from these strategies!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.

🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

☕☕️ Love this content and want to buy me a coffee to help support me? Click here.

How Much Do You REALLY Need to Retire?

Wed, 19 Feb 2025 10:50:08 -0600

Retirement planning isn’t one-size-fits-all, and the question of “How much money do I REALLY need?” can feel overwhelming. But don’t worry—I’ve got you covered!

In this episode of Early Retirement Roadmap, I’m diving deep into the essential factors that determine your retirement number, including:
✅ How to calculate your annual retirement spending 🔢
✅ The 25x rule (and why it’s not enough for early retirees) 📊
✅ The impact of inflation, healthcare, and lifestyle choices on your savings 💸
✅ Common mistakes that can derail your retirement 🚧
✅ Smart strategies to make your money last 35+ years ⏳

I’ll also share my personal experience retiring at 55 years old, the lessons I learned along the way, and how you can create a plan that gives you true financial freedom.

👉 Want to stress-test your retirement plan? I highly recommend Bolden (think TurboTax for retirement planning) to model different financial scenarios and see if you're really ready. Try it here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🔔 Don’t forget to subscribe for more tips on early retirement! If you found this episode helpful, please leave a review—it really helps the show grow!

🎥 Watch the visual version of this episode on my YouTube channel: Early Retirement Roadmap .

☕ Enjoyed this show? Support me! Buy me a cup of coffee here!

🌐 MikeUpland.com – Connect with Mike & explore retirement resources

🚀 Start planning your dream retirement today!

Ready to Ditch the 9-to-5? Your Early Retirement Checklist

Wed, 19 Feb 2025 10:49:21 -0600

Are You REALLY Ready to Retire Early? This Checklist Will Tell You!

🚀 You dream of ditching the 9-to-5 grind—but are you truly prepared to take the leap into early retirement? In this episode of Early Retirement Roadmap, host Mike Upland (early retiree at 55) walks you through the ultimate early retirement checklist—covering both financial and lifestyle readiness so you can retire with confidence.

🔹 Do you have enough savings to sustain a long retirement?
🔹 Is your investment strategy strong enough to outpace inflation?
🔹 Have you planned for health insurance and unexpected expenses?
🔹 More importantly—are you mentally and emotionally ready for this big life change?

Mike breaks it all down and shares personal insights from his own early retirement journey—so you don’t have to figure it out alone. Plus, listen to the next episode, where we’ll dive deeper into how much you really need to retire early.

🎧 Subscribe now so you don’t miss it!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 Resources & Links:
🔗 MikeUpland.com – Connect with Mike & explore retirement resources
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.
☕ Enjoy the show? Support me! Buy me a cup of coffee here!

10 Powerful Reasons to Retire Early (Don't Wait Too Long!)

Wed, 19 Feb 2025 10:28:46 -0600

🚀 What if you could reclaim your time, health, and freedom—starting now?

In this episode of Early Retirement Roadmap, host Mike Upland, a seasoned early retiree, shares 10 powerful reasons why retiring early might be the smartest move you can make. From prioritizing your health to maximizing your time, he breaks down how early retirement can lead to a life of freedom, fulfillment, and opportunity.

🔹 Feeling stuck in the daily grind?
🔹 Wondering if you can really afford to retire early?
🔹 Dreaming of a life with no alarms and total flexibility?

Mike shares personal insights, expert advice, and mindset shifts to help you take control of your future. Whether you're already planning for early retirement or just starting to explore the idea, this episode is packed with actionable takeaways.

🎧 Next up: In the next episode, we’ll cover financial and non-financial signs that you’re ready to retire early, and after that, we’ll dive into how to determine how much you really need. Don’t miss it!

Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!

✅Get these Free Resources available too on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

🎙️Enjoying the podcast? Help keep it going!☕Buy me a coffee here.

🎥 When you’re not on the go, check out my Early Retirement Roadmap YouTube channel for more insights and inspiration. And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real.

👉 Connect with Mike at mikeupland.com and check out his YouTube channel Early Retirement Roadmap for even more tips.