Early Retirement Roadmap

Early Retirement Roadmap

Welcome to the Early Retirement Roadmap podcast — a practical guide for people planning for early retirement, navigating financial independence, or learning how to thrive after leaving full-time work.

I’m your host, Mike Upland. I retired at 55 in 2024, and this podcast shares the real-world lessons I’ve learned before and after making the leap into early retirement.

If you’re in your 40s, 50s, or early 60s and wondering whether you can retire early — or if you’ve already retired and want to make the most of your freedom — you’re in the right place.

Each episode explores practical, relatable topics like early retirement planning, retirement income strategies, health insurance before Medicare, Affordable Care Act planning, taxes, Roth conversions, Social Security decisions, withdrawal strategies, market risk, spending, purpose, mindset, and the emotional side of life after work.

You’ll hear candid discussions about the victories, challenges, surprises, and trade-offs that come with early retirement — along with actionable ideas to help you build a financially secure and fulfilling post-career life.

For all my media in one place, check out the Early Retirement Roadmap YouTube channel and visit mikeupland.com.

Support the channel and get bonus resources on Patreon: https://www.patreon.com/cw/earlyretirementroadmap

Your early retirement journey starts here — subscribe or follow now so you never miss an episode.

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Jaksot(73)

I'm 57 Now.  Here's What I'd Tell My 40-Year-Old Self.

I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.

After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health, work, freedom, and family. When I was 40, I t...

17 Elo 23min

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

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

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 thro...

10 Elo 17min

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

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

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...

3 Elo 11min

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

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

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 sh...

27 Heinä 15min

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

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

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...

20 Heinä 17min

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

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

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 ex...

13 Heinä 12min

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

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

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, ...

6 Heinä 17min

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

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

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 m...

29 Kesä 16min

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