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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Avsnitt(65)

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

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

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 fe...

22 Juni 21min

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

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

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 epis...

15 Juni 20min

Working Past 55? 6 Hidden Costs Most People Miss

Working Past 55? 6 Hidden Costs Most People Miss

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 wor...

8 Juni 18min

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

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

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 l...

1 Juni 14min

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

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

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 b...

25 Maj 14min

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

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

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 ...

18 Maj 18min

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

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

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 ...

11 Maj 30min

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

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

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 ...

4 Maj 25min

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