Early Retirement Roadmap artwork

Investing · Mike Upland

Early Retirement Roadmap

by Mike Upland

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.

Latest episodes

Showing 20 · updated from the feed

Retiring in the Next 5 Years? Get These 5 Things Right

The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you prepare for ear

Sep 28
24 min

I Retired at 55—Why It Felt Wrong

I retired at 55, but early retirement still felt wrong. In this episode, I explore why retiring before 65 can bring guilt, social pressure, and the uneasy feeling that yo

Sep 21
12 min

I Paid Off My Mortgage—Then I Learned About This Scam

Paid off your mortgage? Deed fraud, deed theft, and home-title fraud can still create a costly mess. I explain how this property deed scam works—and the free alert that c

Sep 14
16 min

I Quit the Rat Race at 55 — Here’s What I Got Back

I quit the rat race at 55 and retired early. Nearly two years later, I’ve learned that life after work gives you back things you may not even realize your career has been

Sep 7
15 min

Why Gen X is So Burned Out at Work

Why is Gen X so burned out at work? After decades of corporate America, constant connectivity, doing more with less, and watching work consume more and more of our lives,

Aug 31
20 min

Why Gen X is Quietly Done With Work

Why is Gen X quietly done with work? As an early retiree, I break down 7 reasons Gen X is rethinking careers, early retirement, financial independence, and the value of t

Aug 24
17 min

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,

Aug 17
23 min

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

Aug 10
17 min

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 re

Aug 3
11 min

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 movin

Jul 27
15 min

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

Jul 20
17 min

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

Jul 13
12 min

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

Jul 6
17 min

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 wh

Jun 29
16 min

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 sha

Jun 22
21 min

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 spendin

Jun 15
20 min

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, mone

Jun 8
18 min

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.

Jun 1
14 min

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

May 25
14 min

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 thi

May 18
18 min

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