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

I Retired at 55. We've Got Retirement Backwards.

I retired at 55, and early retirement changed how I think about retirement planning, the traditional retirement age of 65, and the real cost of waiting to enjoy life. Af

Nov 2
25 min

I’m Gen X, Retired, and I Just Don’t Care

I’m Gen X, retired at 55, and enjoying life after retirement on my own terms. Here’s how early retirement changed my priorities—and why I’m done proving myself. At 57, I

Oct 26
17 min

I Retired at 55—How I Knew I Had Enough

I retired at 55. How did I know I had enough to retire early? I looked at whether our retirement plan could pay for the life we wanted, bridge the years before Medicare,

Oct 19
14 min

I Retired at 55 — 8 Regrets I Refuse to Have at 80

I retired at 55, and I’m thinking about the retirement regrets I want to avoid by 80. These 8 early retirement lessons cover spending, taxes, cash, health, travel, marria

Oct 12
19 min

Gen X Followed the Rules. Then the Rules Changed.

Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk with author Ma

Oct 5
26 min

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

Chart trend

Position in the Investing chart (US), last 90 days.

#162
all-time peak
31
days in the top 200 since Apr 2026

Chart positions

Where Early Retirement Roadmap ranks today in each Apple Podcasts chart (US, Nov 3, 2026).

#196 NEW Investing US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

This podcast has been essential support my early retirement strategy and my mindset leading into it which few podcasts delve much into this aspect. Mike’s voice is smooth and his delivery is at a pace and tone I can appreciate. Give a listen!!

Aam1972 · Aug 2026

I have been binging Mike’s podcast recently. So much valuable information for people like me that have retired early and for those who aspire to do the same. Thanks Mike!

Davidnprogress · Mar 2026

I’m so grateful for this broadcast. Mike does such a great job explaining the basic and not so basic lessons around retirement. I love the depth of his research and the way he explains things in a way that it’s easy to understand. I don’t have a plan to retire soon and yet I’m finding this so valuable. Thanks Mike.

Carpelearn · Jun 2025

I have only listened to 4 or 5 so far but this is exactly what I was hoping for! I find myself taking notes as reminders from all the great advice and spot on commentary to the questions I’m asking myself in this transitional sdd te age of life.

3g-SCguy · Jul 2026

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.

More podcasts like Early Retirement Roadmap

Popular shows in Investing, for your next listen.

Browse charts by category

Daily updated Apple Podcasts rankings for the United States.

About Early Retirement Roadmap on Reason.fm

Here you find the Apple Podcasts chart positions of Early Retirement Roadmap, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

Contact

Questions or issues? Reach us at hello@reason.fm

0:000:00