Early Retirement Roadmap
Mike Upland
Publishing Details
About This Podcast
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.
Social Media
Explore Statistics
Recent Episodes
S4E4 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…
S4E3 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…
S4E2 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…
S4E1 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…
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…
S3E19 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…
S3E18 I Retired at 55: 10 Things You Need to Know
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…
S3E17 The Hidden Social Security Math That Changes Early Retirement
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…
S3E16 Your Roth Conversion Window Closes Faster Than You Think
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,…
S3E15 Retiring Soon? Don’t Make this Mistake
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…
S3E14 Your Net Worth is the Wrong Number
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…
S3E13 I Retired at 55: 7 Early Retirement Mistakes I Missed
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…
S3E12 How Much Do I Need to Retire Early? 5 Numbers That Tell You
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…
S3E11 Retire Now If You Can Answer Yes to These 6 Questions
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…
S3E10 Your First 5 Years of Retirement Decide Everything
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…
S3E9 The Cash Runway Plan: Build It, Store It, Refill It
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…
S3E8 ACA Subsidy Payback: The Tax-Time Trap
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…
S3E7 Choppy Markets? Use This Retirement Defense Plan
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…
S3E6 ACA Premium Shock? Pay Less All Year
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)…
S3E5 2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)
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…
Frequently Asked Questions
Early Retirement Roadmap has published 63 episodes since February 2025, covering topics in Business, Education.
Early Retirement Roadmap is currently highly active with new episodes weekly. Average episode length is 13m.
Similar Podcasts
The Ramsey Show
Ramsey Network
180 episodes
BiggerPockets Real Estate Podcast
BiggerPockets
1,317 episodes
Earn Your Leisure
iHeartPodcasts
1,483 episodes
The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network
The Investor's Podcast Network
1,189 episodes
How to Money
iHeartPodcasts
1,156 episodes
Money Guy Show
Brian Preston and Bo Hanson
1,299 episodes