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Hosted by Mike Upland · 🇺🇸 US · EN-US · 72 episodes
Established thought leaders with verified media credentials.
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, challenge
Mike Upland hosts Early Retirement Roadmap, a business show with 72 episodes published.
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 thought retirement pl
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 through five problems ou
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 money is only one p
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 share the seven parts
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 this episode, I sha
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 expected. Before I ret
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, I had a retirement b
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 miss. Retirement calc
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 feels like after leavi
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 episode, I’m sharing 10
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 work. In this episode,
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 looks simple from the
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 been asking myself a
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 information is power
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 kept asking myself:
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 Boomers, retirement
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 retired at 55, I thou
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 Social Security can change
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, Social Security, IRMAA, t
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 Medicare, withdrawal st
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Early Retirement Roadmap is hosted by Mike Upland. The show is categorised under business (investing) and has published 72 episodes.
Early Retirement Roadmap has published 72 episodes.
Early Retirement Roadmap regularly covers business, investing, education. It sits in the business category, with a investing focus.
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Episodes of Early Retirement Roadmap average 19 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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