Hosted by Mike Upland · 🇺🇸 US · EN-US · 66 episodes
Established thought leaders with verified media credentials.
Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55 in 2024. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way. Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, health insurance, tax strategies, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building and managing wealth, and inspiring stories to help you navigate your own path to early retirement or thrive in it if you're already there!
Mike Upland hosts Early Retirement Roadmap, a business show with 66 episodes published.
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
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 people ask, “How much net
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 avoid costly retirement
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 retirement bridge years, and h
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 you can honestly answ
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 are the lessons to ge
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 rules. If you’re retiring
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 fix it, and how to pre
Sponsor detection runs nightly. Check back soon.
No public pitch examples yet for this show.
Generate your own personalised pitchBased on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:
Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.
Shows with the most semantically similar episode content. Pitch one, pitch all; producers cluster.
To pitch Early Retirement Roadmap, visit https://earlyretirementroadmap.podbean.com for contact information, then craft a tight one-paragraph hook that ties your expertise to a gap in their recent business coverage.
Early Retirement Roadmap is hosted by Mike Upland. The show is categorised under business (investing) and has published 66 episodes.
Early Retirement Roadmap has published 66 episodes.
Early Retirement Roadmap regularly covers business, investing, education. It sits in the business category, with a investing focus.
Early Retirement Roadmap is accessible for guests with genuine business expertise. A personalised, episode-aware pitch will still outperform a generic one every time.
Early Retirement Roadmap hasn't explicitly signalled guest openness in recent episodes. That doesn't rule out pitching. your hook just needs to be especially compelling and relevant to their recent content.
Episodes of Early Retirement Roadmap average 19 minutes. a focused format where a clear narrative arc and tight preparation matter most.
Our data rates Early Retirement Roadmap's guest bar at 80/100 (Premium tier). Established thought leaders with verified media credentials. Sign in to PitchCentric to see how your own Pod Score compares against this show.
Methodology. Booking Probability™ blends Listen Score, 30-day Virality, open-to-guests detection, and Apple ratings. Data refreshed every 60 minutes. Listen Score and Booking Probability are calculated by PitchCentric. Last enriched yesterday.
