Early Retirement Roadmap
Claim This Podcastby Mike Upland
Podcast Authority
Beta
Podcast Overview
<p><strong>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.</strong></p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>For all my media in one place, check out the Early Retirement Roadmap YouTube channel and visit mikeupland.com.</p> <p><span>Support the channel and get bonus resources on Patreon: https://www.patreon.com/cw/earlyretirementroadmap</span></p> <p>Your early retirement journey starts here — subscribe or follow now so you never miss an episode.</p>
Language
🇺🇲
Publishing Since
2/19/2025
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Recent Episodes
June 15, 2026
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 spending is actually for. In this episode, I’m sharing 10 money traps I avoid in retirement — including convenience spending, boredom shopping, status spending, supporting adult children without boundaries, long-term care insurance, retirement products that become obligations, housing decisions, car payments, and more. Some of these are things I avoided before retirement, which helped me save more and retire earlier. Others are things I’m even more careful about now that I’m retired and living on the other side of the paycheck. This isn’t about being cheap or saying no to everything. It’s about refusing to waste money on things that don’t make retirement better — so you can spend more intentionally on the things that actually matter. ✅ Free resources available on my Patreon: All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more.To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there. If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space. 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ DISCLAIMER: This episode is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.
June 8, 2026
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 work. In this episode, I’m sharing what I got wrong after retiring at 55 — not because early retirement was a mistake, but because the transition is more complicated than most people admit. We spend so much time planning the financial side of retirement: saving enough, investing wisely, managing healthcare costs, and figuring out withdrawal strategies. But the emotional and lifestyle side of early retirement can matter just as much. If you’re thinking about retiring early, planning for retirement in your 50s, or wondering whether you’re truly ready to leave work behind, this episode may help you think through a few things before making the leap. I’ll share the lessons I’ve learned since retiring early, including what surprised me, what I underestimated, and what I would think about differently if I could do it all over again. ✅ Free resources available on my Patreon: All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more.To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there. If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space. 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ DISCLAIMER: This episode is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.
June 1, 2026
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 looks simple from the outside. One day you’re working, and the next day you’re done. But once you actually retire, you may realize work was providing more than just a paycheck. It may have also provided structure, routine, identity, social connection, and even the emotional permission to spend money. That’s why a slower transition into retirement can make sense for some people — especially early retirees who need their money to last longer, may need to bridge the gap to Medicare, and may still be adjusting to life without a regular paycheck. In this video, I’ll share why I think I could have handled my own retirement transition differently, how part-time work or consulting can soften the landing, why health insurance matters so much before Medicare, and how to think about retirement as more than just a financial decision. Retirement isn’t just about asking, “Can I retire?”It’s also about asking, “How should I retire?” ✅Free Resources available on my Patreon!: 📊Free MAGI calculator Excel template 📊Free 12-Step Early Retirement Planning Checklist 📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long 👉 To get these free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap then click Join for Free, then click on the Tools collection. You can download any of them there. 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ DISCLAIMER: This episode is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.
64 total episodes available
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- What is Early Retirement Roadmap?
<p><strong>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.</strong></p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>For all my media in one place, check out the Early Retirement Roadmap YouTube channel and visit mikeupland.com.</p> <p><span>Support the channel and get bonus resources on Patreon: https://www.patreon.com/cw/earlyretirementroadmap</span></p> <p>Your early retirement journey starts here — subscribe or follow now so you never miss an episode.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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