Early Retirement Roadmap
Claim This Podcastby Mike Upland
Podcast Authority
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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
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Publishing Since
2/19/2025
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Recent Episodes
August 3, 2026
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 retiring at 55, I’ve learned that money is only one part of the retirement decision. Time, health, energy, and actually being able to enjoy the life you worked for matter just as much. In this episode, I share 5 lessons that changed how I think about retirement, spending, work, and the danger of waiting too long. We talk about high-energy dreams, the difference between protection dollars and life dollars, why “good enough” planning matters, the true cost of work, and why retirement only works if you’re building a life you actually want to enter. I’m not saying everyone should retire at 55. I’m saying the risk of retiring too early gets plenty of attention — but the risk of retiring too late is real too. If you’re planning for early retirement, thinking about retiring in your 50s or 60s, or wondering whether one more year of work is really worth it, this video may help you think through the decision differently. ✅ 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.
July 27, 2026
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 moving parts. In this episode, I share the seven parts of my early retirement plan that I deliberately keep simple. That includes how I invest, why I use a small number of investments with clear jobs, how I avoid trying to predict the market, and why I treat retirement calculators and Monte Carlo simulations as tools—not guarantees. I also explain why I don’t try to optimize every tax year, how I built flexibility into my retirement spending plan, and why every retirement strategy should pass the “spouse test.” A retirement plan shouldn’t require perfect forecasts, constant monitoring, or dozens of complicated decisions to keep working. My goal is not to have the smartest-looking retirement plan. It is to have a resilient retirement plan that is easy to understand, hard to break, and flexible enough to handle market downturns, unexpected expenses, changing tax rules, and real life. In this episode, we’ll cover:• Why I prefer low-cost index funds and ETFs• How cash, stocks, bonds, and taxable accounts each have a clear job• Why I don’t make retirement decisions based on market predictions• How I use Monte Carlo retirement projections without obsessing over the score• Why minimizing taxes every single year is not always the best long-term strategy• How spending guardrails make retirement more adaptable• Why your spouse or another trusted person should be able to understand your plan ✅ 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.
July 20, 2026
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 connected than I realized. In this episode, I share six signs that work may be taking more from your life than you realize—including the most dangerous one, because it can sound completely responsible. I also walk through the five-part off-ramp I would build if I were still working today: defining what “enough” means, reducing the amount your paycheck must support, creating a financial bridge, building a meaningful life outside work, and giving “one more year” a clear purpose and expiration date. This isn’t about quitting recklessly or pretending money doesn’t matter. It’s about recognizing that working longer is not always the risk-free choice—and that your time, health, and energy are valuable forms of capital too. If you’re feeling burned out, questioning how much longer you want to work, or trying to build a realistic path toward early retirement, I hope this episode helps you think through what work is costing you—and what you want the rest of your life to look like. ✅ 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.
71 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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