Early Retirement Roadmap

Mike Upland
  • 4.6 (21)
  • Investing
  • Updated Weekly

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.

  1. 6d ago

    Retiring in the Next 5 Years? Get These 5 Things Right

    The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you prepare for early retirement. Many people spend decades saving for retirement but wait too long to pressure-test how they will actually leave work, cover their expenses, access their investments, manage health insurance, and handle a bad market. In this episode, I walk through five areas to get right before you retire: 1. Choose two possible retirement dates and define three levels of spending 2. Create a withdrawal strategy before the paycheck stops 3. Plan your healthcare bridge and manage MAGI before Medicare 4. Prepare for sequence-of-returns risk and a bad early market 5. Rehearse both the financial and lifestyle sides of retirement I also explain why two households with the same net worth can have very different abilities to retire, why one “normal” year is not enough to create a reliable retirement budget, and why a retirement calculator cannot tell you what Tuesday at 10:30 in the morning will feel like. If you are within five years of retirement—especially if you are considering retiring early—use this episode as a practical checklist to identify what is still vague in your plan and where your attention belongs next. ✅ 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.

  2. Sep 21

    I Retired at 55—Why It Felt Wrong

    I retired at 55, but early retirement still felt wrong. In this episode, I explore why retiring before 65 can bring guilt, social pressure, and the uneasy feeling that you haven’t worked long enough. Being financially ready for early retirement doesn’t mean your work habits and sense of responsibility disappear overnight. After decades of being rewarded for staying productive, making yourself useful, and showing up for others, stepping away from work can feel uncomfortable—even when your retirement plan is sound. I share why age 65 has become such a powerful dividing line, how friends and coworkers can unintentionally add to early retirement guilt, and why leaving your job doesn’t mean leaving behind purpose, contribution, or connection. I also discuss one of the hardest adjustments to retirement: enjoying your free time without feeling that every afternoon must be productive or justified. The freedom to do less isn’t something to feel guilty about—it’s part of what you spent all those years working toward. If you’re retired, preparing for retirement, or wondering whether you’ve worked long enough, this episode may help you separate genuine retirement-readiness concerns from the guilt and expectations you carried over from your working life. ✅ 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.

  3. Sep 14

    I Paid Off My Mortgage—Then I Learned About This Scam

    Paid off your mortgage? Deed fraud, deed theft, and home-title fraud can still create a costly mess. I explain how this property deed scam works—and the free alert that can help you catch it early. After paying off my mortgage before retiring early, I assumed my house was one part of my retirement plan I could stop thinking about. Then I learned that criminals may target mortgage-free homes, forge property deeds, and use fraudulent records to pursue loans, rentals, or sales. In this episode, I separate the genuine risk from the sensational headlines. A forged deed does not automatically make a criminal the lawful owner of your house—but it can cloud your title and leave you with an expensive legal mess to resolve. You’ll learn: • How deed fraud actually works • Why paid-off, vacant, rental, and second homes may attract scammers • How to find a free county property-fraud alert • What deed-monitoring alerts can—and cannot—do • Other protective steps involving credit freezes and title insurance • What to do if an unfamiliar document is recorded against your property • Why property monitoring belongs in a solid retirement plan Check for participating counties at: https://www.propertyfraudalert.com/ If your county isn’t listed, visit the official website for the county recorder, county clerk, register of deeds, or comptroller where your property is located. Search for “property fraud alert,” “recording notification service,” “fraud notify,” or “document alert.” ✅ 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.

  4. Sep 7

    I Quit the Rat Race at 55 — Here’s What I Got Back

    I quit the rat race at 55 and retired early. Nearly two years later, I’ve learned that life after work gives you back things you may not even realize your career has been taking from you. After decades of working, saving and planning for retirement, I thought I had a pretty good idea what early retirement would feel like. I didn’t. In this episode, I share six things I wasn’t fully prepared for after leaving the rat race — including how much mental space work had been occupying, why I don’t miss my job nearly as much as I expected, how differently time feels when it actually belongs to you, and why retirement forced me to rethink productivity and purpose. I also talk about one of the biggest decisions anyone considering retirement eventually has to make: when does “enough” actually become enough? Working another year will almost always give you more money and make a retirement plan look safer. But at some point, more money begins costing you something you can’t replace — time. For me, retiring at 55 wasn’t about eliminating every possible financial risk. It was about reaching the point where I believed our retirement plan was strong enough and another year of my life was worth more to me than another year of income. If you’re burned out at work, counting down the years until retirement, considering early retirement, or simply questioning how much of your life you want to keep giving to the rat race, I think you’ll relate to this conversation. ✅ 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.

  5. Aug 31

    Why Gen X is So Burned Out at Work

    Why is Gen X so burned out at work? After decades of corporate America, constant connectivity, doing more with less, and watching work consume more and more of our lives, many Gen Xers are starting to question whether the tradeoff is still worth it. My last YouTube video that published this past weekend on 8/16/26 and titled Why Gen X Is Quietly Done With Work, sparked hundreds of comments from people saying the same things: they’re exhausted, frustrated, counting the days until retirement, and increasingly unwilling to let work control their lives. In this episode, I look at 8 reasons Gen X may be reaching a breaking point with work — including America’s unusual relationship with work and vacation, how technology made us constantly available, the corporate obsession with “doing more with less,” and why our perspective on time begins to change as we get older. I also share something retirement taught me that I didn’t fully understand while I was still working: I didn’t necessarily want to stop working. I wanted work to stop owning my time. Financial independence isn’t only about reaching a retirement number. Ultimately, it gives you something much more valuable: control over your time and the freedom to decide how you want to spend it. ✅ 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.

  6. Aug 24

    Why Gen X is Quietly Done With Work

    Why is Gen X quietly done with work? As an early retiree, I break down 7 reasons Gen X is rethinking careers, early retirement, financial independence, and the value of time. I retired at 55, and being on the other side of work has changed the way I think about the trade between earning more money and having more control over my time. In this episode, I look at why so many Gen Xers seem to be stepping back from the corporate grind, caring less about the next promotion, and thinking more seriously about retirement or simply making work a smaller part of their lives. I cover 7 reasons I think this shift is happening — from the independence many Gen Xers grew up with and changing attitudes toward corporate loyalty, to decades of cumulative work fatigue, greater awareness of limited time, declining tolerance for workplace nonsense, and the financial independence that can eventually make work optional. And perhaps the biggest reason of all: at some point, time can become more valuable than another dollar. This isn’t about saying everyone should retire early or that every Gen Xer hates their job. It’s about recognizing that after decades of working, saving, investing, and building a life, the definition of success can start to change. For me, retirement has become much less about simply having enough money to stop working and much more about having enough freedom to decide how I want to spend my time. ✅ 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.

  7. Aug 17

    I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.

    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 planning was mainly about reaching the right financial number. Now that I’m 57 and have been retired for almost two years, I see it very differently. In this episode, I share eight lessons I would give my 40-year-old self—including why time disappears faster than we expect, how work can quietly take over our lives, why money only becomes freedom when we define “enough,” and why health, relationships, and purpose belong in every retirement plan. We’ll also discuss: Why another year of work is also one less year of retirement How consistency matters more than finding the perfect investment Why stress and poor health compound just like money The importance of building a meaningful life before retiring  How to prepare financially without postponing everything that matters Why financial independence is an opportunity—not the ultimate finish line Whether you’re preparing to retire early, pursuing financial freedom, or already retired, these lessons can help you think differently about money, time, work-life balance, health, relationships, and what you want retirement to make possible. ✅ 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.

  8. Aug 10

    I Retired at 55—5 Problems My 401(k) Couldn’t Solve

    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 our 401(k)s alone could not solve and why having money in a taxable brokerage account, cash reserves, Roth accounts, and other accessible sources gave me the flexibility to retire early. We’ll cover how account location can affect: • Access to money before age 59½ • ACA health insurance subsidies and reported income • Sequence-of-returns risk during a market downturn • Tax flexibility from year to year • The ability to delay Social Security without feeling pressured to claim early I also discuss the longer-term challenge of having a large amount of money in pretax retirement accounts, including required minimum distributions, possible IRMAA surcharges, and losing control over when taxable income appears. A 401(k) is still an excellent wealth-building tool. But early retirement taught me that the location of your money can matter almost as much as the total amount you’ve saved. The 401(k) helped build the wealth. The brokerage account helped build the bridge. Cash provides stability, and Roth accounts create additional tax flexibility. ✅ 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.

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4.6
out of 5
21 Ratings

About

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.

Information

  • Creator
    Mike Upland
  • Years Active
    2025 - 2026
  • Episodes
    79
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Early Retirement Roadmap

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