Early Retirement Roadmap

About Early Retirement Roadmap

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.

Publisher

Mike Upland

Category

business · education

Language

en

Explicit

No

First episode

19 Feb 2025

Latest episode

5 Oct 2026

Latest episodes

80 episodes in the feed.

1. 

   5 Oct 2026

   Gen X Followed the Rules. Then the Rules Changed.

   Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk with author Mark Ross about work, retirement, time, success, and the Gen X experience. Mark is the author of Generation X and the Life Nobody Explained, a book that really resonated with me because so much of it reflects what I’ve experienced — and what I’ve been talking about recently on this channel. We discuss how the relationship between employees and employers changed, why so many Gen Xers stopped trusting the old career model, what happened to retirement parties, why the 401(k) shifted so much responsibility onto individuals, how technology consumed more of our time, and why hobbies, craftsmanship, and even our definition of success changed along the way. We also talk about what comes next. For many of us in Generation X, the second half of life is becoming less about chasing titles, promotions, and money — and more about freedom, time, health, curiosity, relationships, and deciding what we actually want the rest of our lives to look like. In this conversation, we cover:• Why Gen X entered adulthood with one “map” and ended up living by another• How employment shifted from a relationship to a transaction• Why work began consuming more of our time — even outside work • What happened to hobbies and unstructured time• Why retirement became less certain• How the 401(k) changed the responsibility for retirement• Why Gen X is redefining success• Why the second half of life may be the most important chapter yet📘 Click here for Mark Ross’s book: Generation X and the Life Nobody ExplainedDisclosure: This is an affiliate link - I earn a small commission if you purchase the kindle or paperback version of Mark's book. This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ✅ 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. 

   28 Sept 2026

   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 spending2. Create a withdrawal strategy before the paycheck stops3. Plan your healthcare bridge and manage MAGI before Medicare4. Prepare for sequence-of-returns risk and a bad early market5. Rehearse both the financial and lifestyle sides of retirementI 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.

3. 

   21 Sept 2026

   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.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

165,349

Score snapshot 15 Sept 2025

Apple Podcasts (US)

4.6 / 5

20 ratings

Spotify

4.0 / 5

8 ratings

Podcast Authority Score: 40 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

32

Social presence

0

YouTube

86

Engagement

32

Contact Early Retirement Roadmap

Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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