I Retired at 55: Here’s What I Wish I Did First

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 [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 [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/ [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.

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 [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 [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/ [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.

I'm 57 & Retired: America Feels Too Expensive.

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 question I never expected to take seriously: Is America becoming too expensive to retire in? In this episode, I talk about how rising costs feel different once the paycheck stops — groceries, property taxes, home insurance, auto insurance, healthcare, and everything else that can chip away at retirement confidence. This is not a political episode. It’s a practical and personal look at how retirement in America feels right now, and why more retirees and near-retirees may be thinking about options they never considered before — moving to a lower-cost state, downsizing, renting, spending part of the year somewhere else, or even retiring abroad. I’m not saying I’m leaving the United States, although I’ve been thinking about it as a future possibility. I’m not saying everyone should move abroad. But I am saying retirement planning is about more than hitting a number. It’s also about flexibility, quality of life, and whether the place you live still supports the retirement you imagined. ✅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 [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 [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/ [https://mikeupland.com/] ☕ Support: [Buy me a coffee](https://buymeacoffee.com/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.

I’m 57 and Retired: 5 Things I Never Tell Anyone

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 powerful. And once you share it, you don’t always control where it goes, how people repeat it, how they interpret it, or how they use it. In this episode, I’m sharing five broad categories of things I’m very careful about sharing now that I’m retired — and many of these apply even if you’re still working and planning for retiremen We’ll talk about why I don’t share exact financial numbers, salary, net worth, retirement income, exit plans, private opinions, personal vulnerabilities, passwords, identity information, social media, politics, religion, and even certain personal goals. This isn’t about being secretive or trusting no one. It’s about knowing the difference between your inner circle and everyone else. Because not everything private is secret. Sometimes, it’s just none of their business. If you’re planning for early retirement, already retired, or simply trying to protect your peace, this is a conversation worth having. ✅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 [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/ [https://mikeupland.com/] ☕ Support: [Buy me a coffee](https://buymeacoffee.com/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.

I Retired at 55: My 7 Layers to Avoid Running Out of Money

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: What if I’m wrong? What if the market crashes, healthcare costs more than expected, inflation stays high, taxes surprise me, or I live much longer than planned? I’ll cover: • Knowing your real spending floor • Building a cash runway • Stress-testing your retirement plan • Understanding why retirement spending is not a straight line • Why the 4% rule is only a starting point • Planning healthcare and taxes together • Building backup levers into your retirement plan • Reviewing the plan without obsessing over it This episode is especially helpful if you’re planning for early retirement, worried about sequence of returns risk, trying to manage Affordable Care Act health insurance before Medicare, or wondering how to create a retirement plan that can bend without breaking. 🎧 Episode mentioned during this podcast listen to next: The Cash Runway Plan: Build It, Store It, Refill It (Season 3, Episode 9) 📊 Department of Health and Human Services 2025 FPL Levels (2026 ACA uses 2025's FPL levels): https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf [https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf] 📊Michael Kitces' research mentioned in video: https://www.kitces.com/blog/the-ratcheting-safe-withdrawal-rate-a-more-dominant-version-of-the-4-rule/ [https://www.kitces.com/blog/the-ratcheting-safe-withdrawal-rate-a-more-dominant-version-of-the-4-rule/]   ✅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. 📌 New companion tool for this episode: I created The 7 Layers Retirement Confidence Checklist to go with this episode. It’s a worksheet designed to help you review your own retirement plan, score each of the 7 layers, identify weak spots, and turn the vague fear of running out of money into specific planning actions. It’s available in my Patreon Tools Collection for any paid membership tier. Link to my Patreon here and click the Membership button to check out the different membership tiers: https://www.patreon.com/cw/earlyretirementroadmap    💼 My Favorite Retirement Planning Tool, and that I mentioned in this episode! 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 [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/ [https://mikeupland.com/] ☕ Support: [Buy me a coffee](https://buymeacoffee.com/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.