My Gen X Retirement Doesn’t Look Like a Boomer’s

I’m 57 & Retired: What I Actually Do All Day

Wondering when you retire, what you're going to do all day? And is that fear of being bored one of things holding you back from retiring? I’m 57 and retired, and I’ll share what retirement actually feels like after leaving work behind. One of the biggest fears people have about early retirement indeed is boredom. What do you do all day when you no longer have a job, a boss, meetings, deadlines, or a work schedule telling you where to be? In this episode, I share what my daily life looks like after retiring at 55 and now on my second year of retirement — but more importantly, I talk about what retirement actually feels like once work no longer organizes your life. I’ll cover the simple pleasures of retirement, why I haven’t been bored, how my routine changed, how I spend my time, why health and purpose matter, and why retirement planning does not end once you stop working. It simply changes. We’ll also talk about the emotional side of retirement, including identity, spending from your nest egg, letting go of a career, and avoiding the “one more year” trap if you’re already financially ready. If you’re thinking about retiring early, planning for retirement, or wondering whether retired life will feel boring or fulfilling, this video may help you think beyond the numbers and start planning the life you actually want to retire to. Retirement is not just about having enough money. It’s also about having enough health, purpose, freedom, structure, and meaningful things to do with your 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 [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: 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 [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.

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.