Early Retirement Roadmap

ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize premium tax credits/subsidies. In this episode, we calculate ACA MAGI step-by-step using a real early-retiree scenario and show you how to keep ACA premiums low by hitting your MAGI “sweet spot.” You’ll learn: • What counts in MAGI vs. what doesn’t. • How to add back non-taxable Social Security benefits, tax-exempt interest, and excluded foreign income. • How Roth conversions, IRA withdrawals, dividends, interest, and capital gains flow into AGI and then ACA MAGI. • Form 8962 (reconciling with 1095-A) essentials. • How to plan for the 2026 subsidy cliff as the 400% FPL cap returns. 🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 📊 Resources mentioned in this episode:  More information on Traditional IRA contribution limits and the ability to deduct them: Traditional IRA Contribution Limits for 2025 - NerdWallet IRS Publication 501: 2024 Publication 501 2025 FPL Levels based on household size: detailed-guidelines-2025.pdf Click here for the ACA Cost Estimator 🎧 Podcast episodes mentioned:  This podcast episode where I talk about about using the ACA cost estimator and saw amazing results, including cost sharing reductions by controlling MAGI, titled: How Early Retirees Can Pay WAY Less for Health Insurance! This podcast episode on how a taxable brokerage account can be a superhero in reducing MAGI for ACA, titled: The $12,900 Health Insurance Loophole for Early Retirees! This podcast episode that goes into detail about the enhanced ACA subsidies likely expiring at the end of 2025, and the 400%FPL cliff returning in 2026, titled: Will ACA Subsidies Disappear After 2025? What You NEED to Know! ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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.    

Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost you ACA health insurance subsidies before Medicare. In this episode, I’ll break down the trade-off, show you real examples, and share strategies to balance Roth conversions and Affordable Care Act subsidies. Retiring before 65 means health insurance is one of your biggest expenses. Should you save thousands on ACA subsidies today, or avoid massive RMD taxes later with Roth conversions? I’ll cover how subsidies work, how Roth accounts impact your Modified Adjusted Gross Income (MAGI), and what happens if enhanced subsidies expire after 2025. What you’ll learn: • Why Roth conversions are so popular in retirement planning • How ACA subsidies are calculated and why MAGI matters • Real-world examples of couples facing this Roth vs. ACA trade-off • Strategies like partial Roth conversions to protect subsidies • What changes when enhanced ACA subsidies end in 2026 This is one of the most important — and overlooked — retirement planning dilemmas. Listen to see if protecting ACA subsidies or prioritizing Roth conversions is smarter for your retirement strategy. 🎧 Listen to the following episodes mentioned in this podcast for more info that you'll find as show episodes:  - Health Insurance Options for Early Retirement: What You NEED to Know - How Early Retirees Can Pay WAY Less for Health Insurance! 🎧 And listen to these other episodes about health insurance in early retirement that are full of great information you can't miss!:  - The $12,900 Health Insurance Loophole for Early Retirees! -  Will ACA Subsidies Disappear After 2025? What You NEED to Know!   📊 Here is the link to the ACA cost estimator tool mentioned : https://www.healthcare.gov/see-plans/#/ 📊2025 Federal Poverty Level Guidelines: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #RothIRA #ACASubsidies #EarlyRetirement    

Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement planning, healthcare costs, spending habits, and mindset shifts that can make or break your retirement years. Retiring early isn’t just about saving enough money — it’s about knowing how to spend wisely, manage healthcare, and protect your peace of mind. If you’re planning for early retirement (or thinking about retiring at 55 like I did), these insights will help you avoid regrets and set realistic expectations for the journey ahead. What you’ll learn in this video: • Why retiring early feels different than expected • The financial and emotional lessons I wish I knew before retiring • How healthcare, spending habits, and mindset can shape your retirement • Tips for avoiding common regrets in early retirement ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #retiringearly #earlyretirement #retirementplanning

Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing. You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Medicare premiums eat into those extra earnings, and why your healthiest years may be slipping away. Plus, I’ll share real-life examples, surprising data, and a practical framework for deciding when it’s truly time to retire. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! Resources Mentioned: 📊 New York Life Study: https://time.com/3821757/this-is-the-retirement-regret-nobody-talks-about/ 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #WorkingPast60 #RetirementPlanning #EarlyRetirement

Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE implications for retirees, early retirees, and anyone planning for financial independence. 📌 Here’s what you’ll learn: 🏦 2025 retirement tax changes that lock in the 2017 Tax Cuts and Jobs Act (TCJA) permanently 💰 Extended income tax brackets, standard deduction increases, and the brand-new senior tax deduction 🧾 Detailed breakdown of Child Tax Credit enhancements, AMT exemption, SALT cap increase, and capital gains tax stability 🚗 New 2025-2028 deductions for auto loan interest, tip income, and overtime pay 🏥 What the bill didn’t do: the ACA subsidy cliff and how it could affect early retirees in 2026 💼 How to optimize Roth conversions, HSA contributions, and long-term retirement planning This is the 2025 retirement tax update you can’t afford to miss — I did all the research so you don’t have to! If you’re nearing retirement or in early retirement, these tax changes for retirees in 2025 could seriously impact your strategy. Make smarter money moves with clarity and confidence. ✅ ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #RetirementTaxChanges #2025TaxUpdate  #EarlyRetirementPlanning, #SeniorTaxDeduction #OneBigBeautifulBill

Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retirement plans—but beware, the rules are strict and the risks are serious. ✅ We’ll cover: How IRS Rule 72(t) works with IRAs and 401(k)s Eligibility requirements and account types How long you must commit to fixed withdrawals Major risks including sequence-of-returns and tax traps When Rule 72(t) makes sense—and when it absolutely doesn’t If you're aiming for early retirement and don’t qualify for the Rule of 55 or have limited brokerage/Roth options, Rule 72(t) could be your lifeline. But it can also backfire if you’re not careful. ⚠️ Don’t attempt this without consulting a tax pro or retirement planner—this is one of the most complex strategies out there. 🎁 Download my free guide: 12 Must-Do Steps to Retire Sooner and Smarter. Whether you're just getting started or refining your plan, this free guide will help you take the next step! It's a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q  I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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.   #EarlyRetirement #401kWithdrawal #IRSRule72t #RetirementPlanning #FinancialFreedom

Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning. In this retirement planning video, you’ll discover: How to pick the ideal retirement age (55, 59½, or 62) to maximize your retirement savings and avoid penalties. Essential budgeting strategies for retirement, including accurately planning for healthcare expenses before Medicare. Proven methods to calculate your FIRE number, going beyond the standard 4% rule for early retirement success. Powerful risk-management techniques to protect your nest egg from sequence of returns risk and market volatility. Crucial insights about when to claim Social Security, and how avoiding a common trap could save you thousands. Get started with my free checklist, "12 Must-Do Steps to Retire Sooner and Smarter," to ensure you don't miss a thing as you prepare to retire: 👉 https://payhip.com/b/IBj3q Stress-test your retirement plan using the highly recommended retirement planning software (Boldin) mentioned in the video: Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com DISCLAIMER: This podcast 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.  #CountdownToRetirement #RetirementPlanning #EarlyRetirement #RetirementChecklist #SocialSecurityTips

Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money. Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 reasons to retire early,” this episode takes it further—showing why waiting even one more year could cost you more than just money. We’ll explore the opportunity cost of continued work, how your health and freedom are affected, and why arbitrary retirement goals may be holding you back from the financial independence you’ve already earned. I retired early at 55, and in this episode, I’ll share the reasons that finally made me take the leap—and how it’s changed my life, and that you should consider too. 👉 If you’re ready to rethink your retirement timeline, this video is for you.  ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 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 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! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #earlyretirement #retireearly #financialfreedom #retirementplanning #retirement

🚨 Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER! In this episode, I break down why Roth conversions in 2025 are more important than ever—and how early retirees, those already retired, or those thinking about retirement could face massive tax regret if they don’t act soon. Whether you're already in early retirement or planning to retire soon, you'll learn: ✅ Why the 2025 Roth conversion deadline is a critical tax planning window ✅ How losing ACA subsidies in 2026 could spike your health insurance costs ✅ What triggers Medicare IRMAA penalties—and how to avoid them ✅ How to run your Roth conversion numbers the smart way - all the things you need to be aware of to avoid potential pitfalls ✅ Estate planning, tax brackets, and how strategic Roth conversions can save you six figures 🔥 Don’t miss this Roth conversion opportunity—use it before it disappears. Resources mentioned or for more information: 📊 Department of Treasury, U.S. National Debt: https://fiscaldata.treasury.gov/americas-finance-guide/national-debt/ 📊 Charles Scwaab Conversion Calculator: https://www.schwab.com/ira/ira-calculators/roth-ira-conversion 📊Boldin Conversion Calculator: https://www.boldin.com/retirement/roth-conversion-calculator/ 📊Bloomberg Government: 2025 Tax Policy Crossroads—What Will Happen When the TCJA Expires?: https://about.bgov.com/insights/elections/2025-tax-policy-crossroads-what-will-happen-when-the-tcja-expires/ 📊Thomson Reuters: What to know about TCJA expiration: https://tax.thomsonreuters.com/blog/what-to-know-about-tcja-expiration/ 📊Mariner Wealth Advisors: Early Retirement and Roth Conversions: https://www.marinerwealthadvisors.com/insights/early-retirement-should-you-consider-a-roth-conversion/ 📊Kiplinger: Benefits of Roth IRA Conversions Early in Retirement: https://www.kiplinger.com/retirement/benefits-of-roth-ira-conversions-early-in-retirement 📊Investopedia: How Much Tax Do You Pay on a Roth IRA Conversion?: https://www.investopedia.com/articles/retirement/08/roth-conversion-2010.asp 📊Wells Fargo: Roth IRA Conversion Rules and FAQ: https://www.wellsfargo.com/investing/retirement/ira/roth-ira-conversion/ 📊Money With Katie: The Roth Conversion Ladder: https://moneywithkatie.com/blog/how-to-use-your-401k-in-early-retirement-without-a-10-penalty ❤️ Like, Subscribe, Follow, Share and leave a review if this helped! 💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com   DISCLAIMER: This podcast 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.  #rothconversion #retireearly #retirementplanning #taxplanning #taxesinretirement #earlyretirement

Are you constantly worried about running out of money in retirement? You’re not alone—and the good news is, the truth might surprise you! In this podcast, I reveal what most people get wrong about retirement spending, how rare it actually is to run out of money, and the real strategies that work—especially if you're retiring early. We’ll break down the 4% rule, portfolio withdrawal strategies, the guardrails approach, and real-world data that shows how most retirees end up with more money than they started with. Whether you're planning for early retirement or already living it, this episode will help you stop worrying and start living! Learn how to make your money last, without the stress. 🔍 Topics covered: ✅ How to stop worrying about running out of money in retirement ✅What the 4% rule really means (and its limitations) ✅The truth about retirement portfolio longevity ✅How guardrails can give you more flexibility and confidence ✅Common mistakes retirees make with money Resources Mentioned: 📊 Michael Kitces article on why most retirees will never spend their entire retirement portfolio: https://www.kitces.com/blog/consumption-gap-in-retirement-why-most-retirees-will-never-spend-down-their-portfolio/ 📊Michael Kitches article regarding implementing retirement income guardrails: https://www.kitces.com/blog/implementing-retirement-income-guardrails-to-facilitate-the-right-spending-raises-and-spending-cuts/ 📊Retirment Planning Tool I Use, Boldin.com: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!   ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast.   ❤️ Like, Subscribe, Follow, Share and leave a review if this helped! 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #retireearly #earlyretirement #retirementplanning #financialfreedom #financialindependence

Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk. We’ll break down what it really takes to sustain $10,000 in monthly retirement income spending —whether you're aiming for early retirement, following the 4% rule (and why the 4% rule should really be used only as a very rough ballpark estimate), or just want a comfortable, worry-free lifestyle. You’ll also learn how to reduce your savings target without sacrificing your standard of living. You’ll learn: ✅ How much you need to retire with $10K/month in spending ✅ Why withdrawal rate and account types can make or break your plan ✅ How Social Security and other income reduce your savings target ✅ What risks like sequence of returns and inflation really mean ✅ Strategies to optimize taxes and healthcare before Medicare 🔧 Tools Mentioned: Boldin.com: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you! Resources: 📊 Morningstar, 3.7% Starting Withdrawal Rate: https://www.morningstar.com/business/insights/research/the-state-of-retirement-income 📊 Morningstar: Re-evaluating the 4% Withdrawal Rule: https://www.morningstar.com/retirement/morningstars-retirement-income-research-reevaluating-4-withdrawal-rule 📊Charles Scwaab – How Many Years of Cash Reserve: https://www.schwab.com/learn/story/market-volatility-retirement-what-if-you-havent-prepared 📊 More about bond tents: https://www.thegoodlifejourney.com/home/bond-tent-early-retirement-strategy? & https://www.kitces.com/blog/managing-portfolio-size-effect-with-bond-tent-in-retirement-red-zone/ ❤️ Like, Subscribe, Follow, Leave a Review, and Share if this helped! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺When you're not on the go, watch the Early Retirement Roadmap channel on YouTube: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This video 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. #retireearly #earlyretirement #retirementplanning #financialplanning #retirement

⚠️ Are ACA subsidies really going away after 2025? If you're planning to retire early or already living off your investments, this could impact your healthcare costs in a big way. In this episode, I explain exactly what's happening with ACA subsidies in 2026—what's expiring, what's staying, and how you can still qualify for financial help through smart retirement planning and income strategies. You’ll learn: ✅ What the “subsidy cliff” is and how to avoid it ✅ How to use MAGI planning to stay eligible for ACA tax credits ✅ What changes after the Inflation Reduction Act ends ✅ Why taxable brokerage accounts and Roth strategies are your secret weapons.  Even if the enhanced subsidies go away, you can still protect your early retirement plan—if you know how to plan ahead. 📉 Don’t get surprised by skyrocketing ACA healthcare premiums in 2026. This episode breaks it all down. 🎯 If you’re aiming to retire before Medicare kicks in, this is a must-watch. Episodes to listen to next: 🎧 This episode about health insurance options for early retirement, title of: Health Insurance Options for Early Retirement: What You NEED to Know -- Click here to listen on YouTube: https://youtu.be/3lxFC-ob2E4 🎧 This episode about slashing ACA premiums by strategically funding your retirement income to reduce MAGI, where a taxable brokerage account in particular is the big hero, title of: The $12,900 Health Insurance Loophole for Early Retirees!  Click here to listen on YouTube: https://youtu.be/rvbxNVaW3iM 🎧This episode where I talk thru the results I achieved on the actual ACA Estimator Tool on heatlhcare.gov, using the strategy, with 3 case scenarios, from the episode directly above!, title of: How Early Retirees Can Pay WAY Less for Health Insurance! Click here to listen on YouTube: https://youtu.be/2QqresmHRCg Resources Mentioned/Further Reading: 📊 Commonwealth Fund Article: https://www.commonwealthfund.org/publications/explainer/2025/feb/enhanced-premium-tax-credits-aca-health-plans 📊 Kaiser Family Foundation Articles - lots of current articles/happenings pertaining to the ACA: https://www.kff.org/tag/marketplaces/ 📊Medicare Rights Center Article: https://www.medicarerights.org/medicare-watch/2025/04/17/congress-must-act-to-continue-affordable-care-acts-enhanced-premium-tax-credits ❤️ Like, Follow, Comment, Subscribe, and Share if this episode helped you!  💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺 When you're not on the go, watch the Early Retirement Roadmap Channel on YouTube and subscribe: https://www.youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #earlyretirement #retireearly #healthinsurance #financialplanning #retirementplanning  

If you're in your 40s, 50s, or 60s, listen to this! In this podcast, I share 25 life lessons from people over 70 — timeless wisdom for navigating midlife, retirement planning, relationships, purpose, and happiness. These life lessons are based on the powerful research of Dr. Karl Pillemer, author of 30 Lessons for Living, who interviewed over 1,000 older adults to uncover the most important advice they would pass on. I’ve distilled those insights into 25 practical lessons tailored especially for those of us between ages 45 and 65. Whether you’re thinking about retirement, already retired, or simply looking to make the most of your next chapter, this episode is packed with real-world advice from those who’ve been there. 👉 Watch now to learn how to: Worry less and enjoy more Nurture relationships before it’s too late Prioritize time over things Age with purpose, clarity, and peace And much, much more! 🧠 Don’t miss these life-changing insights from 70+ year-olds — especially if you’re in your 40s, 50s, or 60s! 📊See more about Dr. Karl Pillemer's book, read reviews and purchase here: https://amzn.to/45g8ziF Disclosure: The link above is an affiliate link, which means I may earn a small commission if you make a purchase — at no extra cost to you. Thank you for supporting the channel! ❤️ Like, Subscribe, Follow and Share if you found this episode meaningful. 💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺When you're not on the go, watch the Early Retirement Roadmap channel on YouTube: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast 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. #lifelessons #advicefromoldpeople #midlifewisdom #retireearly #retirementplanning    

Many early retirees forget to factor in their adult children when planning retirement. From weddings and tuition to ongoing support, the financial impact can be substantial—especially when you no longer have a paycheck coming in. In this episode, I’ll walk you through how to plan for potential financial support, set healthy boundaries, and protect your own future—without guilt. Learn why planning ahead can be the difference between peace and pressure in retirement. 👇 Comment Below: Have you had to set boundaries with adult kids or struggled with it? I’d love to hear how you handled it! 📊 Resources Mentioned: • CNBC 50% of parents support adult children: https://www.cnbc.com/2025/03/25/half-of-parents-financially-support-adult-children-report-finds.html • 2025 Zola average wedding cost: https://www.zola.com/expert-advice/whats-the-average-cost-of-a-wedding ❤️ Like, Subscribe, Follow and Share if this helped! 💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 🌐 Visit: [mikeupland.com](https://mikeupland.com/) DISCLAIMER: The information presented is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals. #retireearly #earlyretirement #retirementplanning #adultchildren #financialboundaries

Should you claim Social Security early, wait until full retirement age, or delay until 70? In this podcast, we walk through a real retirement case study and run the numbers to show how your claiming age affects your investments, taxes, and even your health insurance premiums. 📊 See why delaying may not always be the best choice—and how opportunity cost could erode your nest egg more than you realize. 💡 You’ll learn: ✅The real math behind claiming at 62, 67, or 70 ✅Why investment returns matter more than you think ✅How taxes and ACA premiums are impacted ✅What most people overlook in Social Security planning 👉 Don’t make a decision until you understand these trade-offs! 📊 Resources: • Social Security Benefit Reduction Chart by Claiming Age: https://smartasset.com/retirement/social-security-early-retirement-penalty-chart 💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. ❤️ Like, Follow, Subscribe, and Share if this helped! 🎧  🌐 Visit: [mikeupland.com](https://mikeupland.com/) ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals. #socialsecurity #socialsecuritybenefit #retirementplanning #retireearly #financialfreedom  

Want to pay WAY less for health insurance in early retirement? This follow-up to my previous very popular video (link below in watch next) shows how smart retirees legally slash ACA premiums by strategically managing their income. You'll learn how MAGI impacts subsidies, and see real scenarios using Healthcare.gov. Don’t overpay for healthcare—plan smarter and keep more of your money! Here is a link to the youtube version of this podcast so you can see the actual demos using the ACA estimator tool on healthcare.gov: https://youtu.be/NXEaYYjQKdI And here is the link to the youtube video this episode was a follow up to (or listen to my podcast titled "The $12,900 Health Insurance Loophole for Early Retirees!" : https://youtu.be/lxdNnUpdZ-Y 📊 Resources: ACA Cost Estimator to run it for yourself: https://www.healthcare.gov/see-plans/#/ 2025 Federal Poverty Level Guidelines: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf ❤️ Like, Subscribe, Follow, Leave a Review or Comment and Share if this episode helped you!  💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. DISCLAIMER: This content is for educational purposes only and is based upon my personal experience and research. Before making any major retirement decisions, please consult with qualified financial, tax, investment and legal professionals. #earlyretirement #retireearly #healthinsurance #retirementplanning #financialplanning  

Are you wondering why it feels like everyone else is retiring early — and you're not? In this episode of Early Retirement Roadmap, we uncover the real reasons people delay early retirement, even when they have enough saved. Learn how to avoid the "one more year syndrome," stop chasing unrealistic retirement numbers, and discover 5 proven strategies to retire sooner than you think. If you want to know how much you really need to retire, how to build financial confidence, and how to create a realistic retirement plan, this episode is for you. We cover the average 401(k) balance by age, how much guaranteed income like Social Security can help, why stress-testing your retirement plan matters, and how redefining retirement could be your key to freedom. 🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.  Episodes to listen to mentioned in this episode:  🎙️Episode 3, How Much Do You REALLY Need to Retire 🎙️Episode 6, The One Retirement Mistake that Could RUIN YOU 💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast.  🎥 When you’re not on the go, check out my Early Retirement Roadmap YouTube channel for more insights and inspiration.    🌐  Visit mikeupland.com – Connect with me & explore retirement resources including all my videos and blog articles.

What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break down the smartest way to structure your income before age 65 to maximize your ACA subsidy. You’ll learn why your taxable brokerage account might be your biggest retirement superpower, how MAGI works, and how to avoid the dreaded “coverage gap” in non-Medicaid expansion states. Perfect for anyone eyeing early retirement with a sharp eye on healthcare costs. 🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.  💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast.  🎥 When you’re not on the go, check out my Early Retirement Roadmap YouTube channel for more insights and inspiration.    🌐  Visit mikeupland.com – Connect with me & explore retirement resources including all my videos and blog articles.

If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experience, hard-earned lessons, and recent data. From not saving early enough to underestimating healthcare costs, I break down how you can sidestep these pitfalls and build a retirement that’s not just financially sound, but fulfilling. Stick around for the final regret — it's one even savvy retirees often miss. 🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.  💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources

You’ve worked hard, saved diligently, and now retirement is here! But nobody warns you about the six major things that disappear the moment you leave the workforce. If you’re not prepared, these changes can hit harder than expected—but the good news? You can replace them with something even better! In this episode of Early Retirement Roadmap, I’ll break down: ✅ The six things that vanish when you retire—and why they matter 🏆 ✅ How to rediscover purpose and avoid feeling lost 💡 ✅ Why having structure & routine in retirement is crucial 📅 ✅ How to replace career achievements with new personal goals 🏅 ✅ The surprising impact of losing your work identity—and how to rebuild it 🎭 ✅ How to maintain social connections when your work network disappears 👥 I’ll also share my personal experience transitioning from my 30-year career to early retirement and the lessons I learned along the way! 🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.  💼My Favorite Retirement Planning Tool. If you're serious about planning for early 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.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real.  🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources 🚀 Retirement isn’t the end—it’s a new beginning. Let’s make it amazing!