Early Retirement Roadmap

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!
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap
 
💼 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.
 

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/
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon:  https://www.patreon.com/cw/earlyretirementroadmap
 
💼 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!
✅Get these 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon:  https://www.patreon.com/cw/earlyretirementroadmap
 
💼 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.
👉To get the free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap
 
While you're on my Patreon, you may want to download these other free tools too: 
📊Free MAGI calculator Excel template
📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long
 
❤️ 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. To get the free download, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap
While you're on my Patreon, you may want to download these other free tools too:
📊Free MAGI calculator Excel template
📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long
 
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!
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon:  https://www.patreon.com/cw/earlyretirementroadmap
 
📺 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

Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working?
In this episode of the Early Retirement Roadmap Podcast, I bust the top 10 retirement myths—with real data and practical advice. These are the beliefs that could seriously derail your plans and cost you thousands if you fall for them.
We’ll cover myths about:
Retirement savings goals
Taxes in retirement
Social Security and Medicare
Downsizing and expenses
Longevity and lifestyle in retirement...and much more.
I retired at 55 and have seen firsthand how common these myths are—and how dangerous they can be. Listen now to plan smarter and retire with confidence.
 
Resources Mentioned: 
📊 Myth #10: Federal Reserve Study reports 5% of households have $1 Million Saved and under 2% have 2 million saved, and median savings: https://www.retirementliving.com/do-you-really-need-1-million-to-retire
📊Myth #9 SmartAssett.com – Is Social Security Income Taxable?: https://smartasset.com/retirement/is-social-security-income-taxable
📊Myth #8: Schroder’s Retirement Study: https://www.schroders.com/en-us/us/institutional/media-center/schroders-retirement-study-finds-inflation-taking-toll-on-retirees/
📊Myth #8 Retirement Researcher, Retirement Spending Smile: https://retirementresearcher.com/retirement-spending-smile/
📊Myth #7: National Council on Aging (NCOA), Social Security Only Replaces 37% of earnings, on average, see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/ 📊Myth #7: Kiplinger, Average Social Security Benefits in 2025, see: https://www.kiplinger.com/retirement/social-security/how-to-get-the-maximum-social-security-check
📊Myth #7: The Center On Budget and Policy Priorities, average social security income: https://www.cbpp.org/research/social-security/top-ten-facts-about-social-security
📊Myth #6: Kiplinger, regarding social security running out of money: https://www.kiplinger.com/retirement/social-security/when-will-social-security-and-medicare-trust-funds-run-out-of-money
📊 Myth #5: Fidelity, 2023 Estimates of Healthcare Costs Medicare Parts A & B Don’t Cover: https://newsroom.fidelity.com/pressreleases/fidelity--releases-2023-retiree-health-care-cost-estimate--for-the-first-time-in-nearly-a-decade--re/s/b826bf3a-29dc-477c-ad65-3ede88606d1c
📊Myth #4: National Council on Aging – 64 percent of retiree retired sooner than expected, see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/
📊Myth #3: Merrill Lynch and Age Wave Study – Many retirees don’t downsize as reported by CNBC: https://www.cnbc.com/2021/04/13/op-ed-more-boomers-are-choosing-to-upsize-their-homes-in-retirement.html
📊Myth #2: 1 out of 3 65-year-olds will live until at least age 90 – see: https://www.ncoa.org/article/debunking-the-top-6-financial-myths-about-retirement/
📊Myth #1, People are Happier in Retirement, and not bored, see: https://www.massmutual.com/global/media/shared/doc/2024_massmutual_retirement_happiness_study.pdf
 
❤️ 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!
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap
📺 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. 
 
#retirementmyths #earlyretirement #retirementplanning #personalfinance #financialfreedom

🚨 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!
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon:  https://www.patreon.com/cw/earlyretirementroadmap
 
📺 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!
 
✅Get these Free Resources available too 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, click Join for Free, then click on the Tools collection, and you can download any of them from there. Here is the link to my Patreon:  https://www.patreon.com/cw/earlyretirementroadmap
 
 
❤️ 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
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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/
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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