Early Retirement Roadmap
Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way. Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building wealth, and inspiring stories to help you navigate your own path to early retirement. Whether you’re just starting to explore early retirement or fine-tuning your existing plans, this podcast provides the roadmap you need to build a financially secure and fulfilling post-career life. For visual guides and additional content, be sure to check out the Early Retirement Roadmap YouTube channel, where I share complementary videos and resources to support your early retirement journey. Your early retirement journey starts here—subscribe now to ensure you never miss an episode!
Episodes

Tuesday Jul 01, 2025
🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!
Tuesday Jul 01, 2025
Tuesday Jul 01, 2025
🚨 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 ChecklistWhether 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/IBj3qI 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

Tuesday Jun 24, 2025
STOP Worrying About Running Out of Money in Retirement!
Tuesday Jun 24, 2025
Tuesday Jun 24, 2025
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 ChecklistWhether 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/IBj3qI 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

Tuesday Jun 17, 2025
How Much Do You REALLY Need to Retire on $10K a Month?
Tuesday Jun 17, 2025
Tuesday Jun 17, 2025
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 ChecklistWhether 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/IBj3qI 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

Tuesday Jun 10, 2025
Will ACA Subsidies Disappear After 2025? What You NEED to Know!
Tuesday Jun 10, 2025
Tuesday Jun 10, 2025
⚠️ 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 ChecklistWhether 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/IBj3qI 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

Thursday Jun 05, 2025
If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds
Thursday Jun 05, 2025
Thursday Jun 05, 2025
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 ChecklistWhether 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/IBj3qI 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

Wednesday Jun 04, 2025
How Your Kids Can Derail Your Retirement (Unless You Plan for It)
Wednesday Jun 04, 2025
Wednesday Jun 04, 2025
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 ChecklistWhether 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/IBj3qI 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

Tuesday May 27, 2025
Claim Social Security at 62, 67, or 70? The Answer May Surprise You!
Tuesday May 27, 2025
Tuesday May 27, 2025
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 ChecklistWhether 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/IBj3qI 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

Tuesday May 20, 2025
How Early Retirees Can Pay WAY Less for Health Insurance!
Tuesday May 20, 2025
Tuesday May 20, 2025
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 ChecklistWhether 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/IBj3qI 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

Wednesday May 14, 2025
Retirement Stats That’ll Make You Rethink Working Another Year
Wednesday May 14, 2025
Wednesday May 14, 2025
Is working longer really worth it?
In this episode, I break down 3 retirement stats and insights that could completely change the way you think about work, wealth, and health in retirement. If you're planning for early retirement, these numbers might just shift your whole retirement strategy.
Here's what you'll learn:
• Why 63.9 years is a critical number for your retirement health
• How the average person works 90,000 hours in their lifetime and reclaiming some of that time
• What research says about retirees who never spend their savings
If you're in your 40s, 50s, or early 60s, and you're serious about retirement planning, this video is for you.
👇 Comment Below: What would you do if work became optional tomorrow?
📊 Resources Mentioned:
• [World Health Organization (WHO) – Healthy Life Expectancy (HALE) at Birth] (https://data.who.int/countries/840)
• [• National Bureau Of Economic Research - Consumption and Saving After Retirement](https://www.nber.org/system/files/working_papers/w29826/w29826.pdf)
• [Institute for Fiscal Studies Report](https://ifs.org.uk/sites/default/files/output_url_files/BN236.pdf)
❤️ Like, Subscribe, 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 ChecklistWhether 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/IBj3qI 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/)
☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

Monday May 05, 2025
Why You’re Closer to Early Retirement Than You Think
Monday May 05, 2025
Monday May 05, 2025
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 ChecklistWhether 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/IBj3qI 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.









