Early Retirement Roadmap

⚠️ 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!
✅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 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!
✅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 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!
✅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
 
🌐 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!
✅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, 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!
✅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
 
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
 

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!
✅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
 
🌐 Visit: [mikeupland.com](https://mikeupland.com/)
☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

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!
✅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 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!
✅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 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!
✅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 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!
✅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 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!