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

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.

Monday Apr 28, 2025
The $12,900 Health Insurance Loophole for Early Retirees!
Monday Apr 28, 2025
Monday Apr 28, 2025
What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break down the smartest way to structure your income before age 65 to maximize your ACA subsidy. You’ll learn why your taxable brokerage account might be your biggest retirement superpower, how MAGI works, and how to avoid the dreaded “coverage gap” in non-Medicaid expansion states. Perfect for anyone eyeing early retirement with a sharp eye on healthcare costs.
🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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.

Tuesday Apr 22, 2025
5 Retirement Regrets You’ll Want to Avoid
Tuesday Apr 22, 2025
Tuesday Apr 22, 2025
If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experience, hard-earned lessons, and recent data.
From not saving early enough to underestimating healthcare costs, I break down how you can sidestep these pitfalls and build a retirement that’s not just financially sound, but fulfilling.
Stick around for the final regret — it's one even savvy retirees often miss.
🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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 Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.
🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources

Monday Apr 14, 2025
What Vanishes When You Retire (And How to Get it Back!)
Monday Apr 14, 2025
Monday Apr 14, 2025
You’ve worked hard, saved diligently, and now retirement is here! But nobody warns you about the six major things that disappear the moment you leave the workforce. If you’re not prepared, these changes can hit harder than expected—but the good news? You can replace them with something even better!
In this episode of Early Retirement Roadmap, I’ll break down:✅ The six things that vanish when you retire—and why they matter 🏆✅ How to rediscover purpose and avoid feeling lost 💡✅ Why having structure & routine in retirement is crucial 📅✅ How to replace career achievements with new personal goals 🏅✅ The surprising impact of losing your work identity—and how to rebuild it 🎭✅ How to maintain social connections when your work network disappears 👥
I’ll also share my personal experience transitioning from my 30-year career to early retirement and the lessons I learned along the way!
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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 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!

Monday Apr 07, 2025
Thinking About Retiring Early in 2025? Think Again.
Monday Apr 07, 2025
Monday Apr 07, 2025
Planning for early retirement in 2025? Before you hand in your notice, this episode of Early Retirement Roadmap is your essential guide to navigating the biggest risks facing early retirees this year.
In it, I break down three critical threats — sequence of returns risk, rising inflation, and high market valuations, yes, even with the market downturn due to the Trump tariffs — and I share practical strategies to protect your retirement portfolio. From building cash reserves to using TIPS bonds and dividend-paying ETFs, you'll learn how to retire with confidence even during market volatility.
Whether you're part of the FIRE movement or just ready to leave your 9–5, this episode will help you build a plan to retire early AND STAY retired.
What You’ll Learn:
How a market downturn at the wrong time can destroy your retirement plans
Why inflation silently eats away at your wealth over time
Key investing metrics like the CAPE ratio and Buffett Indicator
How to create a resilient early retirement strategy that lasts decades
🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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 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

Tuesday Apr 01, 2025
The Retirement Wake-Up Call: What the Study AND My Story--Reveals!
Tuesday Apr 01, 2025
Tuesday Apr 01, 2025
Thinking about early retirement or already living it? This episode is your wake-up call — and your roadmap.
In this powerful and personal episode of The Early Retirement Roadmap, I talk about the retirement truths no one warns you about. Discover the real challenges behind the dream — from unexpected loneliness and identity loss to the surprising truth about pre-retirees' expectations vs. reality per a recent study by MassMutual (Mass Mutual).
You’ll learn:
Why retirement feels unstructured or even empty for many
The #1 activity most retirees do daily (hint: it's not what they planned)
How to prepare emotionally, socially, and mentally — not just financially
The 3 characteristics of thriving retirees
Mike’s candid and honest sharing of his own retirement experiences
If you’re searching for early retirement advice, wondering how to build purpose after leaving work, or asking what makes a meaningful retirement, this episode is for you.
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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 Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.
🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources.

Monday Mar 24, 2025
Monday Mar 24, 2025
Investing in index mutual funds sounds like a safe bet, right? Well, I thought so—until I got hit with an unexpected $17,000 tax bill.
In this episode of Early Retirement Roadmap, I break down the hidden tax trap in taxable mutual funds and why an ETF might be the smarter choice. Plus, I’ll share how tax-loss harvesting helped me fix my mistake and avoid future surprises. If you’re serious about early retirement, financial independence, and smart investing, you won’t want to miss this!
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.
💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin. It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy. I personally use it and highly recommend! Try Boldin here: https://go.boldin.com/earlyretirementroadmap
Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you!
✅ FREE Early Retirement Planning 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 Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.
🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources.

Monday Mar 17, 2025
The Perfect Retirement Announcement: A Step-by-Step Guide
Monday Mar 17, 2025
Monday Mar 17, 2025
Planning to retire? Announcing your retirement isn’t as simple as picking a date and telling your boss—it’s about strategy, timing, and setting yourself up for success. In this episode of Early Retirement Roadmap, I’ll guide you through the complete retirement announcement process, so you can make a smooth, professional transition.
🌟 Here’s what we’ll cover:✅ Choosing a date keeping tax benefits, health insurance, and bonuses 📅💰 in mind✅ How to maximize PTO payouts and avoid leaving money on the table 🏖️✅ How much notice to give (and why too much can backfire) 🚨✅ How to handle your boss’s reaction and preparation 🤯✅ What to expect from co-workers’ reactions and how to respond—from excitement to skepticism 🤔✅ The importance of planning ahead for a stress-free, rewarding exit 🚀
I’ll also share some of my personal experiences announcing my early retirement at 55.
🔔 If you found this helpful, please subscribe & leave a review!
💼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 Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.
☕ Enjoyed this show? Support me! Buy me a cup of coffee here! 🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Make your retirement announcement with confidence!

Monday Mar 17, 2025
Scared to Retire? Overcome Your RETIREMENT FEARS!
Monday Mar 17, 2025
Monday Mar 17, 2025
You’ve run the numbers, planned your finances, and dreamed of early retirement—but fear is still holding you back. You’re not alone! What if I run out of money? What about healthcare costs? Will I be bored? These fears are completely normal, and in this episode of Early Retirement Roadmap, I’ll help you tackle them head-on.
🌟 Here’s what you’ll learn:✅ The #1 financial fear of early retirees—and how to overcome it 💸✅ How Monte Carlo simulations can give you confidence in your retirement plan 🔢✅ Why healthcare costs don’t have to be a dealbreaker 🏥✅ Eliminate debt for a stress-free retirement ✅✅ The secret to avoiding boredom and creating a fulfilling post-career life 🎨🌍✅ How to handle criticism from family & friends who don’t "get" early retirement 🤔
I’ll also share my personal experience retiring at 55 years old and how I knew for sure that I was ready.
👉 Links to Resources 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!
✅ 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.
✅Empower
✅Article: Best Retirement Calculators
✅ Watch my video on all your healthcare options prior to Medicare or listen to the podcast
🔔 If you found this helpful, please subscribe & leave a review!
🎥 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.
Support me by buying a cup of coffee here! ☕🌐 Visit MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Your dream retirement is possible—don’t let fear hold you back!