Early Retirement Roadmap1 Apr 2025

The Retirement Wake-Up Call: What the Study AND My Story--Reveals!

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!

✅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.

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Episoder(73)

I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.

After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health, work, freedom, and family. When I was 40, I t...

17 Aug 23min

I Retired at 55—5 Problems My 401(k) Couldn’t Solve

I retired at 55, and I learned that a large 401(k) alone doesn’t solve every early retirement problem—especially access, ACA health insurance, taxes, and market downturns. In this episode, I walk thro...

10 Aug 17min

I Retired at 55 — Here’s the Risk Nobody Warns You About

The big question that's always asked when it comes to retirement planning is do you have enough money? But the risk nobody warns you about is retiring too late. After retiring at 55, I’ve learned that...

3 Aug 11min

I Retired at 55. My Retirement Plan Is Intentionally Dumb.

I retired at 55 with an intentionally dumb retirement plan—simple retirement planning built around low-cost index funds, cash reserves, flexible spending, and fewer moving parts. In this episode, I sh...

27 Jul 15min

I Retired at 55—6 Signs Work Was Taking Too Much From Me

Working too much can quietly drain your time, energy, health, and relationships. After retiring at 55, I saw how burnout, work-life balance, and early retirement are more connected than I realized. In...

20 Jul 17min

I’m 57. I Retired at 55. Why Am I Still Afraid to Spend Money?

Retirement spending, early retirement, and the fear of spending money can feel strange after decades of saving. I retired at 55, and even with a solid plan, spending from the pile was harder than I ex...

13 Jul 12min

I Retired at 55: My 7 Budget Rules That Survived Real Life

Retirement budget rules matter even more when you retire early. I retired at 55, and in this episode I’m sharing the 7 budget rules that helped my retirement plan survive real life. Before I retired, ...

6 Jul 17min

I Retired at 55: Don't Let a Calculator Keep You Working

Retirement calculators, Monte Carlo simulations, and probability of success can be useful—but they can also keep you working one more year. I retired at 55, and here’s what I think calculators often m...

29 Jun 16min