All Episodes

April 1, 2025 13 mins

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 Checklist Whether 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/IBj3q 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.

🎥 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.

 

Mark as Played

Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.