Early Retirement Roadmap

Early Retirement Roadmap

Welcome to the Early Retirement Roadmap podcast — a practical guide for people planning for early retirement, navigating financial independence, or learning how to thrive after leaving full-time work.

I’m your host, Mike Upland. I retired at 55 in 2024, and this podcast shares the real-world lessons I’ve learned before and after making the leap into early retirement.

If you’re in your 40s, 50s, or early 60s and wondering whether you can retire early — or if you’ve already retired and want to make the most of your freedom — you’re in the right place.

Each episode explores practical, relatable topics like early retirement planning, retirement income strategies, health insurance before Medicare, Affordable Care Act planning, taxes, Roth conversions, Social Security decisions, withdrawal strategies, market risk, spending, purpose, mindset, and the emotional side of life after work.

You’ll hear candid discussions about the victories, challenges, surprises, and trade-offs that come with early retirement — along with actionable ideas to help you build a financially secure and fulfilling post-career life.

For all my media in one place, check out the Early Retirement Roadmap YouTube channel and visit mikeupland.com.

Support the channel and get bonus resources on Patreon: https://www.patreon.com/cw/earlyretirementroadmap

Your early retirement journey starts here — subscribe or follow now so you never miss an episode.

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Avsnitt(65)

The Top 10 Retirement Myths That Could Cost YOU Thousands!

The Top 10 Retirement Myths That Could Cost YOU Thousands!

Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working? In this episode of the Early Retirement Roadmap Podcast, I bust the top 10...

7 Juli 202522min

🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!

🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!

🚨 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 reti...

1 Juli 202511min

STOP Worrying About Running Out of Money in Retirement!

STOP Worrying About Running Out of Money in Retirement!

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 ret...

24 Juni 20258min

How Much Do You REALLY Need to Retire on $10K a Month?

How Much Do You REALLY Need to Retire on $10K a Month?

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 ...

17 Juni 202512min

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

⚠️ 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 e...

10 Juni 20256min

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

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, ...

5 Juni 202511min

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

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 long...

4 Juni 20257min

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

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 a...

27 Maj 20259min

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