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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Episoder(68)

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 Jun 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 Jun 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 Mai 20259min

How Early Retirees Can Pay WAY Less for Health Insurance!

How Early Retirees Can Pay WAY Less for Health Insurance!

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 strate...

20 Mai 202512min

Retirement Stats That’ll Make You Rethink Working Another Year

Retirement Stats That’ll Make You Rethink Working Another Year

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 ...

14 Mai 20257min

Why You’re Closer to Early Retirement Than You Think

Why You’re Closer to Early Retirement Than You Think

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 ...

5 Mai 20258min

The $12,900 Health Insurance Loophole for Early Retirees!

The $12,900 Health Insurance Loophole for Early Retirees!

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 dow...

28 Apr 202511min

5 Retirement Regrets You’ll Want to Avoid

5 Retirement Regrets You’ll Want to Avoid

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 experie...

22 Apr 20256min

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