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Early Retirement Roadmap

Hosted by Mike Upland · business · EN-US

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About this Podcast:

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, challenge

Pitch Analysis

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Contact path

Public web form

Booking probability

32%

Guest openness

Selective

80/100
Required Score

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Questions about Early Retirement Roadmap

What is Early Retirement Roadmap about?

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.

Who hosts Early Retirement Roadmap?

Early Retirement Roadmap is hosted by Mike Upland. The show has published 82 episodes to date.

What has Early Retirement Roadmap covered recently?

Recent episodes include "I’m Gen X, Retired, and I Just Don’t Care" (26 October 2026, 17 minutes), "I Retired at 55, How I Knew I Had Enough" (19 October 2026, 15 minutes), and "Gen X Followed the Rules. Then the Rules Changed." (5 October 2026, 27 minutes).

How often does Early Retirement Roadmap publish?

Early Retirement Roadmap publishes roughly weekly, with episodes averaging 18 minutes across 82 episodes.

How hard is it to get booked on Early Retirement Roadmap?

Booking probability for Early Retirement Roadmap is 32%, and the host is rated Selective on guests. Early Retirement Roadmap requires a Pod Score of 80 or higher. Early Retirement Roadmap's contact route on record: public web form.

Who should pitch Early Retirement Roadmap?

The strongest fits for Early Retirement Roadmap are Investing & Wealth Management and Lending & Credit Cards. Early Retirement Roadmap has a business audience.

About the host

Mike Upland hosts Early Retirement Roadmap, a business podcast with 82 episodes published.

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Recent episodes

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  • Oct 26, 202617 min

    I’m Gen X, retired at 55, and enjoying life after retirement on my own terms. Here’s how early retirement changed my priorities—and why I’m done proving myself. At 57, I’m getting more particular about who and what gets...

  • Oct 19, 202615 minS5

    I retired at 55. How did I know I had enough to retire early? I looked at whether our retirement plan could pay for the life we wanted, bridge the years before Medicare, and hold up in a bad market. I started with the...

  • Oct 5, 202627 minS5

    Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk with author Mark Ross about work, retirement, time, success...

  • Sep 28, 202624 minS4

    The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you prepare for early retirement. Many people spend decades saving...

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  • Aug 31, 202620 minS4

    Why is Gen X so burned out at work? After decades of corporate America, constant connectivity, doing more with less, and watching work consume more and more of our lives, many Gen Xers are starting to question whether...

  • Aug 24, 202618 minS4

    Why is Gen X quietly done with work? As an early retiree, I break down 7 reasons Gen X is rethinking careers, early retirement, financial independence, and the value of time. I retired at 55, and being on the other side...

  • Aug 17, 202624 minS4

    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 thought retirement...

  • Aug 10, 202618 minS4

    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 through five problems...

  • Jun 22, 202621 minS4

    Wondering when you retire, what you're going to do all day? And is that fear of being bored one of things holding you back from retiring? I’m 57 and retired, and I’ll share what retirement actually feels like after...

  • Jun 15, 202620 minS4

    I retired at 55, and these are 10 things I refuse to waste money on. Retirement doesn’t mean you stop spending money. It means you get more honest about what the spending is actually for. In this episode, I’m sharing 10...

  • Jun 8, 202618 minS4

    Early retirement at 55 sounds like the dream — but after retiring early myself, I realized there are things I wish I had understood sooner about retirement planning, money, purpose, and life after work. In this episode...

  • Jun 1, 202615 minS4

    <p>In this episode, I talk about the retirement strategy I wish I had seriously considered before leaving my career: easing into retirement instead of making it a hard stop.</p> <p>For many people, retirement looks...

Recent guests

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