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Artwork for Early Retirement Roadmap

Early Retirement Roadmap

Mike Upland
Retirement Planning
Early Retirement
Health Insurance
Affordable Care Act
Social Security
Financial Planning
ACA Subsidies
Investment Strategies
Taxes
Retirement
Financial Independence
Modified Adjusted Gross Income
Health
Roth Conversions
Life Lessons
Inflation
Sequence Of Returns Risk
401(k)
IRA
IRS Rule 72(t)

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, ... more

PublishesWeeklyEpisodes74Founded2 years ago
Number of ListenersCategories
InvestingBusinessEducationSelf-Improvement

Listen to this Podcast

Artwork for Early Retirement Roadmap

Latest Episodes

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 of work has changed the way I... more

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 planning was mainly about reach... more

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 our 401(k)s alone could not sol... more

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 money is only one part of the retirement decisio... more

Key Facts

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Host

Mike Upland
Host of Early Retirement Roadmap

Reviews

4.6 out of 5 stars from 28 ratings
  • Great information

    I have been binging Mike’s podcast recently. So much valuable information for people like me that have retired early and for those who aspire to do the same. Thanks Mike!

    Apple Podcasts
    5
    Davidnprogress
    United States6 months ago
  • Mike's podcast is great! He effectively and efficiently packs a lot of useful info into each episode, and it is clear that he enjoys sharing the knowledge he gained while preparing for his own retirement. Highly recommended, even if you are not planning to retire "early"!

    Podcast Addict
    5
    Jesse V
    7 months ago
  • Short and sweet but good content

    I really like this podcast. It has good content and is broken up into consumable chunks. Thank you Mike for putting in the time to do it.

    Apple Podcasts
    5
    Krugalug
    United States7 months ago
  • So valuable!

    I’m so grateful for this broadcast. Mike does such a great job explaining the basic and not so basic lessons around retirement. I love the depth of his research and the way he explains things in a way that it’s easy to understand. I don’t have a plan to retire soon and yet I’m finding this so valuable. Thanks Mike.

    Apple Podcasts
    5
    Carpelearn
    United Statesa year ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise practical, experience-based guidance and clear frameworks for retirement planning.
Fans appreciate approachable explanations of complex topics like ACA planning and Social Security.
Episodes are described as valuable and well-researched, helping both aspiring and current early retirees.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#187
United States/Business/Investing
Apple Podcasts
#70
Singapore/Business/Investing
Apple Podcasts
#117
India/Business/Investing
Apple Podcasts
#196
New Zealand/Business/Investing
Apple Podcasts
#200
Norway/Business/Investing
Apple Podcasts
#205
Singapore/Business

Talking Points

Recent interactions between the hosts and their guests.

The Cash Runway Plan: Build It, Store It, Refill It
Q: How would you suggest someone nearing retirement go about building a cash runway?
Consider reducing 401k contributions, selling invested assets, or curtailing spending, as each has its pros and cons.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Early Retirement Roadmap

What is Early Retirement Roadmap about and what kind of topics does it cover?

The show centers on practical, real-world strategies for achieving and thriving in early retirement. Episodes frequently tackle planning for retirement income, health insurance before Medicare, ACA considerations, taxes, Social Security, withdrawal strategies, and managing market risk, all through a hands-on, experience-based lens. Listeners can expect clear frameworks, personal anecdotes, and actionable steps to balance money, health, and purpose, with a strong emphasis on mindset shifts, deliberate spending, and designing a meaningful post-work life. A notable strength is the host's transparent sharing of his own early-retirement journey, accessible budgeting tools, and a willingness to address both financial math and the emotional side o... more

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Which podcasts are similar to Early Retirement Roadmap?

These podcasts share a similar audience with Early Retirement Roadmap:

1. Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)
2. Ready For Retirement
3. Retirement Answers
4. Retirement Starts Today
5. Stay Wealthy Retirement Podcast

How many episodes of Early Retirement Roadmap are there?

Early Retirement Roadmap launched 2 years ago and published 74 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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