HeyJaredEarly Retirement Roadmap
Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement!If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom,…
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- Sep 7, 2026
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Latest episodes
I Quit the Rat Race at 55 — Here’s What I Got Back (opens the original)
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I quit the rat race at 55 and retired early. Nearly two years later, I’ve learned that life after work gives you back things you may not even realize your career has been taking from you. After decades of working, saving and planning for retirement, I thought I had a pretty good idea what early retirement would feel like. I didn’t. In this episode, I share six things I wasn’t fully prepared for after leaving the rat race — including how much mental space work had been occupying, why I don’t miss
Why Gen X is So Burned Out at Work (opens the original)
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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 the tradeoff is still worth it. My last YouTube video that published this past weekend on 8/16/26 and titled Why Gen X Is Quietly Done With Work, sparked hundreds of comments from people saying the same things: they’re exhausted, frustrated, counting the days until retirement, and
Why Gen X is Quietly Done With Work (opens the original)
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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 think about the trade between earning more money and having more control over my time. In this episode, I look at why so many Gen Xers seem to be stepping back from the corporate grind, caring less about the next promotion, and thinking more seriousl
I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self. (opens the original)
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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 reaching the right financial number. Now that I’m 57 and have been retired for almost two years, I see it very differently. In this episode, I share eight lessons I would give my 40-year-old self—including why time disappears faster than we expect, how wor
I Retired at 55—5 Problems My 401(k) Couldn’t Solve (opens the original)
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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 solve and why having money in a taxable brokerage account, cash reserves, Roth accounts, and other accessible sources gave me the flexibility to retire early. We’ll cover how account location can affect: • Access to money before age 59½• ACA health insur
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