Don’t drift into retirement. Design yours.

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What happens when you finally get everything you worked for…and realize something is missing?

In this powerful and deeply honest conversation, Darrow Kirkpatrick shares what early retirement can really feel like — beyond the spreadsheets and freedom headlines. After leaving his software engineering career, he found himself confronting something he didn’t expect: the loss of identity and clout that work had quietly provided. He discovered that early retirement wasn’t just about having time—it was about creating meaning. Instead of retreating, Darrow leaned into challenges. From launching a successful retirement blog Can I Retire Yet? to spending nights alone above 12,000 feet, to confronting his lifelong struggles with fear and panic, Darrow’s journey, chronicled in his new book Two Sticks, One Path, reveals the surprising truth about what can make retirement fulfilling.

If you’re within a few years of retirement — or already there — this conversation will make you think differently about what comes next –  and why the challenges we choose to take on may matter more than the comfort we think we want.

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Bio

Darrow Kirkpatrick is the author of the new book Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail. Darrow is an early-retired civil and software engineer with five decades of hiking, biking, and technical rock-climbing experience, including first ascents in the Shawangunks of New York and the sandstone belt of Tennessee. He climbed three big walls in Yosemite Valley, California: The Shield and The Nose on El Capitan, and The Regular Northwest Face of Half Dome. In 2011 he founded “Can I Retire Yet?” — winner of the 2019 Plutus award for Best Retirement Blog. His personal finance books include “Retiring Sooner” and “Can I Retire Yet?”

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For More on Darrow Kirkpatrick

Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail

Can I Retire Yet?

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Podcast Conversations You May Like

How to Prepare Mentally for Life After Work – Joseph Maugeri

The Inspired Retirement – Nathalie Martin

Lessons Learned in Early Retirement – Chris Mamula

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There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.

Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University.

In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Wise Quotes

On the Value of Challenge in Retirement

“I find 100% of the meaning that I found in early retirement has come from the challenges I’ve tackled.”

On Meaningful Pursuits

“The things I did pay attention to starting Can I Retire Yet, a successful personal finance blog, a bucket list item hiking the Colorado Trail, even though I had to do most of it on crutches, those things are incredibly meaningful to me, writing a memoir about it. I think I would have really regretted if I had stayed at my corporate desk through all those years instead of reaching for those bucket list items.”

On Adaptation

“I did have a series of chronic injuries in my lower body, which got worse. I had a bad hamstring injury, was in bed for a few months, one summer. And as part of the recovery from that, a doctor friend suggested I start using forearm crutches… I wound up realizing I needed to just keep using the crutches on the trail, because they would keep me safe. They reduce the impact on my body, they prevent falls. And if I had any hope of doing a trail as difficult as the Colorado Trail, I needed all the help I could get.”