February 20, 2023

Darrow Kirkpatrick: Beyond Doubt on the Colorado Trail

1 hour 18 minutes

Today on episode 55 I’m honored to welcome Darrow Kirkpatrick, former engineer, climber, investor, author, and the creator of the popular blog CanIRetireYet.com. Darrow began serious saving and investing in his mid-30s and retired at age 50 in 2011 from a career in software engineering.

In this wide-ranging interview, we explore why Darrow stepped away from personal finance writing after creating a popular blog, his adventures on the Colorado Trail and the inspiration for a memoir, and the journey and struggle to finding meaning and purpose at any stage in life.

Darrow Kirkpatrick: An Introduction

Darrow was eager to share the methods and values of frugality and simple personal finance in the early days of his retirement, leading to the creation of his blog. Over time, though, his interest in the subject slowly waned, replaced by the need for more adventure. He partnered with Chris Mamula, eventually releasing the reigns of the blog to Chris.

In the intervening years, Darrow has spent considerable time in contemplation of purpose and meaning in retirement, an often under-discussed and potentially difficult reality. This spiritual journey ultimately led him to pursue a boyhood dream of hiking the Colorado Trail. To achieve this lofty goal, he faced mental and physical hurdles, including walking the length of the trail with forearm crutches. Darrow has been busy writing a memoir of that experience, titled Rain and Fire in the Sky: Beyond Doubt on the Colorado Trail. Additionally, he has created a new website dedicated to cataloguing and reviewing other trail memoirs, at trailmemoir.com, where you can keep up with the latest on his upcoming book.

This interview offers a unique perspective on the softer side of financial optimization. We can be masters of technical methods of saving and investing, but ultimately none of that matters without clear direction, purpose, and meaning in our lives. As a retiree of twelve years and counting, Darrow has plenty of lessons for us all.

Topics Discussed with Darrow Kirkpatrick:

Darrow’s climbing life: early free climbing and first ascents
Darrow’s career: becoming a software engineer and working remotely, long before either of these career options were commonplace
Finding a path to financial independence in a time before widespread blogging
Darrow’s key philosophy and methods to achieving financial independence
Why Darrow sold CanIRetireYet.com to Chris Mamula
Finding meaning and purpose in retirement and deciding to hike the Colorado Trail
Darrow’s physical and mental hurdles in life and on the trail, and specific methods to address these struggles.
How Darrow leveraged financial strength to take a mid-career break for struggles with anxiety
Reflections on trail life, solitude in the wilderness, and writing a memoir of that experience
Balancing life on the road and a home life
Social connections for retirees and for those relocating to new towns
Messaging early retirement in social situations
So much more!

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Show Notes and Links at Clippingchains.com

Get in Touch with Darrow Kirkpatrick

CanIRetireYet.com

Trailmemoir.com