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!
Get in Touch with Darrow Kirkpatrick
Related Posts and Interviews
EP 17: Michael Langer: Hiking the Pacific Crest Trail (Clipping Chains)
EP 18: Kenzie King: Hiking the Pacific Crest Trail (Clipping Chains)
Fear and Limping (Alone) in Las Vegas (Clipping Chains)
Eudaimonia: Key Pillars of the Meaningful Life (Clipping Chains)
EP 53: Lee Cujes: No Free Lunch on the Life We Really Want (Clipping Chains)
Peruse all Clipping Chains posts and interviews here.
Darrow’s 2023 Investment Portfolio (CanIRetireYet)
Finding Your Purpose in a Long Retirement (CanIRetireYet)
Over the Hill (Darrowkirkpatrick.com)
Other Resources Mentioned
Critique Circle (online writing critique)
Books
A Walk in the Woods: Rediscovering America on the Appalachian Trail (Bill Bryson)
Wild: From Lost to Found on the Pacific Crest Trail (Cheryl Strayed)
The Wanting Was a Wilderness: Cheryl Strayed’s WILD and the Art of Memoir (Alden Jones)
How I Found Freedom in an Unfree World: a Handbook for Personal Liberty (Harry Browne)
Fail-Safe Investing: Lifelong Financial Security in 30 Minutes (Harry Browne)
The Making of the Atomic Bomb (Richard Rhodes)
Thousand-Mile Summer (Colin Fletcher)
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