The Problem with Bucket Lists and How to Be Happy with Less

It’s often said that happiness equals what you have minus (or sometimes divided by) what you want. When our wants are many, what we have is of little consequence. That is why there are hordes of unhappy millionaires and high achievers who quietly suffer (yes, suffer) under the weight of lofty and insatiable desires and ambitions. Western ideals place great importance on the “haves.” And despite an anecdotal feeling that my greater social circle is less materialistic, I’m less certain that we’ve diminished our appetite for having things. The things look and feel different. Less like fancy watches or cars or gaudy showings of riches and more like spreadsheets full of countries and crags unvisited, food not tasted, status not yet achieved, or routes not sent. We believe subconsciously or otherwise that by checking items off our bucket list we will arrive at some sense of blissful satisfaction. But biology and evolution suggest otherwise.

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Dr. Jim Dahle of the White Coat Investor on Building the Ideal Life

Jim Dahle is the founder of the White Coat Investor, a widely consumed personal finance and investing blog and podcast specifically designed for physicians and other high-income careers. What Jim created in 2011 as a simple blog has grown into a multi-media empire that now employs fifteen people and hosts content from a range of columnists.

Jim has cut back from his full-time (plus) emergency physician career and White Coat Investor responsibilities to focus on what makes life worth living, and that’s where I wanted to pick up this conversation. Jim is a climber, husband, and father of four. Today we discuss how he’s managed to step away, at least slightly, from his hard-charging career and blogging days to what he’s now describing as his ideal life.

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Jeff and Priti Wright: You Might Need a Sabbatical

Today on episode 64 I’m excited to welcome Priti and Jeff Wright, two accomplished young professional alpinists from Seattle, WA. In 2020, Priti, a software developer, and Jeff, a mechanical engineer at Boeing, embarked on a year-long sabbatical to travel across the globe and climb alpine objectives in Patagonia, France, and Pakistan, finishing by the beach in Hawaii.

The trip was wildly successful, even amid the raging pandemic, including ascents of the Cerro Torre, the six classic North Faces of the Alps in a single season (including the Eiger North Face in winter), culminating in the first ascent of K6 Central and the third ascent of K6 West—both 7000+-meter peaks—in the Karakoram Range of Pakistan.

In contrast to early retirement, Priti and Jeff make the compelling case for a traditional career peppered with sabbaticals. This episode is filled with lifestyle and career philosophy, planning concepts, detailed financial considerations, and just a damn good time. And they are even planning their next sabbatical in 2024, which will look drastically different than their trip in 2020. You won’t want to miss this one.

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What You Need to Know About Financial Advisors with Chris Mamula

Today on episode 60 I’m pleased to welcome back Chris Mamula, who you may recall from episode 3. Chris is a writer, author, and partner at CanIRetireYet.com, who achieved financial independence at age 41 to pursue a life centered around family and the outdoors.

Beginning in early 2022, in search of a new challenge, Chris completed the education and exam necessary to become a Certified Financial Planner (CFP). Two questions emerge from this development:

  1. Why would someone who theoretically doesn’t need to work begin a new career?
  2.  How can someone who harbors admittedly dogmatic views against the financial advice industry find a comfortable home working in this field?

Today we discuss the different kinds of financial advisors, the nature of complex incentives in professional financial advice, Chris’s recommended approach to choosing a financial advisor, and so much more about behavior, psychology, and the tangled emotions of money management.

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Five Lessons from Three Years of Financial Independence

One evening, circa 2011, I sat over dinner with my future wife in our small and sweaty Houston, TX rented bungalow. I was and still am an occasional cheap bastard, so the air conditioning was almost certainly set to engage on an “as-needed” basis, far from anything resembling comfort. The concept of financial independence wasn’t on the radar.

During downtime at work—I told you I was distracted—I was scouring numerous free WordPress blogs documenting the travels of zealous climbing dirtbags. They were camping and climbing and making whatever money they needed along the way. People were even starting to live and travel in vans, something I associated with sixties and seventies surfer culture. I wanted that life.

At this point in my late twenties, I was maybe barely a year into my career as a geologist in the oil and gas industry. But I could see the writing on the wall—this would not and could not be my career for the next 35-40 years. In fact, at that moment, I couldn’t see myself lasting my target three to five years until I expected to return to school for a career in academia. And there was a new problem: I’d kind of grown obsessed with this new hobby of rock climbing.

Twelve years later, I finally found a very different path to a life of freedom, if such a thing even exists. After three years of financial independence, what follows are some key lessons I’ve learned along the way.

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Darrow Kirkpatrick: Beyond Doubt on the Colorado Trail

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.

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Lee Cujes: No Free Lunch on the Life We Really Want

Today on episode 53 I’m pleased to welcome back Lee Cujes, this time as a podcast guest. Some of you may recall the written interview with Lee back in late 2020. Lee is an elite Australian climber and route developer, with multiple 5.13+ and 5.14 first ascents to his name. But most importantly as it relates to this platform, Lee has managed to climb and develop routes continuously while carving a unique career niche and embracing a long-term investing strategy, an approach that provides the ultimate work and life balance.

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QA8: What If We Run Out of Water?

We’re back to the digital mailbag to answer your questions!

For this week:

  • Thoughts on the bear market
  • Getting invested with a Health Savings Account
  • Paying for education with retirement accounts
  • My philosophy on rest from climbing
  • How to develop financial mentorship in the climbing community
  • Travel and rescue insurance ideas
  • Determining a cost-effective approach to climbing destinations
  • Should I open an IRA if my employer doesn’t offer a 401(k) match?
  • How to not get wrecked moving from sport climbing or bouldering to trad climbing
  • The risks of owning property in an area that could be running out of water
  • Getting a home loan with inconsistent income history
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