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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The Power of the Four-Hour Work Day (even in retirement)

We live in a distracted world where depth of investigation is discouraged. Despite increases in scientific spending, the number of publications, or the amount of PhDs being awarded, major discoveries in science and engineering have declined significantly in recent decades. The new-music market is shrinking, and old hits are dominating. We are working more days and longer hours, but US productivity growth is way down. A society that produces meaningful output is a healthy society, but meaningful output is arguably on the decline in many fields.

I argue that distraction and “noise” are key inhibitors to a healthy and progressing society. In the nearly three years since I quit my job, I’ve been forced to examine my strong tendency toward distraction. What follows is a discussion of methods that I’ve found incredibly useful in retraining my brain for deep and focused work and why that matters so much today. Our peak potential resides in no more than four hours per day.

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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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The Great Transition of the US Housing Market

Since the pandemic began in the spring of 2020, we’ve witnessed an unparalleled explosion of price growth in all forms of housing. Until the peak in June 2022, single family home prices rose 45%. But prospective home owners weren’t the only ones biting their nails. Rents also rose over 15%, peaking in late 2022.

The culprit behind this price shock is fundamental: low supply and high demand. Today we examine the origins of these conditions and whether or not it’s a good time to buy.

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Joy and Tyler Black on Career, Money Mindsets, and Parenting

Today’s guests on episode 51 are Joy and Tyler Black. Many of you may be familiar with Joy, who has rapidly built a successful online business as a coach for pregnant and postpartum rock climbers. If you follow Joy on Instagram, you know her as a fun-loving and engaging mother of three, with a reputation for solid technical and personal coaching. Tyler on the other hand, is not a climber at all. He’s a biologist with a contrasting, yet highly complementary personality. In that way, they make for fantastic interview subjects on the discussion of relationships, money, career, and parenting.

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QA9: What Is the Point of Financial Optimization?

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

For this week:

  • Hot Seat Questions: My favorite blogs, podcasts, articles, and books. Musings on my biggest financial mistakes and the advice I’d give my younger self.
  • How do my wife and I keep meaning and purpose in our lives without traditional careers?
  • To sell or not to sell a home that was purchased in 2021
  • How to sell investments and minimize taxes
  • The proper hierarchy of investment accounts
  • Roth vs Traditional 401(k): Which is better?
  • I-Bonds: Should we be buying more?
  • Saving strategies for a home down payment
  • Receiving inheritance in a foreign currency
  • Critical nuance on withdrawal strategies in a high inflation/poor market return environment
  • So much more!
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Eudaimonia: Key Pillars of the Meaningful Life

Thinkers and philosophers of ancient times sorted out much in the way of living a meaningful and purposeful life. But after thousands of years of progress, material growth, and convenience, we largely fail to find meaning in our modern lives. Today we examine the philosophy of eudaimonia and how we can truly develop our sense of meaning and purpose (for free).

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The Anticipation Of The Thing Is Greater Than The Thing

We are prone to believing that outcomes will have stronger emotional impacts on us than they often do. This state of expectation, or impact bias, highlights why anticipation of an event is a much more palpable emotion than the event itself. The impact bias can lead to behaviors that make us less content despite our best efforts for happiness.

Let’s learn more about how to recognize this bias and make better decisions for our future.

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It’s Not All Hard Luck with Shay Skinner

In her late teens and early twenties, Shay Skinner was disowned from her family. She struggled with crushing mental illness, which ultimately culminated in a suicide attempt that left her in financial ruin. From this dismal situation, Shay filed for bankruptcy and began a long and fruitful climb toward being whole again. How can we summon the courage to take such measures of personal accountability?

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Can The 4% Rule Actually Work For Early Retirement?

The 4% rule suggests that a retiree who withdraws no more than 4% of their portfolio each year could have provided for a 30-year retirement window during most historical retirement windows. And that is true! The problem is that the FIRE community, however, perpetuates at least two misconceptions when discussing the 4% rule. Today, we address those common misconceptions about utilizing investment income. And, most importantly, we discuss how to use a flexible withdrawal strategy to weather bear markets and/or reduced future returns.

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