QA10: Bear Markets and Bank Failures

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

For this week:

  • Are new investors part of an “unlucky cohort” that won’t achieve financial independence in the often-cited timelines?
  • Is it worth it to hire a tax professional? And if so, how should I find one?
  • Can you help me understand all these confusing public sector retirement accounts?
  • Should I do a Roth conversion now or just make a contribution to a Roth IRA?
  • Thoughts on the recent bank runs and instability in financial markets
  • So much more!
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Lean Out: The Achievement Paradox with Dawn Baker

Today on episode 57 I’m pleased to welcome Dawn Baker, a board-certified anesthesiologist, wife, mother, climber, coach, and now the author of a new book about the perils of, as she puts it, an intense need to achieve. And Dawn has walked the walk. After years of hard-driving pursuit of linear improvement in both career and climbing, she suffered crushing fatigue and malaise, and ultimately faced a major health crisis during her residency. If that wasn’t enough, she was then plagued with infertility problems. The result was expensive and demoralizing rounds of in-vitro fertilization, an approach that ultimately proved successful and led to the birth of her daughter.

The need for achievement and success is so pervasive in our culture. And this interview is not just for downtown or medical center careerists. This is as much a discussion of climbing and our hobbies, which can so often derail into something quite different from our original healthy and recreational pursuits.

Today, Dawn’s life with her husband and daughter is so different. Through evaluation of her core values, married with a strong financial position, she now works “very part time,” and has moved with her family to a homestead in the high plateaus of southern Utah. But in choosing to step away, or lean out, as Dawn says, we risk our position and standing in the social hierarchy. This is much a discussion of status as it is of lifestyle.

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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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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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Three Important Myths on Delaying a Career

A combination of economic and cultural influences are propelling the trend of delayed adulthood. Through low-commitment job grazing, one can pursue recreational pursuits into the years previously occupied by traditional adult responsibilities: marriage, careers, parenting, and even home ownership.

Some might say YOLO. Life isn’t as short as we think, but our ability to get ahead might be.

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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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