The Great Comfort of Longevity in the Stock Market

Since the financial crisis of 2008, two dominant views on stock market investing have emerged:

  1. Stock market investing is volatile and risky, akin to gambling.
  2. Stock market investing is reliable and free money.

The Great Recession produced a decline in overall equity values in the range of 50%+ from 2007 to early 2009. The event created a lasting and widespread change in mindsets around personal finance, even what it means to be securely middle class. However, for those that stayed the course, the subsequent Great Bull Market produced exorbitant wealth for almost anyone investing in almost anything.

If there’s a lesson to be learned here, it’s that market growth and declines are cyclical. These cycles are influenced by a complex blend of fiscal policy, business practices, and perhaps most important of all—animal spirits: human behavior and emotion. To balance risk and reward, one should invest broadly in the market as a whole and increase the investing timeline. The latter in particular is easier said than done. In this post today, we quantify the power of longevity in the market. We have reason to rejoice, so long as we can hang on!

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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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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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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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Earning to Buy Time with Meghan and Jeff (A Way to FI)

Today’s guests on episode 44 are Meghan and Jeff, two Colorado climbers who are at very different positions on the spectrum of financial independence. Jeff achieved financial independence along with his wife, Rose, over four years ago. Meghan, along with her husband, were inspired to get serious about their personal finances after meeting and learning from Jeff and Rose. Jeff and Meghan now write about their experiences and learnings at awaytofi.com.

Today we discuss their different origin stories, long-term goals, and shed some light on the fraught balance between work, money, family, and the seemingly elusive control of our time.

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