The Illusion of Skill and How to Make Better Predictions

Imagine being faced with the daunting task of predicting the future with nothing but incomplete information and a handful of hunches. Perhaps you’re considering new experiences, like travel or moving to a different town. When I imagined quitting my job, I envisioned a happier world, free from the perceived burden of corporate work. In the following months, however, my expectations were shattered upon realizing that I still largely felt the same despite my newfound freedom. In recent years, this recognition has remained vivid, sparking my curiosity about why predicting outcomes in the face of uncertainty is so difficult.

Whether anticipating a geopolitical event, forecasting stock market trends, or simply contemplating life’s next move, accurate prediction is an ever-present challenge. As I began to journal in earnest some years ago, I uncovered a fascinating trend hidden between the mundane details: my predictions were fraught with overblown concern and startling inaccuracy. Delving into the complexities of prediction and expertise, it becomes clear that many factors—from biases and cognitive distortions to the whims of randomness—shape our perceptions of certainty and accuracy. Despite these hurdles, new research offers a glimmer of hope.

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A Therapist on Satisfaction in Sport, Life, and Love

If you haven’t noticed, the concept of achievement and even competitiveness has weighed heavily on my mind as of late. A gift of the nontraditional life is the opportunity to step back and see the world around us with a degree of unusual clarity, far from the treadmill. For years I valued athletic and professional progress in ways that weren’t making my life better, but I thought they were. I searched for and implemented solutions to the wrong problems. Meanwhile, what truly mattered—mainly my relationships—withered on the vine. The journey toward rectifying these tendencies continues today.

My guest today, Lincoln Stoller, is a former mountaineer who now specializes in psycho-, hypno-, and neurofeedback therapy, in tandem with numerous other counseling and coaching services. Lincoln holds a PhD in Theoretical and Mathematical Physics from UT Austin, including a post-doc assignment at UC Berkley. Lincoln eventually moved from quantum physics to create a management and automation software platform for businesses, learned to build Norwegian log homes, traveled and lived abroad in far-flung foreign lands, and is even a certified pilot. To say Lincoln lives well outside of the bounds of normalcy is probably a half-truth at best. As he says in the interview, we should “just keep doing out-of-the-box stuff. And if people aren’t calling you a little crazy or a little nutty, then you probably aren’t exploring enough of the boundaries.”

Today’s conversation revolves around the high-risk potential of hard-charging performers and achievers, whether they exist in sports, business, or other areas of life. While these individuals hold our collective attention and admiration, Lincoln outlines how their psychological roots run shallow. They often struggle to stay satisfied with themselves or those around them. Lincoln might even say he holds an anti-hard-man philosophy. I think you’ll see why.

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All Work and No Play Makes You…Normal

Play Clipping Chains

The concept of play conjures the image of my three-year-old (and blonder) self, plastic shovel in hand, amorphous stains down the front of my pants. And certainly slobber. Lots of slobber. That three-year-old was certainly not concerned with social hierarchy or status, lacking a whiff of ambition to put the best version of himself forward. He played with a shovel in the sand because something needed to be dug and that was all that mattered.

As we age (and start to exhibit bladder control) the nature of play changes but is not altogether lost, at least not at first. Instead of digging in the sand, we might play a game of Twister, something I played as late as my college years. I challenge you to toss out that board on the floor—putting your head through someone else’s legs—and try and stay serious and stoic. It’s impossible. You’ll be giggling like a child. And that’s the point. We need more play.

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Four Years of Financial Independence: The Slow Growth

For four years I’ve watched something slowly bloom. In my old life, the “before time” you might call it, I moved from task to task. If I wasn’t working, I unknowingly made a practice of turning recreational or hobbyist pursuits into something that, from an outsider’s perspective, looked an awful lot like work. Goals and accolades were everything, and the more quantifiable, the better. But the farther I’ve separated myself from this life in space and time, the more clarity I’ve gained. 

Grasping for metaphors, I was tempted to explain this budding awareness as a slowly growing flower. But for perhaps all the wrong reasons, I hesitated to describe my growth and awareness as floral, preferring to drop the metaphor. But I can’t quite shake it, because I have watched something slowly grow. It’s not me that has bloomed–again, all the wrong imagery–but it is the world I could not see then. I could not see the flawed logic buried in the cold and wet earth because I identified with it. It was my life, so I could not reject what protected me. And four years later I’ve watched something slowly take root.

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Mike Piper: Down To The Essence Of Smart Money Management

Mike Piper is a CPA and the creator of the Oblivious Investor blog, where he teaches a philosophy of simple and low-maintenance investing.

Mike’s simple philosophy distills down to three primary principles:

  1. Diversify your portfolio
  2. Minimize costs (commissions, fees, mutual fund expenses, taxes)
  3. Ignore the noise.

Mike began his career as a CPA before realizing he could support himself by writing books. Surprisingly, he left his secure job during the 2008 financial crisis. He has gone on to publish seventeen books and is widely considered an expert in social security, tax, and a number of other personal finance topics. His work has been featured in the Wall Street Journal, Forbes, and Morningstar, to name a few.

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The Blue Dot Effect: Pessimism in a Beautiful World

As I’ve recently mused, financial independence won’t solve life’s problems. We will never “arrive.” We will never achieve perfection. An impactful 2018 study, nicknamed the Blue Dot Effect (a stand-in for the more lumbering “prevalence-induced concept change” title), helps us to understand the mind’s tendency toward finding problems, even where none exist. The results have broad implications for individuals and members of a progressing society.

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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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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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