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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The Psychology Behind Poor Investments and Other Important Decisions

When we make important decisions, we are often not as rational or objective as we’d like to believe. The base rate fallacy is the tendency to misjudge the probability of a situation by not accounting for all relevant information. This cognitive bias affects everything from first impressions to voting preferences to broad market behavior.

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QA12: Will A Life Of Financial Independence Meet Expectations?

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

For this week:

  • An update on markets and our personal finance situation
  • The role of dividends in growth and withdrawal assumptions
  • Expectations vs reality on a life of financial independence
  • Our experience with health insurance without employer-sponsored plans
  • Real estate investing: an update on our experiences and economics as remote landlords
  • Health insurance considerations for long-term travel
  • Short- to medium-term savings goals (like a house) versus saving for retirement
  • Loss of purpose without a traditional job
  • So much more!
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The One Time to Be Average with Dave Rosen

Dave Rosen is a climber and ophthalmologist in his final year of residency. And Dave grew up like so many of us: broadly exposed to the importance of money and taught a thing or two about saving, but investing was a foreign concept and his lack of knowledge was a source of shame.

While Dave skimmed over it, he’s no slouch as a climber. He has bagged a pile of double-digit boulder problems up to V12, sent 5.13c, and developed numerous boulder problems, particularly in the South Mountain area near Phoenix where he and his wife lived for medical school for four years. He is hard-working, analytical, and pragmatic in his career and life approach. 

In this conversation, we discuss how Dave found climbing from the world of canyoneering, his early exposure to money and how that has markedly changed in recent years, the constant pull of greener grass, working backward from an ideal lifestyle, and the ethical and moral dilemmas of early retirement.

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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 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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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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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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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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