The Life-Changing Practice Of Self-Made Billionaires: Self-Skepticism

Six steps to upgrade your thinking

Barry Davret
May 18 · 5 min read

In 2016, Warren Buffet gambled. He invested heavily in four major airlines, surprising many observers after years of shunning the industry. For a while, it looked like his bet would pay off.

Four years later, at Berkshire Hathaway’s recent shareholder meeting, he announced that he had sold all his airline holdings. “We made an understandable mistake,” he told the audience. He was open-minded enough to assess the future of airlines, determine its dim prospects, and admit that he had erred.

Fellow billionaire Ray Dalio shares a similar philosophy. In his book Principles, he writes, Open-minded people approach everything with a deep-seated fear that they may be wrong.” He points out that our blind spots — gaps in our knowledge and expertise — and ego get in the way of recognizing and admitting to our errors.

Both billionaires demonstrate the virtue of self-skepticism.

The practice of questioning and objectively evaluating evidence that might disprove your beliefs or expose your flawed decisions — self-skepticism

Whether you despise or revere people like Buffet and Dalio, they both embrace a vital truth that helped make them successful: humans are imperfect beings who will be proven wrong about things they are sure about.

Most of us struggle with recognizing and admitting to our errors in judgment. It’s not your fault. Our culture reveres those who exude perfection and those who remain steadfast in their beliefs, no matter the contradictory evidence.

But you can develop the practice of self-skepticism. It may not make you a billionaire, but it will help you succeed in whatever facet of life you apply it.


How to Develop Your Powers of Self-skepticism

These six exercises will help you develop the attitude and behaviors to question and challenge your decisions and beliefs.

1. Be aware of your defensive weapons

When we come across evidence or information that challenges our judgment, we react with defensiveness. This behavior manifests in one of three ways:

  • Dismiss the evidence as inaccurate or fake news.
  • Dismiss the source of information, thereby rendering the content questionable.
  • Reinterpret it to fit your narrative.

As Julia Galef spoke about in her popular TEDx Talk, Why You Think You’re Right — even if you’re wrong, some ideas feel like our allies and some feel like our enemies. She calls it the soldier’s mindset — the unconscious process of seeking out and destroying information that conflicts with your beliefs. But you don’t have to follow this playbook.

Instead, take a pause. Allow the tension to dissipate. Then, imagine putting down your weapon and putting on your detective’s badge; you’re now focused on following the evidence, wherever it takes you. It sounds silly, but it allows you to evaluate information with objectivity.

2. Avoid labeling yourself

Once you label yourself as part of a particular group, you will feel pressure to fall in line with group expectations. Worse than any group label, are ones that denote a status.

The most debilitating of the status labels is that of the expert. The expert stamp (or any of its cousins) can drain your desire to explore and learn. We waste too much of our energy defending our title.

If you must label yourself, tweak the label to give yourself some individuality.

  • A self-reflective republican
  • A curious democrat
  • An amateur expert

3. Publicly state your skepticism

Be the kind of person who professes a belief but qualifies it with skepticism. Always show a willingness to change your mind should new information warrant a revised opinion.

“Here’s what I believe based on what I know, and if further news contradicts it, I have no issues with revising my stance.”

One of the barriers to changing your mind is the pain of admitting your errors in judgment, and when tied to your worldview, it feels like it invalidates your existence. If you’re open about your skepticism, there’s no agony in acknowledging your mistakes.

4. Assess beliefs using the witnessing technique

It’s hard to assess yourself objectively. The witnessing technique helps you judge new information with an open mind.

Pretend the scene plays out in a theater or on a movie screen. Change the optics of the debate to something less emotional. If you’re evaluating an issue about the Coronavirus, pretend you’re watching the same argument play out during the 14th century Black Death. This approach allows you to witness as an impartial observer.

5. Create or rewrite your mission statement

When I got serious about my writing career, I created a mission statement:

“Find solutions to universal desires.”

A year later, I changed the verb to something that reflected my belief in self-skepticism.

Search for solutions to universal desires.”

The word search, instead of find reflected my changing views. You can never find a final answer to universal desires or questions; you can only discover better answers. A healthy skeptic will find a solution but recognize that a better mouse-trap will eventually prove superior.

6. Change your hyper-local culture

No, you can’t change the global or national culture. But you can change the culture of your family and peer group, and possibly even your organization.

Be the leader who welcomes evidence that disproves what you believe. Thank others for new information that reveals flaws in your decisions. Set the example for others to follow. By influencing the culture of your inner-circle, you make it easier for you and those around you to seek and accept the truth.


No matter how smart you are, some of your beliefs and decisions, in time, will be proven wrong. Not all of them but some of them. Don’t insist on being right; commit to self-skepticism.

Cultivate a willingness to question your decisions and worldviews, and if necessary, admit you erred. Adopting this attitude gives you more freedom to try new things and risk being wrong.

Take it from another self-made billionaire, Sarah Blakely, who said,

“It’s important to be willing to make mistakes. The worst thing that can happen is you become memorable.”


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Thanks to Michael Thompson, Jordan Gross, and Evelyn Martinez

Barry Davret

Written by

Writer. Experimenter in life, productivity and creativity. Contact: barry@barry-davret dot com.

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

Barry Davret

Written by

Writer. Experimenter in life, productivity and creativity. Contact: barry@barry-davret dot com.

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

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