Prevent Self-Deception by Challenging Your Own Convictions

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In the 1970s, a psychologist named Leon Festinger discovered “cognitive dissonance”—the discomfort we feel when reality conflicts with our beliefs. Investors desperately want to feel right, so they ignore or dismiss evidence that contradicts their favored stocks or strategies. Social psychology reveals that this drive for consistency is so strong we’ll even cherry-pick data to support our views.

Behavioral finance studies by Daniel Kahneman show that confirmation bias—seeking only validating evidence—leads investors to hold losing positions too long. Nobel laureate Richard Thaler found that investors who invited contrary views outperformed those who didn’t by 25% over a decade. Simply put, arguing with yourself—honestly—uncovers costly blind spots.

The best investors build “devil’s advocate” into their process. Warren Buffett credits Charlie Munger with forcing him to rethink “buy wonderful businesses at fair prices,” shifting away from “fair businesses at wonderful prices.” Seeking disconfirming evidence became a tool for better decisions.

By systematically inviting qualified critique and weighing hard data, you weaken your brain’s instinct for confirmation. That opens the door to smarter, more adaptive investing.

First, write down three key assumptions guiding your investments. Next, line up two or three people—an advisor, colleague, or friend—who disagree, and ask them to explain their perspective. Weigh the evidence side-by-side, noting where your beliefs may be blind spots. Finally, update your assumptions with humility and document the new views in your playbook. Doing this regularly will protect you from self-delusion. Give it a try this week.

What You'll Achieve

Internally, you’ll develop intellectual humility, reducing the stress of defending fixed ideas. Externally, you’ll make better-informed investment decisions by exposing blind spots and adapting strategies based on broader evidence.

Invite Constructive Conflict

1

Identify Your Core Beliefs

Write down three investment assumptions you hold—like ‘tech always outperforms’ or ‘bonds are for retirees.’

2

Find Qualified Critics

Reach out to a financial advisor or peer who disagrees with each belief and schedule a brief call to understand their reasoning.

3

Weigh the Evidence

Openly compare the pros and cons you and your critic have gathered, highlighting any blind spots in your original view.

4

Adjust with Humility

If the critic raises valid points, tweak your assumptions and document the updated belief in your investment playbook.

Reflection Questions

  • What’s a core investment belief you’ve maintained despite mounting contrary evidence?
  • Who in your network challenges your views most constructively, and how can you involve them?
  • How might your portfolio look different if you updated one key assumption today?

Personalization Tips

  • A new homeowner lists benefits of keeping cash for renovations, then listens to a financial planner urging early mortgage paydown.
  • An entrepreneur maps the perks of going public, then talks with a C-suite friend who warns about IPO lockups.
  • A parent saving for college consults a CFP recommending a 529 plan against a robo-advisor favoring tax-deferred IRAs.
Unshakeable: Your Financial Freedom Playbook
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Unshakeable: Your Financial Freedom Playbook

Anthony Robbins 2017
Insight 6 of 8

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