80-Year-Old Self Test

A decision-making framework focused on evaluating life choices by imagining how your 80-year-old self would view them, based on insights from successful entrepreneurs and business leaders.

Core Philosophy

• Make decisions your 80-year-old self would be proud of
• Focus on avoiding regret rather than chasing prestige
• Prioritize meaningful work over purely financial gains
• Optimize for freedom and enjoyment rather than status

Key Decision Criteria

• Long-term Impact vs Short-term Gains

  • Consider the historical significance of opportunities
  • Example: Bezos leaving hedge fund job to start Amazon because internet was revolutionary
  • Focus on playing a role in transformative technologies/movements

• Freedom vs Money

  • Sam Zell's advice: "Optimize for freedom"
  • Freedom allows you to choose what you do
  • Having fun leads to being really good at something
  • Money naturally follows when you excel at what you enjoy

• Lifestyle Sustainability

  • Balance professional success with personal wellbeing
  • Avoid trading time for money once financially secure
  • Focus on maintaining sanity over maximizing wealth
  • Create guardrails to prevent overextension

Warning Signs to Watch For

• Chasing Prestige

  • People rarely think about you as much as you think
  • Prestigious roles often don't lead to fulfillment
  • External validation shouldn't drive major decisions

• "Never Enough" Syndrome

  • Many wealthy people constantly want more
  • Getting rich isn't as hard as staying sane
  • Money alone doesn't create life satisfaction

Implementation Framework

• Do what you genuinely enjoy
• Don't let promises of power/money derail your interests
• Consider impact on family and relationships
• Maintain work-life boundaries
• Focus on long-term sustainability over short-term gains