Post-Exit Depression

A common pattern emerges among entrepreneurs who achieve significant financial exits - they often experience depression and loss of purpose despite financial success. This psychological challenge stems from the sudden removal of a driving force that previously consumed their energy and focus.

Key Observations:

• Post-Exit Depression Pattern:

  • Many successful entrepreneurs feel depressed 6 months after selling
  • Even with $20M+ exits, people struggle with purpose
  • Can't openly discuss due to perception ("boohoo poor millionaire")

• Psychology Behind the Struggle:

  • Humans need purpose and direction to channel energy
  • Money alone doesn't provide fulfillment
  • Type A personalities particularly struggle with lack of challenges

• Common Coping Mechanisms That Don't Work:

  • Playing video games all day
  • Floating in pool
  • Reading books
  • These activities don't provide meaningful contribution

• Successful Recovery Pattern:

  • Most find happiness by starting new ventures
  • Focus shifts from size/scale to solving interesting problems
  • Need for camaraderie and daily challenges remains

• Financial Management Strategy:

  • Invest bulk of exit money and "forget about it"
  • Maintain modest checking account for daily life
  • Create artificial scarcity to maintain drive
  • Use ongoing business cash flow for lifestyle

• Key to Happiness Post-Exit:

  • Take time to rest and reflect
  • Don't stay idle too long
  • Find new ways to contribute
  • Accept that next venture might be smaller
  • Maintain hunger by creating artificial constraints

• Psychological Framework:

  • Work like a lion - sprint, feast, rest, observe
  • Important to enjoy the win
  • Equally important to start hunting again
  • Rest period should be intentional but not permanent