When Thinking About Quitting, You're Already Late

When to quit is a decision that most people delay far too long, with significant opportunity costs.

The Psychology of Quitting Too Late

• We face the same uncertainty in stopping as we do in starting, but with additional psychological barriers:

  • Sunk cost fallacy: "I've already put so much into this, I can't walk away now"
  • Endowment effect: We overvalue things we've built or own compared to identical things we don't own
  • Identity concerns: Fear of being seen as (or feeling like) a failure
  • Need for certainty: Most people won't quit until it's no longer a decision - when things have completely fallen apart

• By the time you're thinking about quitting, objective signals likely appeared much earlier

  • As Richard Thaler noted, "Most people won't quit until it actually isn't a decision" - when you've already "fallen into the crevasse"

The Hidden Costs of Not Quitting

• Continuing with something that isn't working has two major costs:

  • Direct costs of pursuing something not worthwhile
  • Opportunity costs of not being able to pursue better alternatives

• The Stewart Butterfield example demonstrates this perfectly:

  • Had $6M in the bank, great investors, 5,000 die-hard users
  • But customer acquisition was unsustainable (95-99 people left for every loyal user)
  • Realized it wasn't a venture-scale business despite positive signals
  • Shut down Glitch despite having runway and momentum
  • Only after quitting could he see the opportunity that became Slack

How to Quit Better

• Use premortems with kill criteria to make quitting decisions more objective:

  • Identify signals that would indicate failure in advance
  • Pre-commit to specific actions when those signals appear
  • This creates structure that helps overcome psychological barriers

• Ask yourself: "Would I start this today knowing what I know now?"

  • If the answer is no, everything you put into it going forward is the actual waste

• Remember that waste is a prospective problem, not a retrospective one

  • The resources already spent are gone regardless of your decision
  • The question is whether future resources will be well-spent

• Consider the opportunity cost of continuing

  • What else could you be doing with your time, energy, and resources?
  • Like Butterfield, you can't see your "Slack" until you quit your "Glitch"