Anticipated Regret as Wisdom

10 years from now, what will you regret if you don't learn it or do it now?

Chip Conley
Chip Conley on joining Airbnb at 52, working with Brian Chesky, and the Modern Elder Academy

Anticipated Regret as Wisdom

"10 years from now, what will you regret if you don't learn it or do it now? Anticipated regret is a form of wisdom, and it's a catalyst for taking action." - Chip Conley

What It Is

Anticipated Regret is a decision-making framework that uses future projection to overcome present-moment inertia. By imagining yourself 10 years in the future and asking what you'll regret not having done, you can break through the "I'm too old for this" or "it's too late" mindset that often prevents people from learning new skills or pursuing new experiences.

This framework leverages the psychological power of regret—one of the most painful human emotions—to motivate action in the present. It transforms the vague sense of "I should do this someday" into an urgent realization that time is finite.

How It Works

The framework operates on several psychological principles:

  1. Future self projection - Imagining your future self creates emotional distance from present obstacles

  2. Loss aversion activation - The pain of imagined regret is often stronger than the pleasure of imagined gains

  3. Time horizon expansion - 10 years is long enough to make meaningful progress but short enough to feel real

  4. Inertia disruption - Breaks the default assumption that "there will always be more time"

The key insight is that as we age, we often talk ourselves out of learning new things ("I'm too old to learn Spanish"). This framework flips that logic: the longer you wait, the more you'll regret not starting now.

How to Apply It

  1. Ask the question regularly - "10 years from now, what will I regret not learning or doing now?" Make this a quarterly reflection practice.

  2. Challenge "I'm too old" thinking - When you catch yourself saying "I'm too old for this," run the anticipated regret test. If you'll still want it in 10 years, start now.

  3. Make a regret avoidance list - Write down 3-5 things you'd genuinely regret not pursuing. These become your priorities.

  4. Use it for skill investments - Chip used this to learn Spanish and surfing when he moved to Baja at 56. Both seemed "too late" in the moment but would have been regrets if avoided.

  5. Apply it to relationships - Relationships often suffer from "we'll get together someday" thinking. Use anticipated regret to prioritize connection.

  6. Pair with action commitment - The question alone isn't enough. Follow up with "What's the smallest step I could take this week?"

When to Use It

  • Major life decisions about career changes
  • Evaluating whether to learn a new skill
  • Deciding whether to take on challenging experiences
  • Midlife reflection and life audits
  • Overcoming fear of failure or looking foolish

Source

  • Guest: Chip Conley
  • Episode: "Chip Conley on joining Airbnb at 52, working with Brian Chesky, and the Modern Elder Academy"
  • Key Discussion: (01:01:51) - Using anticipated regret to learn Spanish and surfing at 56
  • YouTube: Watch on YouTube

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