Anticipated Regret Decision Test
Ask '10 years from now, what will I regret if I don't learn or do this now?' to unlock action.
- Difficulty
- Starter
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 90%
A single forward-looking question - 10 years from now, what will you regret if you don't learn it or do it now - converts a future self's likely regret into present-day motivation. Conley frames anticipated regret as a form of wisdom and a catalyst for action, especially useful against age-based or fear-based excuses.
Origin
One of Chip Conley's core MEA (Modern Elder Academy) questions; he used it personally when deciding to learn Spanish and to surf after moving to Baja at 56.
Core principles
- 01Anticipated regret is a form of wisdom and a catalyst for taking action
- 02Projecting to your future self converts abstract fear into a concrete cost
- 03The question dismantles 'too old' or 'not enough time' excuses
- 04It works precisely because the horizon (10 years) is long enough that inaction has a visible price
How to run it
- 1
Surface the excuse
Name the thing you're telling yourself you can't or shouldn't do (e.g. 'I'm too old to learn Spanish').
- 2
Project ten years forward
Ask: 10 years from now, what will I regret if I don't learn it or do it now?
Pro tip Picture your actual future circumstances - Conley imagined still living in Baja, which made the regret concrete.
- 3
Read the regret as a signal
If the honest answer reveals real regret, treat that as wisdom pointing to action.
Watch out If there's genuinely no regret, that's also a valid answer - the test can license letting go, not only doing.
- 4
Act now
Convert the anticipated regret into an immediate commitment to learn or start.
In the wild
Moving to Baja part-time at 56, Conley believed he was too old to learn Spanish or to surf. Asking what he'd regret in 10 years - given he might still be living there next to a surf break - flipped the decision.
→ He learned both Spanish and to surf, treating anticipated regret as the catalyst.
Common mistakes
Using the present self's comfort as the judge
The excuse ('too old', 'no time') is the present self talking; the test deliberately hands the decision to the future self who bears the regret.
Is it for you?
Best for
People in midlife or any transition talking themselves out of learning or starting something new.
Not ideal for
High-frequency trivial choices where deliberate regret-projection is overkill.
From the transcript
“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 so and it's a catalyst for taking action”
“I had a mindset which was I'm too old to learn Spanish. I'm too old to learn to surf. But when I said 10 years…”
From the episode
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school
Chip Conley (founder of MEA)