The Regret Disclosure Conversation
Push past the awkwardness and tell your team one regret. It'll be the best conversation you have this year.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 85%
Pink's most practical prescription, and the one he tested on himself first. Push past the awkwardness, gather your team or a group of friends, and tell them one regret you have — plus what you learned from it and what you're going to do about it. He almost guarantees it'll be one of the richest, most interesting conversations you've had all year. His confidence comes from having been wrong: he assumed nobody wanted to talk about regret because it's taboo, and instead found people leaning in, literally, wanting to talk. The three-part structure is what separates it from a confession booth — the lesson and the action turn disclosure into the 'outward' step of a working process.
Origin
In 2019 Pink very, very sheepishly mentioned a few of his own college regrets to a few people, against his better judgment, expecting the topic to be taboo. Instead there was a dam breaking — 'oh my God, you have that regret, I have that regret too.' The physical tell was people's bodies moving forward. He later got 21,000 strangers to do the same thing on a website, confirming that the appetite is real and universal.
Core principles
- 01Everybody has regrets, and everybody wants to talk about them — the taboo is imaginary.
- 02Disclosure is a form of unburdening; the act of speaking converts a vaporous emotion into concrete words.
- 03The structure is three parts: the regret, what you learned, what you'll do about it. Without the last two it's just confession.
- 04The leader goes first. Someone has to break the dam.
- 05The barrier is awkwardness, and awkwardness is not a valid reason to skip it.
How to run it
- 1
Pick the group
A team you work with or a group of friends. It needs enough trust that disclosure won't be weaponised.
Watch out Don't run this where a regret could become performance-review material.
- 2
Choose a real regret
One genuine regret — foundation, boldness, moral, or connection. Not a strategic non-weakness.
Pro tip Pick one you've actually processed, so you can supply the lesson honestly.
Watch out A fake regret produces a fake conversation and kills the exercise permanently.
- 3
Structure it in three parts
Tell them the regret, tell them what you learned from it, and tell them what you're going to do about it.
Pro tip The 'what I'm going to do about it' is what invites others to bring something actionable rather than just raw.
Watch out Regret with no lesson and no action is wallowing in public.
- 4
Push past the awkwardness and go first
Someone has to break the dam. Pink did it sheepishly and it still worked. The awkwardness is the whole cost and it's smaller than you think.
- 5
Let it run
Stop talking. Pink's finding is that people lean in and want to talk. Don't fill the space or steer it back to business.
In the wild
After his daughter's graduation, Pink very sheepishly mentioned a few college regrets — wishing he'd worked harder, been kinder, been gutsier — to a few people, expecting the topic to die.
→ A dam broke. People said 'you have that regret? I have that regret too' and leaned in physically. It launched a two-and-a-half-year book project.
The World Regret Survey asked only for age, gender identity, and location. People volunteered marital infidelity and childhood bullying to a complete stranger.
→ 21,000+ regrets from 109 countries — proof that the appetite to disclose is universal, not a quirk of Pink's social circle.
Common mistakes
Assuming nobody wants to hear it
This was Pink's own error, stated plainly: 'I was wrong. I thought nobody wanted to talk about regret.' The taboo is a prediction, and the prediction is false.
Disclosing without the lesson or the action
Drop either and the exercise becomes a confession booth. The three parts are what make it the 'outward' step of a process rather than a performance.
Is it for you?
Best for
Leaders who want a genuinely different conversation with their team, and friend groups stuck in small talk.
Not ideal for
Low-trust environments where disclosure would be used against people, or a regret involving someone in the room.
From the transcript
“One of the most useful things to do is... push past the awkwardness. And if you have a team that you work with or a…”
“I can almost guarantee that you will have one of the richest, most interesting conversations you've had this year because I was wrong. I thought…”
“They leaned in, that as their bodies move forward in wanting to discuss this. And that's a very good sign.”
From the episode
Daniel Pink: Turn Regrets Into Gold, Understand Your Emotions, and Live Your Best Life
Daniel Pink