What is What I Would Have Done?
What I Would Have Done hands the room a box of life events — prom, a trip, a job — one per folded scrap. Draw one, tell the true story behind it, then describe the version you'd try instead and why. Nobody keeps score; the two versions side by side are the whole point.
It works because the two-part turn does double duty: the true story gives the room something concrete to react to, and the imagined do-over shows what someone actually wanted, not just what happened to them.
It leans on real personal history, so give it a pass with a brand-new group that hasn't built any trust yet — a "what would you have done differently" prompt can drift toward regret if nobody sets a light tone first. For a room that already knows each other well, the box of scraps still turns up stories nobody's shared before.
The rules
- Write different life events on scraps of paper — prom, a sport, a trip, a job — and drop them in a box.
- Fold or cover each scrap so the event can't be seen until it's drawn.
- Each player draws one scrap and reads the life event out loud.
- They share what actually happened, then the version they'd try instead — and why.
- Keep turns short so everyone gets a turn.
- There's no winner or loser — the goal is discussion, not correct answers.
Before you start
- Group size: 2–10 participants. Small enough that every turn gets full attention, wide enough for real range in the stories.
- Materials: paper, a pen, and a box. Tear the paper into scraps ahead of time — one life event per scrap.
- Write events the whole room can speak to. Prom, travel, sports, a job — pick events that are broadly relatable, then fold each scrap so it can't be read from outside the box.
- Set the tone before the first draw. Say upfront that there's no winner and no wrong answer — that's what keeps the sharing honest instead of guarded.
How to run it
- Write and box the life events beforehand
Write different life events on scraps of paper, fold them, and drop them in a box. Prom, a sport, a trip, a job — anything broadly relatable works.
- Draw and read one aloud 30 sec each
The player draws a scrap from the box and reads the life event out loud — that's the topic for their turn.
- Share what actually happened 1–2 min each
Talk through the real story behind the drawn event — what happened, and what it was like.
- Share what you'd try instead, and why 1–2 min each
Name a different path you'd have taken with that same event, and explain why it appeals to you now.
- Rotate to the next player 10 sec
Keep turns short and move to the next draw — everyone gets a turn, and there's no scoring to slow things down.
← the redo is the real answer.
Facilitator tips
Why it works
Reflection questions
For classrooms, trainings, and teams that want the debrief — these turn the draw-and-share format into a real conversation about choices and change.
- What was one life event you drew that resonated with you the most?Gets people naming the draw that actually stuck, not just the one they answered.
- If you could have done one thing differently in your past, what would it be and why?The most direct route to the game's real subject — choices and second chances.
- How did it feel to share something you might not normally share with a group?A quick read on how safe self-disclosure feels here — useful before you run this again.
- Did any of the answers given by others inspire you or make you think differently about a particular life event?Rewards active listening — the answer usually names a specific line someone else said.
- How can you apply what you've learned from this game to your own life and relationships?Moves the game from a nice hour to something people actually carry out of the room.