Take some plan or goal you have and imagine a brilliant success. Everything went great, and now you’re in the future celebrating. Maybe your team is there, or your family and friends. You may even be giving a speech regaling everyone with the story of what happened. So then try asking yourself: What must have happened in order for this success story to come about? Try to be as concrete as possible, point out things that an impartial observer can identify. This is pro-hindsight, essentially an inversion of pre-hindsight. Rather than imagining failure, we imagine success.

For the past year or so, I’ve been focusing on getting better at connecting with people. Both those familiar to me as well as strangers. To look back and have succeeded at this, I would need to become someone who can make others feel instantly comfortable. To be able to walk up and put someone at ease. I’d be at ease opening up and having deep conversations — sharing things about myself that most people rarely do. By painting this picture of success, I immediately notice outcomes that I can target. These tie to specific skills I can develop. To get better at this, I’ve started experimenting with ways to practice these individual skills (for many, by granularizing).

Like with pre-hindsight, there are “obvious” things that pop out once we imagine concrete scenarios and reason about their prerequisites. We often daydream of success scenarios — “fantasies” — but fail to go one step further and ask what must happen to get there. Maybe because this often deflates the fantasy, and if we’re having fun then let’s not do that. But if it’s something we really want to achieve, this move is helpful.

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