I've had two big decisions to make lately, and something clicked for me while I was working through them.
At some point during the pandemic (Who can remember when anything happened in the past 3 years? What even is time anymore?) I read Thinking in Bets by Annie Duke. It put a name to a way of thinking about things in percentages rather than as binary. I often focus on the outcome of a decision rather than the likelihood of that outcome, and my emotions get in the way of making the best decision. This shows up in two ways:
When I stop myself from focusing on the outcome and consider the percentages of how likely one outcome is, it breaks me out of this mode. I find I'm much happier no matter which way things go if I put myself in my own future shoes. I imagine dealing with the unhappy outcome. Even imagining myself in what I think is the happy outcome can be a good gut check - if I feel less excitement (or more dread) than I expect, that's a signal to investigate!
OK, I'll get a bit more concrete here, because I think it will help. I had the opportunity for a new role at work. It will likely be career-altering to some degree, so I'm not taking it lightly. It's been a complicated decision, one which I can't easily back out of, and which I probably won't fully know how good or bad the decision was for a few years.
So how does thinking in percentages affect this decision? It allows me to fully commit to something even when I'm not 100% sure it's the right decision. This is huge! It lets me check in with my gut without giving my gut too much control. It also gives me a baseline, and then see how new information pushes the decision one way or the other.
As an aside: I suppose complex, unclear decisions are just the reality of reaching a certain point in your career. Early on the path is well-trodden and the next steps are clear. Later it becomes highly situation-dependent and there's no playbook anymore. Even if I stay in my current path, continuing to grow will mean my role will look very different than it does today.
Weighing the short- and long-term pros and cons, I was about 60/40 in favor of taking the new role. That is way less than 100% certainty. I wasnt comfortable with that level of uncertainty (and I still had some time), so I went in search of more information. I reached out people who had been in a similar position, a few of whom I wouldn't normally reach out to. That's another advantage of being realistic about the chances: It encourages me to get more information to push the decision in a direction. I got some great input from someone, both positive and negative, and when the decision deadline was looming I was somewhere around 70% confident I was making the right call.
This is still way less than 100%. But it means if I made the same decision with the same information 10 times, I believe I would be making the right decision 7 of those times, more than double the number of "wrong" decisions. But of course those three times are not zero times. I could still be wrong.
Big decisions are rarely simple, and it's rarely obvious which way to go. By allowing yourself to be comfortable with less than 100% certainty, you can make more decisions more confidently. We're always acting on incomplete information. Even if you made the exact right decision based on all the information you had at the time, you could still be wrong. And that's fine! What's more important is that you learn, use the decision you made as an input for your next decision, and try to bounce back.