Should I start this business? Apply for this job? Move states? Buy this expensive thing?

Here’s how I like to think about big, risky decisions. I put myself into the future (two years or five years or whatever makes sense) and imagine:

I didn’t do the thing
I did the thing and it didn’t work
I did the thing and it did work

In each scenario I imagine what I would think and how I would feel. If I would be full of regret if I didn’t give it a try, and I would be OK with doing it and failing, then it makes sense to do the thing.

On the other hand, if I’d be OK not having done it and the thing not working out would be pretty bad, then probably not.

And finally, if in doubt, have a crack. We generally regret the things we didn’t do more than the things we did.