A lot of my best decisions don't really look like decisions at all in hindsight:
- Going to MIT - applied early, got in, and didn't apply anywhere else. In retrospect I had confused it with Cal-tech after seeing Real Genius as a small kid and not seeing it again until college. I did visit MIT as a junior and really liked it at the time, but I really didn't give other schools much of a chance.
- Meeting my wife - she looked super intriguing to me in our freshman picture book and so I decided to just reach out one day. Fate? Easily my best decision ever.
- Getting married - planned a bit of a proposal but just seemed like the right time (few years out of undergrad).
- Starting NamesDatabase - did a random one day side project and then many months later that side project turned into that company.
- Starting DuckDuckGo - similarly, side projects merging into something that seemed tangible. One day just decided it's fun so why not work towards a launch of something.
That is, there was no deliberation or even much explicit consideration at the time these decisions were made. No pros and cons lists.
You could say I just went with my gut. I couldn't really argue with an even more whimsical interpretation. Perhaps underneath is a long trail of implicit decision making that makes the end decision seem somewhat arbitrary or obvious. I'm not really sure.
For some of them I can certainly reconstruct a trail of events that arguably led up to the final one. Or maybe you can say I'm picking an arbitrary final point and it really was (and continues to be) one big fluid decision.
The same is true for company decisions as well like the DuckDuckGo billboard. The idea popped into my head one morning, my wife said it wasn't totally insane (good litmus test) and so I immediately started to make it happen.
Of course I've done the opposite as well.
- Moving to PA - came out of a pretty intense calculation and visiting process.
- Selling NamesDatabase - deliberate decision to embark on the process and then really thought hard about all sub-decisions.
I'm not really advocating one approach over the other, but I just find it interesting. I have no idea how everyone else operates.