Part of hitting your later twenties is wrestling with what success looks like. In a race, you've won when you cross the finish line first. In chess, when you take the king. The rules are narrow and the outcome is clear.
I vacillate between definitions. Sometimes winning looks like my former boss seeing what I've built and saying 'oh, wow.' Or the kid from college I never liked, watching me get into a great business school and thinking — damn, maybe he is smart. That might be gratifying but is that really winning? Would I be truly happy if I defined my goals through what I thought would impress other people? I doubt it. Gratifying, maybe. But not winning.
I am trying to triangulate winning by stating the following three things, clearly, then basing decisions off of that 1) Here are the things that make me really happy that I want to prioritize and 2) Here is what I am okay not being, or what I want to stray away from and 3) Here's something in my gut telling me if I don't do this I will be disappointed in myself.
Things that make me happy I want to prioritize:
- Emily
- Being in great shape
- Reading
- Deep friendships
- Working a job with upward momentum
- Making good money
What I am okay passing on:
- Being a Fortune 500 c-Suite exec (if I could even do that)
- Leading "strategy" or being a Chief of Staff or any other job that would be a massive ego-boost but I'm not sure I would enjoy
- Not being the most credentialed person
- Not being defined as successful immediately by people who I want to know "I won" (i.e. my former boss)
What I need to do in my gut:
- Build something that gets some measure of attention
- Make enough money to not be worried and to be happy with where we are financially
- Hit some metric of external validation/success that not everyone needs to know about but I know for me is "winning"
- Move out of DC at some point (I don't want to spend the next twenty years here without ever leaving)