A Map to Career Capital and a Compass to Guide You
How my partner and I built a map and compass for her career
My partner came over for date night (I made stew) and, as usual, we ended up talking about her career. This is a pretty normal date night conversation for us, my friends jokingly say we’re a “Power Couple”. She’s at a bit of an inflection point in her startup and is trying to figure out whether she should push for more responsibility or leave and seek that elsewhere. Somewhere around 9pm I was trying to figure out how to explain to her that I thought one of her assertions didn’t contribute to her stated goals. Over the last few conversations we had built up the concept of “Career Capital” with the notion that one earns career capital through known accomplishments. I in turn had built an expected value model in my head for a number of possible scenarios she might encounter in the coming years. My initial impulse was to tell her directly what I thought, but one of my major goals these days is to ask, not tell. So I asked her if she was up for playing a quick game with me to help me understand how she’s thinking about the different scenarios. She said yes and I grabbed my notebook and scribbled out something like the below table.1
I filled in the top left most cell with an arbitrary number of 10 to provide an anchor point and asked her to fill in each cell with how much additional career capital she expected to earn in the scenario. My original intention was to simply get her to tell me how she valued each of these possible outcomes, but as she worked I realized this plan was creating something much greater. As we added different scenarios, we began to build out a projection of potential earnings. When the doc was finished, we’d built her a map AND her desire for Career Capital had become a compass!2
I pointed this out to her and the “Aha!” moment was magical. We discussed a few additional scenarios and I pointed out that she could calibrate this compass / map by talking to a handful of people. If she cold contacted ~30 people on LinkedIn with a spread of CEOs, VPs of Eng, Investors, Early Founders and Series B Founders she could probably get thirty minutes with one of each. In that time she could ask them for their perception of the relative weightings between these scenarios and that would help her build confidence in the map.
Once she had confidence in the map, she could start to make really meaningful tradeoff decisions about her career using it. This compass should last years and allow her to quickly make really big decisions.
Needless to say, I’ll be doing this for myself at my next major inflection point.
Thanks to Cherry Yang for her input on this piece.
For those curious, here’s the original notes.
This concept sits at the intersection of Designing Your Life and Never Search Alone, two books I’ve read recently.