Your Next Gig

More recently, I've been spending time in pretty deep conversations with good friends about how they should think about their next gig. In almost every one of these cases, the good friend finds themself at a crossroads, and has options open (i.e. be a founder (again), get some experience by joining a fast-growing startup, full-time investing, etc.). Wanting to give them the best and most actionable guidance I could, I thought hard about what to tell them (as opposed to the usual self-help fluff). Then I went to my Moleskine and visualized my advice:

I prefaced this by telling my friends that it's a great time to be choosy right now: economic conditions continue to improve, and the appetite to support and fund great teams with compelling ideas is high. Had this been a deep recisionnary period, I'm sure it would have impacted my advice. But it's not, and the universe has conspired to give you this window of time to really invest yourself into something that will naturally drive you. The Venn is self-explanatory. It's not hard to think of opportunities that are a real, sizable pain point, but do you really care about food delivery, or last-mile logistics, or analytics? Do you have an unfair advantage, something you know that few others do?

Don't settle. Especially today. Life is way too short to burn cycles of time doing things you are on the fence about. We all need a paycheck, but if there was a chance to get one for something you deeply cared about, possessed an edge on, while alleviating a very big pain point, wouldn't you take it?