(Note: this post is not actionable. Sorry!)
I’ve described my professional activities in many ways. During the transitional periods, I’ll often be congratulated and wished good luck. This has always bothered me and today I realised why.
First, it implies that the activities are discrete, which isn’t the case. Countless types of changes exist within the startup world.. you can switch companies and ideas, or between freelancing and founding, or between VC and bootstrapping, or from coding to sales. But those are all relatively superficial changes. Even in the most extreme case (which is tanking a company and switching roles/careers), all the important stuff stays the same: your network, your reputation, your skills. Being congratulated suggests a big leap, a new life path, but it’s really just the next leg of the same road.
There’s a bit in Siddhartha where he is being a bit uppity to his merchant boss Kamaswami, who shouts, “I taught you everything you know!” Siddhartha replies, “You taught me prices and interest rates, but not how to think.” Likewise, the talents of real value to a startup guy will stay with you between gigs. Domain knowledge is certainly important, but in most cases it’s readily available and quick to acquire.
Second, “good luck” hints at a terrible risk. If you’re young and/or comfortable freelancing, there’s literally zero downside to starting (and tanking) a company. The downside is probably negative, since even in the worst case, you’re accumulating the aforementioned assets.
[The writer Trollope] “woke in darkness and wrote from 5:30 a.m. to 8:30 a.m., with his watch in front of him. He required of himself two hundred and fifty words every quarter of an hour. If he finished one novel before eight-thirty, he took out a fresh piece of paper and started the next.” The New Yorker, June 04
In place of books to write, we have companies to build. You work at it every day, and when you finish one due to either good or bad circumstances, you continue on with the next. The putting down of one and picking up of another requires neither consolation nor congratulation.
Trollope wasn’t writing one book. He was a writer.