A week ago (Friday) was my last official day at Pro Bono Net. I spent the last five years working there, and, as the saying goes, put a good deal of blood / sweat / tears into it with an ever-alternating sense of cynicism and hope. I’d like to think I did a passable job of moving the needle on access to justice in some minuscule way. Maybe a good one, maybe not. But I’ll settle for passable.
I’ve been slacking on this Substack newsletter the past 2 weeks. But as promised: five big thoughts in general, since job moves always get me thinking deeply:
Don’t confuse a job with a career. Don’t confuse a career with a purpose. These can be separate things; sometimes they have to be separate things. Jobs come and go. Careers can change. Even your purpose can change, or be clarified by time and experience. Both my career and purpose have changed / been clarified over time. As ultrarunners say, “find your why.”
Good enough is, well, good enough. Don’t let the perfect get in the way of the good. There’s the old saying: “Do you want to be correct, or do you want to be happy?” My point can be similarly phrased: “Do you want to make something perfect, or do you want to make something people will actually use?” 99.999% of the time you can’t have both.
Start. Try. Fail. Try again. Fail. Start again. I’ve seen so many examples in Legal / Legal Tech / A2J Land where the fear of failure prevents people from trying. Yes the stakes are high - but don’t misinterpret high stakes as a prohibition on trying new things. Over the long term what matters is the number of inputs and creating feedback loops. Try things out. Create an embarrassingly bad beta version. Show it to your friends. Test and test again. Improve it.
No one is an expert. The longer I live, and the more I learn, the more I realize that there’s more I don’t know than I do know. The people who have the loudest and most definitive opinions on something often know the least about it. Truly understanding what this means is like a gateway drug to offering your own opinions and perspective in whatever forum you wish. That’s valuable. But don’t get high on your own supply - always, always, be open to changing your mind.
The only real moat is execution. That’s more true now than it ever was, when anyone with access to ChatGPT, Claude, or Gemini Pro can create a website, application, deep research report, etc. The last mile is the longest one. Execute. As they say in for-profit software land, ship.
As for me, I’m on to something new … more on that later I’m sure. For now, stay cool out there.