AI Made Me Braver

A few months ago, I overhauled our contracting infrastructure to support AI generated contracts, DOCX templates that fill in the things we’d need, and correct-but-unsupported DOCX detection1 Two years ago, taking on a big daunting project would’ve been a measured decision. AI has made building things faster. That changes the calculus of what projects you can take, and how ambitious you can be with your bets. A big overhaul doesn’t take weeks. It can be done overnight, which means you can experiment much faster. This is all true, and lots of people have talked about it. I don’t want to talk about it here. What I do want to talk about is the unexpected surprise of how AI has made me braver. The fear hasn’t gone anywhere Every time I start work on something ambitious, there’s a knot somewhere in my tummy. I call it the fear of the unknown. Not knowing exactly how I’ll do something leads to uncertainties. And uncertainty is … uncomfortable. That hasn’t changed. I don’t think it ever will.…