“Stories and lessons from an unexpected journey in finance.”

I started surfing this year. I am bad at it.

Not charmingly bad. Bad in the way where you spend forty minutes paddling, catch nothing, and come in with your arms shaking and sand in places sand should not be.

I have spent thirty years being the person in the room who knows. Companies hire me specifically because I have seen it before. That’s the whole value proposition of a CFO — you don’t have time for someone to learn on the job.

Then I paddle out and I am the worst person in the water. In public. In front of strangers, several of whom are children.

The physical part isn’t what’s hard. The hard part is that there is no version of this where I get to be competent quickly. I know what I’m supposed to do. I’ve watched the videos. My body simply will not do it yet, and no amount of career makes that go faster.

Here’s why I’m writing about it in a finance newsletter.

I’ve written four posts this year about why finance teams struggle to adopt AI. Tool sprawl. Automating broken processes. Pilots that never scale. All true, all real.

But there’s a simpler explanation I’ve been circling.

Senior people stop doing things they’re bad at. We get good at something, we get promoted for being good at it, and then we quietly arrange our lives so that we are never visibly incompetent again. It’s not laziness. It’s self-protection, and it works — right up until the job requires learning something new in front of people.

Then we delegate it. We ask for a demo instead of trying it. We send someone junior to the training.

I don’t think most AI adoption problems are technology problems. I think they’re ego problems wearing a technology costume.

When did you last do something you were genuinely bad at, where other people could see?

I’ll be in the water Saturday. Still bad.

#TheAccidentalCFO #Leadership #AIAdoption #FinanceLeadership #INERSEC