One post tagged with "skin-in-the-game"

I spent three weeks building my retirement plan with AI.

Not a rough sketch. A proper plan — asset allocation across account types, tax-loss harvesting sequences, Roth conversion ladders, withdrawal ordering optimized for bracket management, Monte Carlo scenarios run from first principles. By the time I was done, I had something that would have cost several thousand dollars at a fee-only advisory firm.

Then I hired a human financial advisor anyway.

I've been thinking about why ever since, because the honest answer surprised me. It wasn't that the AI plan was wrong. I couldn't find anything technically wrong with it. It was something else. The plan had no gray zones. Every decision was clean, optimized, defensible. But when I imagined actually executing it — moving real money, locking in real choices — something wouldn't let go. What I eventually realized: if this plan goes sideways in five years, the AI moves on to the next query. The advisor loses a client, maybe a reputation, maybe sleep. That asymmetry matters. I didn't know how much until I was staring at a plan I couldn't quite trust.