People assume that after you restructure a company, bet on Daikin in 2008, and write a book, you start choosing easy problems. I do not. I still love solving hard problems — the ones where the comfortable answer is wrong, where the room wants certainty, and where the fix costs ego before it pays revenue.
That is not masochism. It is where I am useful.
Hard problems reveal character
Easy problems let you hide behind process. Hard problems strip the paint — is this client-first or not? Does this agent help the customer or deflect them? Is this SEO or your agency's dead version? The 320 to 38 cut was a hard problem. So was admitting our model was broken too. I tell that story in From 320 to 38 because the problem was never headcount math. It was identity.
Why AI-era problems excite me
Entity files, AI-ready infrastructure, agent-mediated buying — these are hard because they require systems and soul at once. Bolt-on chat is easy. Building revenue engines clients own, with entity MD truth machines can verify, is hard. I love it because most vendors will sell the easy thing until owners get hurt.
Hard problems are also where curiosity pays — if you stop learning, you start selling yesterday's fix. I wrote Why I Never Stop Learning because hard problems never stop arriving.
The problem is not hard because the technology is exotic. It is hard because honesty is expensive and brochures are cheap.
Hard personal problems count
Losing over 100 pounds was a hard problem — discipline, identity, years — changed more than health. Leadership as a grandmother — time horizon, legacy — read what Dallas changed. Confidence built in evidence, not affirmations — building confidence as a female CEO. Same pattern: refuse the comfortable story, do the work, stack proof.
What I refuse
Problems that exist to protect vendors — fake AI readiness, rankings theater, fear-based teardown sales. Problems solved with slides instead of infrastructure. I still love solving hard problems because those are the ones that change a customer's Tuesday — and because the easy lies are what broke the industry in the first place.
If you are stuck in a hard problem — restructure, model change, entity rebuild — I wrote Hands Up for you. I speak about it on stage. And I mean it when I say: the hard problem is the one worth your life right now. The easy one is what keeps you invoicing until the world passes you.