Thoughts on the inner life of capable people.
A long letter, every other week. Sometimes shorter pieces in between. No promotions, no course launches — just the thing I'm thinking about and the work it took to think it.
The deals you won't let die
We keep dead deals alive in the pipeline because closing them out feels like admitting we were wrong — and that quiet dishonesty costs us the live ones.
Everyone's using the same AI, and your prospects can tell
AI made it effortless to send personalized outreach at scale. It also made every cold email sound identical — and buyers learned to tune it out.
The day I stopped taking the deal back
Promoting your best rep into management rarely fails on strategy. It fails because nobody warns them how much they'll have to stop doing themselves.
AI didn't make me a better closer — it made me show up prepared
AI didn't sharpen my pitch or close my deals. It did something quieter and more useful — it made sure I showed up to every call actually prepared.
Most deals die in the room you weren't paying attention in
Deals rarely collapse in negotiation. They quietly bleed out during discovery, in the moments you assumed were going well.
When your life doesn't fall apart, it just gets fuller
The trap of capable people is not collapse. It's the slow accretion of obligations — and the version of you that built the life is not the version that needs to live it.
The cost of optimization without meaning
Performance frameworks fail when they assume you already know what's worth performing for. Optimization without a destination is just acceleration in place.
What I look for in someone before we start working
Coaching isn't for everyone, and it's certainly not for the people who want it most. Three things I quietly assess before saying yes.