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Short, story-first essays on raising self-directed kids, the credential trap, and a working world that keeps changing faster than the advice we hand our teenagers. Published weekly on Substack — every post lands in your inbox.
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Pathbreaker Playbook · 6 of 10
She was bored by accounting in school. Then she started a candle company named after her rescue dog, and taught herself the whole thing.
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You will never agree on everything. But there are three anchors you both have to hold before you can free your kid from the path.
Every decision your kid will ever make is a bet, and almost no one teaches them how to place one.
The label kids protect versus the effort they're willing to risk. A Stanford study that changed how we praised our daughters.
What matters is whether they're thriving at 25 — which is why we told them grades don't matter.
No curfew, no phone checks — just four rules, and the long game behind them.
When my daughter Brooke was nineteen, my wife and I kicked her out of the house. Here's why — and what these conversations are about.
You'd never hire a sitter based on a diploma. So why do we tell teenagers the opposite?
The formula I taught my daughters — and why I taught them to run it backward.
I wrote the book in 2024 and named AI once. Two years later, it's the whole argument.
In 1985, 1 in 5 adults had a college degree, at an all-in cost of about $64,000. Today it's 2 in 5 — at $140,000.
I'm not anti-college. I went. We still go back. I'm anti-sending a young adult out there unprepared.
Hard, soft, time, opportunity. We ask kids to make the biggest financial decision of their lives having considered roughly none of them.
"What do you want to be?" is an impossible question. Here's the one we asked instead.
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