Pathbreaker Playbook · 4 of 10
The Pathbreaker Playbook, Part 4: We Taught Them to Place Bets
Every decision your kid will ever make is a bet, and almost no one teaches them how to place one.
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Pathbreaker Playbook
The Pathbreaker Playbook, Part 3: 'Smart' Is a Label They Fear Losing
The label kids protect versus the effort they're willing to risk — a Stanford study that changed how we praised our daughters.
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The Pathbreaker Playbook, Part 2: We told them grades don't matter
What matters is whether they're thriving at 25 — which is why we told them grades don't matter.
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The Pathbreaker Playbook, Part 1: We Had Only Four Rules
No curfew, no phone checks — just four rules, and the long game behind them.
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Why I'm Here and What This Is
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.
The Credential Trap
The babysitter test nobody applies to their own kid
You'd never hire a sitter based on a diploma. So why do we tell teenagers the opposite?
Mindset
Happiness = Reality − Expectations
The formula I taught my daughters — and why I taught them to run it backward.
The Future of Work
I mentioned AI exactly once. Then everything changed.
I wrote the book in 2024 and named AI once. Two years later, it's the whole argument.
The Credential Trap
Twice as common, twice as expensive
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.
The College Question
We go back to App State every fall
I'm not anti-college. I went. We still go back. I'm anti-sending a young adult out there unprepared.
The Real Cost
The costs teenagers are never taught to weigh
Hard, soft, time, opportunity. We ask kids to make the biggest financial decision of their lives having considered roughly none of them.
Self-Direction
What do you want to try first?
"What do you want to be?" is an impossible question. Here's the one we asked instead.
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