
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?
3 min read
Read on Substack ↗The blog
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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The Credential Trap
You'd never hire a sitter based on a diploma. So why do we tell teenagers the opposite?
3 min read
Read on Substack ↗
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 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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