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The Conviction Gap: The Career Skill AI Cannot Replace (And Most Professionals Don’t Have)

Quick read: Most mid-career professionals plateau at the same spot — somewhere between senior individual contributor and director. They produce great analysis, structure problems beautifully, and write competent memos. But they never quite cross into leadership. This piece is about what’s actually going on, why it’s getting worse in the AI era, and the three habits that close the Conviction Gap.

Read the rest “The Conviction Gap: The Career Skill AI Cannot Replace (And Most Professionals Don’t Have)”

The Borrowed Brain

Quick map: this is the long-form essay. There’s a tighter Medium version, a 9-minute video, and a 60-second cut. Read first. The AI-Resistance Self-Assessment link is at the end.

On outsourcing grief, the seven-second window, and what I learned the hard way when I stopped

I want to write about something I have been avoiding writing about for a while, because I am still inside the embarrassment of it.Read the rest “The Borrowed Brain”

The Case for Ordinary Proof (And Why AI Can’t Fake the Chair)

The short essay that started all of this is on Medium. The 3-minute version is on YouTube.

In 2026, the detail you’d cut is the detail that earns. Here’s why.

Why the smallest details in personal writing are doing the most work — and why most writers, including me until recently, have been ignoring them.

Read the rest “The Case for Ordinary Proof (And Why AI Can’t Fake the Chair)”

Kierkegaard Named Your Anxiety in 1844. Wellness Coaches Now Charge $200/Hour to Repeat It.

Read time: ~12 min. Also available as a shorter essay on Medium and a 7-minute video on YouTube. The companion journal — The Door Audit — is available if this lands.

The Danish philosopher who saw your panic attack coming before electricity did.

Why this matters now: Anxiety diagnoses in adults under 35 have climbed for fifteen consecutive years — and most of what we’re selling as treatment is repackaged 19th-century philosophy.… Read the rest “Kierkegaard Named Your Anxiety in 1844. Wellness Coaches Now Charge $200/Hour to Repeat It.”

Read time: ~12 min. Also available as a shorter essay on Medium and a 7-minute video on YouTube. The companion journal — The Door Audit — is available if this lands.

The Danish philosopher who saw your panic attack coming before electricity did.

Why this matters now: Anxiety diagnoses in adults under 35 have climbed for fifteen consecutive years — and most of what we’re selling as treatment is repackaged 19th-century philosophy.… Read the rest “Kierkegaard Named Your Anxiety in 1844. Wellness Coaches Now Charge $200/Hour to Repeat It.”

You’re Not Anxious. You’ve Been Trained to Absorb Everyone Else’s Stress.

Last week, someone left a passive-aggressive comment on something I’d posted online.

It wasn’t even mean. It was that worse, smaller thing — a polite “actually…” that implied I had no idea what I was talking about. My chest got tight.Read the rest “You’re Not Anxious. You’ve Been Trained to Absorb Everyone Else’s Stress.”