Think Big Pig - Rewriting the Rules of a Life That Actually Fit
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The Tyranny of What Works (or, How Success Starts Writing the Rules for You)

The Tyranny of What Works (or, How Success Starts Writing the Rules for You)

21 Oct 2025 9 min read
I was standing in the produce section of a Trader Joe’s on a Tuesday evening, still wearing my work clothes, holding a bell pepper and experiencing what I can only describe as
Why Cross-Functional Teams Can't Understand Each Other

Why Cross-Functional Teams Can't Understand Each Other

14 Oct 2025 13 min read
Have you ever found yourself in a meeting¹ watching someone two levels above you try to explain your team's roadmap to a visiting executive, and suddenly realized: they're not
The Game Theory of Pointy Things: Careers, Catastrophes, and Missing Well

The Game Theory of Pointy Things: Careers, Catastrophes, and Missing Well

07 Oct 2025 11 min read
I was twenty-four when I turned down the dream job. Not the job I dreamed about as a kid (nobody dreams about enterprise software sales) but the dream job in the sense of
Why the Manual You're Following Might Be the Thing That's Holding You Back (With Apologies to All the Manuals)

Why the Manual You're Following Might Be the Thing That's Holding You Back (With Apologies to All the Manuals)

01 Oct 2025 10 min read
There was a period in my mid-twenties when I carried a small notebook everywhere, not the Moleskine (Or is it Leuchtturm now?) kind favored by people who want you to know they'
Why the Same Person Feels Different in Every Room (Especially When That Person Happens to Be You)

Why the Same Person Feels Different in Every Room (Especially When That Person Happens to Be You)

24 Sep 2025 9 min read
I was standing in line at the grocery store last Tuesday when the woman ahead of me started apologizing to the cashier. Her credit card had been declined¹, and she was frantically digging
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