Late last year I was lost. I’d spent the better part of a decade away from the tech space, and somewhere in those years I’d misplaced …
The Strange Privilege of Being Born Between Two Worlds
I was at a concert recently. Great band, perfect venue. And as I looked around, all I could see was a sea of phone screens — …
The Quiet Belongs to the Rich
Spend an afternoon walking through the wealthy part of any city you’ve lived in. Then walk through the cheapest one. Notice what’s missing in the first …
The Old Car and the Wrong Place
I came across a story the other day that stopped me. A father said to his daughter: “Congratulations on your graduation. I bought you a car …
After 20 Years of Blogging, Here Is How I Think About Publishing Online
TL;DR: After 20 years of blogging, I’ve learned that not everything belongs in the same place. Your blog, social media, private communities, local notes, and AI …
5 Things That Will Happen in the Next Few Years
I keep a list of things I think will happen in the next few years. When I share it with people, most of them think I’m …
The Human Skills That Become More Valuable in the AI Era
There’s a version of the AI conversation that goes like this: automation is coming for everyone, and the only way to survive is to learn to …
Don’t Just Surround Yourself With Smarter People
One of the most repeated pieces of advice in business and personal development is simple enough: “Surround yourself with smarter people.” It sounds good. It flatters …
What Arguing About Big Topics Actually Costs You
I’ve spent years arguing about things that didn’t matter to people who weren’t listening. It took me until my forties to fully see the pattern. Something …
High Agency Is How You Win
There is more competition than ever in almost every industry. AI tools are cheap, distribution is wide open, and barriers to entry keep falling. Yet despite …
Long-Term Optimist, Short-Term Pessimist
One phrase captures how I approach life, work, and investing: long-term optimist, short-term pessimist. At first glance it looks contradictory. In reality, it is the only …
I Prefer to Be Happy Than Right
Over the years, I’ve come to realize something that’s quietly changed my life: I prefer to be happy than to be right. It didn’t happen overnight. …
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