Pick any of my posts on entrepreneurship—or ask what I’ve been up to this year—and you’ll see I’m as enthusiastic about designing and building new ventures as I was eighteen years ago when I launched my first business. Ever since regaining some breathing space from my last enterprise in 2023, I’ve been asking myself a simple but unsettling question: Where do great enterprises really come from?

For all the content out there on job seeking, career change, entrepreneurship, or the business of being a creative, there’s a remarkable emptiness on one crucial topic: how do you choose between two or more paths you’re already pursuing? Most books and training materials focus on the drawing-board stage. They typically lead you to take stock of three things, or a combination of: your assets, what you’re chasing, and what you want to escape from. At best, they offer frameworks to compare options before you’ve invested deeply in any one of them…

I had never heard of Seth Godin until June 15th. He’s the author of 21 worldwide bestsellers, translated into 36 languages (I can’t even name 36 languages), writes a blog with over a million readers, hosts a top-ranked podcast with 200+ episodes, and—lest anyone think he only talks—has built and sold multiple multi-million-dollar companies. The joke was on me.

A few years back, I added a small atomic habit to my to-do dashboard: on the first of each month, I pick up a book from the library of those I’ve read and chosen to keep (roughly one in three makes the cut), and flip through all the pages I previously marked with one of my trusted Stalogy sticky flags.

The bad news first. Entrepreneurship is not a finite game. There are no goalposts to tell you how you're doing, or how far you’ve come. Succeeding once—or several times—is no guarantee of a rerun. Failing once—or several times—doesn’t say much about whether this is the right path for you…

Last Monday, I spent an entire day running an airtight background research operation. My target: a YouTuber who has no idea I exist — and likely never will…