Should You Fire This Newsletter?

The value of a piece of analysis is threefold: 

1. It’s accurate. 
2. It’s entertaining to read.
3. You learn something new. 

Technology newsletter writers compete on their ability to deliver value along these dimensions. I’m worried I’m bad at all three.

Part of me knows this is irrational. I’m one of the very few human beings on the planet whose bills are paid via the written word. “Napkin Math” and my public profile continue to grow, and I should have every reason to be confident in what I’ve done over the last year. My dad has even stopped telling me to go back to school to get my Master’s degree. 

Nevertheless, the feelings of inadequacy won’t go away. Self-doubt and anxiety are my closest companions. Some weeks I’m physically sick with worry. On bad days, I can’t look at a Google Doc without my skin getting clammy. As a sign of God’s twisted sense of humor, these feelings have only intensified the more successful I’ve become. I had no concern about my ability when I was writing for my initial audience of 30 random readers. Now that thousands of people pay for this newsletter, I somehow feel like I’ve gotten worse.

The healthy way to dissuade this feeling is probably therapy, maybe drugs. Instead, I’ve chosen public self-flagellation. Accordingly, this post is the "Napkin Math" on whether I’m good at my job. I’ll go through my predictions for the last year, score their accuracy, and see what I got wrong.

I believe that all writers should do this exercise. Being accountable to the audience on whether the product they are paying for is worthwhile. Too many writers skate by on reputation and cultural cache. My goal is that you pay me for accuracy. This post is about whether the investment is worth it.

The analysis