When founders get stuck, they tend to blame it on circumstances or people—sometimes including themselves. But debugging problems this way often leads to more stuckness. It's like engineers blaming a computer for crashing when their code has a giant memory leak. Still, it’s a widespread perspective. My experience running Hipmunk included times of paralysis, panic, petulance, and paranoia. As I work…
This is the third essay in the Anxiety Algorithm series. Click here to read Part 1 and Part 2 . When I ran Hipmunk, I noticed a pattern in how events affected me. When things were going smoothly and something good happened, I felt good about it. But when something bad happened, like our sales missing expectations (or a bad night’s sleep), good news didn’t seem as good. Over time I came to see this…
This is the second essay in the Anxiety Algorithms series. Click here to read Part 1. A paranoid is someone who knows a little of what’s going on. William S. Burroughs When I ran Hipmunk, I would often feel like small setbacks meant disaster. When our first employee quit after a few years, I worried everyone was about to quit and that we’d never recover. That didn’t happen. Later, I spent some…
I learned that courage was not the absence of fear, but the triumph over it. Nelson Mandela You started a company a few years ago. The company now has sales, employees, and some buzz. I ask you, “Would you rather have the business you have now, or had 2 years ago?” “Now, obviously,” you say. “Look how much bigger we are!” “Ok, were you more anxious then or now?” I ask. “Definitely more anxious…