How You'll Know When it's Time to Move On

When I was a kid, my mom used to joke that I never did anything more than once, If Jay wasn't good at something right off, he didn't want to do it anymore, she would say. I, of course, didn't appreciate her good natured ribbings and wasn't shy about letting her know it. She, of course, would point to things like my one season of T-Ball1, among others, to counter my whining.

It wasn't until much later that I finally stumbled on why I took such offense to her categorization of me as a quitter. It wasn't because I wasn't a quitter, I genuinely quit a lot of things, so my mom had a point. No, the difference was I thought of quitting those things as eliminating distractions so I could focus on spending my time doing things I enjoyed.

For every one season of T-Ball there were multiple seasons of soccer. Behind every discarded toy there were hours spent building crazy lego creations. It was true I didn't have much tolerance for things I didn't enjoy, but when I found something I wanted to spend my time doing, I could dedicate hours to it a day.

I bring this up because it lead me to notice a pattern that largely dictates my happiness with certain parts of my life and my desire to stay engaged with those parts. Basically, every interaction I have with someone--or something--goes into a bank account, and positive experiences increase the balance of that account, while the negative experiences subtract from it.

The trick is, as long as that account stays positive, I don't mind spending my time there, but as soon as the lows start compounding faster than the highs can offset those losses, I tend to get anxious to quit and move on.

It's similar to the hedonic treadmill Barry Schwartz talks about in The Paradox of Choice:

In the same way that we each have our own internal thermometer for registering sensation, we each have a “pleasure thermometer,” that runs from negative (unpleasant), through neutral, to pleasant. When we experience something good, our pleasure “temperature” goes up, and when we experience something bad, it goes down.

People fight, I've had fights with my parents, siblings, wife, and child. Yet, I still talk to my parents and my siblings, my wife is still married to me, and my daughter is, right now as I type this, chilling next to me2.

This is why I can get into an all out yelling, screaming, fight with a member of my family on one day and be perfectly normal the next, because even though we just experienced a low point together, the highs are always so much higher that the account isn't even close to going into the negative.

This also explains how a smart, opinionated startup team is able to move past intense arguments about the product and still function as a team, be happy, and get stuff done. I've experienced working environments where the highs no longer tipped the balance into the positive and one of the biggest regrets of my professional career is I let the balance get more and more negative instead of moving on right away3.


  1. To be clear here, I really hated T-Ball, I only lasted one season not only because I wasn't good, but because I had no desire to become good, and that was the problem. 

  2. What's interesting about my daughter is that in the first moment I spent with her, when she wrapped her little hand around my finger, her bank account balance went so high I'm not sure she could ever dip to a negative balance, no matter what she does in the future, hopefully she won't test that though. 

  3. I've also watched good friends' companies descend into madness and ultimate failure because the lows kept going lower and lower each and every day.