While it’s definitely not the answer to all my cringe ToDos, I’m going to second “bignoseduglyguy“‘s suggestion of “Never Do It” and even suggest stronger words: “Exorcise This!”

Seriously. A couple years ago, I realized that there were some “I really should” things always in the background of my brain. I realized one day that they represented sort of a religious fascism, my own I’m-not-jewish jewish guilt junk, things that I had unconsciously picked up along the way that I thought I was supposed to do. I realized:

1. I never, ever want to go to church again. Period.
2. I love her dearly, but I don’t, in fact, want to call my mom once a week.

There have been many more mundane Exorcise This! to-dos since then that I’ve rooted out like, and some even related to my business and other areas, but those first half-dozen ones struck me like a bolt of lightning.

So, once every couple months, I look through my list of supposed Really Important™ to-dos, especially at the ones that make me cringe, and see if any of them need the ol’ exorcise treatment.