#210: How to Pick a 365 Challenge You Can Finish w/o Going Crazy

June 18, 2020—Doing something every day for a year is bold as hell, but you need to be sure your goal is doable. Here’s how I chose the right challenge.

Last November, I randomly decided to start drawing comics every day for a whole year. At the time, it felt like another of Andrew’s classic “start and bail” operations, but, miraculously, I’m now on day 210 of 365.

Committing to something that big was scary, first and foremost because I kept thinking…What if I choose the WRONG CHALLENGE??

I went back and forth between drawing, writing, and music for a few weeks, but there are two requirements that ultimately helped me commit to comics…

1. Natural Talent: For whatever reason, I’ve always been good at drawing. I’m not talking about technical proficiency, I mean raw talent. I can sketch things quickly with no effort, which is important because a 365 Challenge is exhausting. You have to deliver under any and all conditions.
2. Social Interest: I’ve been drawing comics since I was in kindergarten. I put them in thank you letters, birthday cards, and emails. I never thought much of my illustrating abilities, but people just seem to love the silly things I sketch. Let people make your choice for you.