Tools for less thought

issue no. 0013

If you’re reading this, you probably overthink more than you underthink. In writing this, I’m probably overthinking. Overthinking about underthinking is an appropriate amount of headassery for me…

Behaviors serve some sort of purpose, they just might not be the purpose we tell ourselves. For me, overthinking serves a few purposes:

1. Procrastination. Overthinking is just like endlessly reorganizing your desk. For me, there’s twoish drivers of procrastination:

   1. I don’t actually want to do the thing but am unwilling to admit it.

   2. Preventing emotional pain. If I actually do the thing, I might fail. If I strategize enough, I can simultaneously increase the chances of success (narrator: not true) while also delaying a true evaluation of whether I’ll succeed.

2. Cleverness and/or perfectionism. If I just do the obvious thing¹ what’s the point of deploying the Super Elite Special SWAT Team member? Wouldn’t it be great if I could anticipate every objection and have a slide that mitigates each²? If I get this perfect, nobody can criticize me. I’ve also worked for enough ex-consultants who sold packaged pearls of wisdom for a living, and have absorbed some of their neuroses.

3. Labeling the unknown is comforting. It usually doesn’t actually change the outcome, since most of the time what happens is fairly obvious. This might be a sub-form of procrastination.

There’s hundreds of productivity and note-taking apps out there that encourage overthinking. The personal-SaaS-industrial-complex would like you to think that for $9.99 a month this can be solved. The truth is most tools can only help you do what you already wanted to do, marginally faster or better.

I’m not going to build or sell something to encourage underthinking. But if there were something for underthinking, what would it look like? What does it look like in the real world? I’m deliberately spending 10 min thinking about this, and that’s it.

• The writing industry actually has some interesting takes on this problem. There’s the writing app that deletes everything if you stop typing for 5 seconds. iA Writer has “focus mode” that only shows what you’re working on.

• In recruiting, exploding offers timebox overthinking (usually not to your favor).

• Twitter (sometimes) prevents overthinking with character limits, though they’ve steadily eroded that mechanism with new features.

• Stories (Snap, IG, etc. etc.) lower the stakes, which helps lower the activation energy required to make a post.

• TikTok’s duets, remixes, lenses, songs, etc. all provide rails that make it easier to create content.

What’s are common threads?

1. Artificial deadlines

2. Templates and/or rails

3. Lower psychological stakes

4. Remove additional context

I’m going to try some of these on the meat computer and we’ll see how it goes.

Thanks to Matt MacInnis for coaching me to think less ;)

1. One of my favorite lines from Masters of Doom: “Carmack read up on the topic but found nothing adequate for his solution. He approached the dilemma as he had in Keen: try the obvious approach first; if that fails, think outside the box.”

2. Experience teaches me that there will always be objections and there is generally not much value in anticipating them. There are objections for the sake of objections. There’s a time-honored technique of leaving a small mistake as bait for people to correct.