In high school, I was the debate moderator. It was a lot of fun and very intellectually stimulating.

Each week, I got to pick the topic, who would make the pro and con arguments, who would get to ask questions, and who would make the supporting arguments. At the end, everyone (except me) would vote to see who made the best argument and which side won the debate.

My role was to be a disinterested observer of the debate—just set the topic, run the meeting, and then sit back and listen to smart people make one-sided arguments. I never had to weigh in, and I never had to make any final determinations.

These days, I still try to bring that same mindset into intellectual endeavors. I try to be a dispassionate observer of the arguments as best I can.

But I’m no longer in the role of merely sitting back idly and watching the debate; I generally have to make decisions after considering several arguments. I have to be more active and come to final determinations.

…

We were not the typical debate club. Yes, it was a room full of straight-A students, but it was lighthearted, silly, and fun. It was playful. Today, I still try to be playful by taking on all the roles in the debate. 

I like to think about a pro argument and try that on for a bit. Then I like to switch gears and make a one-sided con argument. I ask follow-up questions and make supporting arguments. It’s hard to be objective if your role is to make a one-sided argument from the get-go. That’s why it’s helpful to play with various arguments.

Then I sort of vote. I almost never 100% conclude anything. My current understanding is an unfinished, un-calculated probability. 

What’s important, though, is that I have to make decisions even when I’m not 100% sure. This is a challenge emotionally because people like to feel settled. It’s comfortable to come to a conclusion, to definitively know what you think.

But 100% certainty means you’ve stopped taking in new information. That’s very likely to be a mistake. There’s always more to learn.

So you need to figure how to feel at ease without being certain. You need to figure out how to make a decision without being sure. You need to continually question everything without feeling unsettled.

…

It’s more of a two-step process now, where I still maintain a lot of that “distant observer” perspective as I listen to various one-sided arguments, take them in and weigh them, and come to my own determinations.

– Evan