No One Knows What They're Doing, Part 34

This past week, I found myself down a YouTube rabbit hole of Conan O’Brien videos, which is sadly not a rare occurrence. Eventually, I stumbled across this video of Conan being interviewed by then-Harvard President Drew Faust.

She asked: “I’ve read that you are still an avid reader of nonfiction and that you use that in some ways as a context within which to think about the kinds of questions and issues you want to raise in comedy.” 

Conan responded that he didn’t know exactly how history factors into his comedy, but he said, “I'm convinced that it's good fuel.” He then added this insight:

“If you read history over and over and over again, you get the essence of what I'm trying to tell you, which is: Nobody really knows what they're doing. And people in charge make terrible mistakes. People in charge of the military—the Germans and the British and the French and the Russians in World War I don't know what they're doing. Everyone in charge doesn't know what they're doing. [...] All of Lincoln’s generals—he had to go through like 15 before he found one who knew what he was doing. Over and over and over again, you learn that lesson.”


I think “no one knows what they’re doing” is a frequent theme of this newsletter because I work with leaders precisely on the areas of their lives where they have the most doubt—i.e., where it seems like everyone else has it more together than I do

I find that notion comforting, since my job entails people asking what I think about things, which causes me to have to ask myself, “Do I really have a basis for ‘knowing’ the answer, or am I just making it up?”

One of the things I like about Conan O’Brien is just how upfront his is about his own self-doubt. His larger message to the students during the interview with Drew Faust was that there’s no magical point in life in which people get their stuff together. It’s all messy.  

A student asked: “You talked a lot about checking the list down and finding that one thing that you have [to contribute to the world] and just kind of knowing if it's something that you're meant to do, but… did you ever feel sometimes that maybe you had that one thing wrong? And what did you do when you felt like you were forcing it to get through it?”

I thought Conan's response was helpful.  He said, “Yeah, I think everybody has that. You're not human if you're not questioning. [...] Out of whatever I've done in my lifetime, 3600 hours of television or something, you can have three [shows] in a row that don't go well, and you start to seriously contemplate, ‘What am I doing?’ I think that's everybody.” 

He added: “Nurture that feeling of insecurity, of being lost, of not being sure. That's a healthy sign. That's a sign that you're on your way.”


Leadership Wisdom

Last year, Gabrielle Union was on J.J. Redick’s podcast (I was listening to it this week), and had this delightfully profane statement about the concept of work-life balance:

“[B]alance is b***s*** that I firmly believe is an extension and arm of the patriarchy meant to make women feel like they’re constantly failing at something else. [...] You can’t be a boss b****, a sexpot, a great mom, a great wife, a great friend, a  housekeeper, a chef, a driver, a philanthropist, a community activist. There’s 24 hours in a day. You can’t be all of those things. It’s legit impossible.” 

HBS professor Quinn Mills makes an almost identical statement in Having It All…And Making It Work: “Don't try to be Julia Child in the kitchen, Martha Stewart in the living room, George Soros on the trading floor, Don Juan in the bedroom, and Michael Johnson on the running track.”

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