• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to secondary sidebar

Billy Oppenheimer

  • Newsletter
  • About
  • Blog

SIX at 6: A Certain Daring, A Stupid Bravery, Finding Dwight, That Period Of Not Being Good, Being The Freak, and An Underexplored Emotion

A Certain Daring

In 1959, a government-funded research team was exploring ideas for new antimissile technologies—ways to stop incoming enemy missiles before they reached their targets. At one point, the team decided to try to elicit the help of some of the most creative minds of the time. One of them was the prolific science fiction writer Isaac Asimov, who responded with a kind of manifesto on the creative process and the things that promote it. Great ideas, he argued, often seem great only in retrospect. At first, they usually seem foolish, impractical, or just bad. Creativity therefore “requires a certain daring,” a certain willingness “to fly in the face of reason, authority, and common sense.” “Creation is embarrassing,” he wrote. “For every new good idea you have, there are a hundred, ten thousand foolish ones.” For a team trying to do this embarrassing work in front of one another, his advice was that each time they got together, they begin by explicitly acknowledging and welcoming “the foolishness that would be bound to go on at such a session.” “It seems necessary to me,” he wrote, “that all people at a session be willing to sound foolish and listen to others sound foolish.”

A certain daring, a certain willingness to be embarrassed, to sound, look, be, or seem foolish—that’s the theme of this SIX at 6…

A Stupid Bravery

John Mayer was once asked, When you go into the studio, what do you do to generate song ideas? He picked up an acoustic guitar to demonstrate his songwriting process. “Well, I don’t always do it,” he admitted, “because it requires a stupid bravery.” He strummed some chords. As a nice melody began to form, he launched into singing, making it up as he went: “sunlights beating on the corners of the walls / and I’m a Mr. know-it-all / heaven calls / get yourself right / get yourself right now.” The words didn’t really make sense or mean anything, which is why he can’t always bring himself to do this. It takes a stupid bravery to know what you’re singing—or writing, drawing, painting, designing, thinking up—isn’t very good, and keep going anyway. “You just stare at the corner of the wall,” Mayer said, before he improvised some more: “stare at the corner of the wall / try to get it going on / but I can’t sometimes / you just keep going ’til you get something / and maybe I’m a little bit shy / maybe some day I’ll tell you why.” He stopped singing, took a hand off the guitar, and said, “You just keep forcing it, forcing it, forcing it,” pounding the table with each “forcing it” and then with each “fearless”: “You have to get fearless, fearless, fearless, fearless.”

Finding Dwight

In 1997, the actor Rainn Wilson got cast as the lead role in his first Broadway play, London Assurance. In his head, Wilson had this preconceived notion that a Broadway actor must be “some formal ‘classical actor-man,’” he writes in The Bassoon King: My Life in Art, Faith, and Idiocy. So, “I hid my quirkiness and weirdness.” As a result, “I was stiff and disconnected. All my choices were broad, fake, and strangely puppetlike.” He got destroyed in reviews of the show. One critic wrote, “As the young lovers, all that is required of Kathryn Meisle [who played the lead opposite Wilson] and Rainn Wilson is that they be good looking and charming. At least Meisle is good looking.” Another said, “Wilson pushes too hard for comic effect.” In the aftermath of his Broadway bombing, Wilson gave himself permission to be the odd, weird actor he had been trying to hide. “I said, ‘Never again. Never again am I going to hide. I’m odd, I’m weird—I’m going to embrace that. I’m not going to try to be something else to please someone else. I gotta be me, baby.’” Daring to let his weirdness show, Wilson writes, “led to the defining role of my career, Dwight Schrute in The Office.” “Finding Dwight was all about embracing my nerdy weirdness. If I hadn’t totally embraced that, I never would have gotten the role of Dwight,” for which Wilson received three nominations for the Emmy Award for Outstanding Supporting Actor in a Comedy Series.

That Period Of Not Being Good

Colin Jost and Michael Che are the longest-tenured Weekend Update anchors in SNL history. After their third episode in 2014, an NBC executive called a meeting with SNL creator and producer, Lorne Michaels. “Do you think Jost and Che are working?” the exec asked. Michaels replied, “No.” “Oh,” the exec said, “you know?” Yes, Michaels said he was well aware that his new Weekend Update anchors were not performing all that well. “But it’s a thing,” Michaels told the exec. “People have to be bad before they can be good.” He likes to use the analogy of an ugly baby: “All babies are ugly (unless they’re your baby), but after three months, everyone says, ‘What a beautiful baby.’ You just have to live through that period of people not being good.” (File next to: Force Yourself Through The Hardest Phase)

And Yeah, I’m The Freak

The comedian Hasan Minhaj is the son of Muslim Indian immigrants. His father is an organic chemist and his mother is a physician at Mather Air Force Base. “The choices,” Minhaj says of his parent’s expectations for him, “were doctor, lawyer, engineer, failure.” So, “for my first decade as a comedian,” Minhaj says, “it was real rough between me and my parents.” For his first decade as a comedian, he said that even more than things like comedic ability and work ethic, he needed a certain ability—to be okay with being the fool of his family. After he became a big-time comedian, Minhaj would talk about what it took to get there: “you have to be cool with being like, ‘I went to the family wedding, and everyone made fun of me, and yeah, I’m the freak.’”

An Underexplored Emotion

Once, at a party where people were dancing and having fun, the actor Austin Butler was hanging off to the side. He was a little self-conscious about his dancing and didn’t want to embarrass himself. “Somebody very close to me,” ​Butler said in an interview​, “came over, and they said, ‘Embarrassment is an underexplored emotion. Go out there and make a fool of yourself.’” Wow, the interviewer replied, that’s really a mantra to live by. “Yes,” Butler replied. “That ability to just go for it. Like feel that feeling—that fear of cringe, of embarrassment, of being judged—and then go out there and do it anyway. Because everything you want is on the other side of that.”

Primary Sidebar

About

Billy Oppenheimer is a writer and research assistant based in Austin, TX.

Learn more…→

Secondary Sidebar

Sunday Newsletter:

Copyright © 2026 · Billy Oppenheimer

  • Twitter
  • LinkedIn
  • Instagram