It’s all about the struggle
Great things, there is a mentality in showbusiness where people will say “That was great! Do that all the time.” And you think “No”. By its nature the really great stuff has to be rare.
You can even really love Monty Python, but the really great things, it’s not just back-to-back-to-back-to-back. There’s gotta be some quality to something creative. With the really good stuff, it’s not common.
So whenever I do a remote segment, and it’s really good, people will tell me “Man, that thing you did in New York with the Chinese food, that was great! You should do that every night!” Cut to me throwing them out of the window.
Because I think No, these things take a long time to percolate. My only hope is that you are judged by your best work. If you are judged by your best work, I’ll be ok.
Someone explained to me once that your creative life is laying down little tiles, and you can’t see what it’s all making. Sometimes it’s a slightly darker tile than the other, sometimes it’s a really brightly coloured tile. Sometimes you’ll lay down seven grey tiles in a row, but you’re making a much bigger piece which when seen when it’s completed could be quite fanstastic. But you’re doing it tile by tile and day by day, and you can’t know.
So you get humble and feel “Oh we had a show where I didn’t love that”. But they can’t all be [great]. They’re not supposed to be.
Source: Conan O’Brien interview on episode 167 of the Nerdist Podcast