> ## Content Index
> Fetch the complete content index at: https://www.matthewbogart.net/llms.txt
> Use this file to discover other available public pages before exploring further.

# "Did you enjoy it?"
- URL: https://www.matthewbogart.net/2025/11/12/did-you-enjoy-it/
- Published: 2025-11-12T22:55:51.000Z
- Updated: 2025-11-12T22:56:22.000Z
- Author: Matthew Bogart
- Tags: #Jon Stewart, #Conan O'Brien

I've been thinking about [this interview Conan O’Brien did with Jon Stewart](https://teamcoco.com/podcasts/conan-obrien-needs-a-friend/episodes/jon-stewart?ref=matthewbogart.net). They were talking about their early TV years — those first shows where every week’s ratings felt like life or death. The pressure made the job miserable.

Stewart said that a few weeks into *The Jon Stewart Show,* he could already tell it was doomed. 

"We knew this thing's going down. But I had your experience of like, this is my shot. Like, this is it. My name is on \[a show\]. This is a manifestation of who I am as an artist, as a person. If it gets rejected, *I* am rejected. I wasn't sleeping. I was really miserable. I was drinking like a motherfucker. All those different things. And one night in my insomnia, 3 o'clock in the morning, 4 o'clock in the morning, I just remember thinking, you're going to have had your own talk show with your name on it where you could do whatever you wanted \[...\]. **And people are going to say, "Did you enjoy it?"** And I would have to say, *I hated it.* And I think it nearly destroyed me. And what a dumb fucking response. And that morning I got up and was like, *I'm going to enjoy the shit out of this*. Yeah. And I don't care anymore. Yeah. And it was revelatory. And it was such a, I felt it *physically*, like that relief."

The show was canceled soon after, but it's a good reminder for anyone currently doing their dream job — how’s it going?