A few years ago, a bunch of college students visited Conan O’Brien. One asked him, “When does the nervousness and self-doubt end?”

O’Brien’s response was, “I have really bad news for you. There’s always some of that.”

When O’Brien debuted on late night television, nobody knew who he was. “I had to learn how to do the job in front of everybody, and man, people had very strong opinions—many of them negative. Young people really liked it, and I think that that was nice, but I didn’t know that—I was not aware of that—and I only found out about it until much later on, when those young people grew up into and became really successful comedians.”

The people watching his show weren’t even teenagers yet; meanwhile, O’Brien was surrounded by people watching him critically. 

“I would have listened to anybody. I would have been so happy. It took a while… it took a number of years… insecurity, and all those things that that people have. I just like to be really honest about the fact that it never quite goes away. You’re always hoping, ‘Is this good enough?’ ‘Was that okay?’ ‘Could this be better?’”

Some takeaways:

• Even in spite of the internet, the feedback loop in creative work is largely broken. You’ll only get a small amount of what people are actually saying. It’s worth entertaining the idea that you could very possibly be making a difference in somebody’s life; you just don’t know who or how yet.
• The wrenching emotional experience of doubt never goes away; you grow, develop, and maintain your capacity for it. Doubt can be a driving force of creativity, as long as it’s balanced out with a healthy level of energy and confidence.
• If you admire somebody’s work, go ahead and tell them. “People never get the flowers while they can still smell them.” One yes in an ocean of no’s makes all the difference, and can put the battery in someone’s pack. That person may return the favor one day.