If you could go back, what advice would you give yourself at the beginning of your career?
Bob Gill: Double it. Let me explain: I did an ad or a poster for Barbra Streisand once, and her live-in boyfriend came to New York to brief the advertising agency and me. He kept saying, “And Barbra will record the title song, and that’ll bring in $80 million.” Everything was heady figures, I just couldn’t believe it. And then I thought of my mother, who used to say to me all the time, ‘Why don’t you get a haircut?’ But when she’d ask me, ‘What does a haircut cost these days?’ I knew that if I told her the truth, she might drop dead because it seemed so extravagant. So I cut it in half. She still almost had a heart attack, and realized these things are generational.
To you, a dollar is nothing. When I was your age, a dollar was a meal. It was a different thing. So it’s very hard for me; I can’t charge what you would charge, because it just seems astronomical. So, I’m always charging less because of the generational thing. On the one hand, I’m a terrific salesman. But I’m a bad negotiator. I just don’t get what I could have gotten. I don’t know what the answer is, except once in a while my wife says, ‘You haven’t given a price yet. Double it.’ So that’s the advice.
It’s practical, but it’s not very profound.
— (via Twenty Over Eighty)