A bunch of networks passed on Mad Men. How did you persevere?
To create a television show out of thin air, without anybody paying you, requires a certain amount of delusion, and that's taken me very far. I'm easily offended, but nothing deters me. I'm incredibly disappointed by being rejected, but on some level, I thrive on it. I saw what the networks were saying yes to, and I didn't feel like I'd missed the mark.
Mad Men ends next year. How do you know when to say goodbye?
Before people are sick of you. You don't want them saying, "They're still doing this?" But I probably haven't accepted what it really means to end the show. I'm incapable of understanding the consequences of my actions before they happen. That lets me take risks because I don't perceive the danger.
What motivates you now?
I don't know what it feels like to have made it. Last year Don Draper said, and I helped him say this: Happiness is the moment before you need more happiness. I am greedy and insatiable and curious, and always want to keep doing what I'm doing. I would do it for free, though I don't know if that should be in print. I don't expect to get this kind of response to my work ever again, but I would keep doing it no matter what.
What advice would you give the younger you?
Worrying does not make things happen. Expecting the worst because you think it will ease your disappointment does nothing. I look back at my younger self and think my impatience was a great virtue – but the pain I experienced from that powerlessness did not help me succeed. I was on the verge of becoming bitter. And when you're bitter, you cannot achieve anything.
What did you learn from your parents' generation?
A lot. They were roughly the age of Pete and Trudy Campbell on the show. My father is an inner-city physician; my mother worked for the Civil Rights Commission. They were conformists, but conformity was so much more high-minded in the 1950s. There was social pressure to be well-read, to be tolerant, to not be racist. They had a sense of responsibility to improve the country and to help people who were less well off.
What should every man know about drinking?
Don't do it in your car. And it's better with other people.
You won on Jeopardy! What's the secret?
It's hard. I got married and graduated film school at the same time, so I got to impress my new wife by being out of work for the first five years of our marriage. The only money I earned during that time was on Jeopardy!.I only won one day, but I won, and it was a highlight in a very bleak period.
You've had tense negotiations with AMC. What's the secret to negotiating?
The secret is being completely unaware of the consequences of your actions. Know what you want and stick with it, and if you end up with nothing, you'll deal with it then.
How should a man handle regret?
I have regrets about a lot of my personal behavior. I say a lot of dumb things and hurt a lot of people's feelings, with almost psychic precision. If someone says, literally, "Whatever you do, do not mention her shoes," I will come in and say, "Wow, I love your shoes!"
How does a man find his true calling?
You'll know because you really don't need to succeed to feel fulfilled. I was very lucky I knew I wanted to be a writer. My parents thought writers were the best. They valued them – that might have been part of it. But I always felt that that was what I was meant to do. It's been the greatest gift of my life, because I would do anything to make it happen – including fail.
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!