The Best-Laid Plans of Michael Ian Black

Many of us are more insecure than we’d like to admit, merely pretending we know exactly where our lives are going. In Michael Ian Black’s memoir You’re Not Doing It Right (Gallery Books), the comedian hilariously chronicles his own missteps and how mistakes often lead to greatness. Growing up with a gay, über-feminist mom, dreaming of acting success, Alan Alda on TV was the misguided example Black had of how a man should be.

Through his early years, doing improv at MTV and trying to be a ladies’ man while longing for an emotional connection, Black sought comedic personas not necessarily his own. These funny false starts are combined with honest takes on his marriage, children, and moving to the suburbs later in life, a position he confesses to feeling he luckily stumbled into. Whether describing an early Christmas gift—an Easy Bake oven he hated—or disastrous pot-smoking on his honeymoon in Amsterdam, Black candidly captures vulnerability at its most hysterical.

We sat down with Black over tea and biscuits to discuss why dogs are happier than people, why punk rock is boring, Don Draper versus Ryan Gosling, his deepest fears, and why doing it wrong is so much better than getting it right.

ROYAL YOUNG: Why do we imagine lives outside of our own reality?

MICHAEL IAN BLACK: It seems like there’s always something better out there just out of reach. But the peace I’ve come to as a human being is that there’s not. It doesn’t matter what you’re chasing, when you get there you’re gonna be like, “Oh, is this all? It kind of sucks.”

YOUNG: Do you think that’s a feeling specific to entertainers, or could you be anyone and still feel that way?

BLACK: Everybody I’ve ever met feels that way. It’s gotta be something about the human condition, because I don’t feel like animals are like that. I don’t think dogs are like “If only I was a poodle instead of a golden retriever, I’d be totally happy.” Dogs are happy with who they are.

YOUNG: I think so. I’ve never heard of a suicidal dog.

BLACK: Yeah, and I don’t think it has to do with career. I think plumbers are the same as actors are the same as presidents. Like “If only I was president of the world instead of just the fucking United States.”

YOUNG: Talking about realities, and other people’s: I love this idea that sometimes you look at your life and don’t really recognize it as your own. When and why does that happen?

BLACK: Whatever expectations I had for myself, none of them have come to pass. I grew up thinking I was going to be an actor, which I am. But I thought I’d be a very serious sort of Shakespearean guy going from town to town having sex with various Juliets all over the country. I thought I’d be living a much more bohemian life and be very poor. I never thought I’d do comedy or be married living in the suburbs. Every time I try to plan my life out it just doesn’t come to pass, and I think that’s a great experience.

YOUNG: I think that’s better in a way. When you have a plan, and you try to impose that on life, it always fucks up. But when you allow yourself to be open to opportunity, it often leads you to an awesome place.

BLACK: Yes, my experience has been the same. I don’t chase after things, but I put forward the effort and know the rest of it is out of my hands. Then things you never thought were going to turn into something end up being the most important things in your life. You have to learn to not try to control it.

YOUNG: Why is punk rock a boring societal convention?

BLACK: When I look at teenagers and see them struggling to dress themselves in the clothes of their own making, they think they’re the first to ever feel these feelings. The whole idea of punk rock is that you’re dressing yourself in a crazy leather jacket with safety pins and a Mohawk. The idea of being the rebel is a boring societal idea. It’s such a type. And that’s what I was, without knowing it. The things I care about now are the most pedestrian things in the world. I care about good ice cream and being a good dad and a decent husband.

YOUNG: I’m glad I didn’t wear my leather jacket.

BLACK: [laughs] But the other thing about it, is when I see those kids, I feel such a gentleness towards them. Part of me is like “Fuck you,” but part of me just wants to give them a hug.

YOUNG: I also wanted to talk about the ladies’ man and how that is often not true—how often men need to feel an emotional connection. This idea of a more caring gentleman.

BLACK: I never really understood what was expected of me as a man, or how I was supposed to interact with women, but worse, with other guys. I did not relate to them. Part of it is my nature, I’m just not that kind of alpha male, hooting Bonobo monkey. Whatever that thing is where you’re punching each other. I’d look at them and just be like, I don’t know what you’re doing or how to do that. I don’t want to do that. All my friends were girls. Then my mom’s strident feminism for years where men were thought of as the enemy, I just didn’t know what the right way to be a man was. What I’ve learned over the years is just go to the most pre-feminist, chauvinist society. If we could all just be Don Draper, that’s what women want.

YOUNG: But I also feel like there’s this new Ryan Gosling man. Sort of like Don Draper, but he cries sometimes, maybe once a year.

BLACK: Once a year is too much.

YOUNG: Maybe just for a few minutes.

BLACK: A few minutes every four years, if you could schedule it like the Olympics.

YOUNG: [laughs] Are back-up plans for pussies?

BLACK: Honestly, yeah. If you say “I’m going to be an actor, but I’ll get a teaching degree just in case,” when things get hard, you’ll just be a teacher and that’s how you get stuck. I’m enough of an optimist and a patriot to believe that in this country you have a lot of opportunity and can do pretty much anything you want in some form. For me, the idea of failure is far preferable to the idea of regret.

YOUNG: I feel like something that’s come up over and over in our conversation is about getting at vulnerability and how terrifying that can be, but also how amazing it can be too.

BLACK: Yes, my fear is if I expose myself, not so much that I’ll be hurt, but that the reaction will be “Is that all there is? Is that the entirety of you? Because it’s boring.”

YOUNG: [laughs] You’re a shallow pool.

BLACK: [laughs] That’s been my fear all along. That I’m not enough, and I still don’t trust at all that I am.

YOUNG: I think that’s a good thing. I think if you totally trusted that you were, you’d probably be a horrible person.

BLACK: Yeah, I imagine there’s a level of narcissism that goes into thinking you’re enough.

YOUNG: You’ve done so much wrong. What do you plan on continuing to do wrong in the future?

BLACK: There’s things I know I’m good at, and those things interest me less and less. I learn a lot more from doing it wrong than I do from doing it right.