(This interview has been edited for clarity and length.)
Q: What is the place of the celebrity at this moment?
A: I’m pretty passionate about sticking my neck out. It shouldn’t even be sticking your neck out. It should just be standing up straighter and looking around at your neighbors and the people who have been benefiting from a system that’s oppressing another set of people, a whole other race of people. And for us not to stand up and denounce that and demand change, like time’s up on us, you know.
Q: You made a documentary last year called "Hello, Privilege. It's Me, Chelsea." Could you have timed that better?
A: I made it for Netflix last year because I was questioning my own place. I went to therapy for the first time in my life, and I came out of it, and I was like, “Wait, I had a lot more self-awareness than I did when I went in.” And through that lens, I was able to look at my circumstance and understand that my skin color had a lot to do with my success and the ease with which I succeeded. And I got rewarded for a lot of bad behavior that no one of color would ever have gotten rewarded for. But those aren’t the things I was thinking about when I was in my 20s or even in my 30s necessarily. I didn’t think I was part of the problem. But I think what we’re all realizing now is that if you’re not fighting against the oppression, then you are still part of the problem.
Q: But when we hear the phrase "White privilege," we imagine somebody like George Bush going to Yale and being in the secret society Skull and Bones. Your father was a used-car dealer.
A: He would have preferred a used-car salesman. Yeah, it’s different.
Q: So you worked hard, but it's the idea that your skin color made all the difference. And when you say behavior that wouldn't have been accepted . . .
A: My boyfriend from high school, his name is Tyshawn. He’s in the documentary. I revisit him because in high school, when we dated, he was dealing weed or we were smoking weed or whatever, and we got caught with dime bags two or three times. And each time, he was arrested, and they were like, “You go back. . . . You get out of this neighborhood.” And I was let go, and he has been in jail for 14 years. People aren’t looking for me to screw up. Like, they’re not looking to arrest a young White girl. They’re looking for the Black kids to screw up.
Q: I also want to ask about your book "Life Will Be the Death of Me." So much is about your deciding to go into therapy.
A: After Trump got elected, I really got enraged. And I got to a point where my outrage was unmanageable. I’d get on planes and just argue. I couldn’t understand how anyone with a daughter voted for him.
After I got past the fact that he was elected and there was nothing I could do about it, I wanted to harness that outrage into something a bit more positive. And so I decided to see a therapist under the umbrella of being able to talk to conservatives without lurching out of my chair. Then once I got into therapy, I realized my anger was coming from a much different and deeper place, which is that of a 9-year-old little girl. I lost my brother when I was 9, which I thought I had recovered from. What my therapist explained to me is that the destabilization that Donald Trump represented was the destabilization that my brother dying and leaving our family from one day to the next represented. And so it was like a trigger for me. Of course I’m mad about Donald Trump. What an embarrassment for our country. But I’m really actually in pain about something that happened to me as a little girl.
Q: You weren't an easy customer in there with your therapist, right?
A: No, I wasn’t. But I was ready. You know, there are things that work for you until they don’t, like my anger and my drive, which worked for me for a really, really long time until it didn’t. Then it just became too angry. So it was like self-recognition, knowing that I have to go into this place that’s going to be really uncomfortable. I thought vulnerability was a weakness, but the more vulnerable you are, the stronger you are. So I learned a lot, and I wanted to help. I wanted people to get a lot from my book. And it feels like it’s the first book I’ve written that wasn’t just funny, but actually had more profound meaning to it. I’m very proud of that.