Chelsea Handler Knows Who She Is: 'My Feet Are So Firmly Planted'

"Where I am in my life is my feet are so firmly planted in the ground you cannot knock me over."

As a six-time New York Times bestselling author, Chelsea Handler knows the secret to a successful book is to stay true to herself. "All of my books are representative of where I am in my life at that time." And "right now, where I am in my life is my feet are so firmly planted in the ground you cannot knock me over." The comedian just released her seventh book, I'll Have What She's Having. "The point is to highlight how incredible your life can be when you don't subscribe to doing what everyone tells you makes you valuable." Between the book, her podcast Dear Chelsea and her stand-up—she has a new Netflix comedy Chelsea Handler: The Feeling and a Las Vegas residency, Chelsea at The Chelsea)—it's clear Handler has written her own script to her career. "I feel really strongly and passionately, which I always have, that no one is in charge of me." The former host of the late-night talk show Chelsea Lately says, "we all need a reboot for the talk show." But in order to return to the format, it would have to "be the right set of circumstances.... I wouldn't say never."

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Editor's Note: This conversation has been edited and condensed for publication.

What made you want to write this book?

Well, this book came along when I was in the throes of my love affair. My very public and demonstrative love affair with Jo Koy. I had this editor who came to me and was like, "Oh my God, it's so fun seeing you in such love, no one would have ever expected this from you, and to be singing it from the rooftops and acting this way is just so endearing. And I think people would really respond to hearing about this love story." So at the inception of this book, it was to write about falling in love and opening my heart and all of those things. And then we broke up and I thought, "Whoopsie doodle, that's not going to be a book that is going to be a representative of my life anymore, especially with that person." So I kind of sat on it for a few months and thought if there was anything I did have to say. At first I thought, "Let me just pull out of the deal and move on and do something else." And then I thought, "Let me think if I do have anything to say, and I do." I did have something new to say. And my love story with Jo Koy, the other love stories I mentioned in the book are all part of my story. They're not the story, and I think the point of the book is to highlight how incredible your life can be when you don't subscribe to doing what everyone tells you makes you valuable. When you really follow your heart and your purpose and find out what that purpose is and get after it. Like, this is the only chance you have. How much am I willing to get better, but at the same time, knowing really who you are and never compromising the essence of that?

I mean, this is gonna sound so cheesy, but it is kind of a love story with yourself.

No, it is corny. Believe me, my editor came to me after she read the draft and she said we have to come up with a title. I said, "Well, read it and think about it, because I don't have one yet and usually I do." I've come up with every title for every book. And she came back and said we have to call it I'll Have What She's Having. And I said, "Oh my God, I would never." And then more people started to read it in our group and on my team and felt the same way. And they said that's how you feel after reading it, you want a little piece of what you're having, and I thought, "OK," because there's always me trying to kind of infuse in other people confidence [and] self-empowerment. Taking in what is going to make you the best version of yourself and then doing it. Not just having a stint in therapy and being like, "I'm better," or not just meditating for a couple of years and being like, "I've got it." It's a constant growth curve, and you've got to be on top of it. So I think I'll Have What She's Having actually is an appropriate title for this book.

So much of your work is rooted in showing how the expectations put on women to marry or have kids is outdated, and this book is another example of that. Is that an important part of your work?

Yeah, of course. I can't think of how many huge decisions I've made in my life where I've been told not to do such a thing, which I also discuss in the book. Buying my house in Spain, I discuss how many men in my life—my business managers and additional men—said, "This is a terrible decision. You don't want to invest in Spain. The economy sucks, blah blah blah." The economy had a boom in the very next year after I bought my house there and it was absolutely one of the best decisions I made in my life, which I discuss in the book at length.

I feel really strongly and passionately, which I always have, that no one is in charge of me. My frustration at being a young person, which is how the book opens, is about wanting to be free and independent and why am I tethered to all these [people], why do I have parents like this? I felt like a woman when I was a baby. I wanted to just be a woman, you know? I wanted a business, and I wanted to start working. I thought, these people are not my people. As we as we grow up and we grow out, there is that childhood version of us that we're born as, and as we go through the world and get besmirched or get knocked down, we sometimes fall away from that little person that we were. That's really who we were and who I always wanted to remain connected to even as I became an adult and became a woman and became all of the things that I have become. I've never wanted to lose the essence of who I started out as, because I believe that that is the version of ourselves before we start paying attention to what other people are saying about us. Before we are looking in the mirror at ourselves and staring at our outfits and changing a million times before we go, before all of that, there is a person inside of us that is the most truest version of ourselves. And I think everyone could use a nice reminder of that.

And in many ways you have written your own script to your career. It's never felt like you did the expected thing or went in the traditional direction.

Yeah, I don't have a boss very often. Between my podcast, Dear Chelsea, between all my books, my stand-up tours, my specials, no one is giving me notes, and that's the way I like it. I have worked for big corporations and companies and even within those jobs, yes, they've tried, but I'm not somebody that's easily pushed around. I want to be respectful, but I'm also going to do my thing, and my thing is bold and brazen and I'm going to go out there and say the thing that maybe some other people wouldn't say. It comes up in interviews all the time: You created your kind of own path and you do your own thing. I'm very proud of not having to worry about getting a job on a film or as a writer or something. Those things aren't the crux of my career. I never wanted to be beholden to anyone else, and that was always ingrained in me. I just saw it as an example of my parents' relationship and how little agency my mother had. I thought, "No way am I going to be living with some man who tells me how much I'm allowed to spend when I go grocery shopping." Also, I'd rather not go grocery shopping.

What would you say is different about where you're at with this book and how is this book different from some of your other books?

I think all of my books are representative of where I am in my life at that time. My last book, which was a very serious, deep [one]—I mean, obviously it always has funny stories because that's who I am and I always have to find the humor in everything. But the last book was a delve into my therapy and my brother dying and actually coming to terms with my delayed grief. You go to therapy and I went hard, like I do everything. I'm like, I want to know as much as possible, as quickly as possible so I can move on to the next phase.

There is a period after therapy where things start to just settle in, like you kind of absorb everything that you've gleaned during that time. And it's an adjustment period and it's an opportunity for you to grow into your better self. And right now, where I am in my life is my feet are so firmly planted in the ground you cannot knock me over. Like I don't care if you don't like me. It's not my problem. It really never has been, let's be honest, but in a healthy way, not in an arrogant, "Oh, go f*** yourself if you don't like me" way. I totally get if you don't like me. I get it. It doesn't prevent me from liking you. I could still like you. I'm not stuck in what's going to happen or paranoid about the future, and I'm also not worried about if I said the wrong thing to someone ever or I embarrass myself. Even those things, even when I have done those things, it's just not the same anymore because my intention and my groundedness are kind of just this overarching beam of light around me that can't get me too far to one side. Like I am so cemented in a positive way to who I am now that there's really no question. If you know me, if you followed me, you know me. Inside out. There's no way that you're going to meet me and be like, "I wonder what she thinks about this."

That's so true. There's a Joan Rivers quality to what you do. Like fans of Joan's knew what they were getting at a Joan Rivers show, and the same goes for you.

Thank you. I appreciate that. Listen, when I look back, there have been many times in my career where I'm like, "Oh my God, what if this is it? What if I quit E! and then nobody hires me?" Or when my Netflix show ended, "Now what? What if I'm like persona non grata? What if everyone thinks I'm over?" I've had those times in my life. This month I'm gonna be 50-years-old and you get to a point where you realize, whoa, whoa, whoa, you're the reason that you're sitting here today. There's enough data to show that you're the reason that you got yourself here and that there's no reason to be concerned. It doesn't matter if 15 things don't go my way, it's going to be OK.

Well, speaking of your Vegas residency, has stand-up changed with success? Has it changed how you craft your set?

No, I mean it only emboldens me to be more honest and more sharing to know that people have kind of jumped aboard my story and understand what I'm going to be talking about and the subject matters that I tend to lean toward. I tell a lot of really stupid dog stories. I tell a lot of silly referential stories that are not flattering. I'm not afraid to go there. I think the only way stand-up has changed for me over the last 20 years is the political correctness aspect of things, which I don't have a problem with. I like parameters. I wanna know if I'm hurting your feelings. I wanna know from a group of transgender people if this language is hurtful to them, then I'm not going to use it. I like any challenge to become more clever, and if you're a comedian that complains about that, then you're lazy. I mean that's it.

Your podcast Dear Chelsea is different and yet still very much you. What do you love about doing your podcast?

I like talking to real people, so that to me is just the benefit. I love having people call in with real problems. I love people's business. I am so interested. I always think whenever you have a problem and you go to this person, you go to that person, you go to five people and kind of get a survey of what everyone thinks, so you hear what you want to hear. The most effective advice would be from someone who's not involved in your life in any way. And so that's what I provide for all of my callers who are calling in. I'm not involved in their lives, I don't know who they are. And I'm a total big sister in real life to all my friends, I'm always like, "Let me help you. This is what you need to do." I always step in if somebody's falling down. And so for me, it's kind of just giving people the little push and the extra nudge they need after a decision has most likely probably already been made, but they're not willing to say that to themselves. And some of these things are pretty serious that they call in with, and some are banal. I love talking to real people. I love talking to any people and when you like talking to people and you're a good listener, then it's just kind of a no-brainer. It's turned into a Dear Abby of sorts, and I'm just glad I didn't do a regular podcast. That was like, I'm gonna interview celebrities, and it's gonna be the same thing I've always done. And what's what you see on all these other podcasts. This is a different spin for me. And I'm able to take all of the tools and all of the learnings I got out of my own therapy and I continue to get when I read books about therapy and about self-help. I read almost everything that comes my way. I am in a position to give people advice and be like, "Hey, get out of your own a****** and look up."

Chelsea Lately was such a good late-night show, and it's a bummer we don't see more like it and more women in late-night. Do you think that will ever change?

Absolutely, I mean, somebody just has to do it. There have been some reiterations of it, but yes, I think it's all very cyclical. This late-night talk show thing isn't looking very vibrant these days. They kind of have to switch it up, and that's a great way to switch it. Everybody loves a panel. Having a panel of four comedians on, I mean, when you think about comics, they're known for just standing there on a stage without any other people and a microphone. The idea that four comedians could share space and actually listen to each other and riff off of each other, I didn't think it was such a new idea, but apparently it was. That was my life because I was a comic, I was like, "Oh, let's just put this on TV." So it was definitely one of those very easy, lucky, effortless successes. It just made sense and hopefully it will make sense again sometime soon, because I think we all need a reboot for the talk show. We need something a little bit more energized.

A while ago, when you guest hosted Jimmy Kimmel, it was so great. Is that something you'd ever consider doing again?

I mean, I did for a while when we were talking about The Daily Show. I was interested in doing that because it was really fun, did that for a week, had a blast. And then when that didn't come to fruition, I just thought, "OK. I really love my life. I love not being tethered to a studio five days a week, and this really requires a five-day-a-week job, and even if it's one show, even if the show's once a week, you're there a lot and you're tethered to a studio." And from my book, you'll understand how much I love to bounce around and travel and how much my time off is so important to me. So it would really have to just be the right set of circumstances, and I wouldn't say never. But it's not my focus. It would have to just be the most perfect scenario.