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Cindy Chupack on Failure

Cindy Chupack on failure.
Jay Dixit
This post is a response to The Failure Interview Series by Jay Dixit

Cindy Chupack had been married two years when her husband told her he was gay. Though she felt like a failure at the time, the years of loneliness and dating that followed provided the material that led her to become a writer and producer for Sex and the City. "It felt like a huge curse and it was lonely," says Chupack. "But what I'm most proud of in my life was Sex and the City, and it never would have happened had I stayed married, and had he not been gay, and had that not been my backstory."

Tell me about your successes and your tough moments.

My greatest success was the work I did on Sex and the City. That remains the achievement I'm most proud of. I fear it will always be the achievement I'm most proud of—but it's good to have one, anyway. I was doing my best writing and I was in the right place at the right time. It was just following my heart and figuring out where I could do my best work. That that work seemed to touch so many women (and men) all over the world—and it's still something people talk about and use as a reference point, it felt like it became part of the cultural discussion—I felt really proud to be a part of that.

My low point, my toughest moment personally: I found out my marriage was most likely going to be over, and that was because my husband told me he thought he might be gay.

I was a young bride—we got married when I was 25. I didn't really know who I was yet, and he clearly didn't know who he was yet. What was so hard about it was: We just got married, we'd just moved to Los Angeles, and the thought of telling everyone. The long list of things that kept piling up in my head of what I would have to do to get through this. I was distracted from the emotional work I had to do by the long to-do list of everything that was going to need to happen to separate our lives, to tell everyone in my life, to figure out what my new life was going to be, and just to undo everything I felt I was doing.

How did you feel about yourself at that moment?

I felt stupid. Not entirely stupid—because he wasn't quite clear either. He kind of put it to me, "I need to figure out if I am." He had never been with a man. But it was sort of a sneaking suspicion he probably should have investigated before proposing. But nonetheless, he was ready to investigate it then. I felt stupid because my very first impression of him was that he might be gay. But then he didn't think he was, so I didn't think he was.

But I felt like, in telling everyone and in undoing it, I was going to feel ridiculous, and like a failure. No matter how much you believe you're doing the right thing, it just feels like a very public failure. And we did the big wedding and the big white dress. I think I still had thank you notes. It was so embarrassing. I felt very overwhelmed—just how to sort through everything.

Do you think those feelings of failure came partly because you were blaming yourself?

I don't think so. I was out of touch with my feelings and my needs and myself in a lot of ways, marrying young. That was the first time I went to therapy. When this happened, we went together to couples counseling, and it quickly became divorce counseling. I think there was the slight hope that we would talk through this and there would be some other solution.

My therapist said, "Your job is to get through the day." Then she introduced me to the idea of a gut feeling. I never had thought about it or understood what that meant. What that meant in that moment was, everything seemed overwhelming, like, are we going to tell our parents, when do we tell our friends, when do I change my name back, am I going to get a roommate, am I moving out, are you moving out, are we going to try to stay friends, is this a trial separation, what does this all mean? It felt so overwhelming and we had just moved to L.A. so I didn't really have the support of friends that I'd had in New York. I felt very alone.

It was tricky because he wasn't ready to come out, so we didn't really have a good way to tell anyone what was happening. For a while I was respecting that, because he wanted to figure that out first. This was a really complicated time, and my therapist said, in making all those decisions that I just kept getting overwhelmed by—even the smallest ones like, "I can't even tell a friend or my parents, who can I tell about this?" She said, "What's your gut? Just sit with the decision either way." If I'm going to tell someone, and how does that feel? Or I'm not, and how does that feel? And get in touch with your gut feeling.

I still do that all the time to this day. If I'm debating a job, or whether to end a relationship, or whether to go to a party if you're not in the mood—to try to audition either choice and see which one makes you feel good and which one doesn't.

That's a very Hollywood way to put it—"to audition either choice."

I had a friend who said, "I quit my job today in my head, and I'm going to see how it feels." He spent about a week having quit his job without telling anyone, to see if he regretted it or felt better. It's such a useful thing, and it seems funny to me I didn't even understand what a gut feeling was. Now I have a very strong gut feeling about things. That's really when I first developed it. That was the best thing to come out of that.

I probably had a teeny gut feeling when we first met, and definitely during the two years we were married that something wasn't quite right. But I just didn't know enough to listen to myself. So part of the frustration, disappointment... It wasn't so much kicking myself, because I don't think I had a strong enough sense of things. I just felt embarrassed by being blindsided by it.

What enabled you to get through it?

This is what it was: The day after it happened, I went to the self-help section in this little bookstore in L.A., and there was nothing for this situation. There might be now, but there wasn't when this happened. And I remember there was a book called Loving Someone Gay, and it was for parents and teachers. So there just was nothing. And I thought, "This is terrible, I'm totally on my own, pioneering this problem in Los Angeles."

So I got a journal instead, because there was no self-help book. I started keeping a journal that first day. This journal was only for me. I never expected--and never expect still—to do anything with it. But there was this plant on my balcony that was mostly dead except this one little green leaf, and I took a picture of it and put it on the front of the journal and called it "Finding the Green." I was thinking, "That's what I'm doing, is just waiting for the rest of all this dead mess to clear out, and someday this will be green again."

I just started keeping notes about everything I was feeling. There's crazy things in that journal--like I was constantly revising my personal ad, what my personal ad was going to be when I was ready to date again. Revisions of who I was going to be and how I was going to present myself. I had a list of people I'd told, just to remember, because I couldn't remember who I'd told yet and who I needed to tell. And then just what I was feeling and where we were.

There's something about writing when you're in the middle of things and you can't see your way out. The truth is, I knew someday I would be at the end of that book, and everything would seem OK again, and someday I'd look back at that book and remember that at a time when I didn't see a way out, when it felt hopeless, I got through it, and I'd keep that always. I knew that, so even though I was in it, I knew there was going to be some ending eventually to that period of my life and I was just going to slog through it.

It's funny you said that. We actually have a sidebar, tips for getting through tough times, and one of them is keep a journal. There's a lot of research showing that journaling your feelings during tough moments actually helps you metabolize them and put them into a context, and helps you create a meaning for them which then helps you get past them. There was a study, for example, of engineers—male engineers—who had been laid off from their jobs. They had one group keep a journal, and that group wound up getting new jobs much faster and being happier and more successful than the ones who didn't.

I wish I could comfort that person writing the journal, and say, "It's going to be OK." There's something about writing when you're right in the middle of things. Not only is it therapeutic, but there's something about looking back at it. You can never recreate those feelings you had, because you eventually make sense of all those feelings. You put it into context and you see it in 20/20 hindsight. But when you're in the middle of it, it's fascinating to see how you felt, what you felt, and why you felt it. To document that hopelessness. It's useful because we have a selective memory; we have a tendency to think we weren't quite that much of a mess. I certainly laughed about it and told stories about it and, of course, in the aftermath, put it into some sort of context and narrative of my life.

I think if I had stayed married, and he wasn't gay, and we'd had kids and we'd had a regular marriage, I never would have had the long, long years of dating and all the stories that became the basis of my writing and working on Sex and the City, and just everything that's happened to me since then, and eventually missing the guy I am married to who I feel is the right guy for me to be married to. And my ex-husband is married (for all practical purposes) in California, and has two kids. It felt like we found the right destinies. But at that moment, it felt impossible to imagine we were in anything other than a giant mess.

So you think there is some value now in going back and reading the journal and seeing, "Wow, it's worse than I remembered"? "In my memory, I papered over the toughest moments, but actually I see it was that bad." Is that valuable in some ways?

It is, in tough moments. My husband and I have had trouble getting pregnant, and I think because of going through that, re-reading the journal is a good reminder that there will be a happy ending, even in those moments when you can't see it. I always feel that way for my friends, and I felt that way when I was single for a long, long time, and sometimes lonely—that there was going to be a happy ending to the story, you just have to slog your way through the second act. Reading that journal reminded me of that. Because it doesn't necessarily help—even if you feel confident and optimistic that things will work out, it doesn't necessarily make it easier to get through the hard parts—but maybe sometimes reviewing exactly how hard something felt and knowing you got through it is actually helpful.

All of this is resonating with the actual science I've been reading about in editing this article. So there's this whole concept of resilience. The way you build resilience is by going through tough times and coming out of them—and you realize that you're stronger than you thought you were. It's actually better for you. You're far stronger if you've had failures and bounced back from them than if you haven't. If you've never had a failure, then you're kind of brittle. So if you're 40 or 50 and you've never had something really terrible happen to you, if something terrible then happens to you at that point, you just get broken by it. Because you've never had anything like it happen. It sounds like failure really did have that positive effect for you.

I definitely led a very blessed life. I used to joke that I had a guardian angel, because I was the type that could lose my wallet and someone would find it, or I would be able to find a parking space. It always felt like things worked out for me, and friends used to joke about that. Then that happened, and it did feel for a little bit like if I had a guardian angel, he was on vacation for a while, and everything started to fall apart. But it was good to realize that you can get through this, that things didn't always have to go perfectly.

But seeing that other people actually have terrible things happen to them, and there isn't always a happy ending—somebody might get depressed and then kill themselves, people get terrible diseases and die, so there isn't always a happy ending for everyone—so, given that you've seen that, and probably experienced that among people you know, how is it that you have this confidence that there's always a happy ending for you?

I guess it depends on what you consider a happy ending. I've had friends die young, and tragedies happen, and there's no explanation. And I don't even find religion comforting in those moments. Sometimes you're trying to make sense of something and you can't. So my philosophy does not disqualify the possibility that something bad or unfair could happen, and there may not be a way to get out of it.

But my outlook on success is more day-to-day—the currency of happiness and trying to enjoy your life and what we have of it while we're here. Even in great sickness. One friend I'm thinking of in particular who died young was so loved! All she really wanted for such a long time was love in her life, and she met a guy a few years before she died and had a really happy life with him. Not that we didn't all want more of her. And she should have had more. But it's like, "What was your definition of happiness, and were you able to do things you felt like?"

I generally have a crazy, unsinkable Molly Brown attitude that annoys my friends. Because there's definitely times. After my divorce I felt a bit kamikaze about dating. I used to call it kamikaze dating, because it's like you know it's going to end in disaster—most relationships are going to end in disaster. You're going to crash but that is the task. You just have to get in there and get in the plane and in the greatest case it will work out and last forever and you'll be happily ever after. But assume the job is you're probably going to crash.

I sometimes approach life that way. There might be something really hard. I'm sort of trying to approach having a baby like that. There's probably going to be a lot more setbacks before we get it, and it's probably easier to move forward knowing that. So I'm not a blind optimist where everything has to go well and I get upset when something goes wrong. Maybe I'm an optimist in pessimist's clothing. I understand bad things might happen along the way, and that might make you stronger and be part of a larger plan that will make you a better person.

When you say part of a larger plan, I guess you don't mean that in a religious sense.

I play fast and loose with religion. I don't really believe. I'm Jewish, but I like to believe we're in control of things. But I do believe—I don't attribute it to God, but I do believe there's something—how would I say this? I believe for many people there's something you're meant to do, whether or not you believe that's something God meant for you to do, or something because of your talents you're meant to do, or because of your experience with love or what's missing that you're meant to experience. And sometimes I think those are even hardships that you're sort of meant to go through to be tested.

But I believe we're in control of how we react to those things and what we do with those opportunities, and I like to believe we're in charge of our destiny that way. I approach it less like there's a God and more like there's a writer—and maybe that writer is you. And so this life you're leading is your book, and maybe the really hard thing you're going through is an important plot point. But is it the middle of the story or the end or the beginning? You figure that out as you go along.

I was going to ask you what it is about your personality that allowed you to pull through, but I think you answered that question already when you talked about your optimism. Is there anything else you think is an important factor?

I definitely try to have a sense of humor about life, and it's hard to do in the middle of the hardest thing you've ever gone through. But definitely when you try to make sense of it later in some form, that makes it funny. You can at least laugh your way through it.

Writing first-person pieces, and even writing television about some of the harder things I've gone through. Even now, in trying to get pregnant. I wrote a piece for O Magazine that got picked up by CNN.com about the trying nature of trying. A lot of people have written about that after they got their baby, as a nice story with a happy ending. I really wanted to write about it while we were still in it, because I feel like that's what people need to know—what the struggle is, to be honest about being in it. That journal helped me get through my divorce and it wasn't to be published and it wasn't to try to help other people. But I do believe there's some comfort for me in writing something that will be relatable to other people. And for people to read about what it's like being in the middle of something and how do you deal with getting through it.

I guess you'd have to combine somehow my optimism and my personality as a writer. That somehow it helps me digest things, and writing and having people relate helps me feel better about what I've been through. Being able to tell that story about that moment when my husband told me he might be gay and how I got through it and what happened in the month after that, and having people laugh and cry along with you has been very therapeutic.

My last question is about the silver lining. I guess you're saying that your experience actually provided fodder for writing and that then led to your success. Can you tell me about that path?

When it happened I remember thinking, "I can't believe I have to start all over and be single again and figure it all out again." But that journal of being single again and then the long years of dating, that was the experience that directly translated into all the stories I told for Sex and the City. I wrote pieces for Glamour about dating, and I put together a book of essays about being single and between boyfriends called The Between Boyfriends Book. I just look back and think, "If I hadn't had that opportunity to be single again, none of that would have happened." At times it felt like a huge curse and it was lonely, and it wasn't just material, it was my life, and it was hard. But what I'm most proud of in my life was being able to work on Sex and the City. It never would have happened had I stayed married, and had he not been gay, and had that not been my backstory.

Listen to Cindy Chupack telling her story at The Moth and read her story in the Modern Love column of the New York Times.

Jay Dixit is a science writer based in New York.

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