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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.



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