Girl Talk: I Used To Date Men Whose Careers I Envied

I used to be defined by one singular character: ambition. As early as 9th grade, I knew that I wanted to be a journalist who wrote long-form investigative articles. And for nine or 10 years, everything about my life was focused around that one goal: where I went to school, how I spent my “free” time, who my friends were, even whom I dated. It’s not an exaggeration to say my drive consumed my life — and I was perfectly OK, even pleased, with that. I seriously believed that at long last I would finally be happy when people bought magazines with my writing in them.

The thing is, ambition for ambition’s sake turns out to be a hollow way to live one’s life. It’s a means to an end, of course, but considering that the target you are shooting for is constantly shifting, it can also be exhausting. Don’t misunderstand me: I’m proud of my accomplishments — articles I’ve written, interviews I’ve conducted, maybe a few lives I’ve affected. But if I could go back in time and change a few things, I just might do it.

And the first thing that I would change? I would not have dated so many men whose careers I envied. Life is hard enough when you’re putting unreasonable expectations on yourself to succeed, but it’s damn near impossible when you’re comparing yourself to someone you’re sleeping with.

I felt miserable this entire time because, despite being a total workaholic, I convinced myself that everything that I was doing wasn’t good enough.

I had this crazy idea when I was a teenager that I wanted to publish a book before I turned 18 years old. I actually wrote a book when I was 13 and 14 years old about stuff that was happening in my family. With the encouragement of the therapist I saw in high school, I sent the first couple chapters to literary agents. All the agents turned it down, but, luckily, there turned out to be a lot more interesting things happening in high school. I set my book aside, relegated my crazy idea to the back of my mind, and had an adolescence.

Then I started dating other writers during my freshman year of college. A young writer published an essay that I thought was funny, I wrote him a “fan email,” and he introduced me to a small group of young writers who all knew each other. During my freshman and sophomore years of college I dated two of them: an 18-year-old and a 21-year-old, both who were working on their second books. They were nice enough guys, but to be honest, dating them just messed up my mental health. For years, I’d had this goal of publishing a book by age 18 and by the end of sophomore year — when I was turning 19 — I still hadn’t published anything. If they could do it, why couldn’t I? What was wrong with me? What kind of life was I going to have? What kind of career was I going to have if I didn’t start it now? At the end of sophomore year I had my first serious bout with depression and anxiety: I stopped sleeping, stopped eating, dropped weight, cut myself, and did what I guess you could call “self-medicating” with quantities of alcohol and pot that my little body couldn’t really handle.

When I went home for summer break after sophomore year, I visited that same therapist I’d seen from high school. I don’t blame her for not correctly assessing my self-esteem issues, but clearly she had little-to-no experience dealing with neurotic writers. She told me that lots of college students had “what am I doing with my life?”-style meltdowns when they were halfway done with college, convincing me, at least temporarily, to chill out. Still, that didn’t deal with my distorted self-worth, the root cause of my outlandish expectations for myself.

So, things got steadily worse during my senior year of college. Specifically, I had some flirtations with a male magazine writer and being around him only messed me up in the head more. By that point I’d started a freelance writing career and the editor at the main place I wrote knew this guy by reputation. “Oh, don’t be a star-f**ker!” The editor teased me. Star-f**king? Me? What? I thought what he said was offensive at the time, but years later I could see that he saw something happening that I could not yet recognize in myself.

I’ve already written about the relationship I had with a 30-something magazine editor when I was 22; he had been my mentor first and eventually I fell in love with him. I loved him because he was sweet, smart and entirely without ego. But due to the 15-year age difference, I also got a taste for what it’s like to feel proud of yourself for catching someone’s attention. I looked up to this man who I considered to be both a good friend and a great journalist and I felt special that, of all people, he paid attention to me. There wasn’t just the Older Man mystique, but the Successful Journalist mystique. Considering how young I was, even a little taste of the Successful Journalist mystique intoxicated me.

A few years out of college, I’d worked myself into a career that made my resume look great: I had a good job and on the side I wrote freelance articles for places like The New York Daily News and Bitch and Radar magazines. But — cue the cliché plot twist! — I really wasn’t happy. I gained weight, I slept fitfully, I stopped doing laundry, I cried often, and I could spend hours staring at my bedroom walls, thinking about how I didn’t want to live my life anymore. Part of my unhappiness stemmed for working for a boss who was at times abusive and not getting support at that workplace to deal it. It certainly didn’t help that I was entering into my third (and by far the worst and most serious) bout with depression. But really,

I felt miserable this entire time because, despite being a total workaholic, I convinced myself that everything that I was doing wasn’t good enough.

Maybe I wrote for The New York Daily News, but why not The New York Times? Maybe I wrote for Bitch, but why not Marie Claire or Glamour? Why, at age 24, was I not on staff at The New Yorker yet, damn it?!?!

A person could drive herself crazy thinking like that. And I did.

It was not helpful, then, that in the span of about 18 months during that time, I dated three other journalists who were newspaper reporters and bloggers. All of them were “successful” journalists, too — as successful or more successful than me. But I was at such a messed-up place that their “success” was their most redeeming quality for me; much like with the Older Man that I had genuinely cared for, I felt flattered that these writers were even paying attention to me. The problem, though, was that only one of them was a person I genuinely liked: the other two I did not much care for. One guy was cheating on his girlfriend with me and was egotistical, two-faced and rude; the other guy was fickle, an even worse workaholic than I was, not to mention he used “rape” as a verb all the time in completely inappropriate situations (like “I’m going to rape you at Wii tennis”). Even when I was on dates with them or waking up in their beds, I didn’t especially like them. The only thing I liked, really, was living through them vicariously.

It all came to a head in an awful way: One weekend in July of 2008, I basically had a depressive breakdown. All the listlessness and sadness I felt had been building up for months and, finally, the dam burst open. I started crying on a Friday night, kept crying throughout Saturday and cried all day Sunday; I simply could not stop sobbing. By Sunday night, my very scared mom and one of my sisters were able to convince me I really needed to see a doctor.

The thing was, though, I was not alone that weekend: Saturday night and Sunday morning I’d been with one of the journalists that I was dating. He made it pretty clear in the middle of my bout of crying that he didn’t have time for this; when I sent him a text message on Monday morning to tell him I’d made an appointment to see a doctor about my depression, he never responded. And I didn’t hear from him — this man I had been sleeping with, this man who had talked about introducing me to his mother — for months! While I don’t necessarily begrudge any one person for not knowing how to deal with someone who is having a depressive breakdown, it slapped me in the face in an utterly raw way that this man would reject me.

Over the next few weeks and months, I started taking antidepressant medication and seeing a therapist again to figure out how to live with depression. The bittersweet realization was that with each passing week, I could see everything more clearly — my parents, my siblings and my girlfriends had my back, while this guy (and others like him) didn’t. I might have been dating these men I didn’t care for only to revel in their success vicariously, but they proved to be dating me for similarly shallow reasons. I had to weed these people out, which was not too hard.

Eventually I had to teach myself two things: one, to measure my self-worth by something other than accomplishments, and two, to date men for the right reasons. Luckily, what I learned did turn out to be as valuable to my self-worth as it was to my dating life: Using only my resume as a barometer for my self-esteem just wasn’t sustainable for me — and, I would imagine, it’s really not sustainable for anyone for a long period of time. Fortunately I’ve blogged for The Frisky for over a year now and I have enjoyed it more than any other job, I think, because I’ve stopped being so ridiculously hard on myself. I’m not a workaholic anymore; I force myself to leave work at work and have a fulfilling personal life. I will always love writing and be an ambitious and driven person, but my internal monologue when it comes to using that drive has completely changed.

Since I stopped dating men whose careers I envied, dating became more fulfilling, as well. These days, I have a healthy, happy relationship with a boyfriend who runs a tech start-up. I love him and I’m proud of him, but I am not living through him vicariously at all. I know deep down that he’s with me for the right reasons, and I him; “success” does not factor in at all. How do I know this?

More evenings than not, I hear myself say something like, “Let’s not talk about work in bed, OK?”— and it feels really good to know I finally am able to say that.

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