Career Resolutions Based on My Professional Failures

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Photo: Martin Poole/Getty Images

In the start-up world they like to say, “Fail early, fail often.” I vacillate between thinking this is great advice — learn from your mistakes and move on! — and writing it off as a bunch of dudes justifying wasting a bunch of other people’s money. In any case, early career mistakes are pretty much a given, even for those of us who aren’t tech entrepreneurs. Now that I’m a decade deep in my professional life, it’s easy to see why failure wasn’t so bad. Here are five things I had to learn the hard way, and how I’d do things differently if I could go back in time and advise my post-collegiate self.

That time I thought it would be easy to get the job I wanted.

I graduated in 2004, a time when “millennials entering the workforce with high expectations and dismal job prospects” was still a brand-new trend. Armed with some cursory work experience (three internships), a Bachelor of Journalism degree (seriously, my diploma says “B.J.”), and a college-journalism award for an article I wrote, I felt pretty good about my prospects. Over a period of months, I sent my article clips and a cringe-inducingly earnest cover letter to newspaper after newspaper. I heard precisely nothing. I didn’t know anyone who could get me an entry-level magazine job. And I felt I was above fetching some editor’s coffee, anyway. I was going to do serious journalism.

Eventually, faced with the choice between compromising my standards and moving back into my parents’ basement in Iowa, I got real. Even though I’d spent years deriding public-relations majors as future journalists’ less-intelligent and more-money-hungry cousins (wow, I was such an asshole), I broke down and started applying for jobs in communications. And I was lucky enough to get an entry-level job at a women’s-rights nonprofit in New York. They offered me $28,000 a year, and I enthusiastically accepted. I know this number makes me sound like I am ancient, but trust me it was a bad salary even for 11 years ago. The work was easy: I spent my days writing press releases and proofreading web copy and looking for stock photos of women and children who looked sufficiently “real” to accompany reports on domestic violence. I hated it.

But it shook me awake and reset my expectations. And it made me open to other opportunities I wouldn’t have entertained otherwise. Around that time — actually, through the job I didn’t love — I met a group of women who had just started a blog. This was the dark ages, when blogging with some friends could still garner you a bit of attention. It got me comfortable writing for the internet, which is the way I make my living now. As the author and artist Austin Kleon writes, “The truth is that even if you’re lucky enough to make a living off doing what you truly love, it will probably take you awhile to get to that point.” In the meantime, as I learned the hard way, it’s all about accepting an unsatisfying day job and making the most of your after-hours.

Resolution: I will quit being a snob and take the job I can get. Then I’ll look for a great side project.

***

That time I was my own worst enemy at work.

By 2006, things were looking a little better. I’d left the nonprofit job and completed a barely-paid, year-long internship (hey, at least it was in journalism) in San Francisco. I was still writing for the blog in the meantime, and it was the blog — not so much the internship — that helped me land an interview for a full-time job as an editor at a left-leaning political website. I was so excited at the prospect of earning a salary that I ignored my new boss’s flirtatious comments and creepy questions about my sex life … for a few weeks. When I heard about a position opening across the country at a publication where I had some inside connections, and could probably land the job, I gave notice to the lecherous boss. I had only been in the position for two months.

The new job was in Washington, D.C., and I landed it because my then-boyfriend was a friend of the editor who hired me. In my head, I did the math like this: There were two jobs I had gotten on my own merit (the communications gig and the post-grad internship), and two jobs I’d gotten through men who were either sleeping with me or wanted to. This did not inspire self-confidence. I mean, what self-respecting feminist lets her boyfriend get her a job? Even though I wrote about politics quite a bit on the blog, I was convinced that I was not qualified to be an editor at a political magazine.

I tried to put up a good front, but I’m pretty sure I often came across as nervous and defensive. Deep down, I felt I had no credibility. I later learned that this feeling is called Impostor Syndrome. And that most dudes get good jobs because their friends recommend them, too — which is no different than my boyfriend whispering in the ear of my future boss, really. I can’t tell you how much better my work would have been if I just could have accepted that I was as smart as everyone else in the room. But I’m sure it would have been better.

What I also didn’t know then is that the feeling of Oh god, I’m in over my head, is how you can tell a job is a good fit for you. This is a sign that the job is a step up. Take it from Marissa Mayer: “When you have different options, you should choose the thing that looks like it will be more difficult, because that usually turns out to be the right choice."

Resolution: I will accept all promotions or jobs I don’t feel qualified for, and know that I’ve earned the right to be there.

***

That time I got bored and quit — without a next job lined up.

Four years later, I was still in the same workplace. My title had improved, although I’d felt stuck for a long time. I’m not sure exactly what I was waiting for. I didn’t know where I wanted to go, or what I wanted to do next. I was spending chunks of my workday staring at my desktop background, which was a woman in a convertible on a road trip through the West. Pathetic.

I finally found the courage to quit when my boss announced he was leaving. The higher-ups had made clear to me that they would never elevate me to his job. So the only dignified move was to quit, right? Which is what I did. I didn’t have much money saved up — a couple thousand dollars, tops. This was the rickety foundation on which I built my first attempt to go freelance.

After a meandering solo road trip (living the desktop-background dream!), I signed a lease on an unremarkable apartment across the street from a friend’s place in Austin. I had a contract to do some work for my former employer, but it was barely enough to cover rent. I realized I didn’t really know all that many editors who could assign me work. And my transcontinental joyride had depleted my already meager savings. I began to understand why Thelma and Louise chose the cliff.

I don’t know whether I would have made it as a freelancer at that point or not. But I do know that during all those months I felt stuck at work and fantasized about quitting, I didn’t really do much to set myself up for success. Instead of doing more writing — the skill on which I hoped to earn my future living — I did a lot of worrying and panicking. Instead of trying to build my relationships with people who could assign me work, I got caught up in the office politics of my current job. Rather than make a financial plan and use it to set my timeline, I quit when my ego got bruised.

Looking back, I now realize that things could have turned out a lot worse. Just as financial panic was setting in, a mere two months into my new “freelance career,” I got an email asking if I wanted to interview for a new job in Los Angeles. It was basically my dream job, and they hired me. In other words, I got really lucky. Really lucky.

Resolutions: I will invest in my professional relationships, even when I’m not job hunting. I will practice the skills I want to be paid for, not just fantasize about a career change. And I will save a lot of money before I try to go freelance.