Jobs are like relationships: Some are wonderful, some are horrible, and some of them totally screw us (and not in a sexy Top Gun type of way). Like relationships, the jobs we’ve held can teach us valuable things about ourselves. As we work toward our larger professional objectives, no gig is too “small” or insignificant to shape the course of our careers. In the end, we’re all striving for an LTR with our dream occupation, but finding that occuBAEtion can be one of life’s biggest challenges.
I’m currently in the honeymoon phase of my own dream-job LTR. I’m fortunate enough to have a career as a writer, something I’ve worked long and hard to achieve. But the road to my dream was paved with many professional mistakes (and countless hellish day jobs). So, in an attempt to help you avoid the many career face-plants I’ve made along the way, I’ve compiled a list of (gulp) every mistake I’ve ever made...and how to avoid them.
When I first moved to New York City, I wanted to be an actor. I graduated from one of the most prestigious theatre conservatories in the country, and I expected to become America’s Next Top Ryan Reynolds — overnight, of course. But when I didn’t immediately land a lead in a Broadway show, I was forced to become the ultimate NYC cliché: the waiter/actor.
When I first took the server job, I was a bitch to my fellow coworkers: I thought I was better than them, and that this whole waiting-tables thing was a cosmic joke that would clear up soon. Unfortunately, the starring role didn’t come. I realised that all my fellow waiters were actually in the same boat — and it was time to start treating my coworkers with the respect they deserved.
Waiting tables was shitty, exhausting, and ultimately humbling, but it helped me kick my entitlement to the curb. Once I dropped the bratty attitude, I suddenly found myself making strides in my acting career — casting directors put me on their short lists, I made friends with directors, and I actually booked some work.
Takeaway: No one likes a brat. No one wants to work with a brat. And I imagine that even Mariah “Queen of Shade ” Carey was a sweetheart when she first started out (or at least she pretended to be). Divas are made, not born, so until you’ve sold over 200 million records worldwide, you might want to think about being nice to your coworkers. Being a good person will get you a lot farther in life.
Illustrated by Paola Delucca.
Early in my acting career, I was cast in a summer stock production of Beauty and the Beast in the unenviable role of "dancing meat fork." But though chorus cutlery was hardly a dream job, I did find my dream man that summer: Gaston. Yes, Gaston was handsome, muscular, and gay AF. We began our affair in secret, in an attempt to avoid gossip. But things blew up when Lumiere found us out and told the entire cast. Conflict soon erupted, and our affair quickly fizzled. Workplace hookups create workplace drama, and that drama is even worse when it’s set to the relentless soundtrack of “Be Our Guest.”
“Don’t Sleep With Coworkers” is a “no-no” that may seem like common sense. But sometimes the hotness of a coworker overpowers reason, and the janitor’s closet suddenly seems like a great place for the first chapter of a pregnancy scare. But trust me: It’s not worth the awkward and inevitable work-kitchen encounters. If you do decide to risk it and make the leap from coworkers to co-twerkers, just be prepared to deal with the drama like a grownup if things don’t work out (and that might even mean looking for a new job).
Illustrated by Paola Delucca.
I worked for a few seasons as a host during New York Fashion Week, interviewing celebrities and designers for a prominent makeup brand’s NYFW web content. I was sort of a gay/poor man’s Maria Menounos, infiltrating VIP areas in an attempt to interview unsuspecting Kardashians. One of the first things I learned at NYFW: Never ask permission. If you do, there will be a doorman with a bitchy frown ready to give you a firm “no.” The best way to deal with gatekeepers is to simply ignore them. Walk past the velvet rope with confidence and pretend you’re Whitney Port. At a certain point, acting like you belong translates into actually belonging.
Asking for permission gives someone the opportunity to say “no.” When it comes to making big career moves, sometimes it’s better to just do something rather than wait for someone to tell you that it’s okay to do it. If you’re feeling like your career is DOA, perhaps it’s time to find a DIY solution. Kickstart money for your indie film instead of waiting for an executive to greenlight it, self-publish your book after every editor says no, or launch your Etsy store when Barney’s won’t stock your jewellery. Bottom line: Luck certainly plays into career success, but so does sheer grit. Don’t underestimate how much you can achieve just by trying.
Illustrated by Paola Delucca.
After abandoning the whole actor thing, I found a passion for writing. I wanted to write in television, but had a hard time finding work within the scripted TV world in New York. So, I settled for what I thought was the next best thing: a job as a reality TV producer. I came to hate the brutal working conditions and manipulation that the gig required. Despite this, I remained in that job in for many years. I felt stuck; the longer I stayed, the more I felt defined by a career that I hated. I was afraid to leave, and worried I would be unable to find a new job in a different field. After a few years, though, things became unbearable, and I finally quit. It was the best decision I ever made, and a whole new path unfolded before me.
Be careful not to let a job that you hate turn into a career that crushes your soul. Sometimes we stay in the wrong gig for far too long, only to wake up years later and truly question where we’re going in life. If that happens to you, don’t panic: It's possible to change the course of your professional life. Starting over isn’t easy, but with vision, determination, and courage, it’s possible.
Illustrated by Paola Delucca.
By the time I quit my job as a reality TV producer, I’d worked my way up that ladder pretty far. When I finally left that gig, it was to take a job as a writer’s assistant to a famous novelist/screenwriter. Though I sacrificed the seniority I had earned at my prior job, I gained a position in the field I ultimately wanted to enter. I wanted to be a writer, and I learned a great many things about the industry by being an assistant to a mentor I admired deeply. The job was also part-time, and it allowed me the flexibility to put in work on my own projects. In the end, it was exactly the gig I needed to re-route my career and move toward my ultimate professional goals.
Sometimes, a step backward can actually be a step in the right direction. If you’re rebooting your career, it might mean starting at the bottom of a new field (and you might find yourself at the bottom again and again). But that's okay — especially if that field is your Field of Dreams.
Illustrated by Paola Delucca.
When I was offered a job as an executive at a prominent television network, I put my dreams of becoming a writer on hold. I was initially reluctant, until I saw the number of zeros my yearly salary would contain. My lifestyle shifted significantly, and I began earning a considerable amount of money. But I felt, once again, that I was trapped in a career that wasn’t quite right. I worked with a lot of wonderful people and made some excellent contacts, and I don’t regret taking the gig at all. But soon, I got used to all that money, and I stayed at the job longer than I should have (there might be a pattern in my career path). When I was ultimately let go due to corporate downsizing, it was actually a blessing in disguise. Although I spent liberally during my time at that particular job, I also saved a significant chunk of change. I had no excuse to put off my dream of being a writer once I had a nice amount of savings to fall back on.
Money can’t solve all your problems, but it certainly can solve some of them (and also enable you to shop at Opening Ceremony). Bottom line: Sometimes it’s smart to take a gig just for the money. Money can pay for a delicious dinner, end some credit card debt, and shut up Sallie Mae. But money can become a trap when all that cash comes from a job that’s destroying your spirit. If you’re making a ton of dough, make sure to save some for that rainy day when you bail on your soul-sucking job and go for your dream.
Illustrated by Paola Delucca.
After I was downsized from the television network, it was time for my Career Reboot Round Two. This meant confronting a frightening reality: If I was going to make the leap to become a TV writer, I needed to move from New York to Los Angeles. Starting a new career in a new city was one of the scariest things I’ve ever done. I knew few people and came with few contacts. But over the course of the year and a half I’ve been here, I’ve signed with a major management company and agency, and I've pushed three separate television projects into development. By moving to L.A., I boarded the scariest professional roller coaster I’ve ever been on. But it’s also the most rewarding.
In my career thus far, I’ve found that most equations for success have an unexpected common denominator: fear. The periods of life in which I’ve made the most professional progress have also been the scariest. But courage doesn’t mean ignoring the fear we feel when taking risks. It means embracing it. In my own career journey, I’ve found that the moments when I’ve stepped out of my comfort zone and embraced the struggle are also the moments when I made the most advancement. If you have a big dream, it’s going to mean taking big chances.
Illustrated by Paola Delucca.
In addition to writing for TV, I also write extensively for many online outlets. Being a freelance writer means constantly pitching ideas to publications and often coming up against rejection. It has gotten easier, as I’ve developed relationships with outlets and editors who believe in my work. But starting out was definitely a challenge. My first published essay took considerable time to find a home. I pitched it to approximately five different publications, all of which came back with a firm “no.” Refinery29 was the first “yes” I got. They published that essay, which ultimately went viral. This was my first step toward a career as a freelance writer, and one that only came because of my persistence.
There can be a lot of rejection along the way to success, but I’ve learned to use that rejection as fuel for my ambition. The “nos” will come from every angle. But racking up tons of rejection is actually a good thing — it means you’re really putting yourself out there. All it takes is one “yes,” and that “yes” will likely come after a stream of steady “nos.” That doesn't make that final "yes" any less legitimate.
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