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I’m worried I’m going to hate every job I ever have. Not just worried but petrified in a really low-energy, demoralizing, soul-eroding kind of way. I worry this because I’ve at least disliked every job I’ve ever had.
I’m a journalist or a writer or whatever. I’m only in my early 20s, but I’ve had 11 jobs, starting with working as a counter girl in my local takeout place at age 14. Since then, I’ve been to college, which I loved and where I thrived, mostly I think because my learning was self-directed and I got to run my own life.
I interned a lot while at college, I did a year abroad and interned there, I worked on the student paper, I did a radio show, all in the hope that I wouldn’t have to intern anymore once I graduated. Spoiler: I did. I interned some more for nearly a year after I graduated and lived with my mom to help fund it. Then when I finally landed my first job, I wound up working for a big sexist bully who belittled me at every turn and ripped every article I wrote to figurative (and sometimes literal) shreds. I left the company after three months. I felt like a huge failure.
I got another job doing branded content because by this time I’d moved out and couldn’t afford to not have a job, and hey, maybe advertorials would be my thing. Spoiler alert: They weren’t. I hated client work. The department was falling to pieces because of a few poisonous toads that the management refused to deal with and allowed to spit their venom all around. I left after nine months.
I got another job, and I now I write TV pieces for a website. I like the content of my job — I love writing and what I write about; that has always been the one thing that’s kept me going and looking forward. But as I settle in, the more I realize that this job is little better and, as usual, it’s the people I can’t stand (I’m sure they can’t stand me right back).
I think I know what I want. I want to write about a variety of at least semi-meaningful (to me) topics in an interesting way, and I want to go freelance because I can’t stand working in offices, churning out puff pieces.
I’ve worked for start-ups, small firms, and huge corporations, and there’s been bad management, bullying, backstabbing, bitching, and bureaucracy at every one. Not forgetting the big board of fossilized white men belittling everyone.
I’ve come up with a two-year plan in which going freelance is the goal (it was five-year, but I don’t think I can bear to wait that long). I hope to buy a treadmill desk at some point. Thing is, I’m petrified of going freelance, too. Petrified like I just saw a basilisk reflected in a puddle. I’m not sure if that big scary snake is me or the thought of trying to survive off writing alone.
I want it so badly I’d write anything to get by: product descriptions, banner ad copy, words to go on toilet-cleaner labels. Anything. I’m willing to get a part-time job to fund it, too. Except I know it would be a stupid idea to even try before I’ve saved up at least three month’s pay. But as I can only afford to save a little each month, I’ll have to wait two years at least before I’ve amassed that amount. And I can’t start while in my current role as we’re not allowed to take other paid work.
I also don’t feel like I’m ready. I want to be edited still. I still feel like I need a lot of molding before I’d even be close to being able to pull off the kind of pieces I want to write.
So I guess my real question is how do I stop hating my job long enough to quit it and go freelance? And how do I know I won’t hate freelancing just as much? Am I just a thin-skinned snowflake millennial who needs to get over it and accept that this is working life?
A Highly Strung Spurnalist on the Brink
At least once a week, someone new writes to me, worried that they might just be another thin-skinned snowflake millennial. This is a big problem with global connectivity that we didn’t imagine 20 years ago, when the internet was young. We thought it would be amazing for every imagined demographic and subset of society to find each other, but never conceived of the endless waves of stigmatization therein. Today, I’m convinced that social media makes it impossible not to feel deeply self-conscious about literally every trait, every preference, every choice you might make. Things as simple and as understandable as loving Harry Potter or Star Wars or Beyoncé throw you into some embarrassing subculture of predictable humans, with a universe of memes to sum up your deeply flawed existence.
But if you subtract age from the defining characteristics of thin-skinned snowflake millennials, I am also a thin-skinned snowflake millennial, and I want to strongly recommend it as a lifestyle choice. Why? Because it keeps you away from offices, which are places where all sense of time and space evaporate and all connection to your own desires and longings, to your own humanity, to the natural rhythms of existence, steadily erode until your life feels like a shadow, haunting a dim facsimile of what a life is supposed to feel like. (Spoken like a true thin-skinned snowflake, the kind who hasn’t worked in an office for two decades!)
That said, the “bad” people in most offices are a by-product of this obliteration of space and time and natural human connections. Archaic systems, outdated hierarchies, and illogical procedures reign. Stepping into such absurd little fiefdoms in your early 20s is maybe one of the most painful and jarring life transitions — and if you’re an outspoken, make-your-own-rules type (or a “thin-skinned millennial”), you are likely to make exactly the sorts of noises that will have everyone around you rolling their eyes and distancing themselves from your self-styled low-key acts of rebellion. Which is understandable on both sides. You can see how stupid their world is, and they can see how naïve and impossibly unwilling to play nicely with others you are.
My recommendation is that you keep your two-to-five-year plan but, in the meantime, you train some of your energy on learning to eat some shit and play nicely with others. I say this as someone who only learned these skills very recently, who never bothered to slow down and empathize when I was your age. I considered myself a completely different species of animal from the ones who thrive in offices. This was a superiority complex, but it also fed into my insecurities and feelings of persecution. It made it hard for me to take edits with an open mind. It made me prone to writing off a big chunk of the population. It probably also impeded my friendships and my love relationships and kept me petulant and immature for a long time.
The truth is that you can be polite and back down and go with the flow without losing your sense of yourself or losing your ability to see the bullshit clogging up the machinery around you. Lots of people do it. And when people can trust you not to be a hothead who speaks out of turn and criticizes people who are just struggling to get shit done, they tell you about how they balance the contradictions and troubles of the workplace, and you can learn from them. They also pay you better.
You need these people, too. Freelancing is impossible without solid relationships with editors, and my whole career didn’t really take off in the ways I wanted it to until I learned to be consistently kind and polite to all editors, even when they pissed me off. I’m not saying I never revert back to the brat I was years ago, but most of the time I recognize that the people I work for are really fucking busy and overworked and they aren’t dismissive of me or out to get me, even when that’s where my brains used to go on a bad day. So this is the hard truth: You won’t be able to freelance until you learn to be consistently kind and grateful to your co-workers, recognizing that, even though they sometimes reflect the deeply wrong nature of any given workplace, they also have a million-and-one personal challenges that you know nothing about. And yes, that includes the fossilized white dudes in the corner offices.
Moreover, once you trade in all of the stale burning coffee pots and cheap birthday cakes and dull meetings and incompetent goons of office life for a freelance career, you need to know that you are always, always replacing one team of dehumanizing demons for another. Because when you work from home, you have total control over your day. All of the conditions and the people you used to blame for your bad mood and bad work output are condensed into one single source of blame: you. You are your own alternately slack and merciless boss. You are your own alternatively engaging and tedious co-worker. You are the one whose inability to meet a deadline is taking down the whole ship.
And as a writer, when you start to fear your own shortcomings, you access the years of fear that came before it. You experience something like a traumatic flashback to the other times you were paralyzed, unable to move forward. And as a beginner, you might think, “Oh, but once you get used to it …” or “Oh, but once you’ve made a name for yourself …” But it’s not really like that. You don’t just wear a crown and then you’re king and all of your decisions are the correct ones. You are Jon Snow, doubting every move as you make it. You are Daenerys Targaryen, wondering how many innocent humans your dragons will have to incinerate just to take out Cersei.
Because if you’re doing the freelance writing thing the right way, you’re not just writing words to go on toilet-cleaner labels. Over the years, you’re narrowing in on the things you love to write the most. It’s good that you’re prepared to write anything right now, but that may not be the case for long.
And the stuff you love writing changes. You have a beat for maybe five years and then, unless it’s really engrossing, you get burned out. One of the problems with covering TV is that it’s tough to do it forever. You get really good at it and then you’re fucking done. Personally, I can’t go back and analyze the plot structure of another drama, or unpack the same adjectives about some actor’s very good acting yet again. That feels rudimentary now. Most writers crave a new challenge regularly.
But it’s hard to have that kind of freedom as a writer. And even when you have it, it’s still hard. These days, I have three different kinds of deadlines going at once, including this column, a book, and a big project I don’t have a clue about how to complete. All I know is that I have to get up early, walk on my treadmill desk, and drink tea in order to access some functioning brain cells along with the will to make forward progress on any of it. The rest of the time, I pick up my work and say, “What the fuck is this?”
In some ways I was more fearful as an inexperienced writer, and in other ways I’m more fearful now that I know that I can’t stand not to set the bar higher and higher. My fears don’t circle around talent; they go deeper: Are you sure you can do this? Are you actually a quitter in disguise? Are you a charlatan? Are you lazy? Pretty much anything that has ever scared me can be thrown into the mix during a trying period.
But I also love that part of it. I love facing myself, possibly because I’m a masochist. I love having a new chance to create something unexpectedly good each morning, even if that often means creating something unexpectedly bad, too. And look, I’m a strange combination of lazy piece of shit and overachiever. I avoid and delay and I also own a fucking treadmill desk, for fuck’s sake, and I use it.
Having a freelance career is a little bit like buying a treadmill desk. This is a big, expensive thing that has the potential to make you feel guilty around the clock. You have to dive right in and work hard if you don’t want to feel like shit. But it is really, really hard to start walking and writing at 7 a.m. every morning. Your body tells you that it’s an idiotic thing to do. Your brain says, “This is absurd” and “This is too hard” and “What is wrong with you?” But once you commit, once you start, and you’re engaged with your work and you’re also exercising, you feel like the sort of person who can take on new challenges without freaking out. Even though half of the time you don’t feel like that person, you do feel that way after a few hours of writing and walking.
That probably sounds a little esoteric. I guess I’m stuck on the fact that you mention getting a treadmill desk. Even though you’re struggling with the basic dilemma of hating offices but fearing how well you’ll fare on your own, the treadmill part suggests that you love the idea of overdoing it, of hitting it out of the park, of toiling like a motherfucker in silence, away from distractions, away from the bullshit of office life. I mean, that’s what freelancing is. Even though I feel like I’ve willfully turned myself into a mutant by living this way, I really had MUTANT in my sights from a young age forward. I wouldn’t have it any other way. I think I’m capable of joining the world now, but I don’t really want to go to an office and collaborate for more than a little stretch here and there. I don’t want to tie together things I found in the wild with things other people gave me. I want to dig for something strange in a deep, dark, airless pit, alone.
That probably sounds terrible to most people, but if it sounds like you — and just from the style of your letter, I’m going to say it does — you should follow your plan and go freelance once you have a financial safety net and a few more years of working well with others under your belt. Just don’t wait to start writing. Go to your boss and carve out what kinds of writing you can do for other places. You probably can’t write about TV for another publication, but you can write about other topics and it shouldn’t be a conflict of interest. If the rules have completely changed and your employer wants to own every idea you ever have, then (1) That’s stupid and fucked up and (2) You should put on your turbo jets and save like crazy and also write like crazy. So wake up early, brainstorm, write. Make a list of pieces you want to write and keep adding to it. Research. Give yourself weekly deadlines.
And don’t immediately say to yourself, “Oh, look, I have zero ideas, I am failing to meet my weekly deadlines, I must not be cut out for this.” Don’t say, “Oh, God, this fear is horrible, I am bad with fear, I must not be someone who can freelance.” Don’t say, “Oh, Jesus, I’m just a snowflake who hates everything.” Go look up “writer” in the dictionary, and you will literally find “n. a snowflake who hates everything.” It’s good to know at an early age that you’re particularly ill-suited for office life. But you still have to recognize that the people around you are more like you than you think. Offices bring out the worst in everyone. Make it your mission to treat them with compassion and patience, knowing that they’re doing the best they can with their own big anxious brains and oversensitive souls. Cultivating your empathy for the people around you, in spite of their flaws, will help you in more ways than you can possibly imagine.
And cultivate compassion for yourself, too. You want to write, but you’re never really going to believe that’s the case until you’re halfway through your third draft. You’re going to walk around saying, “Maybe I’m just a talentless fuck who hates everything” for the next three or four decades. If you can tolerate that, and still get up in the morning, and still look in the mirror, and still sally forth, then you are made for this life. It’s a good life, but you will work hard. You won’t have tons of cash, and then you will, and then you won’t again. Expect it. It’s fine. You just have to notice how much you love the work itself. Plenty of writers don’t notice that. You have to notice it, as much as you can. You won’t enjoy your life if you don’t.
And honestly, a lot of writers don’t know how to enjoy their lives. They tell the same old story about how much they’re suffering all of the time, how they labor away in obscurity, with zero rewards. They want to tell you about their disappointing book tours, and bitch about how much attention this one writer gets. “But why? He sucks! Why are people so stupid?!” I love this kind of talk, and I don’t abstain from it, not remotely. But for some people, this is the whole picture. The whole reason to write is to matter, to be seen, to be somebody. And you’ll find that even when these people make it by most standards, it’s never enough. It’s not just that they have new projects they want to complete. They want MORE, period. More attention, more money, more fame, more glory, more more more.
No matter what you do for a living, the only thing you’ll get more and more and more of is hard work. So figure out what kind of hard work feels satisfying to you. Learn to enjoy the hard work, and learn to enjoy the times when you’re not working, and you’ll learn to enjoy life itself. And when you have a tough day, by yourself, not writing a word, remember that your goal is not just about one day’s production, or about making a name for yourself, or about achieving perfect independence and financial security. Your goal is to enjoy your life, period. Your path is unique and very difficult, and it doesn’t lead to some promised land. The path itself is all there is. And if that sounds fucked up and perfect at the same time, you’re already on it.
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