hen I think about my relationship to work, I often think of my parents. They both took traditional career paths in fields whose only appeal was their stability and structure. They both worked — a lot; they came home and made dinner; they saw friends on the weekend or watched my brother play soccer, watched me in a play. I remember the year my mom went a bit wild with what I now recognize was boredom: she started spending her evenings at an astronomy class and bringing home bags of fabric to teach herself how to quilt. My dad spent three weeks at a cooking school in Italy one summer and came home with a pierced ear. Their work served their lives, and not the other way around. Today they look at me, a freelancer, with a mixture of pride and confusion, and when I complain about chasing down checks or being dropped by a client, they shyly nudge me back in the direction of a more traditional career path, something that might not keep them up at night.
Yet research conducted by the Freelancers Union shows that more than 55 million Americans work as independent contractors, a full two million more than two years ago. By 2020, 43% of the U.S. workforce will be freelance.
Part of this trend can be attributed to the stagnation of American wages and the decline of reliable pensions, requiring some to rely on the additional income generated by freelance labor. Another factor is the rise of millennials in the workforce, who state a stronger preference for freelance work than any other generation, desiring the flexibility and fulfillment that comes from being able to construct your own career.
I didn’t go freelance because I felt I had anything particularly potent to contribute to the world; what I had was a weird, crystalline moment on the floor of a midtown Bloomingdales. My best friend had called to tell me her dad passed away suddenly, and I had the very clear thought that I was not living the life I wanted to be living. I was making good money in an industry I despised, and I was four years into being single in New York, no closer to the life I knew I wanted. So I quit my job and moved back to Canada to try to realign my work and my values.
But since I went freelance three years ago, there is not a day that has gone by that I haven’t thought, “Wow, this was a spectacularly bad idea.”
This is partially due to the fact that I’m a slippery, jealous eel, constantly being thrummed by that frisson of energy that whispers, “Everyone is doing this better than you.” Since freelancing requires constant hustling, stringing together gigs and clients, there’s the sense that I could always be doing more. But it is also due to what many people cite as some of the allure of freelancing: the freedom, the control, the ability to design your own schedule and watch 17 clips of Say Yes to the Dress in the middle of the afternoon while marinating in old sweatpants, for example. Freelancing asks you to put a lot of stock in the work you do — to treat your job not like a thing you do for money, but rather like a lifestyle, a deliberate choice.
Many people working traditional jobs think the freelance life is incredibly enviable (and in some ways, it is); but there are others who, having done it, wouldn’t go back if someone paid them. (They won’t. You’ll never get paid.) I met Logan when she was editing at The Billfold, a personal finance publication she founded. I was cobbling together a side hustle as a writer while working full-time, and Logan — freewheeling, day-drinking Logan — was everything I wanted to be. Now Logan works at an insurance platform and has a great haircut, and I’m about 4,000 Twitter followers away from any semblance of relevancy. Recently, we chatted about the freelance versus 9-5 binary, to try and find out whether the grass is ever greener on your own side of the pond.
On the fantasy versus reality of freelancing
Logan: Everything I liked about working freelance I basically only liked in theory, and it all revolved around the ability to own my time. I’m still attracted to that part of it, but for me at least, it never really worked out.
The dream was to go on a long walk in the middle of the day, to meet friends who are also freelance in the middle of the day, to not get out of bed until the middle of the day, to knock off for happy hour at 4PM. (To not … work?) Whenever someone Instagrams from Central Park in the middle of the day, or posts a picture of a cake they just baked to procrastinate for a few hours — that’s the stuff that makes freelancing really attractive.
Meghan: There is, of course, an incredible freedom to being able to design your own days, and to be able to do things like go see a matinee or just get your grocery shopping done when the store is empty, but that also means there isn’t really an off switch. So while I might not get going until 11, I also work through the weekend. Freelancing draws such a weird veil over real time. Like, I used to have a 9-5, I recognize that I managed to do that and also do laundry, but now I am completely boggled by that fact. Time is so amorphous to me now. I genuinely don’t know how long I spend on tasks, where days go.
And I don’t take vacations, really — I just work from wherever I am that day. I’ve been able to travel more in the last few years because of that fact, and that has been a gift.
Logan: Yeah, the ability to work from anywhere in the world — this was a big one in the dream column. Even now, I daydream that if I were freelance I could go spend a few weeks working from England or Mexico or whatever. But I snap out if it, because in the three years that I was freelance, I never did this. Mostly because I could not afford to. Rent was enough of a stretch.
I’ve also learned that I operate much better with the clear lines between work and personal life that come with a standard job. I almost never work from home — if I’m sick, I take a sick day and don’t work. If I’m out of town, I take vacation and don’t even kid myself about working remotely. Those lines are important to me, and they’ve really helped me be more productive at work and enjoy my downtime more.
The reality of freelance, for me, was just constant guilt. I couldn’t enjoy doing anything during the day, because I felt like I should be working. I’d do it anyway — sleep in, run errands, fuck around on the internet — but it never felt good. Plus: I often told myself I’d just do the work at night, which was even worse. It got to the point that no matter where I was or when, I was feeling guilty for not working!
Meghan: Guilt, yes — that is definitely a freelancer’s primary emotion. In a lot of ways I have absolutely the worst kind of temperament for freelancing: I love control and structure but I really struggle with self-motivation, and I fall into really ugly spirals of guilt and shame when I’m not working. I think a lot about how wasteful I am — how I have all this time, no real obligations, no children — and what am I doing with it? Not enough, clearly.
On the concept of a “dream job”
Meghan: So, this is meant to be my dream job — I’m making my living (kind of!) as a writer — but what that actually means is that I’m making money doing service journalism, ghost-writing content for brands, and editing powerpoints, and every now and then I get to write a personal essay or two for much less money. I’ve lost contact with my writing as being artistic or creative, because I’ve commodified it, and that makes it very difficult to envision a way forward that leaves room for projects that don’t have an immediate financial reward.
Logan: I don’t even know if I have a dream job. I think if I’ve ever had one, it would be being like, a New Yorker writer who works on long stories, like Kathryn Schulz or Ariel Levy or Elif Batuman. But my freelance writing never looked like that. I think about ideas a lot and then talk myself out of doing them, because I feel like I just don’t have the energy. Like I’m going to work all day and then come home and do interviews? Can’t do it. You may recognize these as excuses, which they are. Over time I realized, you know, if I REALLY wanted to do this, I would do it. Even when I was running on my own site, and could have done literally anything I wanted, but I always let myself get bogged down in the daily work. A post that needs to be up in an hour, I can do. A long story I might post down the line? Always back burnered.
Meghan: I do the same — back-burner long projects, hesitate to start something I won’t be able to finish quickly or that doesn’t have a clear deadline. What is that about?
Logan: I think a lot of this is time management, which I still have issues with. My boyfriend is fantastic with time management, and the past year and a half of living with him has really been an incredible front-row-seat to what is possible if you commit to do a little bit each day. He’s learned Spanish in a year, is writing a novel. It’s rubbed off a little bit, but it’s much harder for me to stick to things. I’m sort of at the point now where I feel like, my innate skill-set does not include time management or bookkeeping, and it’s much better for me if I work somewhere where the bulk of those things are done by someone else.
Meghan: Now that you’re back working full-time, have you created space for yourself to explore things like that — hobbies or creative goals? Part of why I went freelance was because I never made that space for myself — I left work completely drained, and couldn’t fathom the idea of waking up an hour early to work on my novel or stay up into the night typing.
Logan: I did make a goal when I started my most recent to job to write 500 words a day at lunch or at the end of the day. It’s sort of touch and go, sometimes I’d do it, sometimes I wouldn’t. I have about 40,000 words now, but it’s not really clear if it’s anything. I’m at a point in my career and life where I’m figuring out what I’m capable of and what I want to be capable of. My 20s were about surviving, basically, and also dreaming — once I pay off this bill, I’ll do this; if only I had this job, I’d do this. Now I’ve got more data about what I’ve actually accomplished or pursued in different situations, so the dreams have mostly gone away. Like the dream to work abroad for long stretches — I know now that isn’t something I’d enjoy. If I’m going to travel, I’d like to be on holiday. When I read articles and start to think, I wish I could write this, I think about the journey, the sourcing, the research, the interviews, and I feel like I could do it but I’d be so stressed out.
A book contract is a dream I’ve also abandoned. I think I’d still like to write a book, but it’s something I know now that I’d have to fit in around my other job. I know enough people who have written books and are still working full time. Have you seen Can You Ever Forgive Me? There’s a truly harrowing scene when Melissa McCarthy’s character is in her agent’s office asking for anything, the smallest contract, anything at all, and points out that Tom Clancy is making millions, and her agent is like, “You’re not Tom Clancy.” I’m not Tom Clancy! None of us are!
Meghan: I still want to write a book. I do! But you’re right about it not being a solution financially. I mean, look, there’s an immense amount of privilege inherent in being able to choose a job based on what will fulfill you, and not just what will pay the bills. I try to be very careful about being fully honest about the reality of my situation: I don’t have any debt, and my husband has a reasonable salary with good medical coverage. That’s what makes freelancing possible. I was pulling myself along well enough before I got married, but I had savings from my old job and socialized health care. I would never be able to live the life I’m living now if I didn’t have a stable partner. That’s been a difficult pill to swallow, just in terms of my identity as a woman. Of course there are those people who are able to make more money freelancing or designing their own careers than they could in traditional ways, but it is an infinitely less stable path.
On allowing our work to define us
Logan: The default question in our society when you meet someone is “What do you do?” I’ve been laid off, I’ve been unemployed, and when people asked I’d just say something like, “Right now I’m freelancing,” or “I’m in between jobs but I work in marketing.” This has gotten easier to say breezily the older I’ve gotten, as it feels more true. I did go through a period of trying to ask other questions than “what do you do” when I first met people — how do you spend your days, what are you excited about, but I think most people know that the intent is to try to understand a little more about who you are, and not to like, place you on a dot matrix of job worth.
But also — I don’t get my identity from my work. I’ve never had a clear view of a vocation or whatever, and never any larger or cohesive plan. I’ve never said I’m a writer, even though that’s how other people identified me at times. I guess running The Billfold was one time when I did get more of an identity from my job — like, saying I ran a website was the only time I had a cool (“cool”) answer to the question. But I knew the reality — that I was broke and depressed — and so even when people were like, “oh cool, tell me about it,” I’d be like, “IDK it’s fine, can you tell me about your job so I have something to post about? “
I think I spent a long time thinking my job WAS supposed to fulfill me and then feeling bad that mine didn’t. I’ve done the exercises in “What Color Is Your Parachute” or whatever a zillion times, and ultimately it’ll be like, you should be in a helping position, be a nurse! And then I Google what it takes to do that and it’s like, forget it. The thing is, life is hard and then you die, and various things can make life easier — good friends, a good partner, a job you like, a routine you like, a good SSRI — but nothing changes that basic fact. So for me, having a job that doesn’t stress me out and lets me leave work at work is what helps make life a little less hard, for me.
Meghan: The weird thing about trying to shoehorn your passion into your job is that then your passion becomes this pressure, this weight. As a “professional writer,” I produce more, but the work I’m producing doesn’t feel like me — it feels like work, and in order for it to be successful and efficient as such, I have to detach from it to a certain degree. One of the things I really want to commit to next year is to find my way back to the joy of it, but I’m not sure how. In the meantime, I’m trying to find other ways to be creative, to build a bigger picture of who I am: a loving and supportive partner, a giving friend, an attentive sister and daughter. I’m joining lots of clubs and looking to volunteer more. I’ve walked far enough down the path of being a freelancer to know that going back to a more stable job that provided an income and a structure would be difficult, but I entertain the thought all the time. I think, too, that going back would feel a bit like giving up — I couldn’t hack it! I failed! — and that’s another tough pill to swallow.
It’s Friday afternoon. I’m writing this from my best friend’s house in LA, where I flew last night. When I finish, I’ll edit a corporate blog post, log my hours, check to see if my last invoice has been paid. Logan will just be leaving work now — it’s 5 p.m. in New York. I imagine her turning off her computer, walking home through the cold dusk to her apartment, leaving work behind. I’ll snatch hours through the weekend where I can, through Christmas, too, although work has slowed down and I’m nervous about the month ahead. I don’t know how much longer I’ll be able to live this life, or how much longer I’ll want to — whether I’ll start craving the community of coworkers, the structure of a daily schedule, the relief of knowing when and where my next paycheck is coming from. For now, I’m trying to be grateful for this freedom and for the chance to ask these questions.
Are you a freelancer? Do you wish you were? Are you doing what you love — and if so, how did you figure out what that was? Sound off in the comments, please.
Illustrations by Ana Leovy.