You're going to be tired either way
On holding down a day job and still writing
I’m writing this in the 20-minute blocks I have to spare between meetings at my day job with an advertising and marketing firm. I run a team of about 20 writers — mostly ex-journalists — who do an exceptional job of turning rough briefs from big companies into stuff that actually makes sense. I’ve been doing some form of this for the last decade. In-house with tech companies, as a consultant to media companies, and as a freelancer on the commercial side of things. It was actually what I did for a long time before I ever wrote anything as a journalist. As I say to people who ask such things, I started my career backwards.
Just speaking anecdotally, it seems to me that most non-staff writers have some sort of commercial gig to support them. Even though I’ve been writing like a maniac the last 18 months, there’s no way I could have supported myself living in Brooklyn on solely editorial freelance stuff. My NYT work averages out to about a $1/word, and the online writing I do for major outlets comes up just short of a grand most of the time. The very rare print mag work I get is great, but I think that was maybe like $5,000 total in 2024. I’m a little bit of an anomaly in that I have a full-time day job rather than just a smattering of commercial clients, but it’s not dissimilar from what I know is the case with a lot of writers trying to scrape together a living.
The nice thing about having a day job is that I have the financial breathing room to pitch stories I actually want to write about. But the probably annoying truth about my setup is that I work a lot. I work in the gaps in my schedule during the day at my office job, I work before and after that job, I work late at night, I work on weekends, I work on vacations. I once filed a piece for a client from a seafood shack on a secluded Croatian beach where I had my friend ask the Toni Kukoc-sized bartender for the WiFi password. I know I sound like Sam-I-Am in Green Eggs and Grindset, but the dumb secret to all of this is that I have an debilitating addiction to work1. How does that work in practice? There’s not really a secret to any of it. I’m very blessed to have a day job that knows my editorial work is important to me and also trusts me enough to know I’ll prioritize my work for them because they’re paying my rent. There are tradeoffs, especially with scheduling. If I’m working against a deadline for a paper or magazine, I also know that my schedule is more compressed than it would be if I didn’t have my job. I use vacation days to do reporting, and know that sometimes I have to switch interview times at the last minute if a meeting pops up on my calendar. I am always looking for time in the sofa cushions because I have a lot less of it than other freelancers.
I won’t bore you with the details of the psychology behind it, but suffice it is to say that I feel like I’m consistently playing catch up with people who have been in media since they graduated from college. But I also love it, or at least love the pursuit of it. Like, this is what I wanted to do and be and I fear that if I don’t commit myself to it fully the opportunities will slip away completely. I am slowly coming to the realization that perhaps my position is not fully ephemeral and that, maybe, I should sit down and focus on a book proposal or longer projects. We all have doubts about ourselves, and I don’t think that ever goes away.
This is going to sound trite and boomerish: You have to want it really badly. It’s the advice I give to younger writers who ask how I maintain both sides of my life. You have to take stock of what you want from your career and what you want your life to look like and base it against a 24-hour clock that only moves in one relentless direction. Doing things the way I do them is hard, and probably harder than most people’s common definition of hard2. That isn’t a brag; I have cracked myself open several times because of it3. I’ve turned my desire to write into the main gravity sink in my life, the thing I bend everything else around. I think about something
wrote a while back, about her mantra being “When my eyes are open, I’m working.” That in itself is very grindset-coded, but it’s also unfortunately extremely effective. I’ve spent the last 4 or so years of my life in a sort of permanent semi-exhaustion. There’s always one more idea to pitch, one more piece to write, one more assignment to say yes to. I do not suggest doing this to yourself. And I’m not saying that to cloak myself in inscrutability, but this way of doing things comes at a cost and that includes ones I’m probably unaware of. I wish I had more practical advice to offer people who are trying to balance two careers, but most of it boils down to desire and time.Last summer, I had breakfast with the writer André Aciman. He abandoned his academic career in the 1980s after earning a PhD in comp lit from Harvard. There was just no money in it and he had a family. He became a stockbroker and, later, worked in advertising. But he always wrote in the gaps where he could. He published his first book at 44; Call Me By Your Name wasn’t published until he was nearly 60. I had come to André to ask if I should drop my career and pursue an MFA and through a sly little smile he said, “absolutely not.” “You need the day job, both to keep you stable and to keep your desire,” he said. I appreciated the candor of that advice, both because of his stature as a writer and because it reflected a practical philosophy I could immediately identify. Desire can pull you forward or pull you apart and sometimes you don’t know the difference.
And I guess people want to probably hear about money? When I was pure, dedicated freelance in 2021 — and please keep in mind, this was after like a decade of trying to build up clients etc. and people were spending a lot of money on digital content because of COVID — I had to check my tax filings but I clocked $300k which I know is sort of insane but I was also working 80 hours/week half the year and was on the verge of a mental breakdown. 95% of that was from commercial work at agencies and brands. Was it worth it? Idk, I have some nice clothes I bought that year and bought my brothers PS5s. We’re in a totally different moment in “content” right now, though, so I very honestly think that number was lightning in a bottle. I was writing coffee table books for remote productivity platforms in 2021. It was a weird time.
I hate to say this, but I do think there is a misunderstanding of what ‘hard’ is for a lot of younger writers. Listen, this isn’t investment banking. There’s no glory in working 80-hour weeks and your hair falling out to get paid six-figures to go to The Blond every Saturday. But the sense I get is that the amount of work I do before and after my day job is beyond what some writers deem is an acceptable work/life balance—which is totally fine and probably very healthy but not a great way to grow your career sadly.
I’m lucky in that I don’t have much in the way of personal responsibilities, i.e. I’m not a caregiver for anyone.
I was like this and then my doctor told me the reason my legs no longer fell straight and always looked bent was that I’d sat too much. For years. So I’d say: Work hard but take care of the body that has to do the work.
You're the best. I'm so glad you wrote this!