“I’m Winging It But I Have Hope”: Top Freelancers on Freelancing

Anne T. Donahue, Danielle Henderson, and Devon Maloney dish about debt, jealousy, and other features of the writing life


In many ways, Anne T. Donahue, Danielle Henderson, and Devon Maloney have made it: they get to voice opinions for a living and still take the occasional afternoon nap. But how does freelancing full-time work, financially? Practically? They sat down (in a matter of speaking) to have a frank, self-moderated discussion of the pitfalls and pleasures of their chosen path.

This conversation has been lightly edited and condensed.

DH: How long have you been freelancing?

ATD: A solid seven (holy shit) years. Jesus.
DM: I’m going on four, but even that feels like a lifetime.
DH: Five years. Five exciting, nail biting, seat-of-my-pants years!

DH: Tell me about some of your scariest freelance moments: waiting for checks, losing jobs, etc.

ATD: Well, I personally lost my apartment, which sucked a lot. I had no business moving out in the first place (at the time I was 24 or something, and making about $800/month — on a great month), and rent was $1200, so I put everything on credit and it was a disaster. Then one late cheque pushed it all over the edge about a year later, and I was back at home.

That said, I think that also had to do with extenuating circumstances that weren’t part of freelancing at all. I was a mess mentally and emotionally at the time, so I could’ve been working a 9–5 with sustainable salary and I know it still would’ve ended badly. It was bleak.

DH: Anne! I hate that it happened for you but I love that you pulled it together.

I had my scariest moment this year. For the first time in 20 years, I was late with my rent while I was waiting to get paid, and it sent me into a pretty depressive tailspin. I’ve always prided myself on being responsible and taking care of myself since I have no family to step in, and it scared the shit out of me to think that I couldn’t do that, even if it wasn’t necessarily my fault. Some publishers legit do not care if your life is completely upended by their inability to pay you within 30 days. And I’m like wait, you have regular 9–5 employees that you pay every two weeks, right? Why is this so hard?

DM: More like 90% of publishers. Honestly, seeking out “clients” that (a) pay enough, (b) pay on a reliable schedule, and (c) take enough of my pitches on a regular basis is a Sisyphean struggle. You know how they say, when it comes to creative output, there’s cheap, fast, and good, and consumers (or publishers, in our case) can only have two of the three? It never occurred to me until just now that that works the other way, as well.

DH: Are you ever jealous of the way some freelancers make it look like the easiest thing in the world?

ATD: I’m not actually! It makes it feel like it’s something I can do too. Like, “Oh she must be working super hard! I’m going to work super hard too!”

DH: Not jealous per se, but I do wish some writers were more transparent.

DM: Hell, I am. Not that I think it’s ever easy, but I know it’s a lot cushier for people who ventured off on their own later in their careers, just as “freelancing” started becoming the only way a lot of us can make a living. So yeah, I do deeply envy writers with consistent, high-profile contracts. You know, the ones where GQ or wherever pays you X amount a year to do X number of major print profiles? There’s an upper crust in the freelance writer world, for sure, and I have no problem saying I hardcore thirst to be there eventually, hopefully sooner rather than later.

DH: Let’s talk money stuff, including invisible safety nets like parents, spouses, trust funds, etc., that can make it look easy.

DH: Why aren’t more writers transparent about their support systems? You don’t have to tell me how much you have in your bank account, but some people who have these six-month long, career making assignments rely on other people for rent and stability. It seems a little false to me to be like, “I don’t know, I just made it happen!” when that’s not the entire story.

DM: I’ve never experienced that kind of luxury, but I will unequivocally state, for the record, that I could not be doing this without my family’s support. If I added up all the loans my parents have extended to me over the past four years, it would probably equal what I would have saved if I’d moved home instead of keeping my own place. I’ve definitely considered it many times, but I think it’s complicated for both parties: having a fourth grown adult in their little three-bedroom, one-story house (my brother does still live at home) might end in blood. So they’ve fronted me cash when rent was due and I hadn’t been paid yet, and helped with phone bills and utilities here and there along the way.

One of my darkest moments was when one of my credit cards was about to exit its introductory year of 0% interest. I was panicking, but my parents ended up paying it off for me, and now I just pay regular installments to them instead of twice as much to a bank. It’s not a trust fund situation by a loooong shot, but it has meant I have unending admiration for freelancers like you, Danielle, who are doing all this without that kind of lifeline.

DH: How do you manage your workload?

ATD: I get up by 8:00 or 8:30 every day, make coffee, throw a muffin onto a plate and get to work. I keep office hours (at home — I know) because I need structure, so I work until about 5:00 or 6:00, with an hour for lunch or so. Minus today, where an album release has me doing more work than normal, so I’m going to keep going until about 9:00 or so.

DH: Anne, that is so admirable. No matter what time I wake up, I usually get to work around 10:00 am. I answer email and do invoices while I have my coffee, then get to work pitching or working on the task at hand. I take a nap every afternoon because I can. Like, not to be THAT person, but naps are the main perk of working at home, beyond never having to put on pants. Lately I’ve been taking a formal lunch break, which is nice when I work a little bit later.

ATD: For the record, I stand by the choice to nap! Sometimes that’s what my lunch is! Bless rest (and cats who are willing to sleep for a few with you).

DM: Man, reading about my peers’ routines is so soothing, for some reason. I am unhealthy, so I start reading emails and Twitter from bed, as soon as I wake up, usually around 8:00. I try to get online between 9:00 and 10:00, after eating breakfast and making sure my dog goes out to pee and chase squirrels, or whatever he does out there. I’m an obsessive list-maker, so my day’s structure usually depends on whatever is on the docket I wrote out the night before, to organize and soothe my brain before bed.

DH: How and when do you set goals?

ATD: I am a robot that writes down everything I write in a month and then try and beat that number the next month. Basically, I’m competing with myself because I’m a monster.

DM: If that’s true, I’m terrified not to be a robot monster. Does anyone making a living as a freelancer get anywhere without setting those goals and making those spreadsheets? Big ups to Virginia Sole-Smith, another writer whose blog really helped me get my shit in order back in 2012 — I tend to share the links with every new freelancer I talk to, just because her ledger and color-coding systems are so intuitive and life-saving.

Now, just because I set money goals every month, or bigger career goals at the beginning of every year, doesn’t mean I actually meet them all the time, but at least I have a gauge of where I’m at at any given moment.

DH: Literally every day. I use the Bullet Journal style of journaling to organize my month, and then break it down day to day. I set professional goals annually on New Year’s Day, and revisit them each month to check my progress. And for the past 15 years or so, I’ve been making a giant list of 100 things I want to accomplish each year. I don’t accomplish everything, but I like having the roadmap.

DM: … Wait, I just googled “Bullet Journal” and this looks exactly like how I write lists EXCEPT SUPERCHARGED? Holy shit, Danielle, you might have just changed my life??

DH: The Bullet Journal is a life changer!

ATD: Danielle, I think I talked to you about the Bullet Journal at the top of the year! I have a notebook I write my monthly tarot readings down in and those are where my yearly goals are — but I try not to look at them because I like to be surprised at the end of the year.

DH: What are the positive or negative impacts freelancing has on the rest of your life?

DM: Honestly, sometimes I feel like my entire existence is defined by my identity and life as a freelancer. It’s made me crave solitude and struggle to socialize like a normal human being, which for an extrovert is a very weird thing to come to terms with. The truth is, most days I am working at home, by myself, only ever speaking to my dog, and even that’s just me squealing, “You’re so fluffy and cute!” in a weird voice intermittently as he stares at me, nonplussed.

On the bright side, I’ve learned to rely more on myself and less on my desperate need to please others (helpful in school, not so much in a journalism career). Also, I can’t really get fired, so whatever job insecurity exists is more like a perpetual state of uncertainty rather than a fear that I might suddenly be royally screwed over by a specific institution.

DH: I agree, Devon, that it’s a hard job for an extrovert to adjust to sometimes. As much as I love people, it’s really easy for me to isolate, particularly when I’m depressed. Freelancing is murder on depression in so many ways. Diversifying the work I do helps, but it’s weird that I have to remind myself to go outside so often.

DH: Do any freelancers ACTUALLY plan for the future? I feel like I’m constantly winging it and might not ever be able to retire.

ATD: Honestly, so much of my sanity and happiness is threaded through writing that if I couldn’t do it anymore I’d lose it. So for me the future is what type of writing I want to do and how I want my career to evolve and do I want to different types of writing and what would that look like, etc.

DM: I’m really nervous about that too. Like, I wrote a piece about it, and did talk to financial planners who said millennials shouldn’t really worry about it in a traditional sense, but that advice doesn’t really help when you see stories like this one right after (to say nothing about my paltry savings and IRA balances). It’s impossible to put money away when you’re struggling to pay your bills on a day-to-day basis.

DH: Yeah, saving in any organized way is sort of not happening right now. Getting an accountant has helped, but most of what I save goes immediately to taxes. I’m winging it, but I have hope.

DH: How do you motivate yourself to find work?

ATD: I think it’s a mix between challenging myself and appeasing my ego? I want to know what I’m capable of and I like scaring myself and pitching a new place scares the shit out of me. So chasing that high is a huge motivator.

I seriously sound like a sociopath.

DM: Same, honestly. I actually think this is one of the defining qualities of a successful freelancer, just by virtue of the ability to self-motivate with incentives that go beyond money. You have to be desperately hungry for a little visibility and a little glory and a little self-gratification (and also dedicated to working hard, or whatever) for this whole “career” charade to work.

DH: I tend to get performance anxiety around larger projects, because so much is often riding on them (the paycheck, thinking about how it might impact my entire career for better or worse). Is there a way around that? Or is it just the nature of freelancing?

DM: If anyone reading this knows the answer, I too would like to know it. Most of my freeze-ups, though, come when I haven’t been paid for a while. Making good shit can feel impossible when you get stuck in the vortex of, “Why am I even doing this, if I won’t get paid for another six months?” The cause-and-effect of “work hard, get paid” is so unbelievably slow that it can be hard to motivate yourself to keep going in the intervening weeks and months. Kind of like saving for retirement, but it’s your entire income.

DH: Nothing to add here but SAME.

DH: Are you able to take time off comfortably?

ATD: I don’t work on weekends or on most evenings because otherwise I’m useless during the actual work week. But taking time off during the week is hard because I like working. And I like hanging out on the internet and writing and being on Twitter and seeing what everybody’s talking about. But I also liked going to school when school was something I enjoyed. I think it’s just that feeling of being a part of something? At least for me.

DM: Same here. I’ll often work until, like, 1 a.m. on a thing if I’m up against a deadline, or I’ll work a little on Sunday if the piece is due Monday, but that’s just because I wait ’til the last minute on everything. For the most part, I’ve calibrated to the typical M-F work week and holidays, though, since that’s the only way I’ll ever see any of my friends or family. Not that that doesn’t hurt me in the long run!

DH: I think so? I mean, I look at my schedule each week and try to figure out where I can take time off, and occasionally I’ll even go on vacation for a week or so, but I have a lot of downtime most days. I don’t mind working on a weekend if it means I can take that time somewhere else.

DM: Going off DH’s question above, what do you think sets some freelancers ahead of others? It can’t always be how hard you work. Is there something you’ve convinced yourself others must have that you don’t?

ATD: I honestly think it’s a feeling of “FUCK YOU, LET’S DO THIS.” And I don’t even know who the fuck you is directed at, it’s just that mentality of powering up and pep-talking yourself and getting your shit done.

DH: Anne, you’re so positive! I think a lot of it is work, and a lot of it is where you are and who you know, unfortunately. It’s possible to freelance anywhere, of course, but I think some freelancers pull ahead of others by having the ability to be in a place to do the work. And, like I said, above, the fact that they sometimes rely on someone else to take care of them (or a day job that never gets mentioned) while they’re pursuing big projects.

DM: Yeah, I mean, I mentioned my parents before. It’s not like I’m off on weeks-long reporting escapades and living on their charity (god, I wish), but their support has definitely allowed me to focus on working “smarter” — for example, taking a couple high-visibility pieces for mediocre pay now that will raise my profile and help me score better work in the future.

Since I’ve moved away from New York, though, I do feel like my not being there has kept me from getting better, more prestigious gigs. I do have great relationships with my editors there and benefit immensely from the two and a half years I freelanced in Brooklyn, and I definitely don’t regret moving back here to LA, but … it does inspire a little ambient, resentful paranoia.

DM: What are some of the hardest decisions you’ve had to make to survive as a freelancer? Giving stuff up, moving back in with your parents, eating nothing but eggs for weeks on end, etc.?

DH: This is going to sound so ridiculous, but meal planning has helped me out a lot. It took me an embarrassing amount of time to make the connection between my mental and physical health and my ability to work. It’s so easy to just order junk food right to my door each day! I have a schedule for getting groceries, I meal plan every Saturday, and cook my lunch for the week every Sunday. My snack situation is crucial, you know?

DM: *shoves Teddy Grahams box between couch cushions* I have no idea what you’re talking about.

Anyway, I interviewed with a temp agency recently, and applied to a bunch of copywriting and tech jobs. Nothing has come of these yet, but the fact that this life is so barely sustainable has forced me to consider that maybe I don’t want to struggle this hard! Maybe I do want to pay off my debt doing something that is painless and less emotionally taxing while I work on my book on the side. It feels like failing, a little, but I’ll let you know if that’s warranted if my temp contact ever emails me back.

DH: Totally. I recently took a job as a part-time assistant for two authors, and having even a small paycheck I can count on is revolutionary.

ATD: Why do you think we romanticize this idea that writing is super hard? Like, I know it is sometimes, but I think there’s this discourse that’s very, “Writing is so hard and tragic, everything is difficult.” And like, you don’t have to write, so where do you think it comes from?

DH: I think we do it because we still have to legitimize freelancing as an actual job. We hear all of these stories about how painstaking it is for some writers to finish their masterpiece, but not all writing is that way! It’s not hard for me to write about things I love or experiences I’ve had, you know?

ATD: Who do you guys look at when you want to feel motivated? Like, I’ll think of Spotlight or Lin-Manuel Miranda or Beyonce and be like, “Okay! They work hard and now so must I.”

DM: Oh, I really like this question. Definitely have a handful of these. Early on in my freelancing career I listened to the Longform podcast a lot. It was calming to hear about how (usually older) writers I admire work and how they got where they are. It also gave me a very vague roadmap of what I should be focusing on, even if the media landscape has become a parody of itself in the years since they were in my shoes. I’ve stopped now, since a lot of the episodes feature my peers and that feels like it could get really toxic. But yes, still turn to the classics: Ta-Nehisi Coates, George Saunders, Susan Orlean, Ann Friedman (hey gurl), Amy Wallace, Amanda Hess … avoid the Gay Talese one if you don’t want to scratch your own eyes out, though.

DH: Same! I love Longform, but I’m mostly motivated by fellow freelancers. I love seeing in real-time how a person like Heben Nigatu has pushed her career forward, or watching young writers like Safy-Hallan Farah take over the game.

ATD: How do you guys keep learning? Sometimes I think we can get stuck in our niche. How do you pull yourselves out and try something new?

DH: I try different types of writing to keep it fresh, and I read a lot. I went back to college when I was 30, and started my writing career pretty late compared to others, so I feel like I’m always learning just by paying attention? Does that sound hella pretentious? I just mean that pushing myself into different corners of the world is important to me, so I’ve sort of built it into every part of who I am.

DM: Of course it doesn’t sound pretentious. It’s literally how we make a living, after all. I dunno, I bought a tablet recently? I’d posted photos of some doodles I’d done with Crayola markers on social media, and people were so enthusiastic about it, I decided it was time to actually get around to teaching myself digital illustration, even just as a way to shift to a different creative mindset once in awhile. (Still going write the tablet off on my taxes, though. Because duh.) Now I just have to figure out how to afford Photoshop after the trial period runs out … [insert Amazon Wish List link here].

DH: How long did it take you to get your freelance life together? And what does that mean for you?

ATD: I honestly didn’t feel comfortable even calling my career a career until this year — but I also think that has more to do with impostor syndrome and less to do with work/amount of work/etc. I think I’m still in denial that I get to write in general, so I kept thinking of freelancing as a type of “work quilt” I was trying to make. And then my best friend called it a career and I was like, “Oh shit — you’re right.”

DH: This is the first year I’ve felt like I have my shit together. I’ve always been good about meeting deadlines and finding work, but I finally figured out the financial side of things this year. Like, how to keep enough money in the bank to cover the months where I’m waiting for checks, hiring an accountant for taxes. I also realized that I can’t stay up all night working and expect to be productive the next day; I don’t exactly keep office hours, but I try to be done by 7:00 pm most nights.

DM: LOL, am I supposed to have it together by now? If so, can someone please let J.P. Morgan Chase know? They’ll need to forgive my credit card debt.

Support The Billfold

The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by making a monthly pledge on Patreon or a one-time-only contribution through PayPal.