I Quit My Office Job to Freelance—Here’s How I Maximize Working From Home
Don’t get too comfortable.
Published Nov 22, 2019 1:00 AM
There’s something meta about writing this story—about how, ever since I quit my full-time office job to become a freelance writer, I pull off this very task: pitch to a client, fit in a time to produce the work, meet the deadline. I’m honestly giddy that this is my lifestyle now, because ever since I entered the mainstream workforce, I spent every spare moment trying to leave it. From the time I graduated college until this past summer, I worked as a full-time writer and editor for a series of digital media companies. I commuted to their Los Angeles offices, attended their meetings, hit their benchmarks, and churned out hundreds of words of content every day. But offstage, I side-hustled my own projects with my eye on the prize: to publish a book, quit my job, and become a full-time author and freelance writer who could work from home. This year it all happened (my first book, Wordslut: A Feminist Guide to Taking Back the English Language, came out in May, and I’m currently writing my second, a book about the language of cults). I feel like I’ve won the lottery.
I’m not the only one who has decided to bow out of office life: 77 percent of millennials report that flexible work increased their productivity and 90 percent of current #WFH-ers plan to keep doing so for the rest of their careers.
When people ask how I push myself to get stuff done, I put it like this: self-motivation, as opposed to external motivation, is inherently much more stimulating to me. The stakes are far higher when you work for yourself because the consequence of failing to deliver is not letting some big company down, it’s letting yourself down. If you’re a creative or entrepreneur and you don’t meet that self-imposed deadline or go to that networking event, no one cares. And existentially that’s much scarier than your boss “checking in” or “circling back” to see how that presentation is coming.
Of course, no matter how many theoretical pep talks you give yourself, self-motivation is also a practical skill. So I’d like to share a few of my essential secrets for staying productive as a full-time freelancer. I don’t have a Ph.D. in productivity, but these are the #WFH habits that have been working for me so far.
Make Space, Physical and Mental Experiment with your work environment to find a setup that is comfortable but not too comfortable. You want a setting that encourages creativity and output, not napping (for most people, working from bed is a hard no), so you may need to play around a bit to find the right balance. I recently moved to a house with lots of nooks and crannies, which I’ve decorated to feel inspiring and varied. There are books everywhere and tons of seating options so I can move around and work from different locations. But if I feel myself getting too cozy and moving to another space in the house isn’t helping, I nip the urge to do nothing in the bud by heading to my local coffee shop for a change of scenery.
It’s About Making the Right (For You) To-Do List To-do lists are indispensable, but there are helpful ways and debilitating ways to map out what you need to accomplish on a daily basis. I know people who have pricey, high-tech to-do list apps and who get all nerdy about their color-coding and their subcategories. And I know people who set extremely ambitious goals for their everyday output. There’s nothing wrong with that. But personally, I like to keep things simple and realistic. Every day I update my to-do list with achievable goals (setting my sights high, but not too high), and I do this in my Google calendar…nothing fancy or complicated. I set fixed deadlines for projects, but still allow flexibility within that structure. And I plan those deadlines so far ahead that if something winds up needing to get moved, it’s not a fire drill situation. For example, I might dedicate a whole day to executing one or two big tasks, but I won’t specify exactly what time each task needs to get done (unless it’s a meeting or interview) or overwhelm my list with too many daily goals, because then I’m just setting myself up for failure.
Don’t Sweat the Little Things, Outsource Them Learning to prioritize and delegate has been paramount to successfully working from home. For example, if a task is so low priority that I don’t even want to think of it as something that’s “on my plate” (for example, answer that barely important email or order a spare phone charger), I won’t even put it on my to-do list at all. Seeing it there will just make me feel swamped and discouraged, so instead, I choose simply to address the low-priority thing when it occurs to me or when it’s convenient. As for delegation, I pay a virtual assistant to help me with time-consuming tasks that don’t require my creative fingerprint—general research, transcribing, invoicing, typing up and shooting off emails that need to be sent en masse, etc. (I wound up hiring a former intern from my old job.) For me, the time I save and can dedicate elsewhere is more than worth the roughly $70 a week I pay her.
It’s Okay to Blur the Boundaries As a creative freelancer, I’ve found that the work-home separation has almost become obsolete. I’m currently writing a book about cults, but I also genuinely love watching cult documentaries, so sometimes my research resembles something I’d do even if I weren’t getting paid: lounging on the sofa. I’m lucky enough that the lines between my work and my playtime blur in a good way. So instead of regimenting, say, four hours a day for writing and two hours for emails, and making sure to wrap up by 6 p.m., I like to leave the boundaries between work and leisure more fluid. I try not to work myself to terrible distress, but I also don’t force myself to stop writing if I’m on a roll just because it happens to be 10 p.m. on a Saturday.
No Rules Rule I’ll leave you with one last tidbit: If at any point while reading this (or any other piece of career advice) you started comparing your work style to mine in a way that made you feel bad, just remember that being distracted by feelings of inferiority or self-doubt is the number-one enemy of productivity. There are writers who create way more content than I do at a quality level I find so intimidatingly high that if I let myself think about it, I’ll do absolutely nothing for the rest of my life. But whether you work remotely for an organization you love, recently went freelance, or are running your own company from home, just bear in mind: There are no rules out here in the #WFH Wild West, only tips for what might help, and if you care enough that you’ve gotten to this point (in this story and in life), you’re already doing great. Now get off the Internet and go prove something to the world.