How I Turned My Side Hustle Into A Full Time Job

side hustle

Somehow along the way it’s become standard operating procedure to have a side hustle on top of your full-time gig. As if you aren’t tired enough after your 40+ hour a week job, you’re generally expected to have something else to stand out. Perhaps it’s a natural progression for adults that grew up as super-charged kids who had countless extracurriculars from the time you were five. We’re used to being booked all hours of the day and night, so is it any wonder we’re taking on extra after hours work?

Nearly everyone I know has some sort of side hustle, whether it’s the graphic designer who doubles as a music producer, the substitute teacher who freelance writes, the chef with an Etsy shop, the marketing director with a consulting job, the wine distributor with a band, a lawyer with a book blog, the college admin/aspiring chef, or my personal favorite, the editor by day/ past life writer by night. For most of these side hustlers, their night job is generally quintessentially different from their day job. Is it because we’re dissatisfied with our present careers or our short attention spans preventing us from being satisfied by just one job? Is it a side effect of an economy that has fewer jobs available than there are people seeking them, and we need everything we can to set us apart?

For me it’s a little of all of the above. I’ve been working as a marketing IT writer for the last six years and it was not my cup of tea. It paid well and allowed my salary to rise quicker than average, but it was unfulfilling to write day in and day out about enterprise software that would “make your business more efficient, boost productivity, and help you do more with less.” To combat that I decided to fall back on earlier interests in creative non-fiction and editorial writing and start the very online magazine you’re reading today. In many ways I started Literally, Darling to be a creative outlet that was uniquely my own and not something a boss or a corporation could dictate. Yet it was also a way for me to lay the groundwork to be able to change industries.

As anyone who has found themselves in a career they’re unhappy with knows, it can be difficult to prove to someone that your skill set is malleable to other industries. Even in the marketing world, it was nearly impossible to switch away from the IT field or even a different segment of it. I worked in B2B and B2G tech fields (business to business and business to government) which is a far different marketscape than even B2C (business to consumer)—essentially meaning six years of marketing know-how was still never going to get me a more creative job marketing something fun like Kate Spade or J.Crew. So if it was difficult to even change jobs within marketing, I needed to do something big to break into the publishing world that I’d always wanted to be part of. It was a catch-22: Without online publishing experience I couldn’t get a job in the field I wanted, but I couldn’t get experience without working in online publishing.

So like so many of our entrepreneurial generation, I started my own site to get the experience and know-how required to be able to make the jump. What resulted was a leap and a prayer, and what started as something on the side became nearly a full-time secondary job. In the early months as the site was nearly doubling monthly, I was working a 40-hour marketing job and putting in 40-60 hours a week on the site. Coming up on the first year anniversary I’d taken on so much I nearly had a nervous breakdown as I was trying to pull off our Millennial Manifesto, a massive curated project that was taking over the site for a week, a full site re-design, and finding interns. Simultaneously work was firing at all cylinders and the site got hacked. I’m not sure I slept for an entire month and when I finally left for vacation at the end of May, I sincerely questioned whether I had the wherewithal to continue to balance two such massive responsibilities. I was failing at the most basic element of the side hustle—finding the balance between your two worlds.

For many of us working the side hustle, what we do separately from our primary jobs is often our true passion, one that we don’t mind working all hours on, and we exert unnecessary pressure on ourselves to make it work. The college student running an Etsy shop often finds more satisfaction in styling the perfect photo shoot to sell her prints than cramming for an econ test. It can become overly frustrating to have to take time away from what you love, to do what you have to pay the bills (or graduate). When we find success or fulfillment through our side hustle, it often makes the disappointment of droning away at our primary jobs even more unsatisfying. Being lectured to change one inconsequential word in an ad banner when you currently have an article going viral across the world can make you want to scream. What can start as an almost escapist side gig can often become a source of stress that only highlights our current unhappiness more. And when the side gig doesn’t instantly parlay into something more, it can be extremely discouraging and lead to feeling trapped, overworked, and depressed.

Over the past few years I’ve learned to delegate and find balance between my worlds. I’ve brought on more editors and interns, given up avenues of the site that used to be exclusively my own and found ways to equally spread and lessen the work across the board. I still have weeks when the servers go down and I’m trying to pretend I have any idea how to access the FTP Apache error logs; where I’m up all night hating my side job and I have to get up early for the next morning for my main job. However the trick is to not only learn to prioritize and find balance, but not to expect instant gratification.

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side hustle

The side hustle is often a long haul. If you’re a freelance writer it can take months to gain enough clips to start being taken seriously at bigger paying publications, yet finding time to write and pitch when you’re working can be overwhelming. If you’re trying to switch industries then it can take years to gain the amount of experience needed to even be considered for an equivalent role to the one you’re doing for free or for small fees. You might be able to say you have six years experience in your current job, but that’s not necessarily going to count for much when you’re applying for positions outside your field. It’s the experience and skills you’ve learned in the side hustle (and that you have demonstrative proof of) that are going to help you get that next job.

There are times when it will feel like a fruitless endeavor, but don’t fret, if you persevere it can pay off. Approaching three years since the beginning of LD I applied for an editor position for an online publication, and for the first time I wasn’t convincing someone I knew the best way to sell software, but rather I could pull out everything I’d learned about running writers, working with editors, and building an audience. All those sleepless nights, and blood, sweat, and tears were suddenly a valuable and marketable skill. And it paid off. I got the job, I did the seemingly impossible and switched careers and industries and it wasn’t the six years of marketing experience that got me the job. It was the side hustle that’s about to become my primary focus, and I’m not the only one who’s had it pay off. I’ve had writers use LD as a platform to get picked up on even bigger publications, make contacts, and connections that have allowed them to become full-time freelancers. It’s a slow (occasionally agonizing) process, but with dedication and patience, it can turn into what you want it too, whether that’s a new job or a creative outlet to offset your current one. Afterall, a well-rounded kid isn’t going to be satisfied not being a well-rounded adult, will they? So when you’re exhausted and wondering why you put yourself through this, just blame your parents. (But when it pays off, I’d recommend thanking them too.)

What’s your side hustle? Tweet us @litdarling

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