Go get 'em. By Big Cartel.

The Emotional Reality of Finding a Side Gig

The past year has been pretty hectic for me. Actually, that’s an understatement.

It started with a steady job from which I quit abruptly to pursue a writing career. Luckily, with the help of a publishing internship, that was possible. A few months after that, my partner and I (both agriculturally-minded) found ourselves in a realtor’s office drawing up an offer on our dream property in rural Vermont. Our offer was accepted. After another whirlwind month, I happily found myself in a new house with new responsibilities, and a neglected, fledgling career as a self-employeed writer.

Worth it? Of course. Wise? Probably not.

When the dust had settled and business license for our new farm had been granted, I took stock of the vital stats of my creative business. It wasn’t looking good. All of the madness of getting our shared dream on track had overshadowed the progress I’d made in the first few months I had been working for myself.

I buckled up for a cold-pitch bonanza and reached out to as many publications and businesses I could think of that might have, just maybe, needed a writer. I found enough business to get me through a few more months of expenses.

After New Year’s Eve had come and gone, with fresh intentions to get the year off to a good start, I realized I was still feeling the grip on my finances beginning to slip. That’s when Craigslist and Indeed.com re-entered my life. Rather than spending my afternoons pitching and writing, I spent them in a zombie-like state, scrolling through classifieds and mentally justifying a second part-time job to myself. This was exactly the scene that working for myself was supposed to spare me from.

Before I knew it, I found myself interviewing for a server position with a chef at a nearby high-end relais and chateaux. I took home a guarantee of employment, as well as the sinking feeling of failure.

As I waited to hear back about my start date, I pondered. Since when has the promise of employment ever been viewed by anyone as defeat rather than success? How could I be feeling such resentment towards my new employer before even having worked my first shift?

But it quickly dawned on me. I was viewing this job as a symbol of my failure; a concession to the real world due to my lack of talent as a self-employed artist.


Being a self-made entrepreneur is different than any other career path. Your business’ successes and failures are intertwined with your own ego every single day. There’s no clocking out or forgetting your responsibilities when you go home at night. There’s no one else to take the fall for your mistakes if you make them. And a person needs to have a certain amount of gumption to even give self-employment a shot. So committing 24 hours a week to someone else’s business didn’t just take away from my availability to write, it also forced me to admit what I had been resisting: my creative work was not enough to sustain my life financially.

It’s natural to think that must mean I wasn’t cut out for it.

My first week at the new job went about as well as any first week can go. The world of fine dining proved difficult to understand - it’s a place where silver plated cutlery and napkin folds rule us all. I spent my late night drives home scowling through the windshield, upset that this had become my reality. Upset that I was not asleep in bed, upset that my “lack” of business sense had left me here, upset at the relais and chateaux for even existing. I schemed up all the different reasons and ways to quit my new, horrendous job, which I had barely just started to understand. (It was all very dramatic, really. Reminiscent of a well-practiced toddler’s temper tantrum.)

Things began to change my second week in. I was picking up the rhythms of each shift, anticipating problems and solving them, and getting consistent positive feedback from the managers. I was actually getting good at this job. And it sort of, well, felt great. My resistance began to fade as I got to know my coworkers better and receive praise for a job well done. Though I was still exhausted at the end of each shift, I realized that I didn’t need to be upset about this second job or view it as a failure. I could view it as a great opportunity to maintain a steadier income and feel confident in the work I was doing.

As the financial pressure has worn off, as well as the resentment towards my new side hustle, so have my expectations for my own business. I’ve finally had a moment to reflect on everything that’s shifted in my life in the past year. When I look back on it, I can’t believe the amount of pressure I had put on myself to build a sustainable business so quickly. It’s no wonder I was feeling inadequate and behind the ball!

Given the circumstances - quitting a job, buying a house, starting a new career - I now see that my expectations were way too high to be reached. It only took me 12 months to realize it.


Working for yourself requires a lot of self-reassurance to stay motivated, which can be next to impossible when it’s not working out financially. Now, I’m making ends meet. And I’m seeing the added benefit of how positive feedback from my managers carries over into my writing career and helps maintain the confidence I have trouble cultivating on my own. With a little less free time but a lot more financial wiggle room, I can put my energy towards the writing work that I really want to do, for the companies that matter to me.

Sometimes I still grumble on my drives home from work at midnight. It’s only natural. But my bank account has been singing since my very first shift.

Jillian Conner is a freelance writer living in Vermont. She’s an avid backyard birder, snack enthusiast, and aspiring shepherdess. You can follow her on Instagram.