Facing an Uncertain Career Future: 5 Stages of Freelancing

Facing an Uncertain Career Future:

5 Stages of Freelancing

By Sarah Shostak


The Abyss

Graduating with a BA in Marketing, I came back home to NYC with the prospect of locking down a full-time job. As my post-grad months passed, so did my hopes. It was hard enough to even get an unpaid internship. Half the job board listings were scams and I was swimming in a sea of resumes trying to stand out. Believe it or not, I ended up snagging my first freelance opp by means of a babysitting gig through SitterCity…


The Hope

My first boss was starting his own business and asked me, his 4-year old’s sitter, if I could be of assistance. Of course, I had to take it. This was definitely not how I thought I would land my first job out of college, but it turned out to be the only option to work after months of searching. There was finally light at the end of the tunnel. I could now gain that ‘real’ experience most graduates CV’s are missing.


The Hustle

For the next few years, I helped build the start up’s brand, as well as the client base. My social media savvy came to play and I was given many different tasks. I was willing to take anything that came my way, as I was eager to learn. Whether it was building up company’s Instagram's feed or ghostwriting blogs, I was the marketing point person. You have to be hungry for work, especially as a freelancer.


The Drag

At first, I was only putting in about 6 hours a week, that eventually grew within months to 15 to 20 hours a week after proving my worth. These hours could change month after month, making it extremely unstable living in NYC. I was forced to seek out any other opportunities I could find. I landed on Wag, the startup dog walking app. Though Wag was not in my career path, freelancing makes it hard to choose your work when starting off. You need to take what comes until you find that happy balance where you get options. The more I worked random gigs in the marketing sphere the more I realized that happy balance equals #lifegoals.

Some other challenges of freelancing was feeling isolated. I did not have any peers to talk to which was lonely. Google was my work husband. Working remotely, you’d think one would be running all over the city having a ball. Sometimes this freedom resulted in sleeping late and working from the couch. The instability of not having a steady paycheck or health insurance, coupled with the only human interaction being with my local barista, made me crave a full-time role. I wanted the office holiday party, happy hours, and inside jokes with coworkers.


The Flip

My first year freelancing taught me a lot. I enjoyed the freedom, despite the solidarity. I was at least forced outside when walking some fancy Frenchies for Wag and got to check out baller apartments in the village. I got to set my own schedule and pursue different jobs, which expanded my skill set.

When I landed my first full-time job I managed to freelance at the same time, having the best of both worlds. To this day I still freelance where I can, while working the 9 to 5 grind. The more you hustle, the closer you will come to doing what you love.

I currently work full-time in LA as a Producer for Complex. One day I can be on set where we are interviewing a rapper, the other days I making sure an Facebook video is coming to fruition. Working in a fast paced environment and time management are skills I picked up early on in my career, which led me here. For the first time I am working for a company that I was a fan of first and it feels amazing. Through the woes of freelancing, I am now happier than I could ever be and excited for what’s to come.