An Ode to the Freelance Life


Making your own schedule. Sleeping however late you want. Working from your favorite coffee shop (or at home in your pjs). Being able to hop on a plane to go visit your family or friends whenever you want. Sounds like the ideal job right? Yes and no.

This is what it looks like to be a freelance worker. Is it great? Majority of the time. I don’t have to clock in every day, I don’t have to have a closet full of professional clothes, and I don’t have to schedule out my vacations/trips based on how many days off I have. But I also have my own set of problems. Where is my next paycheck coming from? How much will it be for? Do I need to find a part time job? Can I afford to go home for this holiday? Can I go out to eat with my friends or should I stay home and save money?

I haven’t had a normal job in over 4 years when I was still in college. When I moved to Nashville in the summer of 2014 for two internships, I quickly learned that sitting at a desk for 8 hours a day was NOT for me. I don’t like having to ask for permission: permission to go home to Texas, permission to go see my best friend in Florida, permission to have the afternoon off so I can go to an appointment, etc.

I had the opportunity to have a “normal” job with a “normal” paycheck a couple of years ago, and I was absolutely miserable. Turns out the grass is not always greener, and a consistent paycheck was not all it was cracked up to be.

Now let’s get one thing straight: I’m not saying that you need to stay miserable at your job and save a certain amount of money before you go freelance. But work smarter, not harder. Start cutting down hours at work or picking up freelance work that you can complete on the weekends or during the evening while you’re on the couch. Talk to friends or acquaintances that are freelance workers and get their opinions: the good & bad, what they would change, what they did right, tax information, etc. You don’t have to jump in all at once, you can take your time and take baby steps. Join Facebook groups for support, send emails asking people for coffee to get advice, or do a good old fashion google search.  

So I’ve learned to go with the flow. I’ve learned to network, send emails, and not be afraid to ask for what I want. I babysit, sell my clothes to Plato’s, and am always looking for freelance/remote work. Maybe one day I won’t always be on the search for work, but I’m okay with it for now. I have a solid group of friends who understand the freelance life and the struggles that go with that. One amazing thing about Nashville is that I never feel alone in this struggle. I moved here to chase after a dream, and that is what I’m doing. That is what we are all doing in this town. We are dreamers, creators, hustlers.


Kelsey is a proud Texan who calls Nashville home. She tours in the music industry and loves traveling, coffee shops & reruns of Friends.