I Sold Out: Why I returned to the 9-to-5 life

I Sold Out: Why I returned to the 9-to-5 life

After four months of living the freelance life, I decided to take a full time job with benefits. Well, sort of. It’s a full time job with benefits, but I’m also working like four side hustles because I’m me but that’s completely besides the point.

The point is, I gave up location independence to take a job at a brick-and-mortar office, despite that the past several months, I was thriving as a freelancer and contractor. Why? Let me tell you…

Life as a Freelancer

Some of the odd jobs I picked up since coming home in June included:

  • Real estate photographer
  • Assistant director for a web series
  • Marketing manager for a retail and business consulting firm
  • Wedding photographer/videographer
  • Graphic designer
  • Education admissions consultant

To be completely transparent,  I was making more a month than I was at my previous full time job. But four huge storm clouds loomed over my head:

  • I felt very isolated. I thrive on working with teams and building relationships with others. At most of these jobs, I was a one-woman shop. There were only one or two instances where I worked with the same people consistently; the rest of the time I was flying solo or only met the client once before a job was wrapped.
  • I was working all the time. This isn’t anything new; I’m still working all the time. But instead of working on 2-3 different projects, I worked on over 7-8 different things at once. And the pressure to say yes to a job was unsurmountable. Yes, jobs flowed in throughout the summer, but I was worried that things would slow down in the winter, hence the pressure to say yes to everything—even things I clearly didn’t enjoy.
  • I wasn’t traveling. Even though I wasn’t technically required to be at any specific place at any specific time, the highest paying gigs were location dependent (yay, production!). They happened maybe once every week or every two weeks, but it certainly wasn’t worth blowing hundreds of dollars on a plane ticket to travel somewhere, only to have to work on other odd jobs, then fly back to Chicago to work the gig. So I was essentially just working out of my home office. All of the time.
  • No benefits. As you probably know already, the United States is an expensive country to live in. Healthcare is a scam, and social security is not guaranteed to exist 30 years from now. At best, I was able to build a pretty fancy life raft to keep me afloat and navigate around the ocean to visit cool places, but I didn’t really have a destination. And if a storm came and destroyed my raft… well, I’d be fucked.
A very unattractive picture of me climbing a rail in sandals and a dress. Anything for the shot!
Dragging photo equipment across Chicago without a car kinda sucks.
I spent a lot of time sitting in closets taking bracketed shots of beds

With that said, there were plenty of perks to freelance life. I slept in when I wanted, stayed up late when I wanted, and I took advantage of daytime membership at my local climbing gym. My schedule was flexible enough that I was able to meet up with friends anytime, anywhere. And I had a lot of time to focus on my own creative work, which was nice.

Some positives include getting to go to New York for events
Working with awesome people on a web series about relevant topics like gun violence
More filming!
Going on daytime dates. Granted, none of these were actually good. Dating actually really sucks, don’t do it. Flexibility with your time is nice, though.
Planning events in New York with retailers and tech companies around the world
Doing social media, because what else are millennials good for?

Why Work Full Time?

Taking a full time job was not initially part of the plan, but I ended up in one of those “right place at the right time” situations. One of my good friends invited me to an event, where I met her neighbor. We hit it off and ended up having similar professional backgrounds—and she was looking for someone to fill a role in her office in an area that I happened to be an expert in!

It took me an agonizing three weeks to decide whether or not I wanted to give up the flexibility of working for myself. After thinking it over and seeking the insight of many, many friends and colleagues, I realized a few things:

  1. This job would give me the stability I needed to focus on passion projects. I spent most of my day-to-day as a freelancer on business development—finding gigs and convincing people why they should hire me. With a full-time job, I could afford to pick and choose my side hustles rather than chase everything that came my way. Even more importantly, I had the income to fund projects I cared about.
  2. Money is power. It sucks to admit this, but it’s true. Money gives you the ability to purchase a plane ticket to visit family across the country. It enables you to pay for transportation to see your friends who live on the other side of the city. It gives you the opportunity to take care of yourself when you come down with a cold that sticks around for three weeks. Money gives you the peace of mind to bike around the city without the fear of being hit by a bus and being completely fucked if you don’t die.
  3. My job does not define my identity. I am (and have always been) so much more than my job. Just because I decided to work full time doesn’t mean I’m less of a filmmaker, traveler, or adventurer. If I truly want to do something, I’ll find a way to make it work despite having a 40-hour-a-week job.


My highest priority is community. And as sexy and appealing as being a digital nomad or traveling artist sounds, most successful digital nomads will tell you: 1) Their work is isolating; and 2) They are constantly working.

I feel lucky because I found a job in an area that I’m passionate about, in a city I love, in an environment that facilitates growth and innovation. A job that gives me the flexibility to run away to foreign countries (hello, Mexico!). I had a couple jobs similar to this right out of college, but didn’t recognize how well I had it. I’m actually pretty excited that I have the maturity to know how good I have it now. :/

It’ll be awhile before I take another 3-6 month trip around the world. But I’ll for sure be flying out to 1-2 different countries for at least a week each year, plus other weekend trips.

At the end of the day, I realize how lucky I am to even have the ability to decide how I want to live my life. This post may come off to some people as one big eyeroll, and if it does, I encourage you to reach out to me for a conversation. Life has been a weird rollercoaster, especially in the past five years. But if there’s one thing I know for sure, it’s that I know and am comfortable with who I am in a way that I’d never would have imagined five years ago. And for the first time, I feel like I’m in a place where I can truly build the life that I want.

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