7 Jobs I Had Before Becoming A Freelancer

You never forget your first job. Or the one after that. Or the one after that, although maybe you wish you could. Hello, short-lived college stint as a shot girl at Fat Tuesday’s.

From waiting tables (badly) to interviewing criminals, the jobs I had before becoming a freelancer run quite the gamut. Here are a few of the highlights. Although ‘highlights’ is such a strong word…

1. Hostess at Cracker Barrel

You probably know this place because there’s one off of every interstate exit in the continental U.S. They have those fun little pegboard games that I can still never win, even though I had hours of practice during my shifts posted up at the hostess stand.

 

I’d had babysitting gigs and whatnot, but this was my first “real” job. I remember that working alongside real adults freaked me out so much. They would go outside and smoke! They would ask for more hours. Me? I was always the first one to volunteer when the manager would ask who wanted to be cut.

It was a good first job and taught me how punching a clock works, and to this day I can’t resist the call of those buttery biscuits. It’s also fun running into fellow Cracker Barrel alum who can commiserate over the CB stench—the one that would linger in your clothes and hair and make you smell like you’d been roasting honey baked ham on a spit in an outbuilding for the last 12 hours every time you left the place.

2. Waitress at Chili’s

Once I turned 18, I graduated from hostess to waitress and started raking in the tips at Chili’s. Seriously, I made bank for a college freshman, even though I was a pretty terrible waitress.

For starters, Chili’s is a big happy hour spot and I knew nothing about proper cocktails. My experience with alcohol at that point was mostly limited to chugging lukewarm Natty Lites in frat house basements. The after-work crowd would come in and ask for a 7 and 7 (seven what?) or a cosmopolitan, and I’d stand there staring at the computer screen trying for the life of me to figure out how to ring it in until my eyes glazed over. I was slow.

Looking back, I find it amusing how I would always apply for jobs at places where I liked the food, as if it would be more rewarding running plates of crispy chicken tenders because I liked eating them myself. To this day I have all of the respect for servers, because that job is no joke.

3. Washing Hair at a Salon

This might give some people the heebie jeebies, but I loved this job. You guys, there was a while there where I was into hair. These were the Jersey Shore glory days where the higher the bump and the bleachier the blonde, the more beautiful the girl, and I was killing the game.

 

My hairdresser, Gainesville legend Eddie Escalera, hired me as an “assistant.” He could crank out a set of sorority girl highlights in 45 minutes flat, and it was my job to watch the timer and rinse out the bleach when the color was done.

Eddie paid me cash at the end of each shift and bought us lunch most days. The best part of the job was that I could get my highlights touched up any time I wanted in between clients, for free. Sadly, Eddie passed away a few years back, but I remember him and the summer I spent working for him fondly.

4. Sales Associate at Victoria’s Secret

Retail jobs, am I right? If you work retail, I hold a special place in my heart for you.

The long days on your feet. The hours that drag on during slow times. The breaking down of infinite cardboard boxes. The floorsets!

 

I pushed overpriced lingerie at VS for a hot minute between graduating college and landing my first reporting job. I quit over the phone with no notice, and I still want to cover my face in embarrassment when I think about that call.

“Yes, hi, Jane? I’m moving to Colorado to become a TV reporter, so I won’t be coming in for my shift tonight. Or ever. Ok, bye!”

Real profesh.

5. Sales Associate at Victoria’s Secret… Again

It turns out small-market jobs in TV don’t pay very well.

I was brought back down to planet Earth pretty quickly after receiving my first few reporting paychecks, and reluctantly went into the VS in my new town to ask for a second job. Somehow, they gave me one, and I worked there nights and on my days off to help cover my bills.

Working two jobs sucked. It was exhausting, and I was a single 23-year-old with no kids, still on my mom’s car insurance. It gave me some important perspective that I go back to again and again when I hear arguments over a living wage, or employee benefits, or healthcare.

6. News Anchor

Mom, I made it. After slugging it out for two years reporting and producing in a small market, I moved on to a mid-size market and eventually worked my way to the anchor desk for the morning newscast.

This job is hard to describe. News is an alternate universe where regular schedules don’t exist and everything in life comes second to your job.

I learned about everything under the sun, from taxes to public policy to criminal justice. I got to interview celebrities and politicians. I learned to work fast and under pressure. I adopted a regular speaking volume that more closely resembles shouting, and was asked in my subsequent office job to “please use an inside voice on the phone.”

By the end of my contract I knew I wasn’t passionate enough about news to stay in the business, but it was a lot of fun while it lasted.

7. PR Account Manager

After news I got my first true 9-to-5 job at a PR firm. At this point I feel like I’m just giving you my resume, so I swear I’ll wrap it up soon.

This job was important because it taught me how to behave like a normal human in the professional world: filling out invoices, writing emails in full sentences, using delightfully passive aggressive phrases like “per our last conversation” and “circling back.”

It also gave me the experience and the confidence to eventually strike out on my own as a freelancer. Which, incidentally, is the job I’ve held the longest of them all (you can read more about that here). It’s funny looking back, though, at how all of them in some way seemed to prepare me for what I do now.

Tell me: what’s the most interesting, fun, or terrible job you’ve ever had?

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