“What’s with the Series 7 for Dummies book??”

I looked up from the YouTube playlist to turn to my friend Amanda. She was facing away, wine glass in hand, studying the overflowing bookcase I kept next to my fireplace.

I was sitting on the rug in my living room, wedged between my ottoman and the couch. Amanda stopped by for a few hours of country music, alcohol, and end-of-week rants. I hit play on a Luke Combs’ song before looking back up to give my answer, which I thought should be an obvious one. “It’s from when I was studying for my Series 7 license.”

She whipped around, thankfully spilling her wine on the floors I couldn’t give two shits about rather than my rug. She meant the question as a joke, as in who the fuck would ever own this book, but now I had her attention.

“WHEN did you take the Series 7 exam?” Even though Amanda met me at work, she saw me wear makeup all of eight times and a dress exactly once. It was all but impossible for her to imagine a girl who only wore Ann Taylor, refused to leave the house without caked-on foundation, and washed, blow-dried, and curled her hair daily. To me, that girl seems like a different person. 

“When I was twenty-two,” I replied.

Let me tell you about my first two years out of college.

When I first graduated college I worked inside sales for a high-net worth investment consulting firm. My yearly quota was a million. Somehow I passed my Series 7 exam on the first try. Remarkable; considering I all but outsourced Finance 101 in college.

But I don’t want to talk about that job. I want to talk about the job that came after it.

Those who know me well think my second job was working for a paleo platform called Primal Palate. I credit them for teaching me half of what I know about the online space. My bosses, Bill & Hayley, were the first two people who opened my mind to this idea that I could still work and without being “employed,” which is how I make a living today.

But that wasn’t my second job.

There was a four-month gap from when I outright quit investment consulting to when I found Bill and Hayley. Even then, it started with just ten hours a week, taking a full six months to become my full-time gig. 

My second job ever was at a bar in the Strip District of Pittsburgh, Pennsylvania. I left DC one week after I left my job, convinced I couldn’t afford to stay. It took exactly six hours post-arrival to have an all-out panic attack on the phone with my brother, thinking I severed my own legs from underneath me.

The next morning I tossed my laptop in a bag and went searching for a coffee shop with wifi, committed to applying for jobs. I ended up wandering into an empty bar and ordered a bloody Mary, telling the bartender my sob story about throwing my life away. She went into the kitchen and grabbed the owner, who was just five years older than me. He sat down at the bar stool next to me and said, “Well, I don’t have a marketing budget, but do you want to work here?”

I started the next day.

And you guys, I have to tell you—I fucking LOVED working at that bar.

I mean, loved it. For a girl who had precisely zero work friends at my former employer (I think it’s fair to say I hated two-out-of-three guys I shared a cubicle with), I suddenly found myself surrounded by people who gave zero fucks about who I was or where I came from, as long as I was nice and fun to be around. After being on ZERO dates in sixteen months, I got asked out my first shift. After battling brain fog for nine hours a day with eyes glued to a screen, I spent my days upright, walking miles around the restaurant.

I worked almost every shift we were open. At one point, our manager went on a firing spree until the only ones left were my friend Vince tending bar and me waitressing, and the two of us had a BALL. We worked ten-to-ten, six days a week. At 3PM on the dot I changed in the bathroom to run five miles around the city while Vince covered my tables, then I’d half-shower in the sink, thow some deodorant on, and work the evening shift.

That’s how I remember that restaurant NOW, six years later. But if I’m being honest with myself, it’s now how I experienced it THEN.

When I worked in a restaurant, I couldn’t get out of my head that I didn’t work in an office.

I’ll just come out and say it: I thought I was too good for it. And I know that makes me sound like an asshole, and if you knew me personally at that time in my life, you know I totally was. So let’s just all be in agreement with this paragraph and move on.

I smiled on the outside and made nice with customers, but inside I couldn’t forgive myself from what I walked away from. To the things I thought mattered, I was the girl who always did everything right. I think I got two-or-three Bs all of college. I was a D1 scholarship athlete. I got a job where I wore suits to work, which in my twenty-two year old brain was my vision of “making it.”

This insecurity that I threw my life away was never more prominent than each night after work. After we locked the doors and finished our closing duties, bartenders, servers, cooks, and managers propped up on bar stools, grabbed a few bottles from the cooler, and swapped stories or played Never Have I Ever. By the way, I was the only employee who had never done ecstasy.

I couldn’t share a story about snorting coke and the only needle I’d been exposed to was a cortisone shot, so let’s condense six months’ of closing shifts by saying I HAD NOTHING TO CONTRIBUTE TO THESE CONVERSATIONS. And one night over the uproar about the fact that Kara had never done [that night’s topic] my boss choked out, “Kara WHY do you work here!?!”

I had no answer to that question.

Hindsight is the closest thing we will ever have to twenty-twenty vision.

If I could go back to that night around the bar and answer that question, this is what I would say:

I worked at that restaurant because I had a distorted vision of what success looked like, but I didn’t know how to correct it. I worked because I needed the money, and refused to live off my parents less than two years out of school. I worked there because I was unhappy and knew I needed a change, but I needed time to figure out what that change was.

I worked there because I needed friends. Or just the smallest sliver of human connection. For the second time in less than two years, I moved to a new state where I had exactly zero friends when I showed up.

And I found them. In the weirdest ways. I had a group of regulars who refused to sit anywhere outside my section. I fell in love with a boy who worked in the kitchen. Vince made me laugh harder in one shift than an entire YEAR at my previous employer.

More than anything, I wish I could go back, pull my head out from my own ass, and appreciate the process I was clearly in.

I was so concerned about how my occupation appeared to the outside world, and so fucked up in my thought process of what a job should be, it’s like I missed the lessons I was supposed to be learning.

I am proud to say I passed the Series 7 the first go, but I could NOT pass that fucker today. If I opened the book Amanda pointed at, I’m not sure I would understand a single chapter. I did not take that knowledge with me.

But I took so much from that restaurant. Without realizing it.

I learned how to stick up for myself like I never did at the consulting firm. When our sleazy manager suggested I was smuggling booze in my backpack, I opened it up, pulled out my sweaty clothes from that day’s run in front of a group of customers, and told him exactly where he could go.

I learned how to talk to anyone. Even though I worked in sales before, I was never more charming than when I worked at that restaurant. I spent New Years Eve working a party Casey Hampton threw for a bunch of his teammates, and was not the slightest bit intimidated. Whenever Antonio Brown walked in, I was his server.

I spent so much of my time worrying about when I would get the fuck out of there and get a “real job” again, I missed the whole process. It’s like—even though everyone makes this mistake at twenty-two—I expected to graduate college and immediately be in my dream job. I actually thought life worked like that.

I was so fixated on this idea of getting a “real” job, I forgot the whole reason I gave up any sense of security and stability when I left my last one. I left a salary, health insurance, and a 401k because I was not happy. But those crazy nights and weekends when I was so busy sprinting from table to kitchen that I forgot about the whole job search thing, I was happy. I enjoyed being active for twelve hours a day. In fact, the freedom to go on a walk whenever the fuck I want TODAY is one of the things I love most about being a freelancer.

You will go through transitions. And they will feel like a waste of time.

And they will probably seem like a waste of time to everyone surrounding you. I have the most supportive family and friends in this world, yet I cannot tell you how many times I recited, “No, I will NOT go to grad school just for the sake of going to grad school,” because that was a time-filler everyone could rationalize. 

Respect every transition and process you go through. It’s not embarrassing; you’re just worried of what the world will think of you. And frankly, they have too much shit on their plate to worry about a gap in your life.

You will one day look back at those seemingly worthless transitions as some of the most valuable times you went through. Just like now I view that restaurant in Pittsburgh.