When My Career Stalled, I Got A Job At Olive Garden. I Was Shocked By What I Experienced There.
When I landed a job at Olive Garden, I hadn't waited tables in 13 years. They were the only place willing to hire me with an employment gap that wide. For the first time in over a decade, my freelance writing business—which tends to fluctuate along with the economy—had dried up completely. I needed cash, and I needed it fast.
My first official shift fell a few weeks before Thanksgiving. It was also my 37th birthday.
The Fear of Starting Over
At first, I wasn't sure I could physically do the job. Could I still balance a heavy tray? Could I keep track of dozens of orders in my "mom-brained" head? Serving is athletic work, and my body wasn't 20 anymore. I worried about this constantly during training.
But Olive Garden made it easy to relearn the ropes. They deliberately kept server sections small so we could focus on refills, service, and turning tables. My arms got stronger. I mastered the rhythm. I got used to the chaos. I made friends with my co-workers. I even figured out that if I lay on the floor with my legs up the wall after every shift, my feet would stop throbbing.
By Valentine's Day, I felt confident enough to actually think about things other than survival while I worked. And when I started looking around, I was surprised by what I saw.
The Valentine's Day Epiphany
That night, the restaurant was a madhouse. Every surface was a mess. The lobby was packed. We were short-staffed. A fight was about to break out in the kitchen. Instead of the usual three or four tables, I had nine.
In the midst of the chaos, I was struck with a deep sense of appreciation. My anxieties about being "too old" for the job and my writing career falling apart dissipated. I kind of fell in love with the place.
I know Olive Garden isn't considered gourmet by many (some openly sneer at it), but for others, it feels like home. In many parts of the country, it's where people go for Friday night dates or birthday celebrations. It was a favorite night out for me as a kid growing up in rural Ohio—we'd drive 45 minutes just to get there.
Standing in that packed dining room, apron tied and name tag pinned, I saw myself in the guests. I saw big families celebrating love and couples on casual dates. As the server, I wanted to honor that for them. I hit that specific zone of appreciation that exists in the food and beverage profession: the desire to host, to show people a good time, and to let them make their own memories.
I honestly don't know if I've ever drunk the Kool-Aid on a job the way I drank it that night.
The Practice of Empathy
After that shift, I made a practice of working on my empathy skills. I challenged myself to always ask: *What might this person be experiencing?* Especially when they were being annoying. I made it a personal goal to give people the benefit of the doubt.
Olive Garden attracts all sorts. I saw everyone I knew in town eventually. I experienced every genre of restaurant guest stereotype:
* People who ran me ragged and tipped hardly anything.
* People who were rowdy, drunk, or mad at each other.
* Families with messy, wild kids.
* People are trying to get a table five minutes before close.
* People looking for a free meal.
* People who left fake $20 bills printed with Bible verses.
But I also found a ton of people who surprised me with their generosity. I found a deeper well of empathy in myself than I ever imagined, and it allowed me to care about the experience of all of them.
While I was empathizing with the people around me, I started to feel better about my own situation, too. I came to terms with my expectations for life. All my emotions around my writing career eased when I was running from one end of the kitchen to the other. Learning not to be so hard on the people around me made me less hard on myself.
Where Empathy Ends
But the most important lesson I learned was about where empathy ends. Because sometimes, no matter how hard you try to understand a person's motivation, there's nothing there to understand.
Coincidentally, on another Valentine's Day—my last day at the restaurant (though for an unrelated reason)—I waited on the most memorable table I've ever had.
.jpg)
I greeted a man and woman, probably in their early 50s, with my standard welcome. They ordered water and pasta with sauce—the cheapest item on the menu that still came with unlimited salad and bread, and the fastest to prepare. The man asked me to hold off on putting in the dinner order because they wanted to enjoy their salad first. Like ordering light, this was a common request. I told him not to worry; I would take care of the timing.
I brought their salad and bread, served other tables, and waited. When they placed their empty bowl on the edge of the booth, I asked if they wanted more. "Yes, please," they said.
On my way back to the kitchen, I stopped at an open computer and put in their dinner order. Not to rush them, but because the lobby was full and part of my job was to keep things moving. They'd ordered pasta with a spoonful of sauce, so the kitchen saw an easy order and put it out immediately. By the time I returned with their second salad, another server was already placing their dinner on the table.
The guests, who had been perfectly polite up to now, were outraged.
I've never had people so mad at me. (A close second was when I was 16, working at McDonald's, and a woman threw an ice cream cone through the drive-thru window at me.)
"Oh, you'll take care of it?!" the man parroted back to me.
My manager offered them a discount that amounted to $5 on their $20 check, but the guests insisted they'd never come back if they couldn't get their food for free. My manager—a total hero—held the line. He told me later that if they were going to come in, spend $20, and give people a hard time, then it was cool if they never came back. He emphasized that just because they were looking to get something for free didn't mean they were going to get it.
When I summoned my empathy skills to parse the interaction, I felt tricked. Theirs was complete self-absorption—a total disregard for everyone else involved in the Olive Garden experience that night. Sometimes, people are just like that.
The Clarity of Boundaries
There's something about being yelled at by a jerk that brings a sense of clarity. When people get like that, it usually has nothing to do with you and everything to do with their expectations, realistic or not. No matter how powerful empathy can be, simply saying "no" and not letting it bother you is just as transformational.
Today, when I hear about customers being ruder than ever and see footage of people harassing workers at Target or Applebee's, I wish I could tell those workers: **Not all customers are good customers. Not all people are good people. Not all expectations will be fulfilled.** The best way to live in uncivilized times is often simply not to let it ruin your night.
The Safety Net
I moved on to another restaurant after that. I figured if I could master serving at Olive Garden, I could do it anywhere. My new job was at a fancier place with a completely different clientele. The money wasn't really any better, and I left as soon as my writing work leveled out again.
There are so many factors that play a role in making it in freelance work. If anything, working at Olive Garden forced me to become more comfortable with the fact that I can't control many of them. Just like there might be a jerk in your section, countless other things may not work out the way we expect. Shifting political winds, pandemics, changing markets, and technological advances—sometimes no amount of hard work can overcome them.
Things change. Learning how not to be so hard on myself and others has made me better able to accept my own lack of control. And I can't tell you how many times I've told myself that everything will be all right because I can always go back to the Olive Garden.