This column first appeared in CityView Magazine’s “The Summer Issue” June 2026 edition.

Although our daughter is only 12, she has been dreaming about her first summer job for years. She’s told us that she can’t wait for the day that she’s old enough to be able to carry out all the big ideas she has for earning some extra pocket money.

There’s been talk of lifeguarding, camp counselor-ing, dog-walking, babysitting, waiting tables, or becoming a barista. Working at sweetFrog, Texas Roadhouse, or Chick-fil-A, where I can only assume the chief motivating factors are complimentary soft serve frozen yogurt, butter rolls, and chicken nuggets. She’s asked me if she starts saving now, whether I think she’ll have enough cash to buy a brand new Jeep Wrangler by the time she’s 16.

I gently reminded her that she blew through all her birthday money in less than 24 hours on mall kiosk squishies, a bedazzling kit from Amazon, and a snack tab at her brother’s Little League ball field concession stand that probably equated to the down payment on that Jeep Wrangler.

When our career-curious tween asked her dad and me about our earliest forays into the summertime workforce, what she probably wasn’t expecting was a full-fledged family storytime centered around the nostalgia of being a teenage babysitter in the late ’90s/early 2000s, and one young man’s foray into joining the waitstaff at an exclusive country club, and the misadventures that ensued.

I explained to my daughter that while presently, on most days it seems as though I am fighting for my life to feed, nurture, and guide my own two 9- and 12-year-old children as a 40-something woman, there was once a time when I was the newly-16-year-old babysitter to four children under the age of 7 for whom I could care as if I were Mary Poppins herself. 

There were no shortcuts back then. No DoorDash delivery for dinner, no iPads or Netflix to keep little ones occupied, and no cell phone on which I could easily reach their parents in the event of uncertainty or emergency. We had Kid Cuisines and frozen chicken nuggets that I could pop in the microwave and pull from the oven while balancing a baby on my hip and simultaneously playing a game of Twister with the other three.

And after I got all four kiddos to bed without a single tablet of melatonin, white noise machine, vibrating swivel bassinet, or heart- and oxygen-rate detecting infant sock, it was MTV (with commercials) until the parents got home. And they paid me the going rate of $5 an hour, which went straight to gas for my hand-me-down-from-my-dad 1991 Mazda 626.

After my trip down memory lane, my daughter had two questions: “What’s a Kid Cuisine? That sounds fancy,” and “Did they pay you on Venmo?”

And then it was my husband’s turn to recount some highlights from his summer break job as a black-tie-attire-clad waiter at a quite prestigious country club that counts notable politicians, coaches, former athletes, physicians, and business professionals among their members. As I listened to him recount what amounts to a hilarious comedy of errors, it became clear to me that they really must have hired him (and kept him) because of how good he looks in a tuxedo, certainly not because of his prowess as a waiter.

For starters, he once served a large table of elderly women who had just come off the golf course and ordered a round of sweet tea. As my husband balanced the heavy tray of drinks on one hand and attempted to pass a glass down to the table, the tray began to tilt. He froze and watched as one glass slowly slid down the tray and rested ever so slightly on the back edge of one of the lady’s big straw hats. A trickle of tea began to collect in the brim.

My husband waited for a few seconds to see if the brown liquid would start to leak through her hat and onto her white golf shirt. When he realized that the tea was staying put and that the ladies were too caught up in their conversation to notice what had happened, in an effort to salvage his dignity (and maybe his tip), he made the snap decision not to disclose the moat full of sweet tea this poor woman now wore on her head.

I have heard that story a million times and still cringe at the mental image of that lady flinging her sun hat into the walk-in closet of her fancy mansion, a trail of sweet tea splattering the pristine walls.

And there was the time my husband waited on a family of four generations at a birthday dinner and fumbled the great-grandmother’s beverage order tremendously. When he brought her son the bill at the end of the evening, her son said, “I’m sorry, but no one here ordered a vodka soda.” 

My husband pointed at the octogenarian at the head of the table and replied, “She did, sir.” 

Luckily, the table erupted in laughter rather than outrage. “What? She said club soda, not vodka soda! She hasn’t had a drink in 40 years! We were all wondering why she was acting so fun!”

In a notably less jovial encounter with a wealthy club member who was hosting a business dinner for colleagues, my husband was tasked, for the first time in his life, with presenting and opening a bottle of wine for the table. But it was not just any bottle of wine—it came from the man’s personal home cellar, its vintage older than my husband and pricetag more than he had in his entire bank account.

He struggled so badly with the corkscrew and very old cork that, no matter how hard he tried, crumbled back down into the bottle. The red-faced dinner host finally grabbed the bottle out of my husband’s shaky hands and shouted, “Oh, for God’s sake, I’ll do it myself!”

My daughter posed exactly one question to my husband: “How did you not get fired after all that?”

Twenty-something years later, I still make a mean microwave dinner, and I’m happy to report that my husband has to use none of his table-waiting skills in his career as a dentist. We both had a menagerie of jobs throughout our high school and college summers that provided us with the life skills that I’m sure our parents were hoping that joining the workforce at a young age would develop. Truthfully, I was just thrilled to have my very own spending money that was earned and not given.

Give my daughter a couple more years, and she will make a great employee, whether it’s slinging mocha lattes, watching over swimmers in the local pool, ringing up your fro-yo, or saying, “My pleasure!” after she takes a drive-through order.

And I’m just as excited as she is for her summertime side hustle. She already owes me for a set of press-on nails she bought on my credit card with the promise, “I will pay you back with my own money! As soon as I have some…”