Dashing Side Hustles

People Passing Off A Bag Of Delivery Food

Dear Delivery Diary: Did my Crunchwrap survive?

There’s magic to side hustles, especially when they involve late nights, quirky customers, and the unpredictable pulse of delivery apps like Uber Eats, Grubhub, and Amazon Flex. Maybe it’s the mystery of who’s on the other side of that door, or the way drivers gather stories like souvenirs. Either way, if you’ve ever ordered Taco Bell at 1 a.m. or shared an Uber with a karaoke setup in the backseat, you’ve experienced a piece of this strange, charming world.

On one particularly memorable night, I dozed into a deep sleep in my Airbnb around 1 a.m., fully intending to stay awake just long enough for my Uber Eats delivery to arrive. I’d ordered a Crunchwrap Supreme, that late-night delicacy best enjoyed with a dash of sleep deprivation. As I awakened the next morning, the immediate thought that popped into my mind was: Did my Crunchwrap survive the night?

 I stumbled to the door, opening it with a mix of hope and dread. To my relief, the package lay undisturbed by the “nightlife creatures” I’d feared. There it was, my Crunchwrap, mercifully untouched by raccoons, cats, or late-night wanderers.

The Adventures of Side Hustles 

The thing about side hustles is that they create these little snapshots of other people’s lives. Take my friend Zach, for example. Once, he logged into his Grubhub app to deliver a single ice cream cone. That’s right — one cone, one scoop, across town from a convenient gas station. Most people would have expected it to melt before arrival, but a job is a job, right?

Then there’s Amazon Flex, where the job involves more than just packages — it involves tips, sticky notes, and good survival skills. Colby once dabbled in Amazon Flex and shared some personal notes on how to avoid the family’s hyperactive golden retriever or overly anxious Pomeranian.

Others were more direct signage warning things like, “Please knock quietly, new baby inside!” or “Please use the back door, house cat tends to escape.” Every house has its own house rules. Don’t you? 

Then there are the pet sitters and dog walkers who bring tales from the yards and front doors they visit. One pet sitter, who doubled as an Amazon Flex driver, told me about the “rules” that came with each house. Not just the human rules, mind you, but the pet rules. There were charts to let her know which dogs were friendly, which cats would scratch, and which guinea pigs were escape artists. 

And there’s something oddly endearing about delivering groceries through Instacart. Sophie sometimes does Instacart to earn a few extra bucks and swears by the number of times she ended up delivering orders to the right places but discovered later it was the wrong home address. These deliveries were small moments of delight for the residents, but for the drivers, it was another stop on a list that stretched through grocery aisles, late-night fast-food stops, and emergency snack runs.

One of the biggest ironies in this world of gig work is that many drivers who started these jobs to make some “extra” cash ended up working full-time hours. These side hustles are often seen as flexible income boosters, but for some, they’ve become primary sources of income. The drivers themselves are as diverse as the stories they tell, from college students looking to fill in gaps between classes to retired folks who enjoy the extra cash — and the extra company.

The Uber stories, though, are my personal favorites. It’s a mishmash of personalities, from 30-something code developers to 40-something dads. Once, I found myself in the backseat of an Uber with a full karaoke setup. The driver had a mini microphone setup, complete with small iPad screens that played 80s and 90s pop wonders. He said the karaoke sessions brought in tips and kept things lively.

There is nothing as relatable as singing along to “Don’t Stop Believin’” with strangers under neon van lights.

But it’s not just the karaoke Ubers that make the night interesting; it’s the Uber Eats runs that turn chaotic when team projects run late, and everyone decides a midnight McDonald’s run is the answer. You get a collective sigh of relief as everyone piles into a shared order, then the surreal thrill of opening that door past midnight to receive French fries and cheeseburgers as if these delights make the group project more enjoyable. 

Shop Local 

Locally, there is a hidden gem of a local delivery service called CoMo Delivered. It is a locally owned service in Columbia that partners with small restaurants. Unlike the big delivery names, CoMo Delivered is all about supporting local eateries, and it delivers with the same pride that many bigger platforms can’t replicate. The drivers here know the best places to pick up a late-night gyro or extra-cheesy pizzas. 

Side hustles like these keep a person busy and make the distance of a city reachable. Every delivery paints a picture of late-night cravings, tired students, or hardworking parents who just can’t make it to the store, from the Taco Bells to the ice cream cones to the midnight McDonald’s. And sometimes, the customer’s life sneaks in, too — an Amazon delivery with baby supplies, a dog-walking client juggling a high-demanding job, or the college group too exhausted from cramming for finals to cook.

Whether they’re delivering, driving, or just dropping by to walk a dog, these side hustlers are the unsung threads that stitch the city’s story together. While the gigs may not always be glamorous (or even side hustles, in some cases), they create a strange, enduring connection between all of us who’ve ever waited for a Black Bean Crunchwrap Supreme at 1 a.m., hoping it’ll still be there come morning.

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