It was a hot, sticky Saturday afternoon when Leonard, a 32-year-old delivery driver, picked up his phone and saw a new delivery request pinged through his app. The order was from a high-end neighborhood, and the destination was a luxurious gated community. He smiled to himself, imagining a hefty tip waiting for him at the end of the route. Little did he know, this was about to be the most frustrating delivery of his career.
Leonard had been driving for several months now, making deliveries for DoorDash, Uber Eats, and a few other services on the side. He’d had his fair share of awkward encounters—grumpy customers, wrong addresses, and even a couple of late-night food fights—but nothing had prepared him for the disaster that awaited him on this particular day.
The order was simple: a large catering tray of sandwiches, a few drinks, and a dessert platter. Leonard figured it was for a small gathering or a family celebration. No big deal. He confirmed the pickup from the restaurant, loaded everything into his car, and set off. The route was easy, but he couldn’t shake the feeling that something was off. Maybe it was just the heat, or maybe he was just tired after a long day of driving, but his intuition was buzzing.
As he pulled up to the gated community, Leonard noticed a woman standing outside the entrance, her arms crossed and her face locked in a stern frown. He pulled up to the curb, rolled down his window, and waved at her.
“Hi, I’m Leonard, here to drop off your order,” he said, trying to sound friendly.
The woman, who appeared to be in her late 40s, didn’t respond immediately. Instead, she eyed him up and down like he was an inconvenience.
“You’re late,” she said flatly, not bothering with a greeting.
Leonard glanced at the time. He wasn’t late; in fact, he was 10 minutes early. But he didn’t argue. He was used to customers being quick to judge.
“I’m sorry if there’s been any confusion, ma’am. I’m here now,” Leonard said, offering a polite smile. “Here’s your order.”
He opened the back of his car, grabbed the tray, and started walking toward her. But as soon as she saw the food, her face twisted into a scowl.
“Ugh, I asked for the sandwiches to be cut into smaller pieces!” she snapped. “These are way too big. This is unacceptable.”
Leonard froze. He hadn’t been told about any specific request for smaller pieces. The restaurant didn’t mention it, and he hadn’t been informed on the app. He knew it wasn’t his fault, but the customer’s tone was already grating on his nerves.
“I’m really sorry, but I didn’t see any notes about that on the order. I’ll call the restaurant and see what can be done.”
The woman rolled her eyes dramatically. “Of course, you would call them. Why can’t you just fix it yourself? You’re a delivery driver. This is your job. I’m paying for this service, and it’s terrible.”
Leonard’s patience was starting to wear thin. He’d always prided himself on handling difficult customers with professionalism, but this woman was testing every ounce of his resolve.
“Ma’am, I understand you’re frustrated, but I really don’t have the ability to fix the food. I’m just the delivery driver. I’ll contact the restaurant for you.”
The woman scoffed, crossing her arms tighter. “Fine, but don’t think I’m paying you a tip for this mess. You’ll be lucky if you get anything for such poor service.”
Leonard could feel the blood rushing to his ears. His hands clenched the food tray, but he knew he had to stay calm. He forced a smile, knowing arguing wouldn’t do any good.
“Alright, ma’am, I’ll let them know. Again, I apologize for the inconvenience.”
Just as he turned to leave, the woman called out, “Oh, and make sure you get the right address next time. I live on the other side of the community. You almost went to the wrong house!”
Leonard stopped in his tracks, his jaw tightening. He had followed the GPS to the exact address that had been given to him. But instead of arguing, he simply nodded and walked back to his car.
As he drove off, his mind raced. He’d been polite, he’d been professional, and yet this woman had treated him like he was a servant, not a valued part of the service industry. He couldn’t believe how quickly some people would turn on you for something that was out of your control.
Leonard knew this was just one of those days that would stick with him. A few hours later, as he sat in a diner on a break, he checked his app to see how much he’d earned that day.
There was a notification about a tip—one that was far lower than he expected. He clicked into it, and there it was: a message attached to the tip: “Delivery was late, food was wrong, and the driver was rude.”
Leonard’s stomach sank. Rude? He had been nothing but polite. He shook his head in disbelief, realizing that there were just some customers you couldn’t please.
That evening, Leonard drove home, exhausted and frustrated. But as he pulled into his driveway and turned off the engine, he smiled to himself. He’d survived another tough delivery, and the next one could only get better. He took a deep breath and reminded himself that this was just part of the gig.
Tomorrow would be a new day. And with it, a new chance to prove that no rude customer could break his spirit.
Moral of the story: In the world of gig work, not every customer will be kind, but you can control how you respond. Always keep your head high, even when the delivery goes terribly wrong. You never know what tomorrow’s ride will bring.
