from Freelance
by Kevin M. Kearney
Simon waited out the next morning’s pre-lunch lull in the Italian Market, observing the vendors along 9th Street hocking food, fish, and unlicensed Eagles merch. John the Bag Man waltzed by the Subaru and waved, showing off his blistered palms. A Vietnamese family inspected the produce stands’ vegetables, disappointed to find that nearly all of them were already spoiled. Blood-stained butchers from Cannuli’s and Esposito’s loitered on their respective corners, smoking cigarettes and talking shit on the mayor.
Simon’s phone buzzed in its holster. It was a notification from the HYPR app, but there was no passenger listed. Instead, there was just a line of text. Do you feel lucky, Simon?
He’d read about questions like these on HYPR PPL: mini-games, random opportunities to bet a day’s earnings and maximize your profits. The older Dryvers said to ignore them, that they were a waste of time—shiny objects that would only distract you from making money. “If you want to play games download fruit ninja or something jfc,” one user had written. Younger Dryvers claimed they’d had success, though, with one claiming he’d tripled his daily haul on one hand of blackjack. That particular response caused all the old timers to light up the thread: he was clearly lying, clearly a bot, clearly one of HYPR’s stooges sent to infiltrate the forum and stomp out all dissent. Simon wasn’t sure what to believe. He thought anyone who drove for HYPR was at least a little bit of a robotic stooge, himself included. If they wanted to bet their own money, why should anyone else care?
The question sat on his screen, staring at him. Do you feel lucky, Simon?
A 30 appeared above the question, then quickly changed to a 29, then a 28. His mind went blank; all he could do was watch the number grow smaller by the second. He turned away from his phone and looked out the window, but the Market didn’t offer an answer. Instead, there was a man rooting through a trash can. His long, wiry beard looked like steel wool; his t-shirt, a thinning white V-neck, was decorated with what looked like piss stains. If you squint, Simon thought, it almost looks like a pattern.
The phone buzzed again. 10 seconds remained. It was early in the month, and he was already up for the day. That meant he was already up for the month. Which meant he could afford to take a risk. Which meant he could afford to play the game.
It would only take a few seconds of effort and had the potential for a massive payoff. If he won, he could take off the afternoon. If he won big, he could take off the whole week. The opportunity was in front of him, waiting for him to grab it.
He tapped Yes and watched his phone vibrate in response.
Okay, Simon. Are you interested in numbers or trivia?
He tapped Numbers.
In the corner of his eye, he noticed the man with the wiry beard roll a rickety shopping cart towards the car. Since Simon had started driving, he’d learned the homeless in Philly begrudgingly respected the people who ignored them. Their real ire was reserved for the other people, the ones who looked them in the eyes, pouted their lips in faux sympathy, and claimed they didn’t have any cash. Outward callousness was still callousness, Simon figured, but at least it was honest. The bearded man began waving his arms, trying to grab his attention, but Simon just stared at his phone, pretending he didn’t see anything strange.
Okay, Simon. We’re going to play Guess the Number.
When he’d struggled with math in high school, his dad told him it wasn’t all that different from a game of chance. Sitting there in his car, though, he couldn’t remember any of the specifics. All he could recall was his father at the kitchen table, shuffling a deck of cards. “Are you paying attention?” he heard him say.
The app told him that Guess the Number was straightforward. I will think of a number, Simon. And you will try to Guess the Number I’ve selected.
Simon didn’t need to remember his dad’s lesson. Unlike blackjack, or poker, or rummy, or whatever other games the sad, saggy people in casinos played, this one required no real skill. He just needed to pick a number. He just needed to be right.
Simon, I need you to confirm you want to gambling today’s wages. If you do, you’ll be betting today’s earnings ($70.17). Still, you stand to win a lot ($140.34)!
The bearded man was now next to the car, tapping on the glass. Simon didn’t turn, but he could smell him through the window. He was right. The stains on his shirt were indeed piss.
Do you still want to play?
Simon pressed Yes and then turned to the man, hoping to brush him away before the game began. “No cash,” he said slowly, allowing the man to read his lips through the window.
The man locked eyes with him, said something indecipherable. He flashed his teeth, offering a crooked smile. In the top row was a silver cap.
“Sorry,” Simon said, exaggerating a shrug. He realized this was not convincing, but he didn’t know what else to do. “Sorry,” he said again.
The man leaned closer to the window. Simon heard him this time. “Don’t play the game.”
In his few weeks of driving, he’d already witnessed several memorable statements from passersby. A man on crutches in Snyder Plaza told him there was a 5G receiver in his brain. A kid in Kensington with scabs running down his face said Noah’s Ark could be found at the bottom of the Schuylkill River. “The zebras,” he’d said, holding back tears, “they drowned.” But the bearded man didn’t sound deranged. It was too precise for coincidence. The man knew what Simon was doing, and he sounded concerned.
His phone buzzed with another notification. The game had started. What number am I thinking of? Another countdown appeared. Simon had 30 seconds to pick a three-digit number.
The man tapped on the window. “You’re making a mistake,” he said, his voice rising.
Simon didn’t have time to waste. It was odd, disturbing even, but he couldn’t waste any time. The app was forcing him to decide. He needed to concentrate.
There must be a logic to the game, he thought. He tried to recall every communication he’d received from HYPR, every promotional email and spammy text. Was there a significant number throughout the company culture? Was there symbolic code associated with its enigmatic CEO? He thought it might be the day’s date, 915, but he knew that was too obvious for HYPR. The company’s motto was “Disrupting your expectations.” They would not choose a date.
He realized then the absurdity of the game. How many three-digit numbers were there to choose from? This was an impossible task. Maybe that was the key. Maybe it was a bit, a joke about how ridiculous the odds were. Maybe the answer was something knowingly idiotic, like 666 or 420. He considered entering one of those, but quickly decided against it. The thought of losing his day’s wages on such a dumb answer was something he knew he’d regret. 666? You expected that to work?
15 seconds remained. Simon turned back to his window and realized the bearded man was gone. The Italian Market was still going through its motions, but the man and his silver tooth were nowhere to be found.
Simon was running out of time. He typed in 111, knowing it was wrong.
Sorry, Simon. That’s not the correct answer. Do you want to know the correct answer?
He tapped Yes.
The answer was 420.
Simon wanted to laugh. Laughing would’ve meant he was in on the joke, like he’d at least won that small thrill, but his body refused. He tapped through the app, navigating back to his Dryver homepage. It wasn’t a bit: his balance for the day was $0.00.
Good luck next time! the app said.
He massaged his temples and reminded himself that he’d only surrendered the morning rides. It was just a few hours of work. And it had been kind of fun, hadn’t it? It had made his heart pump a little faster after a few dull hours in the driver’s seat. So, all things considered, it wasn’t a total loss. It wasn’t the end of the world. But, he decided, it would need to be the end of the fun. He needed to get back to work.
Kevin M. Kearney is the author of FREELANCE: A NOVEL (Rejection Letters, 2025) and HOW TO KEEP TIME (Thirty West, 2022). His writing has appeared in Slate, Stereogum, X-R-A-Y, and other fine publications. More at kevinmkearney.com.