Pretty Helpful
The wind swept lightly across the manicured greens as the old man stood just outside the clubhouse, one hand gripping his phone, the other fiddling with the strap of his golf bag. He squinted at the sun, his voice tight with skepticism.
“You’ve got to be joking,” he muttered into the receiver. “This is the guy you were raving about?”
A low chuckle came from the other end. “I know, I know. But trust me, man—this guy, he’s something else. You won’t get it right away, but once you spend some time with him, you’ll see what I mean.”
The old man shook his head, glancing toward the clubhouse where a figure was now approaching. “I don’t know. Retirement’s not exactly something I need mentoring for. I just want to relax.”
“You think I did, either?” His friend’s tone softened. “I thought the same way. But I’m telling you, this guy made my retirement better than I ever could have imagined.”
The old man paused, leaning his shoulder against the wall. He wasn’t sure what he was expecting, but so far, this wasn’t it. “Better how?”
A laugh came through the phone, warm but evasive. “That’s the thing. It’s not about the specifics. He just… I don’t know, man. He shifts your perspective. You gotta keep an open mind, alright?”
The old man glanced up again and saw the mentor now in clear view, moving toward him with long strides but no sense of urgency. The man looked like a collection of contradictions. Expensive golf pants, wrinkled as though they’d been stuffed in a suitcase for days. Crocs on his feet. A polo shirt that said Villainous Grappling stretched across a wiry frame, topped off by an unruly beard and hair that made him look like he’d just rolled out of bed after a week on the streets.
“Uh-huh,” the old man grunted, watching the strange sight. “Is this guy for real?”
His friend chuckled again. “It sounds like you found him.”
“I’ll keep an open mind,” the old man said, though he wasn’t sure how much more open it could get.
He ended the call just as the man stopped in front of him, flashing a broad, easy smile and offering a handshake. “Pretty Helpful,” the man introduced himself, like it was the most normal name in the world.
The old man stared at him for a second, then reluctantly shook his hand. “What’s with the clothes?”
Pretty Helpful gave a casual glance at his outfit, brushing some lint off his wrinkled pants, then smirked. “I call it Yacht Thrift,” he said with a shrug. “Comfort of the sea, price of a thrift shop.”
The old man raised an eyebrow, feeling more baffled by the second. “Uh-huh,” he muttered, glancing again at the Crocs.
Unfazed, Pretty Helpful just smiled wider, gesturing to the open fairways. “I got us a tee time,” he said easily. “Wanna get a round in?”
The old man watched in mild disbelief as Pretty Helpful’s golf ball sliced wildly off into the trees. For the fifth time in the last hour, Pretty had driven the ball with all the finesse of a first-timer. They were barely halfway through the course, and the old man found himself torn between amusement and impatience. How could someone be this bad at something they had set a tee time for?
Pretty shrugged as he lowered his club. “I’m terrible at this,” he admitted with a casual laugh. “But I heard you enjoyed golf, so I figured this would be a good way to get to know you.”
The old man raised an eyebrow, lining up his shot. He was still trying to get a read on this character. “You don’t play much then, I take it?”
“Nah,” Pretty Helpful admitted. “But I’m good at reading people. You like golf. Makes sense we’d talk while doing something you enjoy.”
The old man swung, his ball cutting cleanly through the air, landing on the green near the pin. “You’ve got a weird way of going about things. So… how does this mentoring thing work anyway?”
Pretty Helpful’s eyes twinkled as he leaned on his club, unbothered by his disastrous performance on the course. “Simple,” he said, his voice taking on a sudden clarity. “Mentoring’s just about helping people apply knowledge they already know to their lives. You already know the right answers, even if you don’t realize it yet. I just help you take those answers seriously. Empower you to act on them.”
The old man’s swing slowed as he considered the words. “Okay… but what kind of ‘knowledge’ are we talking about here? What’s the simple stuff everyone knows?”
“Budget. Investment. Priorities,” Pretty Helpful answered without missing a beat, his tone so matter-of-fact it almost seemed rehearsed. “The stuff people tend to overcomplicate. But it’s really just that simple.”
The old man shot him a skeptical look. “That’s it?”
“Yup,” Pretty said with a grin. He gestured toward the fairway, a glimmer of mischief in his eyes. “Take fitness, for example. You’re in great shape for your age, and it shows in your game. But why are so many people out there out of shape and hurting? The answer isn’t a secret. It’s discipline and priorities. You’ve figured it out, obviously.”
The old man blinked. It was a simple observation, but Pretty had a way of delivering it that made it seem more profound. There was no fanfare, no long-winded speech. Just a few words that cut straight to the point.
“I guess you’ve got a point there,” he muttered, pausing to watch Pretty Helpful retrieve his ball from the woods with a chuckle.
Pretty reappeared, completely unfazed by his lack of skill. The old man found himself warming to the mentor’s easy confidence. Pretty wasn’t trying to impress anyone, and that was part of the appeal. Against his better judgment, the old man realized he actually liked the guy. But he wasn’t sure why.
Maybe it was because Pretty wasn’t trying to sell him on anything. He wasn’t pushing or convincing. He was just… there.
After another hole, the old man found himself asking the question he hadn’t planned to. “Alright. So let’s say I’m interested in being mentored. What’s the price for this kind of thing?”
Pretty Helpful didn’t skip a beat. “Sliding scale. How much would you be willing to pay for something that’ll impact the rest of your life?”
The old man hesitated. The way Pretty framed it made him think. He thought about his friend’s praise, about how insistent he’d been that Pretty was the real deal. “Well… I could do ten grand,” the old man said, more because his friend had been so impressed than because he was sure. “Just to see what all the fuss is about.”
Pretty Helpful’s smirk widened, but there was no malice in it—just that same relaxed confidence. “Cool,” he said casually. “Then it’ll be twenty thousand for my program.”
The old man’s mouth fell open. “Twenty thousand? That’s double what I just offered!”
“Exactly,” Pretty replied, totally unbothered by the pushback. “Look, ten grand is what you’re comfortable with. It’s what you think is a reasonable cost for this. But twenty grand? That’s gonna sting. And if it stings, you’re gonna take it seriously. You’ll get out of it what you put into it. The more it costs, the more you’ll commit to the work.”
The old man shook his head, trying to process this logic. “You think I need to hurt to take you seriously?”
Pretty shrugged again, still smirking. “I think you’ll only stick with something if it’s valuable enough to you. And that means putting more on the line than what’s comfortable. This isn’t just about a few sessions—it’s about the rest of your life.”
The old man frowned, but deep down, he knew Pretty wasn’t entirely wrong. He hated admitting it, but there was something about this guy’s way of thinking that stuck.