The phone buzzed against his ear as Jack pushed through the revolving door onto Fifth Avenue. October wind cut through his wool coat like a blade. Still, he barely noticed—his boss's voice commanded his full attention, the way it always did, the way it had trained him to respond like some expensive dog.
"Yes, sir. I understand... No, that's fine. I'll handle the Morrison account tonight... Of course. Whatever you need."
He ended the call and slipped the phone into his pocket, shoulders sagging under the weight of another late night ahead. The sidewalk churned with bodies moving in purposeful directions, everyone rushing toward something or away from something else. Jack felt caught between both impulses—trapped in the current of his own making, swept along by choices he couldn't remember choosing.
Only as he fumbled for his car keys did he notice the figure in the doorway of the abandoned newsstand, tucked into the shadowed recess like a piece of forgotten furniture. He almost would have walked past if the man hadn't shifted slightly, drawing Jack's attention to the paper cup positioned hopefully on the cracked concrete.
Jack had passed this building every workday for the better part of a year, but he couldn't say with certainty whether the man had always been there. The thought disturbed him—how many things did he walk past without seeing? How much of the world had become invisible in his rush toward nowhere?
He fished a dollar from his wallet and approached the doorway, squatting to drop the bill into the cup. The man's face was weathered but kind, his eyes holding a patience that seemed almost geological in its depth. The gesture should have been routine, but today the words spilled out of Jack like water from a broken dam.
"You know what, my friend? You have it easy out here, don't you?" He looked into those gentle eyes, startled by their clarity. "No boss calling you to stay late. No PowerPoints, no deadlines, no suits to dry clean. No credit for your work given to others." Jack shook his head, tasting the bitterness of his own choices. "If I had known I'd end up as someone else's puppet, I would have chosen a different path entirely. I always wanted to be an artist, you know? Paint landscapes, maybe. Create something beautiful instead of... whatever this is."
The homeless man met his gaze with a distant but knowing smile, saying nothing. His silence wasn't the absence of sound but space—room for Jack's words to settle and find their weight. Jack stood, brushing dust from his knees, and walked away into the gathering dusk, the man's eyes following him like a rare moment of stillness he'd forgotten he needed.
Three weeks later, Jack hurried down the same street, venti caramel macchiato in hand and checking his watch with the frantic precision of someone perpetually late to his life. The presentation was in forty minutes, and he needed every second to review his notes one more time, to rehearse the words that would satisfy people whose approval had become the only currency he understood.
He was so focused on his phone that he didn't see the delivery cyclist until the bike clipped his shoulder. His drink exploded across the front of his navy suit, the white dress shirt beneath now a map of brown stains spreading like guilt across fabric. The cyclist called out an apology as he pedaled away. Still, Jack barely heard him—he was calculating drive time home, showering time, and the impossibility of returning to perform his small role in the corporate theater.
"Damn it," he muttered, then louder: "Damn it!"
Only then, standing in his ruined suit while passersby offered sympathetic glances, did he notice the doorway again. The homeless man sat in the same abandoned doorway, patient as the stone around him, watching Jack's outburst with eyes that held no judgment. How had he missed him on the way down the street? How did he always miss him until something forced him to stop, see, and remember that other people existed in his carefully curated world?
"Here," Jack said, approaching the doorway and extending the half-empty but still-warm cup. "I won't be needing the caffeine now anyway." The man accepted it with a nod of gratitude that felt more genuine than any thanks Jack had received in months. "You have no idea what it's like, having to dress up for the sake of others. Look at you—you don't care how you look, and that's freedom, right?"
Jack straightened his tie reflexively, knowing a crooked tie was a sign of laziness, tightening it too much, intentionally—that was his penance for such obedience. "If I had just stood up to Walter once, I wouldn't be his puppet. But no, he's probably out on the golf course while I'm scrambling to clean up his mess, wearing his expectations like a uniform I never chose."
The homeless man sipped the coffee slowly, savoring the warmth, his eyes never leaving Jack's face. There was something in that gaze—not pity, but understanding. The kind of look that said he'd seen this particular pain before. Jack turned away, already pulling out his phone to reschedule everything, to apologize for being human.
The call came in the afternoon—the only reason for that knowledge was that Jack had turned down lunch with his colleagues, and they had already gone and returned. The ringtone was Barry Manilow's "Can't Smile Without You," cutting through the overzealous hum of fluorescent lights and recycled air. Jack was presenting when his phone lit up with his mother's contact photo—a picture she'd sent him just last week of her and his father at their kitchen table, his dad's reading glasses perched on his nose as he worked on a crossword puzzle.
Jack glanced at the screen, silenced his phone, and declined the call. The meeting was important, and she usually just called to chat about neighborhood gossip or remind him to eat better, to remember that he had a body that needed tending.
The phone hummed in his pocket, quiet enough that no one could hear, but the haptics made his slacks dance awkwardly. Jack hit decline again, pushing the decline button through his slacks this time and apologizing to his colleagues as if to say sorry, you know how mothers are.
Then came the text, another vibration. This time, he would answer and say stop, but it was a text: "I know you are busy, honey. Sorry to reach out, but it's about your dad."
His blood turned to ice water. The expression on his face must have been alarming, as the room encouraged him to take the call. He left the conference room and called back immediately with shaking hands.
"Jack?" Her voice was small, fragile, like something that might break if he breathed too hard. "Your father... he's gone, honey. He had another heart attack this morning. I'm at the hospital, but... he's gone."
The words hit him like a physical blow, like falling through ice into water so cold it stopped thought. "Mom, I'm so sorry... if I had known, I would have answered. I would have been there."
He walked without direction, letting his feet carry him down the hall, into the elevator, and out onto streets that seemed suddenly foreign, suddenly emptied of purpose. Only when he stopped did he realize where he was—standing before the abandoned newsstand, tears cutting cold tracks down his cheeks. The homeless man sat in his usual spot. He looked up as Jack approached, his eyes soft with understanding that somehow knew what was happening and needed no explanation.
Jack began to pull a few from his pocket—the change he'd gotten from something a few days ago that had made its way back and forth from his nightstand too many times. But at that moment, something triggered a memory. He knelt in the doorway and pulled out his wallet—the same brown leather wallet his father had given him at graduation. He'd made it himself in his workshop, staying up late for weeks to get the stitching just right, his large hands working with surprising delicacy over the leather. When Jack looked inside, he found the dollar that came with the wallet—his dad had told him it was traditional, so the wallet would never be empty. But today, all there was was emptiness.
Then he broke. "I had no idea he was that sick," Jack said, his voice breaking like something poorly mended. "If I did, I would have made it a priority to visit more. I would have made more of an effort." He pulled out a twenty-dollar bill beside that dollar his father had given him, but stopped, looking at the wallet. "I just can't give you that one," he continued, holding up the dollar. "He made this, you know. More than ten years ago. Spent weeks on it, cutting, stitching, and buffing the leather until it gleamed. And I probably said 'thanks' without looking up from my phone or seeing the love stitched into every seam."
The twenty felt insufficient, meaningless. Jack pulled out another bill, then another, his hands shaking with grief and something more profound—regret that had weight to it, substance. He held up the wallet and the dollar bill beside it. "I would have told him I loved him more. I would have listened when he talked about his garden or that fishing trip he wanted to take. I would have..." His voice trailed off as the homeless man reached out and gently touched his shoulder.
The contact was brief but grounding, a reminder that he wasn't alone with his grief, that touch could still heal even when words failed. Jack wiped his eyes and stood, the wallet feeling heavier in his hands—not with money, but with memory, with the weight of love unspoken. He placed the wallet in his breast suit pocket, next to his heart—a corny gesture, but he hoped his dad would know. Then Jack headed down the empty street full of noise.
It was sunny when Jack was on that street again, but he wasn't heading to or from work this time. He had spent some time with his mom for the first few days—bereavement time off dictated three days only of mourning. It was Saturday afternoon, and he'd been wandering through the city, trying to clear his head to prepare for returning to work. But these streets he walked seemed unfamiliar now, different. At first, he thought it was his t-shirt—he hadn't changed from the airport, even though he'd already been home—or maybe the sun breaking through the canopy above for the first time in ages, or perhaps it was just the first time he'd looked up.
As he raised his view, he spotted a woman about his age with auburn hair that caught the afternoon light like copper wire. She stood at the curb with her arm extended toward the flow of yellow cabs. Each taxi that passed her seemed to slow, consider, then accelerate past to pick up someone else further down the block, as if she were somehow not quite visible enough, not quite important enough to stop for.
After the fourth rejection, her shoulders slumped in frustration. Jack felt something twist in his chest—recognition, maybe, or kinship with another person the world seemed determined to overlook.
He paused, pretending to tie his already-tied shoe so he could steal another glance. She was beautiful, but more than that—there was something in her posture, the way she tucked the flyaways behind her ear when the wind caught them, that made his chest tighten with possibility he'd almost forgotten how to feel.
Just walk over, he told himself. Offer to help. What's the worst that could happen?
But instead, he found himself shaking his head and looking toward the doorway where the homeless man sat, watching the entire scene with the quiet attention of someone who had learned to see what others missed.
"Who am I kidding?" Jack said quietly, the words coming out before he could stop them. "She'd never be interested in someone like me. I mean, look at her—confident, beautiful, probably has her whole life figured out. If I had been braver and learned how to talk to women instead of burying myself in work like it was some kind of shelter... If I could risk rejection once, I would be married a hundred times over."
The homeless man looked from Jack to the woman, then back again, his eyes holding something Jack had never seen there before—not just understanding, but urgency. For a long moment, they sat in silence, watching her growing frustration with the taxi situation, watching another moment slip past like water through cupped hands.
Then, the man spoke for the first time in all their encounters.
"My friend," he said, his voice surprisingly warm and clear, like water over stones, "every day you stop here and tell me about everything you wish you had done differently. But you're still young—you still have time. The real problem is you're so focused on the past that you can't see what's still possible." He gestured toward the woman with the slightest nod, a movement so small it might have been imagined. "It's time you got out of the 'woulds' and into what could still be. Otherwise, those possibilities will just become part of your wilderness of 'woulds.'"
Jack stared at him, the wordplay hitting like a revelation, like the sun breaking through clouds after a long winter, out of the woulds. All this time, he'd been lost in a forest of his own regrets, so thick with the branches of missed opportunities that he couldn't see the clearing just ahead or see that he was the one holding the map to his own escape.
He looked back at the woman, who had given up on taxis and was now scrolling through her phone, probably calling for a ride, probably accepting that the world would continue to overlook her until she learned to ignore it in return.
Without overthinking it—without giving himself time to retreat into another "would have," another excuse dressed up as wisdom—Jack stood up.
"You're absolutely right," he said in agreement, possibility.
He walked over to the woman, his heart hammering but his steps steady, each footfall a choice to be present, to be seen, to risk the beautiful danger of being human in front of another human being.
"Excuse me," he said. "I couldn't help but notice you're having trouble with the taxis. I know a trick—there's a better spot about a block down where they must stop for the light. Want me to show you?"
She looked up from her phone, surprised but not unfriendly. Her eyes were the color of coffee with cream, the color of autumn afternoons. "Really? That would be amazing, thank you."
As they walked together down the sidewalk, Jack glanced back at the doorway. The homeless man had already moved on and was rummaging quietly through a small bag beside him. The man looked up at them and smiled like he did every time. There was no acknowledgment, no watching, no sense that he understood the magnitude of what had just happened. He simply was present and patient as he'd always been, offering what was needed when needed, then returning to the quiet rhythm of his existence.
"I'm Sarah, by the way," the woman said, pulling his attention back to the moment, to the present tense of his life.
"Jack," he replied, and for the first time in longer than he could remember, he wasn't thinking about the "woulds". He was thinking about what might happen next. Behind them, the city hummed with its usual urgency, but Jack had finally found his way out of the woods—all of them.
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I’m obsessed with your metaphors! “Geological in its depth,” “spreading like guilt,” so good!
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Thank you for taking the time to leave a comment. It's so difficult to create metaphors that make any sense and aren't overused.
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Lovely. Truly inspirational.
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Thank you for commenting. I appreciate the feedback.
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