Doorman 2.0: Charley’s Exit Strategy

Charley’s job as a doorman wasn’t glamorous, but it was steady. For almost ten years, he stood at the entrance of a mid-tier Manhattan apartment building, nodding at tenants, holding doors, and mastering the art of pretending to care about Mrs. Feldman’s Pomeranian’s latest bowel movement. At 35, Charley had grown so comfortable in his role that he could predict tenants’ elevator arrival times like some sort of lobby Nostradamus.

But lately, comfort had started to feel like a trap.

“I can’t do this forever,” Charley muttered one evening, slumped on the couch in his childhood apartment in Queens. His mom, who had been folding laundry while watching reruns of Family Feud, didn’t even look up.

“You’ve been saying that for five years, Charley.”

He sighed. She wasn’t wrong. Every year, he promised himself he’d move out, get a new job, and finally feel like a grown adult. Every year, he ended up exactly where he started: eating takeout with his mom and dodging Mrs. Feldman’s complaints about her Amazon packages.

But this time was different. Or at least, that’s what he told himself.

Step One: The Job Search

Charley’s first hurdle was deciding what he actually wanted to do. He didn’t have a college degree, but he was good with people and could hold a conversation like a pro—thanks to years of chatting with tenants about everything from the weather to Knicks games. The problem? Most jobs wanted experience.

“What kind of experience do they think I have?” he grumbled, scrolling through job listings on his ancient laptop. “Experience avoiding Pomeranian pee puddles?”

One day, while venting to his childhood friend Max over beers, Max suggested remote work.

“Look, dude, everyone’s doing it now. You don’t need a degree to do customer service or something. Half these jobs just want you to know how to use email and sound nice.”

Charley perked up. “Sound nice? I’m great at sounding nice! I’ve got a decade of nodding and smiling under my belt.”

Encouraged, he dove into the world of remote job applications. The first few were disasters. One cover letter accidentally included the phrase “door-holding expertise” (Max’s fault for proofreading while drunk). Another required a 3-minute video introduction, during which Charley nervously rambled about his favorite bagels before abruptly cutting off with, “Uh, yeah, so… call me, maybe?”

Step Two: The Move-Out Plan

Getting a remote job was only part of the equation. Charley also wanted to move out of his mom’s place—a place that hadn’t changed since the early 90s. The wallpaper was still floral, the furniture still creaked, and the Wi-Fi barely worked in his room.

The idea of paying rent, though, sent a chill down his spine. Rent in New York was no joke, and Charley had grown accustomed to having his mom’s lasagna on demand.

“Maybe I’ll just move to, like… I don’t know, Jersey or something,” he told Max one day.

“Jersey?” Max cackled. “You’re afraid of paying for Wi-Fi, and you think you can afford Jersey?”

Charley groaned. The harsh reality was that moving out would require cutting back on old habits—like his daily bodega sandwiches and Friday night Uber Eats splurges. He tried meal prepping one week but gave up halfway through when he realized chicken and broccoli every day made him want to cry.

Step Three: Breaking the Cycle

The hardest part wasn’t applying for jobs or budgeting for a new place—it was changing himself. Charley was a creature of habit. He liked routine. He liked knowing the exact temperature the lobby got too warm for tenants.

So, when he landed his first remote job interview—a customer support role for a tech startup that sold smart pet feeders—he nearly sabotaged himself by overthinking.

“What if I blow it?” he asked his mom the night before.

She put down her crossword puzzle and gave him a long look. “Charley, you can talk about weather and dogs for hours. You’ll be fine.”

The interview went surprisingly well. Charley managed to keep his rambling in check, and the interviewer seemed charmed by his doorman stories. A week later, he got the job.

Step Four: Life 2.0

Charley’s first week working from home was both exhilarating and terrifying. He set up a makeshift desk in his room, balancing his laptop on a stack of old textbooks. His mom, bless her heart, kept interrupting to ask if he wanted snacks or needed help “typing things.”

But slowly, he found his rhythm. He learned how to handle frustrated customers, write polite emails, and troubleshoot smart pet feeders like a pro. And for the first time in a long time, he felt like he was building something—no, building himself.

Within three months, Charley had saved enough to move out. He found a modest studio apartment in Queens—not too far from his mom, because, let’s be real, lasagna is a hard habit to break.

Epilogue: The New Charley

Charley still struggled with consistency. Some weeks, he fell back into his Uber Eats habits or stayed up too late bingeing anime. But now, when he felt stuck, he had a reminder of how far he’d come.

On his desk sat a little plaque he’d bought himself: From Doorman to Door Opener.

Because for the first time in his life, Charley was no longer just standing at the door of opportunity. He’d walked through it.