In my early twenties, I was a self-obsessed loser whose primary concern was conning everyone into thinking I was doing well.
A friend’s mother got me a paid internship doing grunt work at a bank’s corporate headquarters each summer.
My first year, a high school wrestling teammate and I were assigned to the Online Banking division and got our own office. Really, it was a large closet they’d dropped a desk in. I didn’t mind, because we had a door we could keep closed, which meant I could sleep my hangover off each morning without being disturbed by management.
My buddy was usually quick enough to wake me when a supervisor did show up though. And when he wasn’t, the boss didn’t seem to care. He was in his 40s, rotating the same five ill-fitting collared shirts each week, and dead in the eyes.
I spent most of that summer burning my paychecks in the ShopRite liquor store and getting fat.
The next year I was placed in Mortgage Servicing and there was nowhere to safely nap.
I was seated at a long table with a number of other interns my age. They had graduated from the local Catholic school, and seemed like the kind of guys who intentionally drank Coors Light over Bud. I tried to talk about parties I heard were coming up, or bars that didn’t ID, but they were only interested in discussing lacrosse and their parents’ beach houses.
I asked to have my seat moved, and got my own desk in a sea of cubicles and baby boomers.
Next to me was a persnickety woman named Saanvi, who couldn’t pronounce my name and always pointed out errors I’d made when sorting piles of paperwork. I’d take the stack, apologize, then hand it back an hour later after changing nothing.
The mother of my elementary school girlfriend was a few desks away. Despite the fact that I was disheveled and slightly drunk on most mornings, she always made an effort to talk to me, ask about my family, and say nice things. I often thought that she was secretly thanking God that my relationship with her daughter had ended prior to sixth grade.
Behind me sat Marky-Mark, who’d graduated from my high school a few years ahead of me. When we were teenagers, he was one of the funnier people in our town. But it seemed the fluorescent lights and meaningless work had stunted his personality. Occasionally, I’d distract him from his duties and try to pull the humor out of him. We cracked jokes about Saanvi, and promised each other that if one of us threw a chair through the window and jumped, the other would follow.
I was in the banking world. If I got my shit together and changed my major, I’d likely fall into a career that paid pretty well. But I was dying inside. The highlight of each day was taking the elevator to the executives’ floor, winking at my childhood friend who’d gotten an internship in the investment division, and sneaking a shit in the marble bathroom reserved for VPs.
Leaving a surprise in the toilet for the guys who signed the company newsletters brought me tremendous joy, but every other part of the day-to-day was unbearable.
Office small talk made me sick. The sight of staplers, sticky notes and highlighters drummed up an animalistic rage in me. Whenever Saanvi mentioned that I’d placed a pink sheet where there should have been a yellow, I wanted to find a screwdriver and dispatch her a la Morrie in Goodfellas.
The monotony, the burnt coffee, the conversations about the weather—it all drove me mad.
So, I just stopped giving a fuck.
I started keeping a set of dress clothes in the trunk of my car. If I got too drunk and couldn’t drive home at night, I would just head straight to the office parking lot the next morning and change into a polo and khakis behind the neatly trimmed bushes.
My work day was supposed to start at 8:00 AM. After the first month, I never arrived prior to 8:30. If anyone dared look at me when I strode in thirty minutes late, reeking of cigarettes and discount tequila, I stared back until they were too uncomfortable to retain eye contact.
Lunch was supposed to last thirty minutes, but I always took an hour or two. I liked to drive in circles, smoke Marlboros while listening to Eminem, and tell myself lies about getting back in shape and earning that wrestling scholarship.
Most days at my desk were spent clicking through Barstool or stalking my high school girlfriend on Facebook. I never made an effort to conceal my screen.
It was clear to anyone with eyes that I wasn’t there to work.
None of them cared enough to report me though. They were all miserable in their own right, and just trying to make it through each day without giving in to the urge to stick a letter opener in a coworker’s neck.
But one afternoon I decided to shut down my computer and go sleep in my car till quitting time.
I kicked off my dress shoes, opened all the windows, and propped my feet on the dash. Marky Mark interrupted the afternoon nap with a phone call.
“Dude, everyone can see you,” he said. “You should probably come back inside. Bob is pissed.”
Bob was the big swingin’ dick in Mortgage Servicing. Like everyone else trapped there, he had phoned it in a long time ago, but as the boss, had to maintain some order.
When I got back inside and sat across from him, he asked if I was intentionally trying to get fired. I thought about it for a moment.
I didn’t want to make my friend’s mom look bad. But the answer was yes. I wanted to be fired. I wanted to break a keyboard over Saanvi’s skull. I wanted to play Pantera through a concert amp, flip over every desk, set the file room on fire, and start a revolution that would liberate us all from the shackles of office life.
I squirmed in front of Bob.
“I don’t know man. I wanna make it through the summer. I don’t want to disappoint anyone, but I honestly don’t care. I understand if you fire me.”
He sat quietly for a moment, then leaned over and told me to clean up my act and get back to my desk.
I think Bob respected the honesty. After that, he never said another word, and smiled whenever we passed one another. I made it through the summer without being summoned to HR.
Clearly, I am not a sit-behind-a-desk, yes-sir-no-sir, kinda guy. This wouldn’t work for me long term.
But, I liked being able to show up to dollar beer night in dress clothes with a corporate ID clipped to my belt. I thought it made other people take me seriously.
And that mattered more to me than anything else. My reality was ruled by the way in which I thought others perceived me.
I’d long harbored creative ambitions and wanted to get into the entertainment industry. But the idea that other people might whisper behind my back about me being out of my mind for thinking I could make it, terrified me.
I was positive that everyone I’d grown up with was already commenting on my receding hairline and post-high school weight gain. If I were to start putting myself out there, and tried to write or do stand-up, a hundred different group chats would surely pop off, and together, all of my peers would mock my aspirations in bursts of malicious text messages.
Paranoia, and the delusional belief that everyone was watching my every move, held me hostage. I was scared to walk away from a safe, prescribed path.
So, I kept my dream on the backburner, and stepped into hell once more with another stint at the bank.
This time, I reported to a woman who was the spirit of misery and wickedness wrapped in rapidly-aging human skin. I imagine she’s sitting in a dank, dark room right now, sucking on butterscotch candy, drinking dry gin, and taunting the orphaned children she has chained to a wall.
Each morning, she’d arrive in an ancient purple coat and squawk orders. She had a biting tone, and would slither out from her office to double and triple-check everything I did. There was no faking the funk with her in charge. She rode me every day, and I never got away with not working.
If I saw her on the street this afternoon, it would take every bit of my self-control to not kick her off her broom and spit in her face. But I’m thankful for that miserable bitch.
I stopped caring if people heard I was unemployed. If they talked about me, they fucking talked about me. I just had to get away from the paper clips, the stamp pads and the agonizing whistle that came from between that gap in the she-devil’s teeth whenever she dropped a stack of paperwork on my desk.
I faked an injury or illness (I can’t remember which) and stopped showing up. My banking days were done.
Months later, when there was no more corporate ID to tack to my belt, and no false air of stability to uphold, I took a bus into the city.
The night before, I’d let it slip to a kid I smoked pot with that I was thinking of getting into the comedy industry. He laughed and said there was no shot. I was funny, but not that kind of funny. I was better off in our hometown.
I left before the blunt was finished burning, walked home, and plotted every comedy club in Manhattan on a map. I printed it out, listened to a lot of angry music, and waited for the sun to come up.
Starting near city hall, I walked 60-plus blocks and stopped at every spot to ask for work.
My plan was to get a gig washing dishes or sweeping the floor, so I could attend live shows for free. That way, I’d absorb enough stand-up to ensure that when I finally found the balls to step on stage, my set would be flawless, and no one I went to high school with could say anything negative, or mock me for dropping out of college again and quitting another job.
One place offered me work, and I became a barker, selling tickets to absent-minded tourists in Times Square. My new boss assured me that when I was ready for stagetime, they’d put me up.
I sat silently at a hundred shows, taking notes, waiting for my balls to drop and never getting on stage. The risk of failing and becoming the subject of gossip in my hometown was too much to bear.
But someone I’d met at the club knew the producer of my favorite talk radio show. All the best comics in the country regularly made guest appearances. A few months later I was an intern.
After a year of hustle, I was hired as an associate producer. I hadn’t found the courage to do stand-up myself, but was officially in the business. It would be hard for anyone to see anything but success when they looked at me now.
I had a salaried job in the entertainment industry.
On occasion, I got air time and earned a few laughs.
When the show did live events with large audiences, I was put in charge of coordinating it from top to bottom.
After guests were on air, I wrote liners and got them to sit in a studio with me. People like Brooke Shields, Ice Cube, Henry Winkler, Stone Cold Steve Austin, Billy Bob Thornton and others were reading and recording promos I’d written. Sometimes they laughed or complimented what I’d come up with.
I got to hang with Joe Rogan and Ari Shaffir after they guest hosted. Bobby Lee comped me tickets to one of his comedy shows, and let myself and a date hang with him backstage. Akon hugged me once, Shaq patted me on the shoulder and called me “Big Dog”, and that crazy fuck Gary Busey tried to tickle me when we were taking a photo together.
We got flown to LA to do a few shows. A well-known TV host invited us to drink at the bar in her mansion afterwards. I crushed brews with her husband (the owner of an online broadcast network), who talked to me about where he thought my path was leading. He saw good things.
I won’t pretend I made a major impact, or that I was even close to as talented as the people I worked with. On paper though, I was doing well.
But, a year and a half in, I started to question why I was there. The job was great. I had an incredible mentor who taught me a thousand priceless lessons. He was setting me up for success, and as long as I hung on to his coattails tight, I’d make it.
But did I want to make it? Not really.
Although the work was better than sorting paperwork in an office, I didn’t love it. And I wasn’t doing it for me. I was doing it for everyone else.
I was only there to assure myself, through the opinion of others, that I was worth something. When I ran into someone from home, and they acted impressed that I’d met so many famous people, I lit up inside.
I was still the douche trying to claim some form of legitimacy, though this time I was doing it with a gallery of celebrity interactions on Instagram, instead of a corporate ID tag. And I didn’t want to be that guy forever.
My stand-up aspirations, and my desire to get into the entertainment industry, were byproducts of an intense insecurity and need to cultivate a positive perception of myself amongst my peers.
I did want to do creative work. But I wanted to do it for me and focus on what I was personally interested in. The show had given me a lot, but I didn’t truly care about the product we were putting out.
A new dream started to take shape in my head; one in which I would get paid to do cool shit and tell the stories about it. I wanted to be an adventure writer and answer only to myself.
Still, I worried about whether it was realistic, and most importantly, what everyone would say. It took another year and a half to commit.
It wasn’t realistic, and people would surely whisper about the guy who had very little outdoors experience trying to become the next Jon Krakauer.
But, the entertainment industry hadn’t been a realistic aspiration either, and in my mind, everyone had talked shit on me when I tried that. When I had set aside my paranoia, said “fuck you” to safety, and took a risk, I’d made it work. I could make the writing thing work too.
Shortly after receiving a promotion and pay raise, I quit. A month later I was living out of a tent in Montana and learning to paddle whitewater.
Acquaintances and good friends both called me a fucking nut. That dude in LA who’d talked to me about my potential trashed the decision on his podcast, and said I’d given up a golden ticket. He wasn’t wrong. But that golden ticket was taking me somewhere I didn’t want to go.
Out West I found a subculture I fell in love with, and people who completely altered my perception— dirtbag river guides, climbers and ski bums. They were persistent, wildly unhinged human beings, hell-bent on extracting every ounce of satisfaction from life that they could. Dirtbags refuse to bend the knee to society’s expectations, and put everything into what they love. They express more personality and passion in a single conversation than most individuals do in their entire lives.
In them, I found a group I respected, rather than people I worried about impressing. The risk I took in moving to the mountains laid the groundwork for the first story I sold to a publication, for what I’m now trying to do with The Dirt Lot, and for opportunities that have come my way thanks to the site.
I’m telling this story because a few people have reached out in the wake of The Dirt Lot’s launch to talk about fear and taking chances.
They’ve asked how I’ve been able to write without feeling anxiety over the reaction it might get. A few have mentioned dreams they have, but are too scared to pursue, and asked if I had advice on overcoming the fear.
I’m not an established writer, and my advice shouldn’t hold much weight, but the answer has been made clear to me.
The fear doesn’t go away. You just have to do it.
Write that book. Start the podcast. Put your art on Etsy.
Take a fucking chance, do what you want, and just be you. And not just with creative endeavors.
Log out of that Zoom meeting and get to work on the catering business you’re scared to start.
Train for the marathon your friends say you won't run.
Stand up to your dad and tell him you’re not interested in taking over the family business.
Throw out your coats and gloves, move to Miami, and maybe, tastefully curate some bikini shots on Insta, and start calling yourself an influencer.
Grab the girl that stopped you in your tracks. Admit that yes, her ass is unfair and the thought of those gorgeous eyes tears at your insides when she’s not around. Come out and say that her nipples are damn near perfect too. Then tell her the bigger truth— that in a room full of the world’s most uncommon people, she’d still stand out to you, not because of her preposterous physical attributes, but because of who you think she is.
It might not work. You’re more likely to fail than you are to succeed. And that’s fine. I’ve failed at a lot of things. But every risk I’ve ever taken has paid off somehow.
Prior to The Dirt Lot’s launch, I got on the phone with The Last Professional Broadcaster (my mentor from the radio days). He gave me two pieces of advice that drive me each day:
1. The success isn’t in being successful. The success is in saying I want to do this, and then doing it
2. Sometimes you have to wait for other people to catch up to you.
The Dirt Lot is no major hit. We’re not even a month old, and I'm still not Jon Krakauer. Every time I sit down to write, fear and insecurity hang on my neck. But I do it anyway.
It’s hard to think other people might see what you make, or who you are, and react with rejection. But take comfort in knowing that the dude who’s hating on you, is hating on me too.
He might be reading this right now, taking occasional breaks to glance at the fiancée he secretly hates. She’s splayed out on the couch, cradling that half-melted pint of Cherry Garcia and snoring into her armpit. He wishes he’d had the stones to leave her in college.
Tomorrow, he’ll get up and hate that he’s awake again.
From the drab apartment he’ll go, dragging his Hyundai around the same corners he drives every day, to the soul-sucking cubicle, then back to the miserable bitch that nitpicks everything he does, and never puts the cap back on the toothpaste.
They’ll argue about what to eat, then hold up the line at 7-Eleven as they bicker over who’s paying for the cigarettes and lottery tickets.
After a flavorless dinner, he’ll count the minutes till she’s asleep again. Once she’s snoring, he’ll bathe his Vitamin D-deprived face in blue light, and beat back the pain of an inauthentic, unlived life with help from the internet’s vast archive of hardcore pornography.
He and the wicked witch of domestication don’t matter. And honestly, most people probably aren’t giving you or what you’re doing a second thought. Regardless, they’re not who you’re doing it for.
You’re doing it for you.
If you’re unhappy now, if you don’t really feel like you’re you, staying with what’s safe and sensible will only exacerbate that.
If you hold on to something that you know is already dead and dry—whether it’s a job, a relationship, or specific place— and believe that you’ll somehow find a way to give it new life, that this time it’ll be better, you’ll likely end up dead and dry too.
Safety means warmth and comfort. It also means you never grow, never find out what else you have inside you, and never realize who you could really be, or what you could really feel, if you were only willing to embrace the challenge that comes with risk.
I’m imploring you to give a megaphone to that little voice inside that’s been begging, through gritted teeth, for something new.
Out west, I met an old dude who had regret painted on his face at all times. It came from decades of things left undone and words he’d never said. You don’t want to be him.
The universe might reward your boldness. Or it might not, in which case you just have to get up and keep moving.
I’ve shared a lot of personal things, made some jokes that people might find off-putting, and written extensively about shitting my pants as an adult. It all makes me nervous.
And The Dirt Lot has yet to turn a major profit. But because I’ve been willing to take risks, and been honest about who I am and what I want, I feel an immeasurable amount of satisfaction when I lay down to sleep at night. I’ve never known that before, and I’ll die before I start doing a job that requires a collared shirt again.
Most of the world’s malaise is rooted in stale things we hold on to for far too long, desires never voiced, and dreams not pursued.
So, go be you. Don’t sweat the technique. Just take that chance.