From Craigslist Chaos to Capturing Moments: My Journey to Becoming a Professional Photographer

The Commencement of My Current Self

On the first day of my unemployment by choice, I woke up feeling a profound sense of liberation. I was now my own individual, which meant I could do anything. Anything! I could paint, run, jump, create, play baseball, concoct mac-n-cheese in my bathtub, rise at 3pm, or 3am. Literally everything was within my grasp. The world was my oyster.

By the fifth day, I found myself utterly unhappy.

What in the world does someone do with their time during a random Wednesday afternoon? I mused on such thoughts largely due to living in New York for a while. Just as Californication tends to lower a person’s blood pressure, leading them to wear out the snooze button and diminish the urge to act instantly, a similar effect called New-Yorkification occurred. Unbeknownst to me, New York had instilled a type-A mentality in me, making me wholly unprepared for lounging around in a bathrobe at 3pm.

Consequently, to escape the confines of my home, I began searching for activities. I picked up new hobbies. I engaged in community sports events. I reminded myself of my lack of athletic abilities and stopped participating altogether. Eventually, I found myself on Craigslist, where an advertisement titled ‘Be an extra for Hollywood!’ caught my attention.

As someone who could

I entered a cinema, purchased a ticket, viewed the specified film, exited, and immediately acquired another ticket for a different movie. I had always contemplated what it would be like to be part of one of those films. Even if it meant being just an extra loitering in the background, the concept had always fascinated me. So, I replied to the advertisement and made my way to a talent agency located somewhere on 8th Avenue a few days later.

The lobby of the agency resembled a complete cattle call filled with individuals who seemed to possess minimal to no acting experience; merely aspirations of achieving fame. Dozens upon dozens of people were crammed into the space – half of them sat on the floor as all the chairs were taken.

The atmosphere was largely a cacophony of noise as individuals readied themselves for their interviews/auditions; I distinctly recall a fellow in an Autozone uniform mangling a monologue from The Godfather while preparing for his extra audition. I remember how he continuously pronounced ‘Michael Corleone,’ heavily accented with a Queens lilt, as ‘Miguel Corleone,’ and it was actually quite painful to observe.

Anyhow.

I waited for roughly an hour for my opportunity, was ultimately summoned, and after a few minutes of wandering the halls found myself in a cramped audition room. A woman entered, handed me a slip of paper with a single sentence printed on it, instructed me to read it aloud, and then with what seemed an excessive amount of enthusiasm congratulated me on the fantastic reading I had just completed.

She then gave me another slip containing a name and number that I should call the following day to ‘check if I landed the role.’ I recollect feeling puzzled about ‘landing the role’ since general background work does not involve ‘landing roles,’ but who was I to question it?

Enter Tom the Vampire

I received firm instructions to dial the number the next morning precisely at 8 am. I found this somewhat strange but, once again, held my tongue. Upon calling, a gentleman answered, introducing himself as Tom. Tom sounded, and I say this without embellishment, quite similar to what a vampire would sound like on the phone if you were to contact one about a film opportunity.

He exhaled ‘Joe’ in a breathy tone to verify who I was, and as he did so, I could almost visualize him eagerly leaning closer to the receiver with every passing word, attempting to siphon bits of me through the phone. He queried me a few additional questions to further confirm my identity, and after the fifth or so inquiry, he seemed completely satisfied and then abruptly shifted into an infomercial host persona.

‘Joe! I’ve really gotta tell ya. Everyone at the agency, gosh, we are all SO thrilled about you!’ proclaimed Tom.

As soon as that statement concluded, my heart plummeted, and I recognized that the individual on the other side was poised to attempt to con me into purchasing something. What that something was, I didn’t know, but intrigued and lacking any plans that day (or any day, for that matter), I stayed silently on the line, anticipating Tom to delve into his sales pitch.

Tom went on to express that everyone at the agency was extremely enthusiastic about me. Not that anyone had witnessed my presence, apart from the woman in that small audition room. Or that anyone had actually heard me, aside from that confined audition space.

As Tom unraveled his sales pitch, he began discussing how his agency collaborated frequently with Kevin Bacon. And Liam Neeson. Then he casually dropped a few other well-known names while I sat quietly on the opposite end of the line.

‘Joe! Man, Joe. Everyone here. So excited. Heaps of enthusiasm. Truly mountains of anticipation. Heck, somebody peel me off the ceiling right now. Ha!’ exclaimed Tom.

Then, a brief silence, as Tom inhaled a bit and sounded puzzled. ‘Hmmm…’ said Tom.

‘What’s that hmmmm, Tom?” I inquired, aware that the moment had come for Tom’s scam to make its appearance.

‘Well, you know, Joe. I don’t see any headshots.’

And at that instant, I realized what Tom’s strategy was. He aimed to sell me headshots. Subsequently, he would likely attempt to sell me a multitude of other items. But he was commencing with headshots. Before I could articulate anything further, he erupted into an impassioned discourse on the necessity of having headshots and how, without a professional set, I’d essentially be dead in the water, unable to succeed in the industry.

‘You gotta have headshots, Joe!” – Tom.

I inquired of Tom regarding the cost of the headshots, and with the utmost innocence, confusion, and concern for my well-being one could muster, he replied, very literally, this:

‘But Joe, can you truly assign a value to your career?’ – Mother. Freaking. Tom.

At that juncture, I was pretty much finished with the conversation, and there were merely thirty seconds left in it, but I remained inquisitive about how much he’d attempt to extract from me. I once again asked him what the headshots cost, and he answered that they were ‘only a thousand dollars, Joe!‘

Thus, I expressed some words to Tom thereafter that I would refrain from repeating in front of my mother and promptly hung up the phone.

Back to Craigslist and Into Photography

At that moment, I possessed a Nikon D3200 that I had acquired a few months earlier because I had contemplated entering the field of graphic design after encountering a graphic designer’s blog featuring some stunning photographs of him and his girlfriend taken in Japan with a DSLR, leading me to assume that all graphic designers owned exquisite cameras.

Simultaneously, I had cultivated an interest in reselling second-hand apparel on eBay, primarily due to the unparalleled access to second-hand clothing available in New York, and I thought I might be able to sell items with rare labels that others desired but found hard to obtain. Consequently, I purchased an affordable lighting setup that included a shoot-through umbrella, light stand, and corded sync kit.

Thus, while strolling down the street after my discussion with Tom, I decided then and there that I would begin taking headshots. Although I lacked experience as a photographer (aside from capturing images of myself clad in absurdly expensive attire for eBay listings), I recognized that headshots were a significant aspect in New York City. They were a concept that I did not grasp, but they undeniably existed. To me, having no experience at the time, headshots appeared to be akin to magical income. Someone pays you $800 or more, you spend a couple of hours together, and they depart. And that seemed quite appealing to me.

So I dialed my mom, who was worried about my unemployment and lack of clear direction, and stated, ‘So I’m going to begin taking headshots.’

She responded, ‘That’s wonderful!’

Then she added, ‘I’m not certain what those are, but how marvelous.’

Back to Craigslist I ventured, posting an ad that day titled ‘Free Headshots,’ embarking on a quest to become a New York City headshot photographer, and within just a few short hours began receiving not only responses but an abundance of them. I had no clue what I was doing, yet I started consuming information obsessively about photography (the hours I dedicated to this particular site at the onset of my career could easily be counted in the hundreds) while meeting and photographing numerous strangers in the ensuing months.

After each session, I would upload the outcomes onto a Tumblr (my initial portfolio), and after about a month or two, a gentleman reached out to inquire if I would photograph his wedding. It was a city hall wedding which paid just a fraction of traditional wedding photography rates, but I was still astonished by the notion that someone wanted to compensate me for taking photographs.

Following that, I primarily relied on gig platforms where websites like Taskrabbit, Thumbtack, and Upwork likely contributed to about 80% of my shoots during the initial years while collectively enhancing my skill sets and gaining momentum whenever the opportunity arose.

Eleven Years Hence

Eleven years later, and an abundance of astonishing events have transpired throughout my career that I never thought would be even remotely achievable.

During that eleven-year period, I’ve collaborated with a multitude of prominent brands like Samsung, Docusign, and Google, meeting and capturing images of several distinguished and influential figures such as Jeff Bezos, Reese Witherspoon, Dropbox Cofounder Arash Ferdowsi, Eli Manning, and tomorrow I may very well find myself photographing Martin Scorsese (seriously, how I stumbled into this opportunity is beyond me but no joking, I’m truly amazed).

What I take the most pride in, however, is that I’m entering my fifth year as a studio proprietor, occupying a 1,000 square foot space in Williamsburg, Brooklyn. Maintaining its operation requires relentless effort and often feels like hard work, yet if you cherish what you do (and I absolutely adore what I do), work seldom feels like work, and life appears to be so much more than mere existence.

About the author: Joe Jenkins is a skilled headshot photographer located in New York City. The views expressed in this piece are exclusively those of the author. You can discover more of his work on his website and Instagram.