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7 Lessons Learned from My Journey into Photography

As a writer, I see the world in words. The architect sees things differently than I do, as well as the designer, construction worker, and florist. My craft influences how I see my surroundings and the ways I interact with it, and recently, photography has opened the frames of my worldview and creativity.

I started playing with photography when I moved to Brooklyn in the fall of 2016. Street photography was a way to explore my neighborhood and familiarize myself with an environment that was equally mysterious and—at the time—unappealing. I was resistant to moving to Brooklyn; I was carrying unchecked assumptions and expectations influenced by the hive-like mindset of living in the suburbs. Through photography and exploring this incredible city, my biases were wiped clean and I was able to experience something new.

I remember sitting up on my rooftop (because Brooklyn) after the day’s work, staring out into the city, and telling myself: “I love this place.”

What began as a source of play has taken over my weekends and, also, my dreams. Light is no longer just light. The symmetry in the subway station acts as a frame for a picture. Shadows and lines cast from buildings or objects have moods and stories. And as soon as I got into portraiture, I became obsessed with the intimacy and necessity of cultivating a connection with the subject. Like writing the same sentence 10 different ways, 50 portraits of a person all tell a different story, and that fascinated me.

Photography has opened a floodgate of learning—the power of human connection to create better work; how I miss the smallest of details in the moment and notice it like a grammar error two days later; the ravishing beauty of color and symmetry; and perhaps above all, myself and all of my insecurities, predispositions, hopes, and dreams.

Here are seven lessons learned thus far in playing with photography for less than a year, with some of my work scattered throughout. I hope it inspires you to pick up a new hobby or play with a new craft for the sole purpose of finding out what’s inside of you.

1. Hands-on learning, always

For the first three months, I sat in my room and devoured online courses and YouTube videos to learn how to use a DSLR camera—and I still couldn’t tell you the difference between shutter speed and aperture. If you can’t write about it, then you don’t understand it.

My talented friend, Tory Williams, hosted a small hands-on workshop where five other aspiring photographers and myself learned the fundamentals; it was also my first time working with a model. I walked out of that workshop with a new level of confidence—the camera no longer felt like a machine, but rather a part of me. I thought less about settings and paid more attention to what I sought to capture.

And then I went down the rabbit hole as I tend to do with anything that grips my curiosity.

In January 2017, I signed up for a workshop with the photographer Underground_NYC; his style of shooting in NYC subway stations was so fascinating and different, the way he used symmetry and light in this cacophony of chaos was new to me. The workshop was so valuable that I took it again a month later.

Model: Kelsey Adams.

Over the next three months I learned from Nick Ramirez, Marcus Hyde, and Stephen Vanasco—photographers that I’ve been following ever since I had an Instagram account.

Model: Sian Osborne.

The immediate feedback and sharing of stories trumped the safe method of hiding in my room, devouring online content, pretending that real progress was being made.

Being in these workshops allowed me to fail faster and quickly get the feedback that I needed to hear. I also made friends and connected with people in different states. I sometimes wonder the opportunity cost of not surrounding myself with writers earlier in my career…

2. Community is a catalyst for rapid learning

For most of my career, community was the last thing I thought I needed.

Growing up in the suburbs of New Jersey, my definition of community was the friends I grew up with. I never attended conferences or networking events, and I relied on books and online resources to stretch my skills. I never had a group of writers with whom I could talk about the craft, bounce ideas around, and give feedback. I didn’t see the lack of community as a bad thing.

Seth Godin brilliantly said about associations:

Who you hang out with determines what you dream about and what you collide with.

And the collisions and the dreams lead to your changes.

And the changes are what you become.

Change the outcome by changing your circle.”

Upon coming to Brooklyn and being surrounded by immense creative talent, one of the most surprising realizations was the appreciation of community and how it became the sole catalyst for growth.

A big photo meetup in NYC.

Pursuit of Portraits photo meetup. Photo Credit: @forourseasons

The theory is simple: I wouldn’t have leveled up exponentially if it weren’t for a community, especially at my job, CreativeMornings, and the altMBA.

In less than a year, I was able to attract clients and paid gigs, pitch agencies, and get accepted. The friends I’ve made being in this city, the talent that I’m surrounded by, the photography community that I belong to—all of this was rocket fuel for propelling me into this craft and helping me rapidly learn. Being able to ask professionals a ton of questions—and having them respond genuinely and honestly—is a rare asset that allows you to sidestep needless mistakes and failures. I asked for real talk about rates, contracts, pitfalls, frustrations—all of it—and I was met with transparency and wisdom.

If you can’t find a community to belong to, then what an opportunity to lead one yourself.

3. Calm the ego

There is nothing more reassuring to your ego than hearing praise like, “you’re a natural” or “you’re definitely talented and have an eye for this.”

Real talk: If I didn’t hear this, I probably wouldn’t have pursued photography as ruthlessly as I did. We are social animals who feed off the opinions of others. Even the slightest bit of praise at the right moment can alleviate insecurities, whereas no acknowledgment at all can make us shrivel up and quit.

But over time, I had a check yourself moment where I realized I was more focused on external praise rather than the experience of taking pictures and connecting with my subjects. I would refresh likes on my Instagram as a measure of my worth and art. As soon as I caught myself doing this, I made a conscious effort to disengage with this behavior and get the hell out the door and start exploring.

Whatever creative craft you pursue, the acknowledgment has its place and you determine what your metric for success is—just remember that the beating heart of your work must always come from within, not from the outside.

4.  “What should I do on social media?”

I hear this question from photographers all the time at workshops, and as someone who has done this kind of work for almost six years and serves as the head of content for CreativeMornings, I can hear the question behind the question: How do I get 100,000+ followers like you so that I can get great opportunities? Do I matter? Am I doing all of the right things?

Seth Godin said in this post [emphasis mine]:

What would happen to your customers and to your prospects if you stopped doing your work?

If you stopped showing up, if you stopped selling them something, would they miss you if you were gone?

If the airline went away, we’d just find another airline. If the cookie cutter politician went away, we’d just vote for someone else. If the typical life insurance agent…

Does it matter if it’s you doing the work?”

“Would they miss you if you were gone” as a framework focuses your mind on what’s truly important to your art. This is why a personal website/blog is paramount, because you have full autonomy, it scales, and it’s yours. This is why email lists are still the best thing to grow for any organization or freelancer—it’s personal, relevant, builds trust, and gives you full creative control (if you’ve never read Permission Marketing, do it asap).

Shot during the solar eclipse, 2017.

Instagram is one platform—a blessed one for photographers and visual artists—but to hinge your entire career or life’s work on something that can change and vanish without your permission is playing the short game. You’re at the mercy of rules that are out of your control.

Model: Kelsey Adams.

The pattern that I’ve noticed while studying masters of the craft is simple: They update their website more than they do their Instagram. They focus on growing their email list because that’s where you can directly communicate with your audience. Some of the most impactful photographers of the last six decades don’t even have a large following on Instagram, and it’s sad that many creatives and companies measure the impact of work based on the number of followers. Their work speaks for itself, they’re connected to the right people and communities, and they put in the work to consistently explore their creative range.

I remember the words of Maria Popova in her 2016 commencement speech at the Annenberg School for Communication:

Develop an inner barometer for your own value. Resist pageviews and likes and retweets and all those silly-sounding quantification metrics that will be obsolete within the decade. Don’t hang the stability of your soul on them. They can’t tell you how much your work counts for and to whom. They can’t tell you who you are and what you’re worth. They are that demoralizing electric bike that makes you feel if only you could pedal faster — if only you could get more pageviews and likes and retweets — you’d be worthier of your own life.”

5. Equipment doesn’t matter

At first, this sounded like utter bullshit.

To tell me that there’s no difference between my Canon Rebel T3i ($300-$400) and a $3000 Sony or a $6000 Leica just sounded absurd, like a Honda Civic racing a Ferrari and claiming it’s about the driver. Then I remembered the words of Hugh MacLeod from his book, Ignore Everybody:

Abraham Lincoln wrote the Gettysburg Address on a piece of ordinary stationery that he had borrowed from the friend whose house he was staying at. Ernest Hemingway wrote with a simple fountain pen. Somebody else did the typing, but only much later. Van Gogh rarely painted with more than six colors on his palette. I draw on the back of small business cards. Whatever. There’s no correlation between creativity and the equipment ownership. None. Zilch. Nada. Actually, as the artist gets more into her things, and as she gets more successful, the number of tools tend to go down. She knows what works for her. Expending mental energy on stuff wastes time. She’s a woman on a mission. She’s got a deadline. She’s got some rich client breathing down her neck. The last thing she wants is to spend three weeks learning how to use a router drill if she doesn’t need to. A fancy tool just gives the second-rater one more pillar to hide behind. Which is why there are so many second-rate art directors with state-of-the-art Macintosh computers. Which is why there are so many hack writers with state-of-the-art laptops. Which is why there are so many crappy photographers with state-of-the-art digital cameras.”

I spoke to photographers and learned that they, too, used basic cameras early in their careers and were still able to get big gigs. It didn’t matter about the equipment; what mattered was their ability to see, tell a story, and communicate. What mattered was being in the right moment, at the right time, with the only device in the world that can stop time. What mattered was that they didn’t tell themselves a narrative that their art wasn’t worthy without expensive equipment—in fact, the constraint of working with what they had pushed their creativity to the edges.

The best advice I got was from friend and fellow photographer, Wesley Verhove. The strategy was brilliant and it made me obsess less over what I didn’t have. He admonished,”Gamify it. Use your current camera to earn new clients, and use that money to buy a new camera, rather than using your day-job salary for something that, right now, is just a hobby.” It was brilliant, and it lit a fire within me to pitch myself, raise rates, and work hard.

Within four months, I got the camera I desired, and it was bliss.

6. Learning the language

Every craft has its own language and the deeper you get into the domain, the more you become accustomed to the culture.

The one thing I was most surprised by was a number of inquiries for collaborations. This was nothing like my career in writing. There are two translations of this word:

  1. Trade for photos: This is when a model reaches out to me and asks to collaborate. This collaboration enables me to practice my craft and possibly get some good work out of it, and the model gets (hopefully) some portfolio work, too. A relationship is built and the potential to work again is promising. I did a few of these when I hit my stride because the upside and focus were to just get out there and shoot. Over time, I had to be selective of this because I was investing a lot of hours almost mindlessly with zero appreciation for the collaboration.
  2. Free work: This is when a model or someone who doesn’t do modeling professionally reaches out to me and frames their ask like this (real message): “Hey! Love your photos and the vibe of it all. Would love to collab/model for you sometime no charge…. I’ll post stuff on my page too so its a win win. You get credit and we get experience.”

Instead of being offended by this type of ask, I try to have empathy instead. Here’s this young person with fewer than 100 followers on Instagram—so clearly there’s no benefit for me even if they posted and gave credit to my work—no clear bio, and no modeling pictures in their feed. A quick search on Google yields nothing about them. This person finds my work and says, OK, this guy doesn’t have a huge following but he does have some decent portraits, maybe he’ll want the practice and do it for free; maybe he’s starting out like me. At first, I was angry at this request, baffled by the audacity, but then I realized I probably said far worse things when I was younger.

Whatever craft you begin playing with, you’ll learn the language over time, and it helps to ask a pro for deeper context into this. I asked a lot of the photographers during the workshops what these terms really meant in this industry, and they gave me full context. 

7. Don’t forget: it’s about play

I feel infinitely lucky to have been introduced to photography as soon as I moved into one of the greatest cities in the world. The city as your backdrop and the access to a diversity of people are indeed invaluable assets to a photographer.

I also feel lucky that I didn’t have to worry about survival because this was an avenue for playing while I maintained a full-time gig and freelance work. There were times when I received those outlandish requests to work for free and appreciated the fact that I had the power to say no.

As soon as money entered the conversation, I became careful of how I was growing with this craft. I wanted to be more fascinated by the idea of the shoot rather than the financial reward. I would chase creativity, not commissions.

The first altMBA alumni gathering with over 170+ alums.

It’s important to protect your source of play even if it becomes a full-time career. Indeed, some of the masters of the craft still treat their work like play. They embrace it from a posture of curiosity and with an eagerness to explore the edges of their talents rather than just finishing the job to move onto the next.

One of the most solid frameworks that helps me maintain my sense of love for writing—even when it became a full-time career—are the words of Kurt Vonnegut when he replied to a letter sent from a class of high schoolers. He said:

Practice any art, music, singing, dancing, acting, drawing, painting, sculpting, poetry, fiction, essays, reportage, no matter how well or badly, not to get money and fame, but to experience becoming, to find out what’s inside you, to make your soul grow.

An ah-ha moment that I’m having now as I write this is that maybe it’s not about the act of taking portraits or the act of sitting at a desk and emptying my brain onto a blank page, and more about the act of learning, of becoming, of gaining confidence and self-love through the process. I realize that as long as I’m learning, then it feels like playing; and as long as I’m taking the work seriously and not myself, then it’s worth doing.

Seth Godin making pizza.

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