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Jeff Lipsky: How to Be Ready for Your Big Break

There’s nothing more human than thinking you have a life plan and then watching it evolve into something entirely different from what you thought it would be. For renowned celebrity photographer Jeff Lipsky, a chance encounter with actress Daryl Hannah in the late 1990s turned his world upside down. It pushed him from teaching snowboarding and fly-fishing in Colorado down the path to becoming one of the most sought-after celebrity portrait  photographers working today.

Lipsky was born in Baltimore and attended Boston University. From a young age he had an interest in photography and visual storytelling, but he wasn’t sure if professional photography was in the cards for him as a career. Lipsky says that he got a camera for his Bar Mitzvah and never stopped wanting to take pictures.

After graduating college, Lipsky spent a decade living in Telluride, Colorado and worked as a snowboarding and fly-fishing instructor. He was fortunate enough to have a large client roster and one of his clients was Daryl Hannah. Lipsky and Hannah developed a rapport and in 1998, she invited him to come out to Los Angeles and take portraits of her for The Sunday Times. Lipsky jumped at the chance and that job got the ball rolling for him.

Lipsky used his shoot with Hannah to develop his portfolio and then he began working with different modeling agencies in Hollywood to hone his skills. After Hannah gave him his start, he began working as a first assistant photographer to a well-known photographer in Los Angeles. One day after a shoot, Lipsky was asked by his then boss to drive the photo editor back to her hotel in Glendale, which was at least an hour drive from the shoot location in Malibu, and then another hour from Lipsky’s home in Venice. Lipsky says that driving around Los Angeles for more than two hours wasn’t how he wanted to spend his time after work, but he also knew it was part of the job to make life easier for his boss.

On the drive back to the hotel, Lipsky and the photo editor figured out they had a friend in common, and she offered to look at his portfolio if he came to New York. Lipsky agreed and went to New York the following week. He presented his portfolio to the editor, who recommended him to a contact over at Esquire. And from there everything snowballed in exactly the right way. Esquire hooked Lipsky up with a job at Premiere Magazine and then that led to a job with Outside Magazine.

“Right place, right time,” he says. “Suddenly I started shooting for all those publications and still to this day, I still work with a lot of [them] because of taking one person home and having a connection with them.”

Clearly there is something about Lipsky’s work that people love, which is why he’s become such a heavy hitter in his field. When I ask him about it, we talk about the intersection of talent and ability–what some people refer to as having an eye for something. You’ll hear people talk about someone having an eye for photography. But for Lipsky, it really comes down to personal taste.

“For me having an eye for photography is a personal thing,” he says. “It’s subjective. It’s your personal aesthetic, just like art. I like a particular photograph because it appeals to my style. It appeals to me. And as a photographer, basically you’re taking pictures of things that you like, or the content that you like, so it’s a natural thing. I’m not thinking about composition. I’m not thinking about light, which [are] two very important things when taking a picture … It’s like, a natural feeling almost. I like [the photos]. I like what I’m doing. I just hope that other people like my aesthetic so they hire me to take pictures.”

Today, in addition to the publications he started out with, Lipsky shoots for Vanity Fair, Men’s Health, Women’s Health, and Men’s Journal. His work can also be found on movie posters, billboards, and in print advertisements. If you can think of a major celebrity, there’s a high probability that Lipsky has photographed them. His portfolio includes Brad Pitt, Emma Stone, Jimmy Kimmel, Jason Momoa, Catherine O’Hara, Taylor Swift, Mark Hamill, John Legend, Kristen Bell and Dax Shepard, Kumail Nanjiani, Zac Efron, Chris Pratt, and Dwayne “The Rock” Johnson, just to name a few.

While Lipsky started out shooting landscapes, he likes portrait photography because it gives him a chance to connect with his subjects, even if celebrity photography comes with a certain level of protocols that might disrupt the creative process.

“I’m a portrait photographer, but I did start out taking landscapes of course, living in Telluride,” he says. “That was my first [experience] of taking pictures of the beautiful land and the mountains, and shooting black and white, so that’s what started me off. The hardest part of my job [now] is keeping it simple. You get a job and there are so many people telling you what they need. The celebrity needs something, the publication you’re shooting for needs something specific, and then you as an artist–you want to get something specific for yourself. And there’s so many factors involved like, where can they go? Where you’re going to shoot them. What time of day? The entourage, the people, the equipment … And the reality is you just want to connect with your subject and take a beautiful picture, and you have to block everything else away.”

While photographing celebrities might seem glamorous, it doesn’t come without its own set of challenges. Most celebrities are themselves, their brand, so it’s understandable that some of their own personal desires when shooting would need to be considered as they become reflective of how marketable the photos are.

Lipsky tells me that a lot of the battle is making sure the celebrity is comfortable while the publication is happy. Many times the publication wants the subject to be shot in a certain outfit, or at a certain location that might be uncomfortable, cold, or wet for the subject. There’s a challenge for him to be the intermediary between his subject and the publication that hired him. He’s aiming to keep everyone happy, while not compromising his own artistic integrity.

“[Celebrities] want to be appealing,” he says. “They want to have a sell-ability to themselves. I like to make people look beautiful, organic … Who doesn’t want to look sexy, right? So tastefully sexy … You want men to look cool, so there’s a certain little dance that you have to do. Again, a magazine might say, ‘They need to be in a swimming pool for this shot.’ And you’re like, ‘Really? They don’t want to go in the swimming pool.’ So how do I get that person into the swimming pool? [So the solution becomes,] let’s see what we can do and make it all work for everybody and still take a great image.”

When it comes to mastering photography, or any craft for that matter, Lipsky is a fan of learning in the field. He recommends a hands-on approach where you can watch someone, who is a master of the craft you want to learn, work.

“To me you have to learn in the field. That’s the most important thing,” he says. “You can go to school for photography. But I would say–the way that I came up, and the way that I see most photographers [come up is]–you have to assist. You have to learn hands-on: Being on the set, learning, watching other people make mistakes, or watching other people succeed so you can just be that fly on the wall … Seeing how everyone lights and seeing how they talk to clients, seeing how they talk to the celebrity, and all the ongoings, and in and outs. It takes years. I assisted for years, learning before I started shooting on my own.”

One of the biggest lessons I learned from Lipsky has to do with not judging a book by its cover. There might be some people who would look at Lipsky’s choices out of college, including his own parents, and question his work ethic and whether he was just wasting his time playing around in the mountains. Snowboard instructor is a fun and honorable job, but it is seasonal and comes with its share of limitations.

But Lipsky pursued his interests of perfect powder and fishing in spite of how it looked to everyone else, and that was what led to his big break. The lesson here seems to be that there are many paths up the mountain to the top. Lipsky was in the right place at the right time, but he also recognized when opportunity was knocking and opened that door. He took action, took a chance, and he was on his way.

The other lesson here for me is that nothing we do goes to waste if we don’t discard or diminish it. Remember how irrelevant all that Colorado fly-fishing seemed to be? Well it turns out that filming celebrities on location doing interesting things, like fly-fishing with Jimmy Kimmel, paid off. This rings true for me when I remember being a cashier at Polo Ralph Lauren during college. I learned a lot about sales, customer service, and managing the emotions of upset customers. I can say the same about being a waiter in a busy restaurant and the other less impressive jobs (on paper) I’ve had over the years. Nothing goes to waste if you don’t let it.

What skills are you honing now that you might access later in your career in a high-profile position or running your own company? I wish I had kept a detailed journal of my thoughts and feelings, that would have come in handy many times over the years, I’m sure. Maybe the idea will spark some inspiration and help you in the future? In any case, while I don’t believe the notion that “everything happens for a reason,” I do subscribe to the idea that everything can happen for us if we let it.

Watch my interview with Jeff Lipsky here:

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

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