Risky Business: How to Quit Your Job and Come Out on Top, Jacob Breinholt

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What’s the riskiest thing in the world that nearly everyone has, at some time, considered but few achieve? Answer: Changing careers. Because who in their right minds would give up the  security of a job—the necessity that pays bills and allows for indulgences like that new seersucker suit—for an alternative quality-of-life vision that may or may not pan out? 

Jacob Breinholt is a real estate trust attorney by day and has found a way to monetize his love of fashion photography by night, and lives the life he always dreamed he’d have.

For many risk-takers, hobbies form the foundations of new careers. Utah-born, real-estate investment-trust attorney Jacob Breinholt decided to follow his passion and successfully reimagined himself as a fashion photographer. Using all his vacation days and free time to charm his way into runway events, he turned what was a passing interest into a thriving second career. His work can be seen at Shot By Jake, in countless fashion publications, catalogs and in ads for everything from clothing lines to cell-phone cases. (He’s also an editor at HighSnobiety.com.)  If you follow New York Fashion Week, it’s safe to say you’ve seen Breinholt’s photos.

You dared greatly before you started shooting runways by moving to New York from Utah, right?

Nassau County is quite a big shock coming from Salt Lake! Only in retrospect do I realize what a risk it was: taking on $200 grand in student debt and coming out here without the prep-school pedigree, thinking I could waltz into a Wall Street job.

But you did, becoming a successful real-estate trust lawyer in Manhattan, which is a notoriously all-consuming job. How did you decide to pick up a camera to become a professional photographer? It seems like a giant gamble. 

It’s funny, because I actually consider myself risk-averse. I’d taken photos for the high-school newspaper growing up, and it was always a hobby of mine. When I came to New York, there was so much opportunity here with this stuff. And in my third year of law school, I had a lot of downtime, to put it nicely. So I started working for this streetwear blog out of law school, and was able to meet media people and P.R. people who allowed me the foray into the fashion-lifestyle stuff. I started doing freelance stuff for Hypebeast and HighSnobiety, then I would get invited to a J. Crew preview or something like that. Back then, you saw the exact same content on every single site, so if your website got original stuff, you were scooping everyone else. People reached out to me and I became their guy at the shows.

Before you became “Shot by Jake,” what did you do to build up your cred?

Before I got to that point, I was just hustling, getting invited to stuff even if I didn’t have an outlet for it. I thought, I’m free tonight, I’ll shoot it, I’ll meet people.

There must have been times when you did a lot of work and didn’t sell any photos. How did you deal with rejection?

I was sort of like, how much longer am I going to be able to keep doing this? Do I really have to focus on being a lawyer? But the experience alone is invaluable. And it teaches you to be scrappy. I think that everyone gets nervous when they’re presented with the opportunity to take a chance and it’s sink or swim. And if you know deep down what will happen, then it will.

What’s the line you draw between taking a risk for your photography career and not?

I [realized] I can do this for myself instead of playing the lottery. I got to be creative and learn something, and I wasn’t just tossing money away on a chance to make money. But it’s not worth taking a risk that would be irresponsible, so take risks within reason, where you can still find your way out of the worst-case scenario.

How do you keep your careers—lawyer and fashion photographer—separate from each other?

Lawyering is not my passion. Photography is. It feels much more rewarding to have taken those risks with photography and be where I am now because I feel so passionate about it. One of the things I would do is take vacation days to shoot a gig I was excited about. Instead of traveling with my girlfriend, I would take a week off for Fashion Week to shoot runway.

Is there one mantra that you’ve found to be more useful than others when it comes to starting out in a completely new career?

Meet everyone you can, be nice to everyone—it’s so much about knowing the right people. Some experienced guys who shoot in studios a lot get a reputation for being divas, and there have been a couple shoots I’ve done where people come up to me and tell me how easy I was to work with. I’ve probably gotten more follow-up work just because of that, and not necessarily because my work was better than the next guy’s. Treat everyone well, because it’s a small world, and chances are you’ll cross paths with them again.

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