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New gen bosses: Jessica Pettway on leaving her dream job to become a successful freelance photographer

By Screen Shot

May 16, 2020


New gen bosses is a new series created to guide and inspire more people to go out there on their own, either as new business founders or freelancers. And what better way to do that than to ask the ones that already succeed at it? We want to know about big fuck-ups and even bigger successes, and the risky decisions they had to make along the way. We want to be the last little push you needed.

Job title: Photographer
Industry: Advertising
Company founder or freelancer: Freelancer
How long have you been doing it: 8 years shooting, 1 year fully freelance
Age: 25
Location: New York City

What pushed you to start on your own?

I really wanted to bet on myself and live a life where I could create my own images and my own happiness! Seeing people my age from school and on the internet not only surviving but thriving as photographers gave me some courage as well.

What was the very first thing you needed to do to set everything up?

My first steps were to double down on personal and editorial projects as well as letting people know that I was available for freelance work.

What was the riskiest decision you had to take?

I think the riskiest thing I did was leaving my in-house dream job to pursue a freelance photography career. I was working on some fun projects at Sagmeister & Walsh, but I still felt the itch to take a chance and start my own photography career.

What was a skill you didn’t foresee needing that you had to learn?

I did not have the slightest clue about business—taxes, accounting, net/gross, negotiating, all of it! I learned a lot by making mistakes, talking to people in the community and reading books.

New gen bosses: Jessica Pettway on leaving her dream job to become a successful freelance photographer

At what moment did you realise that this was going to work out?

When I was able to make both my studio and apartment rents with some cushion and not by the skin of my teeth, I knew this was all going to work out.

What did you spend your money on?

I started out with the cheapest lights that wouldn’t catch fire, props, a used Mark III & 24-70mm and a 600EX Canon Speedlite that was my overheating workhorse for a while.

What was your biggest fuck up?

My biggest fuck up was not charging enough and not communicating the value of my work enough. I think when you undervalue your work, you definitely lose out on money and confidence, but you’re also not communicating to your clients the value that you bring to a project.

What was your biggest success?

My biggest success was fully taking the leap and becoming 100% freelance. I was working part-time at a photo studio to supplement freelance work and I was scared to jump into the unknown. It was a huge hurdle and I was super nervous but my work is now better for it and I had a great first year! I still went on travel assignments and built up my kit and studio while working with dream clients like Apple and the publication PDN.

New gen bosses: Jessica Pettway on leaving her dream job to become a successful freelance photographer

What do you know now that you didn’t know then?

Tons of stuff! But I’ll start with business—I think reading about the business of design helped me a lot and maybe I wouldn’t have had to learn as hard if everything had fallen into my lap a little sooner.

What are three tips you would give someone who wants to start on their own?

One: Don’t be afraid to shoot your shot! Let people know what you like, what you’re doing and that you’re available to blow their minds.

Two: Save! Budget! Save! Save for rainy days. Save for flash EQ and supply sales. Save for projects that pay shockingly late!

Three: Find your own path and keep going. I read somewhere that one of the most competitive things a business can do is survive.

Want to discuss taking the leap with other new gens? You’re in luck! We’ve created New Gen Bosses, a Facebook group to continue and expand the conversation started through this new series.