Work when you want, wherever you want, for whoever you want—sounds great, doesn't it? Nearly one-third of Americans are self-employed, for the obvious reasons listed and because the hiring market is getting rigged with more and more obstacles.
You might be thinking about ditching the hunt for the perfect 9-to-5, but you don't know how to pull in clients, build a network, and impress enough to get people to keep coming back for more. Lucky you, we've rallied top freelancers in photography, illustration, and writing to give you some advice.
Alexandra Gavillet
The Photographer
Alexandra's fascination with photography began way back in high school with her Mom's Nikon D80. Once she got to NYU, she was so career-driven that she graduated early to focus on building her portfolio. More than two years later, NYC badas has snapped a cover for The Fader, campaigns for Maybelline and L'Oréal, and captured top artists for Atlantic Records and Roc Nation. On top of her busy shooting schedule, Alexandra's taking a dive into the video world. Oh, and she's only age 23.
Can you describe your job on a day-to-day basis?
I have a pretty strict morning routine, even if I’m not shooting. It’s important I still follow a consistent pattern to keep me sharp and ready for whatever. I always tell people who are freelance to act like they’re working, even if they’re not technically “at work”, or at a shoot. Make work for yourself and create your own opportunities, if nobody’s giving you one.
I usually write down my goals and a to-do list for what I’m trying to accomplish before I go to bed. I get up around 6-7 AM, send out pitch decks, edit if I’m on a deadline, go to some meetings, and plan for whatever shoots I have that week or month.
Can you tell a story about how you landed a particular gig?
Whenever my workflow slows down, my hustle turns up. I use email introductions as a way to introduce myself and my work to companies. I had always wanted to shoot for Billboard, so I shot their awesome photo editor an email about coming in for a meeting. I left that meeting with an assignment to shoot THE Janelle Monáe, which ended up being one of my favorite shoots to date. It just goes to show that you can't wait for people to knock on your door (or email?)—go out and get those opportunities for yourself.
Another when is more recent. I just started a series called #UNMUTED, where we take influential figures down into the subway to uplift and connect all types of people, or strangers, together via a talk about what the subject wants to bring up. The idea sparked after the election this year.
I got stood up on a date (don't worry, I’m fine now) so I wasn’t feeling too hot about going out on a Saturday night. Instead, I decided to email Nick Knight to show him my new series and tell him how his words actually inspired me to start it. He’s been my idol since I was a sophomore in high school. I just tried a few variations of what I thought his email may be, and one of them ended up going through. About a week later, he responded to my email and we exchanged some (really exciting and kind) words. He has been my inspiration for forever, and he ended up posting our project on the incredible SHOWstudio page and Instagram. I was G-A-S-S-E-D!
Do you have any cautionary advice to a photographer just starting out in the freelance game?
My cautionary advice is don't be cautious. A lot of the time, I meet people who are too afraid to reach out, to show their work, to be seen. Do not fear! You must always keep pushing yourself and your work on others. One time a teacher told me that my ambition would come off as bitchiness, but please, PLEASE never think that! Your ambition, and hustle truly excites and flatters some incredible people and companies! You need to get seen, rejected, time and time again, so you begin to understand how this works.
Paul Windle
The Illustrator
Six years ago, Paul ditched his small hometown and moved to New York to get schooled in the graphics world. Now an LA resident, Paul has created illustrations for Adidas, The Atlantic, Adult Swim, and Urban Outfitters, to name a few. The artist is an especially big fan of animation and he's expert in GIF creation. Right now, Paul is working developing visual for a top secret Cartoon Network show.
Why did you pursue illustration?
I drew a lot as a kid. When I was 13, I started skateboarding and I would subscribe to skateboard catalogs and magazines. Getting that stuff in the mail was one of the things I’d always look forward to. I would look over the catalogs forever. I was just really into skate's visual cultures—like the graphics and photos. It was my first introduction to art.
I didn’t really know anything about making a living as an artist or illustrator. I grew up in Arlington, TX where there wasn’t a very prevailing artist community. I then went to college at UT Arlington and studied architecture for 2 years, but the more I learned about it the more architecture seemed like a grind. I was working at a skate shop and I remember this funny illustrated column in Skateboarder by Lori Domiano called "The Learnings Of" and I remember thinking, "this is someone’s job to draw and write this, why can’t that be my job?"
Can you describe your job on a day-to-day basis?
I try to meditate or pray first thing in the morning and then after that I do some free writing in a notebook. I let the writing just be anything, it could be an idea for a story or drawing, what I dreamed about, things that I’ve been thinking about, etc. It's before I’ve had any coffee or even gotten out of my bed, so some weird half-formed thoughts come out in that time. I share a studio space with some friends in Chinatown, Sarah Baugh, Julio Chavez, Lilian Martinez and Daniel Mckee, who all rad artists and makers.
When I'm not doing commissioned work, I’m working on my own stuff I’m usually just writing and coming up with stories and drawing characters. This year I’m focusing on creating an animated short.
Can you tell a story about how you landed a particular gig?
When I was just getting started around 5 years ago a friend gave me Matt Dorfman’s email address, this art director from the New York Times. I was pretty sure he wouldn’t get back to me, but he did like right away. I remember him saying that he’d keep me in mind for future stuff and I just thought that’s what he told everyone, but like 30 minutes later he emailed me again and was like, hey wanna do an illustration for this article? For sure one of the more exciting emails that I've ever received.
What is the biggest benefit of being on a freelance schedule?
Having time and energy to develop ideas and work on personal projects. It’s a lot more difficult when you’re working a full-time job. After I first moved to LA, I was full-time at an animation studio for 6 months and I hardly did any creative work outside of that job. A lot of people can go home and make all this stuff after their day job. I just find it harder.
What is your biggest obstacle as a freelancer?
Making good use of my time—It’s a struggle. Sometimes I’ll get into really good routines, but it’s easy to fall out of them. Also getting paid. A lot of people don’t like paying for stuff—it can be difficult to get paid on time or sometimes at all. It’s important to be careful about who you work with. I try to find out about people that suck at paying through other friends who freelance. If you’ve been screwed over by someone you gotta warn others to not work with those clients.
Molly Young
The Writer
We don't really know when Molly sleeps. She is one of those rare types of superhuman—you know, the ones that somehow manage to balance a full-time job with an equally successful freelance career. When she isn't leading a content team at Warby Parker, Molly is writing cover stories, about the people you love, for publications like New York Times Magazine. She also has a book due out later this year with Penguin Press.
You work full-time on top of freelancing. How do you juggle all the work?
Well...I’m stressed a lot. But I’ve gotten good at metabolizing stress! I go on walks, do crossword puzzles, read books, bake bread. It’s about choosing how you spend your time and not feeling guilty about it. There’s a lot of stuff I DON’T do, like go to the gym, for example. I loathe the gym. And I don’t feel guilty about it, because I’d rather be writing.
Why do you choose to juggle a full-time job along with taking on freelance work?
A full-time job means I'm always surrounded by smart people who have wildly different skills and interests than I do. Also, I’d turn into a hermit if I wasn’t required to be at a physical office every day. The forced socializing is healthy.
Can you tell us the story of how you landed your first paid freelance gig?
I interned at n+1 when I was in college over one summer. I lived in a cockroach-filled Alphabet City apartment with a Craigslist roommate and spent most of the internship ferrying beer and installing air conditioners. It was great. n+1 published my first piece and paid me, I think, $100.
What do you think are the most important characteristics a freelancer should have to ensure success?
Internal motivation and resourcefulness.
Do you have any cautionary advice to an aspiring freelancer?
Turn in your work on time. And always ask (politely) for more money than you think you’ll get. It never hurts to ask!
At my normal job, I work with a lot of freelancers, so I know what it’s like from the other side. I’m grateful when people are prompt, on top of their shit, and easy to work with.
