Becoming a Freelance Photographer in an Uncertain Year

Sara Haile on owning a risky move and succeeding

2020 was not the year to expect a seasoned social media professional with a stable full-time job at a thriving fashion brand to launch a freelance career. Yet Luupe photographer Sara Haile left her post running marketing and social media for Aerie to go out on her own as a full-time freelance photographer.

Haile made a quick transition, using her marketing knowledge working for brands, and her technical photo chops to make it work in stride. Some of her recent highlights include Peloton, Warby Parker, Oprah Magazine, Uber, and Create & Cultivate.

We speak with Haile about her promising career shift, photographing for the Beyoncé x Peloton partnership, and what’s in store for 2021.

© Sara Haile for Warby Parker

The Luupe: You worked in marketing and social media for Peloton and then Aerie, and recently moved into full-time freelance as a photographer. What was it like making the decision to leave a full-time job?

Sara Haile: It was scary but I knew it was right. A lot of people have been discussing how the pandemic made them really assess and take a good look at what mattered, what they’re grateful for, and how they wanted to spend their time and this was really true for me. I really value the people and experiences I had in the marketing world, but I knew that feeling truly fulfilled, challenged, and happy was more important to me than feeling completely safe in a job that I knew deep down didn’t bring me to life the way photography does.

Meet Sara Haile. Photo credit: Issac James

The Luupe: This move comes at a chaotic time, to say the least, and we continue to hear the uncertainty it has given many freelance photographers and creatives. How are you feeling?

Haile: I’ve had discussions with friends about this and one of them pointed out to me that there will never be a “perfect” time to go freelance. Yes, a pandemic presents different challenges but I was grateful to be getting photography work that could be done safely while I still had a full-time job.

In the beginning, there might be some weeks where the amount of incoming work isn’t crazy and that’s okay because I’ve learned how to optimize my time wisely. I think there’s lots of different ways that I can get better as a photographer outside of just shooting (i.e. attending virtual workshops, networking, mood boarding for future shoots etc.) so I plan to use those outlets to always be improving when I’m not shooting but to also help me be prepared for the next project.

Sara Haile’s photos of artist Zaria Forman in Oprah Magazine

The Luupe: Has anyone helped you make the transition or served as a mentor? 

Haile: There have been several friends who I’m grateful for that I have in the industry who have offered me their time and have answered several different types of questions that I’ve had about freelancing which has been really really valuable. In addition to that, just having the support and encouragement from friends, family, and community, in general, has made it so much easier to move forward feeling like I have a solid foundation cheering me on.

Priscilla. © Sara Haile

The Luupe: How does your background in marketing influence how you think about your photography business from a creative and content side?

Haile: It’s made me a better photographer in the sense that I can go into a project already anticipating how the images may be used (i.e. social media, email, website) and it’s helped me be able to ask the right questions in order to know how to shoot technically and to also understand the look and feel of the shoot depending on the concepts and stories my clients want to tell within the finished product. I feel like those advantages allow me to immerse myself in the project so that the images feel as if they fit seamlessly rather than just be an accessory to it.

The Luupe: How about from a business side?

Haile: It’s helped me get a little more creative with how I can potentially pitch myself or structure a project. Knowing how many different marketing arms there can be attached to one campaign, I can get creative with what I can potentially offer clients.

Robin Arzon from Sara Haile’s partnership with Create & Cultivate

 

Peloton instructor Ally Love – © Sara Haile for Beyonce X Peloton

The Luupe: What was your experience like photographing Peloton instructors for the Beyoncé X Peloton partnership?

Haile: It was the best. I got to work with an amazing instructor lineup and production crew for this collaboration who came together to execute one amazing partnership. I had planned for the direction of the shoot to embody the behind-the-scenes and on-stage moments of a Beyoncé concert which I’m proud to say I’ve studied thoroughly (like, REALLY proud to say).

It was a lot of work but it was my favorite project so far within my photography career and I remember on the last day of shooting feeling like I didn’t want it to end. There’s really nothing better than that, right? And for added context, when I worked at Peloton I had a life-size cardboard cutout of Beyoncé right next to my desk, so this felt like a true, full-circle opportunity for me and I’m grateful that the team asked me to be a part of it.

Peloton Instructor Jess Sims © Sara Haile

 

Peloton instructor Ally Love. © Sara Haile

The Luupe: We’re interested in the very real and personal way you see, and specifically how you take that approach when working with brands. From your editorial photos for Oprah Magazine to your work for Warby Parker, the photos could easily be from your personal portfolio – it feels both sophisticated and with a level of appeal to gen-z aesthetics.

Do you make any distinction in how you think of the work you do for brands vs. yourself?

Haile: I’ve been thinking a lot about why photography makes me so happy and I think one element of it is the connection and time you spend with the people or persons you’re photographing whether it’s something commissioned or if I’m just shooting with a friend. I really like to connect and get to know the person because I enjoy that aspect of the job but I also think this builds a lot of trust and encourages anyone, even a professional model, to open up even more.

When I’m working with a brand, there are certain things like a shot list and visual direction that I keep in mind but I believe I always bring that personal aesthetic to my images because it’s in my nature to make that connection.

Musician Sammy Rae. Photographed for Sara Haile’s project People Who Do

 

Sienna © Sara Haile

The Luupe: What are some projects you have in the works?

Haile: Right now I’m working on producing shoots to continue to build my portfolio and evolve my images so that it’s reflecting the style of work I want to get hired for. Also, I’m addressing my weaknesses! Studio lighting, for example, it’s an area where I know there’s room to improve.

I’m tired of avoiding things that are really intimidating so I decided to just face it head-on and work through the challenge. It can be so scary to be vulnerable as a photographer in NYC because the industry can appear to be really intimidating but I’ve met some amazing people who have helped me with this so, lesson-learned: ask for help and don’t feel stupid doing it. It’s the best thing you can do.

Savanah Oshun © Sara Haile

The Luupe: What’s exciting you most about this coming year and your photography? 

Haile: It’s exciting to finally be able to just focus on photography and also to bet on myself 100%. For so long I was working in my full-time role in social media and shooting on the side and it became a lot. It was also difficult to put all of my energy into broadening my photography career and in the past couple of years, I’ve been thinking a lot about narrowing in on what I really love and where my talent really lies.

The Luupe: If you’re comfortable saying so, what are you most nervous about?

Haile: I’m nervous about failing but it’s way scarier to think about never pursuing what I love. I’ve always been afraid of not becoming the photographer I wanted to be fast enough but I’m working on leaning into the process, exercising patience, and doing the hard work that happens behind the scenes.

© Sara Haile for Warby Parker

The Luupe: Any advice to those looking to take the plunge into full-time freelance photography?

Haile: Bet on yourself and have a plan! I’ve recently become obsessed with the documentary Free Solo, a film that features the first person to ever climb El Capitan in California without ropes or safety gear which is pretty terrifying but a huge endeavor. After watching it a second time, I wrote down a quote from it that really stuck out:

“If the ultimate dream is to solo El Cap, I need a good map of what that will take; a mental image of what the hard parts are, what where they are and what they will entail.”

Hearing this really helped me think about how I could make my plan better. Think about what will be hard but imagine and visualize how you can get through those hurdles whatever they may be for you. Also, make sure to visualize the good stuff too like achieving a goal you set for yourself no matter how big or small.

Finally, believe in yourself and your work. For a long time, I didn’t allow myself to see my photography potential landing in certain places and it felt like that world was not attainable for me. I realized that’s up to me to decide that so I had to change my thought pattern. I now have a quote on the background of my phone’s lock screen that says, “Stop assuming things aren’t attainable for you. You decide that.” Work on introducing healthy self-talk or ways to remind yourself that you can do whatever it is that you’re setting out to do because your thoughts will create your reality.