The “Beautifully Terrifying” Art of Chasing a Dream: Interview with Tour Photographer and Artist Manager, Brittany O’Brien
Brittany O’Brien is a professional tour photographer and artist manager. After graduating high school, Brittany moved to San Francisco where she began photographing local concerts. She got her first big break when she was offered the opportunity to go on tour with the band Hippo Campus when they were selected as the opener for Twenty One Pilots. Since then, she has gone on to photograph the tours of artists including Gus Dapperton, Pinegrove, COIN, and many more, as well as expanding into tour managing and artist managing.
Brittany reminded me of what it means to unabashedly pursue a dream while navigating the complex set of emotions and experiences that the pursuit requires (facing rejection, building confidence, believing in yourself, making sacrifices, putting yourself out there). I think she described the sensation best when I asked her about what it was like to take on the new role of artist manager: “Beautifully terrifying.”
I spoke to her about:
Staying afloat in San Francisco while working to make it as a tour photographer
Persevering through rejection
Finally experiencing the feeling of “I’ve got this”
Expanding her skillset
What she’s learned from life on the road
Her advice for pursuing your dreams
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
What are you up to in life right now?
I am currently taking a little break from touring through the end of the year. It’s kind of nice to be home in Los Angeles for a while. I manage a handful of bands now so that has my attention through the end of the year. It’s been a really fun and interesting transition from being a full-time touring photographer into managing bands. My focus is on getting a couple of albums out for other artists. I enjoy directing the creative side of things for bands and then switching over to the logistical nightmare of putting music out. It's always challenging my brain.
I read that you were studying to be a meteorologist before you got into photography. What’s the story there? How did you end up transitioning to what you're doing now?
I always had this obsession with the weather since I was probably 5 years old. And I remember my first favorite movie was the movie, Twister, which is effectively a horror movie about tornadoes. I don't know why, but I was fascinated by the idea of people storm-chasing and going to see these events because they're things we can't control. I think there's something that's always drawn me to things that are outside of human control. I really thought I was going to get into storm chasing and become a full-on meteorologist so I took that path in school. But when I got into the later years of high school, I realized I didn't care about the studying part of school. I was in dance, drama, theater, and choir, and I didn’t want to stop those classes. I decided not to take the history and math classes that were required for me to move forward with getting a 4-year college degree. I just said, “I'm gonna figure out how to not do that.”
What happened after that? Was there a single moment where you said, “This is going to be my career. I’m going all in on photography?”
It took a while. I've always been a big music fan. After high school, I moved to San Francisco. I just cold Turkey left home and decided I’d figure it out. I grew up about an hour north in Santa Rosa, which is a small town. I met some people in a band so I decided I would take photos of them playing music and just have fun with that. I fell in love with it. That band started taking off and was offered the opportunity to go on tour with Twenty One Pilots in 2015. At that point, I was just kind of bouncing around doing whatever I could to stay afloat in San Francisco. Once the band got offered the opportunity with Twenty One Pilots, I decided to go out on tour with them.
When I got back from tour, I was like, “Being a photographer on tour is a job and I'm gonna figure out how to do that.” So I started cold emailing bands with my portfolio from that tour and just said, “If you want someone to come on tour, I’ll do it for free. Just throw me in the van.” That’s how it all started. 2015 was the big moment of starting to figure it all out.
I read an old interview of yours in Sunstroke Magazine where you were asked about what it was like to make it in the industry on your own. You said, “...you have to accept that “no” is going to happen a lot before you get the “yes” that changes everything.” What did you tell yourself to keep going and persevere through the “nos?”
That's a great question. It was really hard, and it’s funny because I have quite a large fear of rejection. Sometimes when I send an email that's a little risky, I'm scared to open my inbox so I just avoid it. I still have that habit all these years later. But the big difference in the beginning was that I was very driven by being able to do what I wanted. I didn't want to have to fall in line and do something that I had no interest in. The passion to control my fate and my own destiny outweighed the petty fears of rejection. Every “yes” that I got was proof that every time I cold emailed someone there was an opportunity waiting. It might not be every time. But every time I got a “yes” I thought, “See? I did that thing. I made something happen out of literally nothing.” All of those little tiny wins, even if they were one-off gigs that paid me 50 bucks, were still a “yes” that enabled me to go do it again. Even now, there’s an email I’m waiting for and I’m scared to open my inbox.
I don't think I really trusted myself when I made the leap to start my own business. It was more like the trust and self-belief came after a lot of faking it until I made it. Does that resonate with you? Was there ever a moment when the “faking it” stopped and you were able to say, “There are still some things that scare me but I know I’ve got this?”
Oh, absolutely. That happened relatively recently for me. There was a time in 2021 when I really felt it switch, and I’ve been doing this since 2015. So it took a really long time. There's always been, you know, some level of imposter syndrome. Thinking along the lines of, “Do I know what I’m doing? I guess, but I’m not 100% sure and I’m gonna keep doing it anyway.” Over time, I realized and saw that most other people, regardless of their status, no matter how high or low in the music industry (or maybe any industry), felt and thought the same things. You can be on the top of the food chain at Universal and still be figuring it out. I saw that everything was just moving pieces, and I had more insight into other people doing things the same way as me, or maybe worse than me. I think I do know what I'm doing, and I think I am providing a service to people who don't have what I have. I was finally able to see that I was creating value. It just took a lot of learning and experiencing other people’s ways of doing things to see it. But that shift did come eventually and with it the confidence that has carried me into being comfortable with my, rate rather than asking, “What kind of budget do you have?” which I did for most of my career. It’s been a nice shift.
You mentioned that you’re managing bands now, in addition to being a photographer. What was it like jumping into a completely different part of the business?
It was beautifully terrifying. It happened very naturally and I'm very grateful to the band Pinegrove. I was tour managing them in 2021 and very much just fell in love with the band and the crew. At the end of the tour the singer, Evan Hall, just took a really big leap with me. He asked me to join the band’s management team which is a very unusual move for an artist, especially because they already had management. Their manager, Tom, has been my mentor through this whole experience. He's the best. Bringing me on was just a very serendipitous learning experience because I was surrounded by 2 people who trusted that I had it in me, even though I was brand new, and helped me expand to a whole new scene of people and knowledge. So it was beautiful, but it was terrifying to think, “Oh, you're putting a record out in 6 months, and now I'm a part of figuring out how to do that, and I don't know anything about doing that.” So it was a lot of learning very quickly which I've always really loved to do. I just hit the ground running figuring it out.
You've now spent a lot of time on the road. What did you learn from life on the road that has translated into the bigger picture of your life?
The first thing that comes to mind is being able to see life all over America. That has been incredibly life-changing in terms of acceptance and awareness. I grew up in a largely white, largely middle-class community in Santa Rosa. There's a lot of stereotyping about different areas of the country. Things like, the south is scary and everyone is horrible there, or New York is overwhelming and you’d never be able to make it there. A lot of stereotypes about places were just thrust upon me as a kid. Being able to go see all of these places for myself and being able to create my own view of the world has translated into my life, in terms of how I see everything. It enables me to go back to the people in my life and say, “Those stereotypes aren’t true. The south is wonderful. There's obviously been a lot of horrible politics there but you can’t just group a bunch of people together and say that’s how it is.”
That’s translated into my life but also helped me in business. It’s super helpful to know the markets and what people are like all over the country. It’s amazing to learn about the kids growing up everywhere and how they're changing the narrative of where they live. A lot of it has been through touring with the band, Hippo Campus, which has a fan base of younger college women. They have all sorts of fans but a heavy base in that demographic. Meeting these bright women who are doing all kinds of incredible stuff all over the country was incredibly cool. Interacting with other people has been the biggest translator for me.
Have there been any cities in particular that really surprised you?
Yes, I love the city of Baltimore. They have some wonderful pockets of art communities. Tennessee was another big one. I remember the first time I went to Tennessee, I thought about how the picture I had of it growing up was that it would be flat with dry grass. In reality, it’s swampy forests and beautiful rivers. I was just blown away when I saw Tennessee for the first time. I still love traveling through Tennessee and North Carolina and the swampy parts of the south. America as a landscape is so stunning and the amount of diversity in the landscape of this country is just so cool.
One thing I always like to ask people about is the concept of making money. With creative endeavors, I think a lot of people get stuck with the idea of “How will I make this work financially?” Having done this for a number of years now, what’s your perspective?
Great question. It’s kind of twofold. One, I really believe that if you stay in the space and really want it, you will make it work. It’s easy to give up if it’s not going well. Sometimes finances dictate giving up, but I don’t think of it that way. I think of it more in terms of sacrifices. If it’s something that you want to be full-time and lasts forever, sacrifices will have to be made. You might continue to pursue it for free while you work on other things and keep building. I think eventually there's going to be something that breaks if you're throwing your whole heart into it. That's coming from my own experience. Every person is different but I do believe that if you want it enough, you can make it happen for yourself.
I will say that the landscape has changed. Things were different when I started in 2015 in terms of competition. Social media was still largely focused on Instagram and photos. There was no TikTok. There weren’t as many people trying to be online and take photos. It’s a much more saturated industry now so I’m sure it’s harder to have a moment. But I still think there are so many ways. Everyone is an individual. I think there’s a way to rise above and find a way that makes you the one to shine. I see a lot of photographers when I'm observing people at shows just pointing their cameras at the stage, clicking, and then hoping that something comes out of that. I feel that if you are the one who wants to make a career out of this, there needs to be a second layer going on of looking for angles, really thinking about the shot, and throwing yourself into it, instead of just hoping something will happen for you. I think the difference is in hoping versus focusing.
That makes me think about what you said about learning a lot from experiencing different parts of the country. You've also experienced a lot through the lens of a camera. How has that altered your perspective?
The biggest thing I've been reflecting on is how hard it can be to be fully immersed in any moment. When I'm either on tour, at a party, or out at a concert with friends, part of my brain is distracted thinking about what something would look like as an image or as a captured moment. That is a blessing and a curse. Obviously, there are a lot of ways that has benefited me throughout my life. But sometimes I get very annoyed at the fact that I can't just be there fully. Then I get lost thinking about being there fully and why I can’t be and how I wish I could focus. And then it's just a spiral from there. When I was younger, I was the kid in school who carried around a little point-and-shoot digital camera before I had a phone with photo capabilities. We were always messing around doing fun stuff and I’d be the one to say, “Well, hold on. Let me just grab this.” So I’ve learned how to live with that. But that is, I think, a big photography curse…always looking at things as though they're already images.
You have so many amazing things going on right now. What’s next for you?
Next year I’ll be doing something I haven’t done before which is a big print store of all the images I've shot since the beginning of my career. I've been working on this long-term project showing all the prints from my first year until now. It's not necessarily something that I think people would want to buy or own because it's more of a personal thing. I'm working on having a little art gallery to gather people. I want to bring some other photographers on to compare their journeys and the growth that people have gone through over the last 5-6 years of their careers. I just think it would be fun because it’s fun to reflect on your creative journey. A couple of bands I work with will be back out doing some stuff next year, and I'll be back on the road at some point. For now, I’m just helping my bands put some songs out.
Has there been anything you’ve noticed in putting that project together that stood out to you in terms of your transformation over the years?
I have always had this weird fascination with wide-angle lenses. Effectively having a larger picture but on a close-up subject. I have seen this reflected in my live work from 2015 through now. I am always really close to a subject, but I shoot them in a way where they look like a giant compared to the landscape behind them. I didn't realize that I've always done that. I thought that was something that I started doing 2 or 3 years ago. I've always been fascinated by depth perception in live music photography.
For anyone out there on the precipice of following a passion or a dream, what are your parting words of wisdom for them?
First, I really want them to do it. The biggest thing is being able to have confidence that you know what you want and are forming a plan for yourself, with a goal at the end that you know is attainable. I think a lot of people get stuck thinking that their dream is not attainable, just based on societal constructs and things that have happened to them in the past. I believe that it is attainable as long as you keep looking at your goal, and you get to that goal by being confident in yourself and knowing that this is your passion. Also being comfortable with rejection in whatever way you can cope with that while knowing that it's gonna happen. You have to learn to have a coping mechanism to push through because you will get beat down. All you have to do is know that you can get back up as long as you see that goal. Those things have carried me along; the confidence, learning how to deal with rejection, and keeping an eye on being free to control my own life. My goal has always been to control my world and be able to do things my way. I got there through rejection and confidence.
