At 51, Lisa Congdon is the picture of a thriving freelance artist. Her client list includes Fortune 500 companies (Facebook, General Mills, Hewlett Packard), tech companies (Airbnb, Sonos), and art museums and universities (MoMA, Harvard), among many others. In addition to her commercial work, she makes, exhibits, and sells fine art, teaches online classes, and has published eight books, including the forthcoming: Find Your Artistic Voice: The Essential Guide to Working Your Creative Magic.
If you’d told her any of this in her early 30s, she would have laughed at you. Growing up, Congdon wasn’t even the creative one in her family (that would be her sister). After college, she went into education: first as an elementary school teacher and then as a staff member at a nonprofit working with public schools. Her life path seemed set.
But at 32, she experienced “a bit of a life crisis” after a long-term relationship with a woman she’d been dating since her early 20s imploded. In a depressive rut, she started seeing a therapist, who helped her begin the the terrifying process of figuring out who she was and what she wanted from life. Congdon didn’t have a lot of answers but, spurred by an unfamiliar urge to make things, she began taking community drawing and painting classes.
In the beginning, art was purely something she did for fun on the weekends. It stayed that way until, in the mid-2000s, she started a blog in which she posted pictures of her work. Congdon met other makers online, some of whom made their living from their art. It was a life she wanted for herself.
The transition wasn’t quick or easy. It wasn’t until 2007, at the age of 40, eight years after she began drawing, that she left her job to focus on her art career. “I did in phases,” she says, seizing opportunities as they came and slowly building up momentum and clients.
Here, Congdon looks back at her unconventional path to freelance success and why she’s glad she found art later in life.
Q. When you started drawing and painting, you did it solely for fun. Looking back, did that mindset help you professionally?
A. To a certain extent, because I wasn’t thinking, ‘I need to make work that’s really conceptual, or totally unique, or groundbreaking.’ I just drew what was around me, and then tried to make it interesting in terms of color palette and how I was arranging and rendering things on the page. My own style developed out of that.
Part of the reason I’m able to make so much work is that I don’t have voices in my head necessarily telling me that this is right or wrong. I just kind of try things.
Q. You also started in your early 30s. For creative industries, the perception often seems to be: if you haven’t established yourself in your 20s, the ship has probably sailed. Were there advantages to finding art later?
A. There are probably a lot of artists who are starting out who don’t necessarily have a strong set of interests yet because they are only 22. I’m not saying all 22-year-olds don’t have a developed sense of interests, but I think one advantage to starting later in life is that I knew who I was already. I understood what I was drawn to, and that really helped me not trip too much about the meaning of my work. I just started drawing the stuff I was interested in and I didn’t overthink it. It freed me a little bit.
I also think that because I came at this at an older age, I have patience with the art-making and creative process that I wouldn’t necessarily have had when I was younger. In order to get good at something you have to work at it. I had experienced that in other areas of my life, and that’s how I approached my art practice.
Q. How did the way you thought about your work and process change as people began to pay attention to it?
A. When I started out as an artist, I was really free because I didn’t have any expectations for myself, nor did anyone else. That definitely morphed into more self-judgement, or more, ‘am I doing this right?’
When I’m working, I try to stay focused on my own vision. I think so often now, what happens to people who are trying to make it in the art or illustration or design world is that we get overwhelmed by what other people are doing. You become part of this community of artists online or in your actual community where you live. You are inadvertently bombarded by their work; we all follow people we admire. But I understood early on that I had to tune that out. That I could admire those people and I even learn from them, but I needed to stay focused on my own vision of what I found interesting or beautiful or weird that I wanted to communicate in the work that I do.
Q. What are some of the strategies you’ve developed for finding inspiration without getting overwhelmed by the work of artists you admire?
A. There have been periods of time that I’ve had to unfollow people [on Instagram]. Not because I didn’t like their work, but because I liked their work—I was feeling a sense of competition or jealousy. I do it less and less because I feel more confident in my own career, but there was a time when I had to block out the stuff that didn’t make me feel good.
I also had to work on embracing this idea that there is room for everyone. Just because someone else you admire has some amazing accomplishment doesn’t mean that your work has any less value, or that your path is any less significant. It’s a really important mindset, and I had to work really hard to get there.
Q. What has your career taught you about the importance of professional benchmarks?
A. You think, ‘Oh, if I only had this client on my client list, I will have arrived.’ I just announced that I did a collaboration with [fashion brand] Comme des Garcons. Everyone is like, ‘That’s amazing!’ But is my life or my illustration process any better because I’ve had this giant client? No, not really. You learn over time, even when you get these great client jobs, that a) sometimes they are hard work and b) they don’t necessarily make you a happier person or make your career any more or less significant.
The more you do something that you want to do in your life, the more you have perspective about it’s true meaning. Some things we think are going to be life-changing for us end up not being [that way], and other things that we never would have imagined are absolutely transformative. I never imagined that all the personal work I do would have lead to the more gratifying projects that I’ve done in my career. In the beginning, I was like, ‘I want to build this cool client list and do cool projects with clients.’ I’ve done that, and while a lot of it has been really fun, it’s not necessarily where I’ve gotten the most satisfaction and meaning.
Q. You kept your full-time job for years after you started selling your art. Is this a path you recommend for other people who are hoping to break into a creative industry?
A. Definitely. The minute you put all of the pressure on your art career to feed you is the minute it becomes extremely stressful. I talk to people all the time who have part-time jobs either as illustrators or artists who work for bigger companies or as a barista or a social worker because they don’t want that pressure. It allows them to take jobs that they want because they want them, not because they have to have them.
If you already have a bunch of work coming your way and you have [multiple] income streams, then quitting your job is fine—do it! But there is this period of time where you need to do three or four different things.
Q. It can sometimes feel like the ultimate goal for any aspiring creative is to do what you’ve done: develop your art career to the point where it sustains you financially. Is that the only option, or can keeping a part-time job work in the long-term?
A. I have a lot of friends who do that to this day. That’s their comfort level. We have this image of the successful entrepreneur or the successful artist as someone who makes their full-time living doing it, who is thriving and gets all this work. There isn’t one way to be an artist; there isn’t one way to be an entrepreneur. There are lots of ways to do it, and to do it well, and to live a happy life, because ultimately that’s the goal. The goal isn’t to have a successful career. The goal is to be happy.