Lisa Congdon is a fine artist, illustrator, and writer living in Portland Oregon. She’s teaches, lectures, hosts a podcast, has written seven books, and creates commercial work for clients around the globe including Google, Schwinn, Warby Parker, Method, Comme des Garçons, REI, and MoMA. In our interview we talk about perseverance, the joy of learning, and the creativity inside all of us.

I really love your message that it’s never too late to tackle your dream and make a career change. Can you tell us about leaving your career in education at the age of 39 and dedicating yourself to art?

I started making art when I was in my early 30s with zero aspiration to become a professional artist. I’d just gone through a big breakup and was looking for things to fill my time and lift my spirits, so I started taking art classes and set up a little “studio” at my kitchen table. I was very much a beginner and my art looked very much like a beginner’s. But I found peace and motivation in making art that I’d not experienced before in anything else. So I just started making a lot of art. This was in the early 2000s when the internet was becoming a space to share your work, whether you were an amateur like me or a professional artist. I began to see that this was something—if I dedicated myself to improving and learning and practice—that I could get good at and maybe do to earn money someday.

Eventually, in my late 30s I left my job at an education nonprofit and went out on my own. At first it was really challenging financially, but I am extremely dogged, and I dedicated myself to figuring out how I could make a living. I found my voice, grew my business, attracted an audience, and began to flourish. I’ve been in business now for 16 years and my practice is divided between fine art (exhibitions of original works) and commercial work (illustration and brand collaborations). I also have a retail arm of my business, and my two employees run that for me entirely. 

Your personal motto “begin anyhow” is so wonderful, and you’re right, most of us can make progress towards our goals with what we have right now. And there’s always an excuse not to start, so why line them up when you can blow past them? How did you find this mantra in your creative life?

Like most people, I get caught up in overthinking my ideas. We might think, “Oh! That idea that popped into my head just really excited me! I should do/make/create that!” But then what happens is that we are faced with actually doing that thing, and we suddenly are filled with doubt. Doubt that we could execute it. Doubt we have time. Doubt it’s a good idea at all. Etc. So we sit on it, and often we do nothing.

I believe most people are incredibly creative. It’s just that their ideas never get expressed because they’re scared. I noticed this in myself when I first started out, and I had this big AHA moment where I realized there is never a perfect time to start anything, whether it was executing a new idea or trying a new medium or just starting a project. So I literally forced myself intentionally to “begin anyhow”—even when I was filled with doubt. I noticed that once I started, it was fine. The difference between most “successful” or prolific artists and the rest of the population isn’t innate talent or some sense of fearlessness. It’s that we feel the doubt or fear and go for it anyway. We push through. We begin anyhow. 

You’ve talked about being open about your successes and struggles, so others can relate to the ups and downs and feel that they are not alone. And the various aspects of your work (artwork, social justice, mentoring, etc.) has certainly uplifted many others. What or who uplifts you?

Thank you for saying that! I am honored to give back to my community, and that certainly uplifts me! I work a lot and have my hands in many pots. So for me, doing something completely separate from making art or managing a busy studio is what uplifts me and keeps me going. I am an avid endurance cyclist, and I have found that having something in my life that is so physically challenging, where I am in my body and pushing myself in a totally different way than I push myself in my art, has been so incredibly important. Being outside, being with other human beings, training, racing, climbing mountains, being in the pain cave—all of those things make me a better artist, mentor, and boss. They give me perspective and help me maintain a sense of humility and a gratitude for being alive. 

You were a real pioneer at the advent of blogs and social media being utilized to share creativity and build community, what changes have you observed over the years?

I love that I have met most of my artist social circle on Instagram, and I am so grateful I entered that space when it was truly a space for visual artists and creators. It’s now become a space for “content” creators and folks who make videos. I built my career on social media and found a community of folks, many of whom I am close friends with now or have worked with—and even folks I have started a nonprofit foundation with.

I am a bit nostalgic for the old days when it was so easy to do that. I am not here to create content that will please an audience or an algorithm. I am here to make art and share it, and to connect with people around social justice issues, art and creativity, and cycling. It’s hard, but change happens. And I am trying to adapt (I am still there and I still use Instagram primarily), but I am also finding other ways to connect with my community and share what I do.

I really appreciate your insight that success doesn’t happen overnight, and that if it did, you wouldn’t be remotely prepared for it. What encouragement can you offer to anyone struggling with their art career, or fearful of beginning one?

Be in it first and foremost because you feel called to do it. That doesn’t mean you have to love every minute or that you have to make your dream work every day. Those goals are not realistic or even healthy. Embrace the discomfort of the creative process. Loosen your grip. Keep showing up. Dig deep. Keep practicing. Find joy and humor in learning, screwing up, and starting over. Keep your eyes focused on where you want to go. And then realize once you are there, a new journey will unfold. 

Find more of Lisa Congdon’s work at and follow her on Instagram at @lisacongdon.