Artist Lisa Congdon On Finding Her Passion and Business At Age 40

Lisa Congdon is a Portland, OR-based artist, illustrator, hand letterer, author, activist, and the list goes on. She has so many creative projects that she is passionate about, and her dedication and talent are truly inspiring. We had a chance to speak to Lisa about her journey to becoming an artist and her work, and we also got an inside look into her awesome studio. Step inside and see for yourself why we can’t get enough of Lisa and her art.

How did you get started in your creative career?

When I was about 32 years old, I went through a breakup of a pretty dysfunctional relationship I’d been in for almost a decade. Even though the breakup was my decision (and it was the right decision), I fell immediately into despair, because I realized when that relationship was stripped away, I didn’t really know who I was or what mattered in my life. I went to an amazing therapist who helped me unravel my sense of unworthiness and emptiness. And in the process of healing, I found that I had a deep desire to create. So I began taking art classes and consuming books about art and design. I had no intention of becoming a professional artist. I didn’t even know that what I do today was even possible. I just fell in love with making. At first, I was just experimenting with all kinds of things, from painting to drawing to sewing to collage. I set up a little “studio” in my apartment. Art filled me up in a way that I had never been satisfied before. I poured myself into making things. A couple years later in 2004, I started a blog and then opened a Flickr account at the same time. I began meeting other artists and makers online, some of them amateurs like me, some of them professional artists. The DIY movement was forming. The internet was becoming a space for creative people to share their work and process online. Seeing this, my mind exploded with possibility. I realized that if I worked at it, I might be able to forge my new hobbies into a career. And from there forward, I worked on honing my skills, finding my voice as an artist and developing a plan for starting to sell my work once I was ready. And that was really how it started. In 2007, I left my job to pursue a creative career full-time. It was rocky at first. I was broke. No one knew who I was. But steadily, mostly through social media and blogging, I began sharing my work and eventually, I began to build a career.

You’re a fine artist, hand letterer, author and illustrator. How do you balance so many creative passions?

In addition to all the things you mention, I also teach, do public speaking, run two shops (one storefront in Portland and an online shop). Some people become overwhelmed by pursuing different directions in their career. I am energized by it. I love having a few different projects going at once. I rarely get bored and they use different parts of my brain. The key to calm for me is making sure I stay organized. I am really lucky that I am a good balance of creative and organized. I think some of that comes from working for so many years in a job before I was an artist where I had to manage projects and develop systems of using my time efficiently. I learned so much in my former career. I’m also a Capricorn, so I’m just sort of naturally organized! The fact that my brain likes to compartmentalize things works in my favor. It helps in making sure I have balance. I keep spreadsheets of all my projects and interests and check in with them every day as I create my to-do lists. I find the more time I spend on organization, the calmer I feel and the more balanced my workday is. Sure, there are days when I feel stretched, but the flip side is that I am always finding energy in my work because nothing is ever the same from day to day. 

Do you feel that being self-taught helped or hindered you in any way?

I sometimes wish that I had discovered that I loved making art earlier in life and that I had gone to art school. Attending art school or studying art at a university can be incredibly valuable in so many ways. But my path didn’t include that, and I have come to accept that. And I do think there are even advantages to being self-taught. First and foremost, I don’t have those voices in my head that say there is a right or wrong way to do something (draw, paint, whatever). I took some painting classes in the beginning and learned some basic skills, but mostly I learned by doing and experimenting. And I think that really freed me up. I have no doubt I break a lot of “rules” and I actually don’t care. I think what matters is what you produce, and while your process is interesting, there is no one or two right ways to make art. And I think art education can instill the opposite perspective in people.

“I think what matters is what you produce, and while your process is interesting, there is no one or two right ways to make art. And I think art education can instill the opposite perspective in people.”

What inspires your work?

On the simplest level, I am really motivated by a lot of things, including things like colors and shapes. And I am inspired in huge ways by folk art and mid-century graphic design, and the places that those two things converge. I think that’s why Alexander Girard is one of my favorite artists of all time. I am also motivated by doing good in the world, and using my work to challenge and inspire others to live with more intention. I found happiness and a sense of agency in my life when began making art. I want to share that with other people.

What were some of the first initial steps that you took to start your own business?

The first thing I did was open an Etsy shop back in 2007.  I am actually currently building my own e-commerce site after 12 years in business, so I will be leaving Etsy soon. But Etsy was a great place for me to start (I started my business back when Etsy was tiny), and it was the perfect place for me to test products and sell things without huge risk. And eventually, it became a big source of income for me after about six years, and it continues to grow. Simultaneously, I was an early adopter of social media. I rarely use Twitter or Facebook anymore, but those were two places where I began promoting my work early on before Instagram. And then Instagram happened. And, honestly, my business wouldn’t exist if it weren’t the work I did to build a social media presence. Eventually, Instagram became the place—and continues to be the place—where people find me! People who hired me to do work for them, people who commissioned me, people who gave me incredible opportunities. Creating a space for people to find and follow and financially support your creative journey is everything. I am so grateful that I came into this career at this time in history.

You started your own business at age 40! Can you share some advice on how to successfully make such a major career pivot?

It’s funny, if you had told me at 30 that I would leave my job at 39 to become a professional artist, I would have told you that you were crazy. And now at 51, I can’t imagine any other life. You never know where your life choices will lead you. And I think therein lies my first bit of advice: make choices that are aligned with what you want out of life. I wanted to be a happier, more creative person. So I started making art. And even though I didn’t know what I was doing half the time (I was teaching myself as I went), I fell deeply in love with the creative process, which motivated me to get better at it. I showed up for it every day. And eventually, years later, I realized I could make a career at it. So by the time I made the career pivot, I had been working at it for several years already, preparing myself financially and mentally and developing my skills. When I made the pivot, I was ready. And there’s another bit of advice: work at what you want to do on the side for awhile before you abandon everything to make a huge change. 

Do you have any advice that you can share with other aspiring artists afraid to make the jump?

One of my personal mottos is, “Begin Anyhow.” Life is super messy, no matter how hard we try to make it clean and smooth and perfect. We often procrastinate on starting new projects or launching this or that or meeting our future goals because we think we don’t have the right amount of money or the right setup, tools or time in our schedule. And then not having the right setup, tools or time becomes just an excuse not to begin. In the end, we can almost always work toward our goals with what we have right now. It’s important to summon courage and Begin Anyhow—despite circumstances not being perfect.

Are you working on anything new that you can share with GG readers?

I have a new book that comes out on August 6 that I am so excited to put into the world. It’s called Find Your Artistic Voice: The Essential Guide to Working Your Creative Magic. Your artistic voice is what sets you apart, and, ultimately, what makes your work interesting, distinctive, worthy of discourse and desired by others. No matter your medium or genre, having your own voice is the holy grail. I wrote the book to help folks understand what it means to have an artistic voice and why having one matters. I also share methods for tricky things like navigating influence and working through fear and practical tips for deepening your voice-finding experience. You can order it online wherever books are sold.

Do you have any routines that you stick to as a busy entrepreneur?

I sometimes get buried in work and I have to remember that taking care of myself—exercising, eating good food, hanging out with my tight group of friends, getting enough rest, taking vacations—are all in service of my career, not a detriment to it. And having a routine that includes all of those things is critical for my sense of well-being and equanimity. I get up at pretty much the same time nearly every morning. I exercise vigorously about six days a week (I am super into road cycling so I either go to spin class at my neighborhood studio or I ride with my women’s cycling team here in Portland). Cycling outdoors is like my church. It’s almost a spiritual experience for me and a great emotional and physical release after sitting and working all day! I go to bed at nearly the same time every night. I am a voracious reader. I spend a lot of my downtime reading or drawing for fun or watching dumb Netflix shows. I have a full social life (sometimes too much of one!). I take vacations periodically, even just day-long vacations where I go shopping in town for clothes or to a vintage shop for things I collect. And when I am working, I am super present with my work. I work in time blocks for efficiency. I don’t make social plans very often during my work hours. I find that disrupting work for lunch dates (even with people I love) throws me off and I don’t get as much done. So I work pretty regular hours and with a lot of focus. Then outside that, I live my life fully. If that sounds easy, it’s not. I have to have really strict boundaries around my time, and that takes a lot of discipline.

How do you keep your home life and work life separate?

Those boundaries have saved my sanity and my relationship. And it took me awhile to figure that out. When I first started out as a solo entrepreneur, I worked all the time and without a real end to my day. I would literally take my computer to bed and it was the first thing I grabbed when I woke in the morning! And found that I had no time to play or relax. So I burned out in a really bad way a few years ago. I am married and my wife has a full-time job with regular hours. So I made a commitment about five years ago to work the same hours as she does so we can have quality time together in the evenings and weekends. Since so much of my work is on social media, I also have pretty strict boundaries about what I share and don’t share. I do share some of my personal life in Stories and occasionally, when it’s relevant, in my feed (sometimes I cannot separate life from my art). But I don’t share too much of my personal life, and that’s because I need privacy. It’s not necessary for people to know where you are at every minute, and it’s also important to give yourself space from your audience and community. As a person with a large following, I’m acutely judicious about what I share and what I keep private. People might thing they know everything about me (and they’ll tell me so!), but that’s simply not true. There is so much more to my life and experience on this planet than my professional life or what I choose to share. Thank goodness, right?


Photography by Chris Dibble – @dibblephoto

Lisa Congdon – @lisacongdonLisa Congdon Art & Illustration

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Author: Wendy Vazquez

Wendy is the Editorial Assistant here at the Glitter Guide. She has a background in PR and marketing, but her true passion is editorial. She enjoys all things beauty and lifestyle.