Lisa Congdon’s Top 10 Tips for Being a Business Boss

HOW Design Live is coming to Chicago in May!

Lisa Congdon is more than an illustrator, artist, and designer: she’s a badass. She’s a keynote speaker at HOW Design Live in Chicago in May 8, and in her talk “Art is Power: Let’s Share It,” she’ll cover her work as an artist, activist, book author, illustrator, Instagram queen, and everything in between.

Lisa Congdon is a legit business boss.

Congdon, based in Portland, Oregon, has a savvy approach to running her own business: As the author of 7 books and a list of clients that include the Museum of Modern Art and Harvard University, she’s got to know her stuff. Her work ranges from book writing to class teaching to selling prints, and through the years, she’s done (and made) it all.

She’s full of information and inspiration, and she gave us 10 tips on being a business boss. Here they are in her own words.

1. Do work that excites you

“I’m a new kind of artist/designer identity, someone who shows in galleries, has done commercial work, wrote books, worked in the world of craft, worked in both wet and digital media, taught. For me, that’s where the excitement is. That’s what makes me want to get out of bed in the morning. Doing the same thing every day for the same purpose would bore me. Pure creativity is a personal expression of power – it is how we feel, how we are connected, how we express our ideas. And there should be no limits to how you express your personal power.”

2. Put yourself out there

“My approach is really to put my work and ideas into the world and to see what happens. And that has worked for me. I make a lot of things, and put those things out into the world on social media. From there, people come to me and say, ‘I’d like to work with you’ or ‘How about we turn that idea in to a book.’ Or ‘I’d like to buy that thing from you.’ I always start from where I am at that moment, and what I love and am passionate about. And the rest unfolds.”

Lisa Congdon is a legit business boss.

3. Drive sales through Instagram

“I would not have a career without Instagram. I realized that there was a golden opportunity there. I began slowly posting more and more work and thinking more and more about the quality and tenor of the images I posted. I also happen to have work that is fairly Instagram friendly. My work is bold and colorful and often contains messages about stuff in life that I think is important. So my work gets shared a lot and tends to get a lot of engagement. It’s where I get most work, where people see my work and then go buy it from my shop (say, when I release a new print). It’s where the customers for my brick and mortar shop find me.” 

4. Think expansively about online sales

“Several years ago, I used to think all the time about how I needed to begin to make other products besides prints of my work because eventually people would stop buying prints. How could selling prints be a sustainable thing? But you know what? Years later, I still sell a lot of prints! People are still buying my prints! I can’t believe it! So I keep making and selling them.”

5. Really push your entrepreneurial pursuits

“I had to figure out how to make money almost immediately pretty much on my own, and so many of my entrepreneurial pursuits were simply a result of needing to figure out quick ways to pay my rent, so it came from necessity at first, and then I slowly figured out which of those pursuits I enjoyed and were also fruitful.”

Lisa Congdon is a legit business boss.

6. Teach an online class

“I make a decent part of my living from online classes, especially my course on CreativeLive about Time Management and Productivity for Artists. That one has really resonated for a lot of people. And my book Whatever You Are, Be a Good One, is the top selling art category title of all time at Chronicle Books (my longtime publisher), and a few of my other books, including Art Inc, have done well too, so I make a good chunk from book royalties. I’ve been very lucky.”

7. Write a book that shares your true voice

“In August, I have a new book coming out called Find Your Artistic Voice: The Essential Guide to Working Your Creative Magic (Chronicle Books). It’s all about finding your creative voice, what an artistic voice is, and how to navigate influence along the path. I cover the importance of showing up, doing the hard work, and managing your time. We can’t develop our voice without making a routine of making work.”

Lisa Congdon is a legit business boss.

8. Don’t be afraid

“In my new book, there is a chapter about fear. It’s the one thing that prevents creativity from happening. And I offer a lot of practical advice for developing your voice. Things you can do to even speed up the process. I’ll be going on an extensive book tour across the US this coming fall for the book, which I’m pretty excited about.”

9. Don’t give up

“I think today we are so easily defeated. It is so easy to fall into the trap of fearing that our story doesn’t matter or that our work doesn’t matter, so why even try? But you have to figure out how to stay inspired, how to tap into that thing or that part of you that has no choice but to be creative. Making art and designing for a living is hard work. You have to take risks, listen to feedback, put your work out there, and eventually form a distinct perspective. That takes a long time. So patience is also important. You have to learn to sit with disappointment and show up to do more work anyway.”  

Lisa Congdon is a legit business boss.

10. Don’t forget to give back

“Last year, I co-founded a non-profit organization in Portland called We Are Here, with Eugenie Fontana and Victor Maldonado. It works to provide mentoring and education to help young underrepresented creatives of color and LGBTQ creatives move into positions of power and influence in the worlds of art and design. This work is especially important to me.” 

Lisa Congdon (and SO many others) will be at HOW Design Live in Chicago on May 8th. Tickets and information can be found at