Behind the Brand: Doodlebooth

Jana Kinsman is the owner and artist behind Doodlebooth, a Chicago company that provides the service of drawing portraits. The WCBC founders met Jana at a party where she had been hired to draw portraits for guests and we were immediately smitten with Jana’s work. We talked to Jana about what it is like to go out on your own and start a business as an artist. Jana also gives excellent advice for people looking to work for themselves.

What services does Dooblebooth offer? We have seen your work on websites, met you at parties drawing portraits, and you mentioned you create save the dates – it seems that your doodles are popular!

Yeah! Doodlebooth offers doodle portraits in a few forms. I can be hired for events where I’ll sit at a table and do portraits of any guests who are interested, kind of like a photobooth. I am also doing something new called Doodledates where we can meet up for coffee and I’ll draw your portrait. That only works if you’re in Chicago, of course. If you live further away, you can send photos to me and I’ll draw from them.


Were you the type of student that was always doodling in class? Did you study art in college?

Haha, YES. I was a very creative kid. Always an illustrator. In 2nd grade I remember winning over the boys in my class by drawing them their favorite dinosaurs. In high school I continued getting better at many different mediums, but I ended up going to college for graphic design where I honed my computer skills. I’m really glad I ended up going that route instead of the regular art school route; right after school it got me a good job that taught me a lot about being a hard worker and gave me a great design sensibility.

What is your favorite part of your job?

My favorite part is definitely getting to meet and chat with all kinds of people. I’m a super-extrovert, and Doodlebooth is the perfect type of work for me. If I have to sit alone in my studio and illustrate things, it takes me a long time and I am easily distracted by the internet or opportunities to go out with friends. Doing in-person portraits really plays well to my social butterfly tendencies!

You are self employed one woman shop, what inspired you to take the plunge into self employment?

Oh boy, many factors. Around 2011, at my former job, I began doing less and less creative work. At the same time, more freelance work started coming my way through Quite Strong, the all-female design collective I started with 4 other women. I decided to leave my day job to pursue the freelance and adventurous life. I didn’t want to work for anyone else anymore, I wanted to travel more and be able to work from anywhere. At a salary job, I could come into work and put off all of that day’s work til the next day, and STILL get paid. I didn’t feel like that was honest. I wanted to be fully responsible for my success and my failures. When I was a kid my favorite phrase was “all by self!” because I wanted to do everything on my own. I don’t think I’ve changed much.

What are the challenges of working for yourself?

The biggest challenge is holding myself accountable. Even though part of the reason I wanted to work for myself was not having to work for anyone else, I still find myself to be a terrible boss sometimes! I’m bad at sticking to routines, which is OK because I enjoy having a different day every day, but it’s bad when I should be checking emails consistently or following up with time sensitive stuff. The resulting guilt can make me feel really bummed out sometimes, so every day I try to be a little bit better with timeliness.


Which female entrepreneurs do you look up to?

This is a hard question, partially because I feel like I’ve been inspired by both genders. The biggest thing that helps me move towards personal fulfillment is to see that every person who has ever done ANYTHING, big or small, is a human being just like I am. Those who inspire me could be categorized as heroes, but instead of putting them on a pedestal and observing them from afar, I immediately try to get to know them on a personal level. I loved watching my mom run her own sewing business when I was in high school. She ran it out of our house and I liked how she didn’t put up a front, she just let our home be the quirky space it was. She taught be to be myself, transparent, messy, and human. Dawn Hancock was inspiring to me in design school for starting her own design business, and the girls of Quite Strong have been a great support and an accessible source of inspiration. A rad woman named Shannon Downey keeps this great blog that is a great source of inspiring women. I check it often.

How have you seen your business grow, and what advice would you give to someone trying to grow their business?
I have seen my business grow very slowly, organically, and honestly. Every day I think about how I can secure it as a source of income and stability, while also making sure it stays small and real. If there’s an aspect to Doodlebooth that I don’t enjoy, I either eliminate it or hire someone else to do it. I hired my friend Justin to do my website because, even though I *could* do it, I just knew it would take me forever and I’d hate it. I waited for the right moment when I had enough money, and hired him. I try to focus on my strengths and what I find enjoyable and make that the core of my business. If you’re on your own and you’re not doing that, then what are you doing?
I would also offer that last sentence as advice to people interested in starting out on their own. Think about what you’re good at, how it might be marketable, and see if there’s a spot for it, culturally. Also, assess your liabilities. I pay cheap rent, don’t own a car, am not married and have no children. It helps that Doodlebooth is not very demanding supply-wise, too; I just need pens and paper. So, I can get by on very little income. If you have a lot of liabilities, take a gradual approach to independent life. Work hard after your 9 to 5 until you think it’s time to devote life to your own work.

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