Maggie Sichter Enterrios is best known for her intricate black ink drawings, inspired by typography and nature.
With a background in graphic design and art direction, Maggie pursued her love of illustration first as a hobby and then as a side hustle, building her business to the point where she was able to take it full-time in 2016.
Based in Chicago, Illinois, Maggie creates and sells art prints and apparel, and works with commercial clients on logos and branding, advertising, packaging, and more. As well as dozens of small business clients, Maggie has created work for the likes of Apple, Colorfy and Sakura of America (makers of Pigma Micron and Gellyroll pens).
Here, she shares her journey to becoming a full-time illustrator, what her weekly schedule looks like, some of the challenges self-employment can bring, and why her process calls for her to be “part artist, part detective”.
1. Can you tell us a bit about your background and story so far. How did you get started as an illustrator?
I’ve been drawing my entire life in a style that is not so far removed from the aesthetic I’m most known for. I went to school with the intention of studying photography, but found myself doodling through all my classes. It became pretty apparent that I should adjust my focus. I switched over to graphic arts, and I got a job in design during my junior year of college that eventually became a career in art direction, where I managed branding and creative strategy in the tech industry.
Illustration was relegated to a hobby for a long time, until one Christmas when I was talking to a friend’s dad — a retired pilot — who, when reflecting on his career said: “If you find a job doing what you love, you’ll never work a day in your life.” You know those moments that stick with you, unshakeably? From that point on I started taking my hobby completely seriously. I was born with a talent, but I had to work to turn that talent into a skill, and eventually into a full-time job.
2. What made you decide to pursue freelancing and how did you find your first clients when you started out?
I’ve been freelancing since late high school. Maybe earlier. I’ve always had a side hustle, whether it was photography or graphic design. I was so nervous I wouldn’t find a job; I hadn’t heard about any of my peers sailing directly into a design career so I recognised fairly early that I may have to design on the side while holding some sort of day job.
Amazingly, I found a temp job doing graphic design at Grubhub even before graduating. My position there quickly evolved into an in-house contractor role, which taught me the ins and outs of managing invoices and self-employment taxes, and gave me the time and opportunity to start building a design vernacular.
The clients I had at that time were mostly friend or work referrals, and almost none of them involved illustration. I said “yes” to anything someone would ask me to design even if it seemed out of my wheelhouse, no matter if it paid or not. Then I’d research like mad and ask my older co-workers for a lot of advice. That direct line of access was priceless.
3. How has your business evolved since then? Can you talk us through your different offerings?
The evolution was gradual but calculated. I knew that I’d someday want to transition exclusively to illustration. I did enough digital work during the day building ad campaigns and web banners, I was desperate to close the computer when I got home. Once I crossed the 30-hour a week freelance threshold (in addition to my art director job) I knew I could make the switch. I learned to finally say “no”, no matter how lucrative a graphic design offer sounded. I decided I had to focus on an aesthetic — the one I loved most — and build that portfolio to perfection.
At this point I am solely an illustrator. Most of my clients are national and in the retail sector: packaging, textile, publication and advertising, and I also keep an active Instagram account for my ink illustrations, which I try to create often enough to keep my followers engaged. In addition, I create illustration-heavy logos for small companies.
4. How do you manage your time across the different aspects of your business? What does a typical day or week look like for you?
My work week is Monday – Saturday and every other Sunday. I balance anywhere from six to 30 clients at a time depending on project size. During a busy week, I spend Monday – Wednesday accounting, building invoices, emailing clients and sending quotes. Thursday through Saturday are spent drawing, usually for 14 hours at a time or more. I like to completely zone out when I draw, and I can rarely do that if I’m in the middle of an email chain, so I break my week into two pieces accordingly.
I learned to finally say “no”, no matter how lucrative a graphic design offer sounded. I decided I had to focus on an aesthetic — the one I loved most — and build that portfolio to perfection.
5. Do you have a morning routine? How do you like to begin each day?
Yes! I am regimented about my morning routine. I wake up before 6am on weekdays, hit the gym for bootcamp or meet up with my running club girlfriends. Because my job is so sedentary, I really require that morning movement and socialisation to stay balanced. I’m back home by 7.30am. I make a full breakfast, a pot of coffee, and begin work by 8am.
6. What does your creative process look like and what tools and materials do you tend to use for your work?
I do a lot of research before anything that I create, and then I build in some room for spontaneity. To give you an idea, I was recently tasked with creating painterly digital illustrations of some very specific plants. First, I tested the style in which I wanted to draw. I bought some flowers and practised drawing them with a few different brushes: watercolor, ink, airbrush.
Once I landed on the winner, I had to find the actual plants and photograph them in a way that was conducive to the style I’d just created – really high contrast and moody. I called around to local botanical gardens and obsessed over finding these plants. I researched the history of them, what they are used for, the Latin root words. After I drew them, I got rid of all reference photography and painted them from memory. I made them interpretive, beautiful and unique. To me, that makes my job so much more fulfilling. Part detective, part artist.
I like to completely zone out when I draw, and I can rarely do that if I’m in the middle of an email chain, so I break my week into two pieces accordingly.
7. You have a gorgeous, distinctive style. How would you describe your work and style and what tips would you give to a fellow artist who’s struggling to develop their own?
Embrace what is naturally coming out of you. Don’t fight it. I am most inspired by other artists who have some sort of quirk to their style – a slight wobble in their linework or a heavy hand. Imperfections in skill are actually what create uniqueness. For me, no matter how hard I try, I cannot draw perfectly realistic subject matter. I get bored or frustrated. And I hated on myself for that for ages. Now, I can see that my half-real, half-imaginary florals are what draw people to my work. They are presented as fact: this is how I draw. Lines are perfect but subject matter is not.
Find something that flows out of you easily and perfect your presentation of it.
8. What’s the most valuable lesson you’ve learned about your creative process so far?
It’s always so tempting to go with your first, impulsive idea, but usually more rewarding to really think it through before putting pen to paper. I am forever indebted to my first senior art director at GrubHub, Mike Wright, for this skill. Every time he presented an idea to a group of stakeholders, he would tell a story and talk through his ideas in a perfectly Don Draper way, painting the picture verbally before unveiling his concept. It was always a hit, and I was in awe time and time again. So, I’ve learned to sleep on it: fully mull my ideas over before putting them out into the world.
I am most inspired by other artists who have some sort of quirk to their style – a slight wobble in their linework or a heavy hand. Imperfections in skill are actually what create uniqueness.
9. What do you do if you hit a creative block?
I keep a list of ideas on my phone. I call it the “if I had time” list. Whenever I have a fleeting inspiration or concept, I throw it on the list. When creative block hits I think it’s best fighting fire with fire, but maybe not on the project you’re working on. So if I’m struggling with a logo concept, I’ll take a day and draw something from my list. Typically, getting those ideas out breeds more, and I’m able to re-inspire myself.
10. What’s been your proudest achievement so far?
Every time I transfer money into my savings account, that’s the biggest achievement. But really, working with Apple on the launch of their new iPad Pro was obviously a dream come true.
11. What’s the biggest challenge you’ve faced in business so far?
I got audited for my first year freelancing, four years later. It took over a year to settle the ordeal, and it really came close to breaking me. But I tried to see a silver lining, and some day down the line I’d love to start writing or blogging for other artists with tips on handling money, taxes, and all the nasty stuff we all hate.
12. What are your top tips for fellow artists looking to set up their own business?
1. Start with it as a side gig. That’s the only way you’ll know if you really enjoy it or not. And figuring out the business side of things is much easier and less horrifying when you’ve got a steady paycheck coming in from somewhere else.
2. Understand that your priorities will completely change. This is something I was excited for, but I know a lot of other creatives that struggled in this area. Free time may not exist anymore unless you schedule it in. Challenges all become self-contained: there isn’t anyone you can pass your problems off to. Any time shit hits the fan, that’s on you to handle.
3. Get an accountant. Thanks Matt!
4. Go for it. Nothing in work will ever be as rewarding.
13. And finally, what does 2017 hold for you and your business?
2017 will be so exciting – I’m getting married! Also, I’m finally going to do a pull-up, and I’m going to finish listening to all of the This American Life podcast. All have been a long time coming.
On the work front, I’ve got a couple big projects launching in the fall – a fabric line and a book! I’m also going to be making the leap into large-scale fine art illustrations. I can hardly wait.
Find Maggie on the web
Maggie’s headshots by Scott Thompson