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Ladies, Wine & Design Nashville

A monthly salon style conversation series for creative women hosted by Lindsey Laseter.

Emily Mills

Emily Mills

Interview by Jess Nelson, Intro by Lindsey Laseter
Photography by Brooke Dainty

While she dreamt of becoming an artist and cartoonist early on, it wasn't until starting a career as a designer that Emily Mills learned she could pursue illustration and live the life she actually wanted all along. Here she shares her experience making the jump to full-time freelance, what she learned from challenging work environments, how she balances her unique career and advice she'd give her former self. 

How did you get into illustration and how long have you been doing it?
I grew up drawing pictures and reading cartoon books. I liked Bill Watterson (Calvin and Hobbes) and Gary Larson (The Far Side) the most and I wanted to be like them, so when I got to high school my dream career was to be a cartoonist. I was the editor for the high school yearbook and created a comic strip for the newspaper for a few years, which felt like good experience to help me move closer to the dream job. But, by the time I had to pick a college I was told cartooning wasn’t a realistic path for earning a living. No one told me I could do illustration, so I didn't pursue it. I wanted to be wise and earn a degree I could use, so I pursued Graphic Design instead, and did the cartoon for the college newspaper on the side for 3 years.

I worked as a graphic designer through college and then after I graduated (2010) for about 6 years. I eventually got tired of design and knew that my heart wasn't in it for the long haul. I felt like it was a fun career, but I also didn’t want  to become the best designer in the world. I was perfectly ok being an “ok” designer, but I didn’t know what else to do and figured I was stuck in the design career path forever. Illustration never went away, though. I made cartoons on my office door whiteboard, which led to a former coworker remembering those and asking me to help him on a whiteboard video for his film studio, which jump-started my career with the company I work for now called The Sketch Effect. Today I’m a full-time freelance illustrator (and sometimes designer) and do it all — live event illustration (graphic recording), sketchnotes, technical illustration, book illustration, and even teaching classes and workshops. I also have a book on visual notes coming out later this year that I’m really excited about!

Is it frustrating to hear people say you can’t be doing things like drawing for a living?
It was frustrating to hear in high school because I felt like my generation was raised being told “You can do anything!”, but then when it came time for us to do it, the same people were telling us “That’s not wise,” and “You should be more stable,” and “That’s not a good long-term plan,” etc. It still frustrates me to hear people rain on others’ dreams because it is possible to do things society says you can’t. Culture and technology are constantly changing the world we live in, and so much is possible that wasn’t before when our parents were making career decisions.

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Do you think that if you had come out of school and immediately started doing illustration, that you would have been as successful?
Yes and no. If I had gone to school for illustration, I think I would be a lot farther ahead skills-wise because I missed out on good drawing instruction in college. The drawing classes I did have to take for the graphic design program were so basic that it felt like repeating high school art classes, and there were a ton of non-art department people in those classes doing “fun” credits for their other majors. I never got the instructor attention that I wanted because they were too busy helping the students who were there for fun and sucked at art! Instructor attention came with upper-level drawing classes, which I never took. I kind of wish I had gone to college for illustration now, but hindsight is 20/20. Now I think it’s pointless to go back to school for that kind of thing because of the internet. I can buy online courses taught by the best illustrators in the world and I can learn at my own pace. Sure, I won’t have a fancy degree attached to it, but I think the art and design fields care more about the skills and execution than they do the piece of paper on the wall.

So where'd you go to college?
The University of Northern Colorado.

So you grew up in Colorado, how long have you been in Nashville?
I’ve been in Nashville over 3 years — I moved in January of 2015. Before that I was in a small town in Texas for 5 years (I moved there for work during the recession). After 5 years in Texas, I thought, “I'm tired of living somewhere that's really hot, has no career growth, and where there's no creative community. Where can I go?” I came up with a list of 5 things I wanted in the next place I’d live:

1) An airport
2) Outdoor adventure opportunities (kayaking, hiking, camping, etc.)
3) Healthy food options
4) Creative community
5) Job and career growth opportunities

Nashville just kept popping up in my head and checked all the boxes on my list, so I focused my job search here.

Did you move here with a job already in place?
I moved here with a job already in place because I'm not naturally a risk taker — I was only willing to move with a job in place. I think applied for about 8 design positions in Nashville. I flew in for a second interview at one place and thought I had the job in the bag, but they didn’t call me back for 3 months! I didn’t want to wait around for them to decide, so I found something after a few weeks of waiting around. I flew back to town for another interview, got the job, and moved to Tennessee 3 weeks later. My job here was at a startup doing design and creative direction. It sounds sexy, but it was awful. I learned a lot from that experience though, and I’m grateful for that.

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Can you tell us a bit about how working there led to going freelance?
When I was in my early 20’s I thought anyone who was a freelancer was foolish because I'd never seen anyone do it right. My association with “freelance” was “failure”. Everyone I had seen go freelance usually did it because they were fired or laid off and couldn’t find something else, or rage-quit but weren’t ready for the leap. They’d all done it for a year or so and then flopped because they didn’t learn the business side, didn’t have a community, or didn’t get help… AND they all suffered alone! I’d see social media posts that sounded a lot like this, in this order:

  1. “I’m pleased to announce that I’ve left my job to pursue freelance!”
    (Translation: I have no idea what I’m doing, but it least it’s not with my old job!)

  2. “Now taking on commissions!”
    (translation: I have nothing to work on. Please hire me. My kids need shoes.)

  3. “I’m pleased to announce I’ve taken on a new role with this company!”
    (translation: Thank God I’m not freelancing anymore! Hooray, money!)


I thought freelancers were just lazy, stupid people, and I was very closed-minded. I just didn't know that you can do freelance successfully! By the time I hit my mid-20’s and I had some work experience under my belt, I considered that I’d actually be good at being a freelancer but wasn’t confident that I could actually go freelance. I made it a stretch goal… something for ten years down the road. Maybe. I started a savings account so I could be ready whenever I quit my job, I planned on the kind of work I wanted to do, and the kinds of clients I wanted to hire me. I thought about how I’d do business — I got an LLC, hired a CPA, and started charging more on my side work. In my mind, if I took the right steps to prepare to quit, it would be easy when I did. It would be seamless and perfect and no-risk (LOL).

So I moved to Nashville with a job so that I could continue building up savings, and building up my network locally, and slowly move towards freelance. I was burning the candle at both ends — I was working the full-time day job about 30 hours a week, and on top of that was doing freelance. I was a workaholic. I had no friends in my new city and it was awful. I was using vacation from my job to do work for The Sketch Effect. Eventually it just came to a head where my job had recently hired a new creative director to be our boss. I had asked to go to a design conference months before, and it was granted. I didn’t even ask them to pay for it! I just needed a few days for the professional development. Thirty hours before I was to leave town for the conference, the new creative director was like, “LOL JK you can't go.”  I think it was a power play for them to get me to quit so they could hire a new team. That was the moment where I was like, “Okay, this bureaucracy isn't for me anymore. I'm ready to go freelance.

Did you rage quit?
I did. My boss had called me after work telling me I couldn’t go to the conference anymore. I told him, “I'm going, so either I have a job when I come back or I don't — it's up to you. Tell me in the morning when I show up to work.“ I showed up to work and everyone was tiptoeing around me and I felt like, “They're totally gonna fire me or ask for my resignation.” They finally called me into a meeting at the end of the day and said “We will accept your resignation.” And I was like, “Oh, I'm not resigning. You have to fire me because I want severance.” So they fired me and I got severance pay.

I was a little scared because I am a rule-following goody-two-shoes who never takes risks! Do I really want being fired on my work record? But then I realized WHO CARES with the semantics of “leaving” and “firing” and “quitting.” WHO CARES because it won’t matter, because my next boss is me, and I don’t care if I was fired, because I asked to be fired. It is unfortunate that I had a lot of bitterness with that company, and that the bridge was burned long before I left. It's just a model with startups that I've seen — they hire a bunch of really good people, then they fire them or get them to quit because the culture changes and you are going a new direction and you don't want to bring them with you. I think that was my situation, where they brought someone in to take us to the next level, and I was not up to their standards, which was totally fine because I didn't really want to be at that company anymore anyway.

If you had to boil it down, what did you get out of that experience? What advice would you give to someone who's just starting their career, maybe in the startup industry?

A few things:

  1. Stand up for yourself because no one else will.
    I'm so anti-confrontational and scared to take risks, but that job forced me to do it because no one else was going do it for me. There was no good HR system set up. Startup culture made things harder.

  2. Fight for your rights at work, get things in writing, and keep your integrity.
    I could go on and on about the problems I had with my job surrounding this topic, but I’ll sum it up with this: Know what your rights are and fight to keep them. Know what is legal and what is not, and don’t do anything illegal even if your company asks you to. Finally, If the company doesn’t keep the word they give to you or anyone else, you probably don’t want to work for them anymore.

  3. It’s not the end of the world if you get fired, or quit, or if you have to start over, or if you try and go freelance and you fail, or you have to get another job.
    I wish I had left sooner! I wish I would've taken the risk of going freelance because I would've figured it out. I could've found another job if I wasn't ready. It’s not the end of the world if you get fired, or quit, or if you have to start over, or if you try and go freelance and you fail, or you have to get another job.

Do you think that if you ever decide to not be freelance anymore, you would go into a job with a different approach?
Oh yeah!  I've seen and experienced a lot of bad stuff in the workplace, which is probably what propelled me towards freelance. I thought, “I can do this work better than everybody else has been doing it.” I think if I were to go back into the corporate workforce, I would be asking a lot of hard questions and fighting for myself and others more than I ever have in the past. I’m not scared of being fired anymore, and that has given me so much freedom to do good work and do the right thing.

What’s the most exciting freelance project you've done?
The most exciting project I've done were book illustrations for a parenting book — every spread had an illustration on one side and text on the other. I got to illustrate parenting tips in a way that would be easily understood with visual metaphors. Some of the illustrations were really easy —  for example, one of them is “If you have 118 weeks left with your kid before they leave for college, use one marble to represent one week, put them in a jar and then at the end of every week, take a marble out of the jar. That way you can visualize how much time you have left with your kid.” That's easy to draw because the visual was already there. But others were more challenging, and I love the challenge of finding just the right image to convey information.

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Are there any side passions that you've worked into your work? Did you have a passion for parenting tips before that book?

No — I’m not a parent so it wasn’t a passion beforehand, but I do care about doing work that has a lasting or great impact. I liked the book illustration project because good parenting has eternal consequences. You can affect someone's whole legacy by how they're parented. So, the meaning and depth of that project was really cool.

As for personal interests or side passions, most don’t get integrated into my work because I’m a little scared of it feeling too much like work. For instance, I love hiking, and sometimes I’ll sketchnote out a hike I go on, but then it feels like work. I like going on hikes and not illustrating it, and just enjoying that it happened without capturing it visually.

Sometimes overlapping passions can be helpful, though. I’ve been learning how to longboard with my husband, and so I've been wanting to make a sketchnote about longboarding so I can learn about the techniques and parts better. I figure if I illustrate it, maybe somebody else would find it interesting too! And, it would also be really cool to get hired to do that kind of work by a longboard company if they found my work. There’s definitely pros and cons to mixing work with pleasure, and it’s something I decide on a case-by-base basis — there’s no formula.

Do your notebooks from high school look like what you create now?
Yes and no. There were probably drawings in a lot of my notebooks, but they're not super doodle-y because I was also a rule follower. I thought, “There's a time for notes and there's a time for art!”, but I'm sure there was some overlap when I got bored.

What’s your approach for the sketchnotes, do you have set rules you follow for those?
I do follow a few different formats for sketchnotes — the goal is that they’re always easy to read and understand. I'm not super free-form or loose with sketchnotes because my goal is always information over illustration.

I feel like every creative feels like they could be better. I don’t know any creatives that are like, "Yeah, I'm at the top of my game". Do you feel like you could be better?
Yeah, I keep going back to, “If only I had more time.” Of course, you have to make time for stuff like experimenting and doing your own passion projects. I've been freelancing for two years and I'm still trying to figure out my workflow, my money flow, and managing my life. I'm more focused on that right now than I am on expressing myself as an artist.

Do you see what you do as more beautiful art or like functional art? Do you ever have that internal debate?
I definitely see it as functional art, again, mostly because the goal is for the information to be easy to read and understand. I do struggle with calling myself and “artist” though because

1) I feel like artists focus on form over function.
2) My work is really simple and fast-created in real-time. It's more about understanding than it is about beauty. I feel like an amateur sometimes because I don’t spend time on my drawings… because I can’t! The work I do dictates that I am fast, and fast means simple.

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Do you travel a lot?
Yes! Last year I was in 20 states. I love being able to work here in Nashville, but because a lot of our work with The Sketch Effect is events-based, we go where the events go, and events often rotate locations.

Would you still want to do newspaper cartoons?
That'd be awesome! I just haven't focused on it because I have other opportunities that I’m excited about like finishing my book and client work. I’d love to do cartoons regularly again but haven’t worked it into my daily workflow yet.

Do you have any other specific long term goals?
I used to have all these goals but going freelance was such a big goal for me that I forgot to plan for goals after that happened! I was like, “Oh! I did it. Now what do I do?” Now I don’t plan ahead as much as I used to, but take things as they come. I feel like my life has gone in a direction that I never could have predicted so I hate planning too much, too specifically. I love planning. I love goals. I love following rules. But, the older I get and the more I work on my own, the more I appreciate going with the flow and redirecting when you need to.

How do you keep balanced?
I don’t! I tend to just overdo it on either end of the spectrum, then pull back and adjust when it becomes too much. That first year where I was overlapping with the day job and freelancing and working 70 hours a week? That wasn’t healthy, but that stage also helped me learn a lot (especially what NOT to do!). Being freelance has allowed me to balance my life more quickly, though. If I’m feeling overwhelmed, I stop working and take a break, or go run errands, or go for a hike. You can’t exactly do that with a day job. My workdays are usually more concentrated, too. I will put in 4-6 hours of intense, distraction-free work per day. It doesn’t sound like a lot, but I’m finding it’s about quality over quantity. I feel amazing doing 4-hour workdays, and I’m not losing money. Being in a relationship has also brought balance. My husband helps me take breaks, and I don’t do work in the evenings when we have time to spend together. I want relationship time to be as focused and distraction-free as work time is.

What about personal life?
I feel like I’m constantly adjusting and learning here. I’ve had a harder time finding friends in Nashville than any other place I’ve lived. I’m not sure if it’s the culture here, or the transiency, or the life stage, or me! I love connecting with others, but I’m constantly learning how to be better at being more plugged into the community and sharing myself with others. Being introverted, it’s really easy to withdraw and not let others in... until I find myself feeling lonely, and at my own fault! Haha.

If you could go back and talk to your eighteen year-old self, what would you say?
That's hard! Take more risks and be open-minded. I was just so sheltered and closed-minded about so many things and didn't know any better. I met someone in college who was going to grad school in another state and that blew my mind! I thought grad school was only for college professors, and I thought going to school out of state was only for rich people. I had just never encountered people so different from me, and that was the thing that opened up my mind to possibilities. I wish someone had been in my life when I was in high school, when I was choosing what to do with college and majors, that had told me, “You can make it as an illustrator, you should do what you care about. Don't listen to everybody else because they’re lame and they're just unhappy about their job and they wish they had done the same.”

What's your favorite kind of wine?
I don't really drink wine... I’m a lightweight, a cheapskate, and just not that into it. Sparkling cider though…

Find Emily on her portfolio and twitter.

Jess Nelson

Jess Nelson

Jenny Luckett

Jenny Luckett