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Becoming an Illustrator: Dropping Out, Getting Fired, and Starting my Own Business; The By Dylan M Timeline

January 27, 2024

If you’ve ever felt poorly built for your dreams, allow me to tell my story.

My Technical Training + Dropping Out of School (2011)

In 2010 I was entering my second year at Eastern Michigan University. In the throes of an eating disorder, I was forcing myself to change my major to Dietetics in hopes that working in the health field would force me to be perfect forever. Instead, I balled my eyes out while signing up for Organic Chemistry and other pre-reqs. My wise and lovely adoptive mom told me her parents had urged her to go to school to get a steady job with the state, which she did, and that she simply couldn’t sit by and watch me nail myself to a profession I was doing for faulty reasons. She helpfully reflected that I loved carrying around our camcorder, loved any and all school projects, and suggested maybe a creative route would be best.

This led me to doing a year long certificate program with a technical school in Michigan that taught me introductory skills for videography, postproduction, motion graphics, graphic design, and web design. We didn’t learn color theory, composition, or story-telling, but I did learn how to operate a camera and function within adobe products – ‘just enough to be dangerous’ was the school motto. For once in my life I was at the top of my class, the one helping others to master Photoshop or get their timeline edits down more quickly, instead of flailing behind in confusion. It was during my time at this non-traditional school that showed me not all paths are right for all people, and that I can trust my instincts and ability to find my own curriculum. So I dropped out of Eastern Michigan University on my conviction that I could cobble together my own learning path, disappointing my entire family along the way πŸ™‚ .

“It was during my time at this non-traditional school that showed me not all paths are right for all people, and that I can trust my instincts and ability to find my own curriculum.”

Working Graphic Designer + Being Someone Else’s Hands (2012-2017)

After finishing my technical certificate I began working as a freelancer right away (I still use the same LLC I formed back then <3). I filmed and edited weddings and promotional shorts for local businesses, I built (shitty) websites for people with too-small budgets, designed app interfaces and advertisements for various companies, and designed wedding stationery and logos for anyone who would hire me. I even moved to New Orleans and back for a stint as a graphic designer for a (fraudulent) solar power company. I was grateful and relieved to have work, yet…

I was just someone else’s hands in whatever creative project I was working on. I wasn’t hired for my expertise or vision – just my ability to execute someone else’s. Not only that, I was struggling with getting my work done. I never wanted to face and implement edits and feedback, I resented clients wanting changes, and generally started to feel like the bad kid trying to keep up. I assumed it was the type of work I was doing, so I decided to try something new.

“I was just someone else’s hands in whatever creative project I was working on. I wasn’t hired for my expertise or vision – just my ability to execute someone else’s. Not only that, I was struggling with getting my work done.”

100 Day Drawing Challenge + Publishing My First Class (2016)

Regardless of my non-existent track record with setting and reaching goals, I decided to set up my own 100-day drawing challenge (thanks to this Skillshare classmy original project is still living there!) where I would draw from reference photos for 20 minutes a day. I still have so much warmth in my heart for this past version of myself because I learned I can surprise myself and do hard things. Not only that but I can follow through with something because I want to, not because others are holding me to it.

All these drawings combined with my skills in Photoshop led me to figuring out how to digitize my sketches. At the same time Skillshare had reached out with an invitation to their teach challenge, an opportunity meant to inspire new teachers to publish classes. I had some video skills, I had some informal teaching experience, and I had this new skill (digitizing my sketches) that felt too exciting and on fire to not share with other people. So I published my first Skillshare class: Digitizing Hand Drawn Sketches with Character. I was hoping to bring in $20 to cover a nice lunch at Taco Bell; to my delight it brought in just shy of $300 that first month. Between actually completing my 100 day challenge and publishing a class that others found helpful, I had finally felt the sweet rush of success on my own terms.

“I still have so much warmth in my heart for this past version of myself because I learned I can surprise myself and do hard things. Not only that but I can follow through with something because I want to, not because others are holding me to it.”

Fired. (2017)

My now husband, Brooks, and I had just moved from Michigan to Arizona for him to pursue producing a Fantasy Football podcast. I was excited but anxious, as my long time graphic design job had laid me off after ensuring I could keep my position remotely after the move. I had landed a new, shiny design job for a company that essentially made pretty Powerpoint presentations for big ole’ companies and their annual meetings and such. The pay was tight, the work sucked, but it was a job and a creative one at that. One day my boss came in and invited me to the center of the public co-working space we were forced to commute to. After roping me into a conversation about baseball he said,”So, today’s going to be your last day. We don’t feel you’re a good culture fit.” My only shred of good from that day was that I didn’t cry in front of anyone and I ate cornbread for dinner.

Here’s the plot twist: I always feared the idea of getting fired. Of feeling your livelihood ripped from underneath you as the expenses to stay alive keep rolling in. And yet I felt…peaceful? I felt open. I recognized I was at a crossroads: one road where I get back on the job hunt, find another “shiny” design job with a title I can brag about when meeting new people, or comfort my family with, and essentially be someone else’s hands, or, I could try something new. In the same way I believed in myself when I didn’t think finishing school was right for me, I felt I could believe in myself to give it a go as an illustrator. Not just share my creative skills with the world, but my creative ideas and vision (and pay my bills with it).

“In the same way I believed in myself when I didn’t think finishing school was right for me, I felt I could believe in myself to give it a go as an illustrator. Not just share my creative skills with the world, but my creative ideas and vision (and pay my bills with it).”

Becoming an Illustrator (2017-present)

With $0 in savings, mounting proof that I’m struggling with ‘normal’ daily things (productivity, routines, money, hygiene, sad list continues, etc), and a nugget of belief in my skills and taste, I took out a just-in-case $16,000 personal loan and got to work on whatever starting spots felt sensible to me:

I published another Skillshare class and was invited to be a Top Teacher; a partnership I still proudly hold today, and one that has helped me continue to pay my bills (and beyond!) and grow my own creativity. Today I have 150k+ students, 21 classes, and more in the works. This teaching and guidance would also lead to me launching my own Patreon group, which today has over 250 fellow artists. We gather multiple times monthly to do art reviews, art dates, and for me to answer your burning questions.

I reached out to my previous design clients and found enough “mindless” design work that I could do for sound pay without losing steam elsewhere. I made sure to remember that this work was strictly transactional for pay and not allowed to eat up more time or brain space than the projects warranted. That was saved for the endeavors I cared about and wanted more of.

I also set my sights on licensing my illustration work to commercial clients. I began sharing my work on Instagram, and also pouring my honest thoughts and heart out into the captions, which thankfully opened the doorway to real friendships with fellow artists, as well as getting noticed by brands. Anthropologie found an illustration I shared on Instagram and licensed it for tea towels. During this time I also set and accomplished a goal to attend Quilt Market and score a licensing deal with a fabric company. Shortly after I was approached by Jennifer Nelson Artists, who eventually became my trusty agent, representing my work and getting it on the desks of art directors for cool projects all over. Today I’ve worked with over 30 brands worldwide including Martha Stewart, Magnolia, Blue Q, Loloi Rugs, Penguin Random House, Red Cap Cards, Papyrus, American Greetings, and Anthropolgie. I’ve gotten to see my work turned into advent calendar boxes, greeting cards, magazine spreads, quilts, apparel, embroidered home goods, and more.

It’s hard to describe this time because on one hand I was absolutely killing it. I was like a character in a movie, moving on up from underdog to success story. I was actually paying my bills with my creativity, I got to set my own schedule, work from home, choose my direction, etc. Yet the lack of parameters only shone a light on my growing distress at being able to handle my day-to-day life. Brooks would leave for work in the morning and I would spend the remaining hours until he returned trying to figure out how to get myself to do any of the things on my list that I needed to do but didn’t want to do. Deadlines were a godsend because I would actually get things done, but only last minute, and usually un-showered. On Instagram I’d see photos of women in their pretty flower dresses sitting in sun-drenched studios, laughing while painting, talking about passive income. I’d turn inward, which helped me make artwork that I could hide behind. Here, look at these flowers, be sucker-punched by these colors, but please don’t look further. I am a crumpled mess.

“On Instagram I’d see photos of women in their pretty flower dresses, sitting in sun-drenched studios, laughing while painting, talking about passive income. I’d turn inward, which helped me make artwork that I could hide behind. Here, look at these flowers, be sucker-punched by these colors, but please don’t look further. I am a crumpled mess.”

Getting Diagnosed with ADHD (2020)

Thank god I overshare. Thank god I made friends on the internet. Thank god those friends gently helped me see that my struggles maybe went beyond normal “creative resistance” and funny memes about adulting struggles. While the world locked-down for a global pandemic, I was learning about my new ADHD diagnosis. About how my issues with planning, showing up, prioritizing similarly-urgent items, and even my rejection sensitivity, were all part of my brain not developing all of its executive functions. And not only that, there were tools for me to use to better my life even with my abundantly-attentive brain.

I joined an adult ADHD support group that helped teach me life skills, and generally dug in deep to learning more about my neurodivergent brain. I shared about my story on this Podcast episode and you guys still write to me with your touching and relatable stories. It affects a lot of us. And even those who don’t have ADHD but consider themselves creative can often relate to the plight of those of us with ADHD, and so it’s strangely been a great bridge for me to connect more deeply with fellow artists and ADHDers. If you’re curious, I highly recommend the book (and list of 90 symptoms) Taking Charge of Adult ADHD by Dr. Russell Barkley.

Finding Human Design (2021)

Leading my first painting retreat at the Smiley Manse

So color me surprised when after two years of ADHD life skills training and CBT STEAR maps and practicing being Dylan 2.0, I’m struggling again to show up for my work. But not just work. Sending birthday cards. Working a “normal” amount of hours. MONDAYS. I had gotten really skilled at hacking my ADHD, yet this deep feeling plagued me of not being able to keep up with the world around me. Of being terribly disappointing. Of burnout. I felt I wasn’t doing anything AND I was burned out. Enter Human Design.

“yet this deep feeling plagued me of not being able to keep up with the world around me. Of being terribly disappointing. Of burnout. I felt I wasn’t doing anything AND I was burned out.”

I started learning about my human design and immediately was relieved to learn that I’m not made like everyone else (no one is! we’re all equal in value, but not equal in build). I learned that my energy ebs and flows (while other people’s energy sort of revs up and sustains them throughout the day), and that I best make decisions quickly and intuitively (some people best make decisions by waiting a day or two). I learned I’m here to value what I see, not what I do. It explained why I couldn’t keep up with other people, and better yet, it relieved me of the duty altogether. I now know how to navigate huge business decisions, I know how to navigate a menu at a restaurant, I only wish people I really like ‘happy birthday.’

Best of all, it’s helped me feel like I know who I am, and she’s not some surprising new version, I’ve always known her, I just didn’t know I’m allowed to be her full time.

“it’s helped me feel like I know who I am, and she’s not some surprising new version, I’ve always known her, I just didn’t know I’m allowed to be her full time.”

If you’d like help learning about your human design and how you best make decisions, I’ve actually sat with over 100 people to help them understand their charts! You can learn more here.

Massive Weeding (2021-2023)

I had to bring human design into the mix for this part to really make sense. Thanks to my bullet journal practice (an ADHD tool I use, I made a class on that too!) showing me the things I schedule and carry around, combined with human design empowering me to navigate my life with my intuition, I started weeding.

If you’re part of my newsletter then you know the year+ drama of me turning down a 31k commission, breaking up with my first client (my fabric client! from quilt market! can you believe?), closing a long-standing art group, breaking up with friends, etc etc. I just started to see that 98% of my business was built in an effort to be impressive and accepted by the external world; to prove myself. So I weeded anything that I was hiding behind. The fire kept burning (in the very best way).

I just started to see that 98% of my business was built in an effort to be impressive and accepted by the external world; to prove myself. So I weeded anything that I was hiding behind. The fire kept burning (in the very best way).”

Sketchbook Artist (2024)

What do all my most successful endeavors have in common? What do all my favorites pieces of art have in common? What do all my favorite people have in common? Sketchbooks.

My most successful endeavors have been in the sharing of not pretty, finished things, but the lessons I’ve learned by making messes and filling pages with those messes (this is part of my human design too!! my 3/5 profile asks me to face failures and get my hands messy in exchange for practical wisdom). My favorite art pieces aren’t on products, they’re tucked into sketchbook pages as intimate as a diary. My favorite people have sketchooks, or love art supplies, or let their creativity eek out in some way or another.

When I started all those years ago, I desired to be a successful illustrator. I wanted to prove I could. Prove to all the people who were wrong about me that they were sorely wrong about me. And I got there.

And when I stopped focusing on all those invisible people I was proving myself to, I got to have some fun and fill my sketchbooks with my life. Get to. Will continue to.

And when I stopped focusing on all those invisible people I was proving myself to, I got to have some fun and fill my sketchbooks with my life. Get to. Will continue to.

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  1. Megan Wenger says:

    Oh goodness! This is such a great post. Thank you for sharing all the details. Thank you for bringing me along on your journey.

    • Showit User says:

      Hi Megan, thank you for taking the time to comment! When I wrote and published it I honestly didn’t think anyone would read the whole thing (but that’s okay, I really wrote it for my own reflection) – so all that to say, you reading it means a lot. Thank you <3

  2. Megan Russo says:

    You are so amazing and bright my Dyl. I think this post is basically what everyone desires: to keep growing and discovering who we really are, not what people think we are or should be. That takes courage and grit my dear, both of which you have had exuding from you your whole life. Love always<3

  3. Lizzy House says:

    Oh Dylan, when is your birthday?

    You and I have seemed to traverse similar paths. We should talk about it some time. Maybe it’s actually a well worn path by the type of person who pursues a creative life out of absolute necessity. I’m really grateful you’ve gotten to a place where you see yourself more clearly and on solid ground. Proud of you.

    • Showit User says:

      Hi Lizzy! Always love to hear from you and see your name pop up πŸ™‚ My birthday just passed on January 2nd. When’s yours?

  4. Martina says:

    Thank you, Dylan! what an inspiring story. So much of it resonates with me, particularly the part about proving others you could make the right decisions about your own path, and your weeding phase – very necessary step but oh so scary! when so much of the old you-identity is tied to things and people that have no reason to stay, weeding is a matter of survival, but at the same time a shedding of something that once was part of you, and so there’s a bit of grieving that goes with it, no?

    • Showit User says:

      Hi Martina! Oh yes! Absolutely a grieving phase. This shedding process has been two years now, and for the first year I really feared I was actually just shutting down and ruining my life, and yet – the ground beneath my feet, my intuition, it felt more correct than the fear. So I let it feel weird and sad AND right. And now I’m in a place where I just feel so light and happy. And I hate to use that word ‘happy’!! Haha. Because there are so many other feelings to be felt, yet I can’t deny that I do feel happy lately. Even when I’m sad.