(My) Creative Professional's Survival Guide

Simple, straightforward advice based on decades of real world experience.

Bookmark this post. Don’t bookmark it because it’s an all-in-one, flawless and concise concentration of brilliance that will solve all your creative problems and answer all your questions. That doesn’t exist. (If it *does* exist, please do share it with the rest of us in the comments.)

Bookmark this post because it’s a personal account, filled with real world experiences and lessons. Some of the generic or popular advice for creatives is pretty good, sure. But personal stories that back up this advice can clearly illustrate and solidify ideas or sayings that are otherwise vague.

Mainly, you should bookmark this post because I believe my story is relatable. And I hope this gives you real confidence that you can find your way with your own creative work. If I can do it, so can you.

I did not go to art school (I went to a state school in North Carolina with a small art department).

I did not live in a hub for creative professionals, like New York (I stayed in North Carolina after graduating college).

I had almost zero friends who were artists, designers, or illustrators (most of my friends were business majors, and those who did major in art did not get illustration-related jobs after school).

I knew nothing about who to contact to begin the journey of realizing my dream of drawing for money (or if such a job could even exist).

My first job out of college was cobbling together tiny websites for regional textile businesses.

My second job was creating 2-inch square classified ads for funeral parlors, family law firms, and pest control businesses for the local newspaper.

But I went on, eventually, to create illustrations for The New Yorker, The New York Times, Nike, Apple, The Wall Street Journal, and The Washington Post. My picture book was bought and distributed by the world’s largest publisher of children’s books, Scholastic. My first iPhone game, White Lines, was a Top-50 bestseller for two weeks. And I created what became known as the industry standard digital brushes for artists around the world (KyleBrush), acquired by Adobe in 2017.

How?

Hindsight really is 20/20 and I can now clearly see what I did to get here. It may have FELT like an accident (see the title of this newsletter), but it wasn’t.

Without further ado, here are some big lessons I learned:

1. Never accept the status quo.

   In college, I needed money. I worked evenings in a tiny office calling alumni and asking them to please consider donating to the school. It was awful. But it paid more than other on-campus jobs; I had no car.

   What to do?

   I noticed there were flyers around campus for tons of events (sports, clubs, concerts, etc.).

   They were ugly.

   I tracked down the central office that accepted all of the event information that was submitted by various organizations on campus. In this office, an overworked employee with no art skills had been producing the flyers in between other job responsibilities. I had created my own versions of existing flyers with custom illustrations and hand-drawn lettering for titles. After showing them these, they created a job position for me producing higher quality flyers, working just four hours a week (I made my own schedule!) and earning the same pay I had been making calling annoying strangers during dinner. Goodbye crowded phone bank, and Hello, tiny gateway into the world of graphic design.

   LESSON

   Study your own community closely and find small opportunities for your creative skills to shine. One small observation can lead you on a path towards something more fulfilling and suited to your talents.

   If you find your way in, SHOW people what you can do right off the bat; telling them won’t be enough.

2. Fake it without lying (too much).

   I was laid off from my third job after college with no portfolio of work. I had been designing websites but wanted to do illustration and design work for print. Beautiful packaging, posters, books, and ads were everywhere around me and I wanted in.

   So, I spent about two months creating a mock portfolio of work for known brands. I never said the work was real. I also never said it wasn’t. I emailed samples all over town to local design and ad agencies and quickly got meetings with art directors and creative directors. Within a few minutes of meeting them, I casually mentioned that the samples of work were invented. I didn’t apologize for it, I simply stated it as an aside. Not one of them cared. They simply liked the work and wanted to pay me to create more just like it.

   LESSON

   If you’re not being paid to make the work you really want to make, make it anyway. Let people see what you CAN do—what you WANT to do. Yes, this might mean working after hours, staying up late, working on a few weekends, but it’s worth it.

   It’s perfectly fine to create work for dream clients, even if they aren’t asking for it. And if your creative ideas are way better than what’s already out there, this just shows others how clever you are. Also, great work for popular brands is just easier to show and to be appreciated; the audience knows the brand and understands its messaging, which takes you halfway to the finish line.

   Finally: nobody can hire you to do the work that excites you if this particular kind of work is absent from your portfolio.

3. Don’t believe the “you only have one chance to get it right” warnings.

   I submitted work to The New Yorker numerous times before I even got an email back from an art director. And that email reply simply told me my work wasn’t right. Instead of giving up, I wrote a short reply asking what I could do differently to at least be in the running for a spot. Fortunately, the art director threw me a bone and told me to create work with less busy linework, bound in a rectangular frame (rather than ‘floating’ on the page), and with “more sophisticated” color choices. I waited a couple of months, so as to not be annoying, and then sent work that followed his instructions, to the letter. Success. Shortly after this, I began a run with The New Yorker, drawing at least one illustration per month for the next three years.

   Getting a picture book published took many attempts over the course of five years.

   And selling my brush business to Adobe? That didn’t happen with my first pitch. I was almost laughed at. Three years later, they announced an acquisition on the Adobe MAX stage in front of the world. Good thing I didn’t stop trying.

   LESSON

   This isn’t the Olympic Trials. Windows of opportunity are plentiful and will often open multiple times. Rejection is part of the game and you can keep knocking on doors if you don’t get in the first time.

   Learn what’s required to gain entry, do the work, be objective in your judgment of your own efforts, and try again when you’re ready.

4. Don’t be afraid to act like a pinball.

   I had been drawing for magazines, books and ads for about six years and business was still growing. iPhone games had just started capturing people’s attention and I was curious about this new market. I spent a few weeks designing a simple memory game that took advantage of the touch screen’s ability to read swiping gestures accurately. Through Twitter, I connected with a wonderful developer and paid him to code the game, using my graphics. The game (White Lines) was a top-50 bestseller for a few weeks and earned me over $20,000 in extra income in just a few months.

   Did I go full-time into iPhone game dev? Of course not.

   It’s not like I wanted to give up illustration, especially when it was going fine. I simply added iPhone games to my list of fun creative things to do for money. My second game, Hot Plates!, was more sophisticated and also well received, cracking the top 50 in the Puzzles category. It didn’t make nearly as much money, though. I quickly realized it was time-consuming and risky, making these games without any guarantee of decent sales, so I made a little directional shift and offered app design to my existing clients as a new service. This way, I knew I would be getting paid for this kind of work, whether or not the apps were successful. I went on to design five more apps over the next couple of years, then made the decision to stop taking on app design projects because my new brush business was growing (and was more lucrative).

   Throughout my career, I have bounced around like a pinball, allowing myself to go shooting off in different directions to see what’s possible. Some directions led nowhere, but this hasn’t been detrimental to my business— far from it. It has only given me opportunities to offer more creative services to more clients, in the end.

   LESSON

   You don’t have to stay in your lane. If things are going fine in your picture book illustration gig, but you just so happen to create a pattern design that gets printed on pillows sold at Pottery Barn … you should seriously consider designing more patterns. It’s not like you’ll suddenly forget how to illustrate picture books; you will simply open up a new revenue stream, and simultaneously create some insurance for your business.

   Things can change suddenly in the creative industry (look at Animation jobs right now). If possible, having two or three revenue streams is highly recommended, as long as you enjoy that work.

5. Be there, physically.

   • I went to an illustration party and wound up with a two-week teaching gig in Berlin (thanks, Rafa!!)
   • At a neighborhood art-swap party, I met an art professor and wound up teaching a life drawing class at his university. This ballooned into my teaching 5 more classes per year and adding a nice chunk of change to my income for over a decade.

   • Playing my sax in a local blues/rock cover band got me an interview that landed me a full-time job.

   • Befriending the owner of a local arthouse theater led to a series of poster illustrations, which then led to my meeting Owen Wilson, who asked for a print of my Midnight in Paris poster when he was filming something else in my town.

   • After months of submitting work via email to The Wall Street Journal, I decided to visit their art department in person. After meeting some art directors over lunch at their office, I walked away with several jobs and continued to work with them regularly for many years. The same thing happened at TIME Magazine.

   LESSON

   Nothing can replace human-to-human interaction. You have to get out periodically and meet people in your industry and have real conversations, in person, if you want to give yourself the best chance to grow in your career. Work on your conversation skills. Learn to meet people, face-to-face and make them remember you.

   We are, all of us, still animals; we cannot be healthy and whole in a digital world, alone.

6. Turn off your phone.

   No cap, as people my age never say: I am more creative, more productive, and just plain unburdened during ANY week when my Screentime report is low.

   LESSON

   You have heard this a million times because it’s true: if you spend more than an hour a day scrolling on Instagram, feeling insecure or unaccomplished because the people you follow seem to always be killing it, then you are doing NOTHING good for your mental health or your productivity. Make your work, share it if it’s good, then make more work. It’s fine to dip in a couple of times a day to see what’s new, but if the social media experience leaves you feeling more inferior than inspired, take a break for a week. We all know our phones are addictive. Turning them off is hard, but worth it, if we want to build something, do real work, and feel better all around.

Want more of these? Shall I keep going? I have more. Is this too long? Please comment below and let me know if this has been helpful. And bookmark it, so you. can come back to it anytime. Also, if you like what I’m doing here, please share!

Extras for You

• The Etherington Bros. are releasing their latest AMAZING drawing book, along with all of their previous books for a limited time only. I recommend them very, very highly. (If you’re on a tight budget, they also generously put all of the content of these books in their blog for free!!)

• I always have free and inexpensive plug-ins, actions, and other goodies on my Gumroad page.

• Oh, speaking of Gumroad — I created their Gumroad Day official art!

• My Adobe Fresco digital art course on Domestika is on sale again for the criminally low price of $5.99. That’s 4+ hours of in-depth instruction and demos for the price of a large fancy coffee. It has a 99% positive rating with the one lone negative review being from a person who liked the course but misunderstood that it wasn’t a full-blown animation course. I’m not mad. I mean, it’s important to read course descriptions. But, I promise, I’m really not that mad. I’m a little mad. Anyway, venting over. Check out the course!

Until next time, take care of yourselves, take care of each other, and I’ll say, Ciao for now.
– Kyle (find me here!)