What I Learned from My Biggest Rejections in Ten Years of Job Applications
Hint: They were an integral part of my career.

I wouldn’t believe that this year is almost over already, but every morning my front yard is crispy with frost and I’ve added A Charlie Brown Christmas to my listening rotation, so there you have it.
The next year in the queue is a big milestone for me. It marks 20 years since I graduated high school and left my hometown in Maryland for parts unknown.
When I finished school, I knew I wanted to draw and write stories for a living. I just had no idea how I was going to get there and an even fuzzier sense of how I was going to make a living.
Two decades later, despite my magical thinking, I’m astounded that I’m doing exactly what I always wanted to do. (Actually, in the last twenty years, I’ve done nothing but draw and write with occasional part-time work.)
My post-graduation career path basically consisted of the following cycle:
1. Hey, this art project looks like fun! 2. Dang it, I’m running out of money 3. Time to plan. Hey, this job looks financially stable! 4. Dang it, I didn’t get the job and my plan failed 5. Hey, this art project looks like fun! (Back to step 1)
These rejected job applications have been a big part of my art career.
Scattered along my path like the tombstones of dearly departed Oregon Trail party members, each passed job opportunity was a big disappointment.
Looking back, though, I’m glad I didn’t get what I wanted.
Here’s a list of my favorite job application rejections. Like manure on a field, each failure led to something good. (Bit of a crappy metaphor, but you get the point.)
2009 — Junior designer at a bunch of graphic design firms in the Washington, DC area
If I had followed the standard 4-year undergraduate plan, I would have finished with a degree in 2006. Instead, I deferred enrollment to study for a year in Germany, spent 2 years on a major at one college, and transferred to another college with a new major.
My future wife and I both graduated with BFA degrees in the dumpster fire of the 2009 economy.
Our supposed shoo-in entry-level graphic design jobs completely vanished. My cute little applications and portfolio rarely even got a “we’ll keep your information on file”.
I struggled to get a few hours part-time at the local bookstore. And in the meantime, Ashley and I got married and started freelancing together as newlyweds.
We’ve been collaborating ever since. It was the greatest career pivot we ever could have made.
2011 — Contract illustrator for several literary agencies
Our self-designed wedding invitation designs led to our first design clients. A year later, our hand-drawn design style led to illustration clients.
Within two years, we realized we wanted to be full-time illustrators. We had our sights set on hip contract jobs with companies like Target, Disney, Starbucks, and drawing for children’s books. Those jobs usually materialize through art directors contacting illustration agencies, so we started sending out inquiries.
The problem was that we had nowhere near the work experience and portfolio to get noticed.
After several unanswered applications, we realized we didn’t have a way forward besides working with what we had, mostly logos and illustrations for small businesses and selling prints of art pieces on Etsy.
We made just enough to get by. More importantly, we began to build the solid foundation of thousands of practice hours that we still stand on today.
2012 — Café worker at Pixar
This one makes me laugh.
Ashley and I are both complete Disney and Pixar nuts. Inevitably, hours of watching behind-the-scenes DVD bonus features led to checking job listings.
When this one popped up, it was completely obvious that the 6 months of part-time work in the deli section of a health food store and 4 months making cookies in a pastry kitchen was going to totally impress the hiring staff at a prestigious animation company on the opposite end of the country. Duh!
Yeah… this was a long shot.
2013 — Middle grade novel pitch to a literary agency
This one doesn’t seem so silly at first. Just wait.
I had found a really good literary agency through an illustrator friend and carefully selected the agent to whom I’d pitch my first middle grade novel. The problem is that I had only written the first chapter of the first drafr.
I didn’t do my homework on the publishing industry, so the natural next step was to send the cart about a day’s journey ahead of the horse. I didn’t realize that not only would they want to see a polished full manuscript from a debut author, but I was also unlikely to make any kind of advance anytime soon.
I’m thankful that she sent back a note with feedback to work on it some more. I finished the book, let it sit for a few months, reread it, and decided that I absolutely hated the story.
2014 — Production Assistant at Pixar
This Pixar application was even more of a long shot than the one in 2012. It grew like a weed out of the dry ground of a bank account drought after Ashley and I quit our wedding photography weekend side hustle.
I worked really hard on the application and even name-dropped a buddy who worked there as an assistant editor.
The only problem? I was applying for a film industry job at an animation company and had absolutely zero experience in film and animation. Needless to say, I did not move to San Francisco for work that year.
2019 — Graphic designer at Disney’s Yellow Shoes
This is the crown jewel of my last round of rejected job applications.
Ashley and I had decided to quit our small business of printing and selling our own stationery and art prints in favor of pursuing full-time illustration. The sales half of our income disappeared, our bank account dried up, and we got desperate again.
The job opening at Disney World’s in-house graphic design firm in Orlando popped up and it seemed like a dream come true: move down to Florida, become a Disney employee, gain a regular paycheck, spend half of it in the parks every month.
I worked really, really hard for this one. Harder than I’d ever worked to win a job. I connected on LinkedIn to everyone from Yellow Shoes that I could find, I sent self-designed postcards to the higher-ups in California, and I specifically reached out to a senior art director I knew personally.
I didn’t get the Disney job. I was kinda crushed.
After this, I got rejected on several more graphic designer applications. One of the more surprising rejections was a design position specializing in hand lettering at American Greetings, which was puzzling because for several years prior I had done freelance hand lettering work for American Greetings.
Then it hit me: I had spent so long as an illustrator that I was too far removed from my college major.
My design portfolio and skills were outdated. I was only qualified for illustration, so I faced the choice to bail out once and for all or to quit quitting and go all-in.
The one that stuck: 2020 — Contract illustrator at Astound Agency
Early in 2020, right as the COVID pandemic was starting to make its way to the South, I sent out my standard round of inquiries to potential illustration clients. I snuck in some casual applications to a couple of illustration agencies.
I didn’t expect much. When you send out cold illustration inquiry emails, it’s pretty standard to not hear anything back from most of them.
Except for this time. One high-level illustration agency wrote back and expressed interest. We sent more work examples. They offered a contract. Within a month we had a couple of new book illustration deals.
A year and over ten book jobs later, we’re only getting started with our amazing agents.
We still sweat over money every month because the compensation per job isn’t spectacular. But we have a long list of book credits and an excellent agent who’s receptive to our author-illustrator book pitches, so the future is bright.
Most importantly, we get to raise our little girls together while we work from home. And I no longer see bailing out and trying to get a “steady job” as a preferable option.
Bonus: here are three really important lessons I’ve learned from these favorite failures.
1. Get humble, bro
When I graduated from high school, I was the quintessential entitled millennial.
The Recession grabbed me by the shoulders and shook that out of me.
I emerged with big dreams intact, but also with expectations proportional to the amount of work I put in, and tempered by the reality of innate skill level and being in the right place at the right time.
2. Independence is worth it.
I learned that I value long-term creative freedom more than short-term comfort.
That means that instead of ceding control to an employer, I retain all of it. The trade off is that I don’t have an employer to absorb the stress of risk.
But I’ve learned that I’d rather live with the discomfort than give up my ability to make all the creative decisions I need to make.
3. Trust the process
Ever heard that (surprisingly positive) Kierkegaard quote about how life is meant to be understood backward but lived forward? My career has borne out that truth.
I don’t think anyone can ever truly plan for the future, but the freelance artist path particularly carries a disproportionate amount of uncertainty.
It takes a lot of faith in the process to start and maintain a career in the arts.
If you don’t trust the process, you’re less likely to take creative risks and make critical discoveries that lay beyond the rulebook horizon. As Ray Bradbury said, sometimes you have to jump off the cliff and make your wings on the way down.
I can’t say this job gets any easier with time. But if you stick with it, you’ll find that your wisdom and strength grows alongside the challenges.
Sometimes falling flat on your face is all you need for a fresh perspective.
I wouldn’t do the last twenty years any differently if I could.
