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How to Cope with Imposter Syndrome As a Freelancer

In this short blog post, I hope to share a story that will illustrate (pun intended) what happens when you are plagued with self-doubt as a freelancer, and decide to go for it anyway. I hope this mini story will give hope to other folks who are contemplating the next move in their career, or maybe a career change all together!

On this Day in 2019

My iPhone reminded me that on this day in 2019 I attended my first book signing as an illustrator, for JOEY & IGGY’S GREAT ADVENTURE by Mary Thero, Maria Cameron & Cassie DiOrio at Barnes & Noble.

I remember how the opportunity to illustrate a picture book fell into my hands because of my super-thoughtful, hometown friend Denise, who had always been a supporter of my creative endeavors and recommended me to the family-author trio. THANK YOU DENISE!

I was also reminded of the imposter syndrome that I had to face-down, in order to open myself up to such a wonderful, life-changing opportunity...


What is imposter syndrome?

Here is a great article by Psychology Today that explains it. Basically I told myself I got this opportunity by pure luck and outside factors, and that I didn't deserve to be doing it-- nor was I equipped for the job. ...Yes, luck is important, but what do they say about luck?

“Luck Is What Happens When Preparation Meets Opportunity."

Photo by Max N. Esposito

This quote attributed to Roman philosopher Seneca, is one that I constantly remind myself in order to fight off imposter syndrome. We easily forget about all the hard work and relationship-building that sew the seeds of luck.

My recipe for luck is:

Step 1: Do the best work you can.

Step 2: Share the work, even if you worry it's not good enough.

Step 3: Build sturdy relationships with clients: showing up on time & do step #1 repeatedly.

Step 4: Keep learning to improve your craft.

Eventually, if you repeat these steps over and over again, it will build up your integrity and the association between you and your craft within your network. People will recall you when random conversations arise, and recommend you for opportunities. Every lucky opportunity or generous recommendation happens this way. It's not just by chance. It just feels aimless sometimes in the pursuit because you don't have concrete evidence that the seeds you are sewing will yield the reward.


Going full-time as a Freelancer - YIKES!

I went from part-time to full-time as a freelance artist in September of 2018, but had no idea I’d end up finding illustration that Winter, and finishing a book by the end of that year. I was so excited to try my hand at a new type of art, after over a decade of hustling to earn a living as a freelance painter-musician.

I bought my first iPad shortly before getting the job of illustrating JOEY & IGGY'S GREAT ADVENTURE. I taught myself some how to translate my traditional painting skills into digital art skills in Procreate, and then began illustrating the book with the basic functionality of the app.

One of the authors, Maria, said to me “Mark my words, you are going to illustrate many more books after this,” to which I thought, ”Yeah, right!”

I didn’t know it at the time, but I had a limited view of myself that didn’t include “wild dreams“ like that. I didn’t think I was capable or that people would want me to illustrate their books. The whole industry of publishing seemed mysterious and hard to access because I was ignorant of how it worked.

But, still, her words caused something inside of me to ask “What if?”

2020 Vision

Just before Covid hit, I had just launched a new mural business, got the agent, bought the domain, and built the website. I had also begun an adjacent business doing corporate art events, like teaching paint parties, when Covid hit. I was also performing as a musician --Then suddenly all public avenues for income were less safe, less appealing and less available to me.

But there was a silver lining to this forced pairing down of my pursuits...

The isolation of lock down and its way of stopping all of my other career engagements was actually the catalyst for focusing on picture books as my main job and making significant progress within a short period of time.

Covid was essentially a pressure cooker.

I realized that the freedom of working digitally from anywhere, and the joy art gave me (see my last blog post) made a future in publishing seem like the most meaningful and logistically-reasonable pursuit. With art, I could set up my future life for success and wellness.

I wanted a future where I could make my own schedule, travel freely, and have a healthy work-life balance. This seemed like the best way to do so, not to mention the passion that was ignited within me to make more books.


10 books in 3 years.

One thing led to another by word of mouth and I ended up working with several other authors, illustrating 10 picture books in the 3 years that followed. I am now working on my 11th, and in addition to that, I’m illustrating several spots and a cover for my first middle-grade novel.

Here's a read-aloud of my latest book, RYAN GOES MOUNTAIN BIKING by Katie Dalton & Craig Friedman, which is coming out in 2023!


The Next Big Dream

I’m actively preparing my portfolio and my writing to find a literary agent and begin the pursuit of working with traditional publishers as both an illustrator & an author-illustrator pitching my own stories.

And you know what that voice inside my head keeps saying?


Here we go again... It's time to take my own advice and deal with the imposter syndrome.

Photo by Kelsey Gayle Photography

The truth is, If I knew back in 2019 how much I DIDN'T KNOW about digital art techniques and the illustration/publishing industry, I probably would have never had the courage to begin. So I highly recommend embracing your ignorance and just jumping into it to learn as you go.

Courage is feeling afraid but acting anyways.

You will learn your best by actually DOING IT anyways. Good comedians "write on stage" and test out material 100's of times at small clubs before their big special.


My next post: How to Quit Your Day Job

I’m going to go back in time before I was an illustrator and explain the steps I took to go from part-time to full-time as a freelancer. I’ve gained some insights from my experience learning and making it up as I go, which I hope will help anyone out there who is considering making a career change.

Thanks for the support and please comment below if you found this interesting or have had similar “kismet” career changes!

Stay tuned & subscribing to my newsletter, where I will eventually be looping everyone in on future blog posts. Clearly I wont be spamming you, because I rarely remember to post, HA! But hoping 1-2 times a month will be the future routine!

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