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The Dream That Was Too Scary to Voice Aloud.

Updated: Aug 25, 2023

And other struggles as voiced by a super famous cartoonist.

giraffa and elephant discussing the merits of being a cartoonist for a living

“What do you love to do?” Tony asked me. “I don’t know. I guess I want to be an art director.”

Tony was an art director at a big agency in Boston. He had been a guest speaker in my advertising class the week prior, and I had tracked him to his office for an interview. He worked at a top-flight agency and was gracious enough to see me, but I could tell he wasn’t overly impressed with my work.

“You guess? No, don’t guess,” he said. “What is it you really want to be?

I was too afraid to say it. It seemed crazy, irresponsible, and out of reach, but I knew what I wanted. I wanted to draw cartoons. I knew I was good. I had already had a taste of the big time. My work had been picked up by a major beer label and I had a contract for more but could someone actually make a living drawing cartoons like that? Was it just a lucky break, a one-time thing, or was there something bigger lying undiscovered?

“I have this friend who does storyboards for a living,” he said. "This guy lives the life. He wakes up when the sun is warm, walks his dog, and works when he wants. He doesn’t punch a time clock and is his own boss. He’s always busy, and he gets to call all his own shots.”

I froze in my chair. “You can just do that?” I thought. “Who does that?... I want to do that!”

I knew the interview with Tony was over, not because my work sucked, but because I was showing an illustrator’s portfolio for an assistant art director's position. I knew there would be no offer, but what I was coming away with was far more valuable.

rock and roll bob on the hood of my old 73 chevy caprice classic
The kid who showed up in Tony's office

My portfolio was loaded with illustration work. Even though I thought of myself as a

budding art director or an entry-level

designer, my work showed I was far more concerned with illustration, cartoon illustration, to be more specific. After that interview, it became clear to me what I was going to do. I was going to be an illustrator, just like that guy Tony knew. I didn’t know how or what it was going to take, but that’s the life I wanted.

So that’s exactly what I did, and I started my journey as a storyboard artist because that’s what I knew best. It suited me well, and I stuck with it for a while, but I wasn’t quite there yet. I needed to let go of my fear and go all in. So I did that too.

All in on illustration.

It was not an easy path, and there were times I questioned my decision, but I did everything thing just like Tony's friend. Maybe it was a subconscious decision, maybe it was planned, but it was my new life. I woke up when the sun was warm, I got a dog and walked him in the morning before I went to work, and I called all my own shots. it was great, but it wasn’t exactly how I pictured it. For starters, it was WAY more work than I had envisioned. There was way more stress too. The pressure of meeting deadlines, getting new work, and getting paid was an even more significant challenge than I had imagined it could be. So I did something completely out of character for me at the time. I went out and got some help.


In the early days of my career, I struggled with confidence. It was a strange dichotomy, the brazened wreckless abandon of youth coupled with the fear of not being able to measure up as a professional artist. I recognized if I was going to get anywhere in this business, I needed someone in my corner. So with that in mind, I leaned even harder into my dream. The dream I was too scared to tell anyone about until now. The dream I had kept to myself for years because it was too precious and too scary to utter aloud. To be a cartoon illustrator.

My dream was to illustrate games and toys, and children’s books. I wanted to draw all my favorite cartoon characters and get paid for it. I had no idea how I would do all that, but I was young and hungry and very, very determined. So I looked around to see what other people who shared my dream were doing and contacted a lot of people along the way. Information was not as abundant or accessible as it is now so it was an uphill climb. There was no internet, no social media, no online courses to explain how things worked. There was just a kid with a dream. So instead of all those things, I bought a book, yes, a book, from the bookstore... where they sell books.

It was full of listings. Artists, agencies, publishers, the works. The only problem with the list was it wasn't mine. Some of the contacts had dried up since it was published others were out of date and no longer interested. A lot can happen between the time a book is written and published. But one of those listings hit. It was an art rep from NY, NY. They liked my intro letter and asked if could send samples. So I sent them my stuff, in the mail, with a terrible cover letter that probably looked as if it had been written by a child, but it worked.

They were impressed with my artwork and signed me that same week. With the help of my new rep, I took a giant step forward toward my dream. Each project I took was another step up the ladder. It was an amazing journey, and one that exposed me to a side of the art world I had been entirely unaware existed. There was a whole world out there where artists, cartoonists, like me could actually make a decent living doing what they loved.

Flying solo

Bob Ostrom with children's book series

Through the years, I found myself working on bigger and bigger projects I never dreamed I would have had the opportunity to work on. My art had been used in almost every capacity I could have ever imagined. It was incredible, but eventually, I grew restless. I know, I know, here I was doing all the things I had wanted to do except one. I wanted to be the guy who was creating the work. You see, until now, my work had gone mainly unrecognized by all but a few people who knew it was me.

Because these were properties owned by huge corporations and conglomerates, my name was rarely seen in association with them. I had largely been flying under the radar. It was always somebody else's dream I was being hired to bring to life, not mine. And while that was very exciting, there was one more step I needed to accomplish to make that unspoken dream of mine spoken. That meant stepping into the role of the main artist, the artist whos work sold the project. So that's what I did.

I found a new rep who was willing to lead me in that new direction. It was all or nothing. Thrilling and petrifying all at the same time. If I failed here, the stakes felt much more real and much more personal and there was a lot more riding on my success. I followed that path for the next ten years, and as my career began to flourish in a new direction, I was rewarded with the one thing I had been searching for since the beginning. To live the dream and to say it out loud. I'm an artist and I have the best job in the world. I draw cartoons for a living. I am a cartoonist!

Cartoonist Prolog

Yes, I am a cartoonist but that's not all I do. I'm a fine artist, I'm a designer, a creative director, teacher, video editor, children's book illustrator, the list goes on, but what these things have in common is that they feature my cartoons. I know, can you believe it? Me either but it's true. I've found a way to feature my cartoon work in just about every facet of my business.

From time to time, I’ve held full-time jobs over the years, but I always find myself going back to what I love, cartoons. What you see on this website is what I do best. I love my job, and I love sharing my art with the people who appreciate it most. I consider myself very fortunate to have been able to have done what I truly love for so many years (the dream that was too scary to say aloud) and I plan to continue for as long as I can.

Now as I approach this stage in my career I find I have a new dream every bit as big and challenging as the first dream and that is to take my art to a new level where I will take on the role of creator. What does that mean? Stick with me as I move into my new role and I'll show you what I'm planning and where it leads.

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