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Self-describedvector art monsterRobert Generette III, aka Rob Zilla, taught for 20 years, most recently photography, before quitting to freelance full-time in the DC area, having worked repeatedly with mega clients like the NBA, ESPN, Xbox, and Adobe. “I was standing on the edge of this cliff for a long time, trying to build up courage. If I was single, I would have done a somersault off that ledge, but I’m married with two kids so I could take that fall, but I was afraid I’d land on my family. It wasn’t a risk I was willing to take at first.”

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Illustration by Rob Zilla

Know when it’s time to go.

It got to a point where teaching got in the way of freelancing, and it became unfair to my students because they didn’t have a high percentage of my attention, and there were opportunities I was turning down.

Do work that’s worth it.

It has to be fun. If it sounds fun, I’m willing to set aside some things like budget, for instance. I also ask about approvals: How many people are putting eyes on this to say yay or nay? If the number gets close to a double digit, that’s a red flag.

I had to change the way I worked after I quit teaching.

It was tough. Last year was my first full year freelancing. I did a lot of yard work and things around the house. That way I could multi-task and mentally escape; just to get the juices flowing mentally I had to do something physical to take the place of teaching.

Make the most of downtime.

I do a lot of work in sports, so I pitch a lot in the offseason. In the dry season, like [in August] when I’m waiting on hockey and basketball to start, I do a lot of maintenance work, updating my portfolio presence on the web and cleaning things up and adding things to get more eyes on projects.

Adapt.

Adobe just introduced Fresco, and it will soon replace Adobe Draw, the vector drawing application I use, which means it’s a different way of working. I pride myself on having a process that can adapt to any project I’m given and know what tools to go to in order to get that job done effectively. Now I have to find a new bag of tricks.

You don’t have to take every job.

I wanted to work for entertainment, pop culture, and sports—and sports has a very quick turnaround. Sometimes they need it by next week, and that’s with revisions. Some teams go as far as getting approvals from players, and I’m like, “Ehh. I don’t know about that.” Those are some of the jobs I turn down—some of the most macho athletes are divas.

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Illustration by Rob Zilla

What makes you stand out are your workarounds.

Everyone has the same tools when it comes to mobile at their fingertips. If everybody has the same tools, it’s how you use those tools that’s going to give you your own voice.

Don’t be afraid to try new things.

But find out how they relate to older things. That can make a whole world of difference. In my process on the iPad I found a way to relate comic book workflow in its traditional form to this new technology.

Think outside the box.

When I first got on Instagram the only thing I was posting were super high contrast photos. One day I was bored and did a drawing on paper, took a pic of it and put it on Instagram and my likes were 10 times more. Now when I look at stuff I try to make it go beyond what it was intended to do.

Don’t respond immediately to criticism.

Give yourself time—you don’t have to respond to feedback right away. Give yourself some time, walk around the house, curse somebody out who’s not there, vent to a friend or someone who’s not in the industry because sometimes the outside perspective makes you see the criticism a little differently.

These aren’t clients; they’re collaborators.

I don’t work for somebody; I work with somebody. That’s my state of mind. I’m working with you because you sold me on your vision and I want to make this happen. I also want to build a friendship because I don’t want to be a one-time hit and quit it type of person when it comes to jobs.

This article originally appeared in the Fall/Winter 2019 issue of Sixtysix. Subscribe today.