His resumé is a zig zag of creative risks. Early on Curtis spent ten years pursuing music and then taught himself design and web software out of desperation after he was dropped by his record label. He rose through the ranks to head up Macromedia’s Flash efforts, then formed his own shop and designed sites for Yahoo and Adobe. Next, he got into short films as a side project and recently completed a feature-length film called Rise, Ride, Roar, about legendary musician and Talking Heads frontman David Byrne. To date, Curtis’ three books - Flash Web Design, MTIV, and Creating Short Films for the Web - have sold well over 150,000 copies and are required reading in design schools around the world. I sat down with him on a recent afternoon in Brooklyn, New York to chat about his facility for reinvention - and the risks, challenges, and fears that come with it.

It seems like you had it made with Macromedia and Flash  - literally writing the book on it - why did you move on?

For me Flash was all about motion graphics on the web, so there was a bit of a connection to film. At the time it was very light on the code end of things, and while I can code, it’s not something I truly wanted to do. And I was having more and more success doing site design, so I decided to pursue that and start my own site design studio. We had anywhere from 5 - 18 full-time employees and started landing these big sites like Yahoo and Met Opera. But I found over time that these types of sites became less and less about design and more about system design. The value was on social networking, database integration, CMS... and the value of things like color, typography, and composition seemed to take a backseat a bit.  As a result, I wasn’t enjoying the work as much. I had started to make short films around this time and one day, after banging my head against the wall while chanting “Expression Engine” over and over, I decided it was time to try my hand at making films.

Having worked your way to the top twice and having had some awful jobs in the process was it daunting start over yet again?

You know it was hard. To answer the phone and say, “No, I’m not doing site design anymore” took me a full two years to get up the courage to do it.  I took on some projects that I probably shouldn’t have and did so mainly for the money. Looking back, those jobs didn’t turn out that well either. It’s one of those things that I should always remember, to try and take the courageous route.

Why leave the web for film?

Around this time of designing these big sites, I found myself just wanting to get back moving images, and I was lucky because prosumer cameras were finally becoming affordable. At first, I left all the settings on auto because I didn’t know how to adjust everything and instead focused on just making movies. I had a tripod, a boom mic, and a bicycle and I would ride around Manhattan doing these short films on different creatives like Milton Glaser, Stefan Sagmeister, Lawrence Weiner – I called it the ‘Artist Series’ – and by doing so, I learned the craft of filmmaking and the technology along the way. Most everything I’ve learned in film or otherwise has been by just diving in and doing it.

Would you say there’s a common thread that runs through all of your work?

The one thing I’ve gotten good at from doing all these different pursuits is finding a central theme in a project. If you can find that theme or story in your subject, the solution will present itself to you.

What’s your theme?

I think it is reinvention.

When you set out to reinvent yourself in a new field, how do you counter the panicked inner voice that says, “I don’t know what the hell I’m doing?”

I think it’s only natural in the beginning to try and assert control over that creative process, and I’m always trying to optimize. When I first got into doing documentary films I would write all the interview questions out and bring them to the shoot. But I found I was getting shitty interviews by trying to impose a linear storyline on the films. The best lesson I got in letting go was when I interviewed Milton Glaser for the artist series. I could sense he was bored as I read my questions. I was asking him the same questions he’d answered a million times before. However, we were in his fantastic four story brownstone that housed all his work, so I decided to wing it, stopped the shoot, and asked if I could have a tour. He agreed and I ended up getting all this great footage of him pulling out sketchbooks he did in Paris in the '50s and reminiscing as he shuffled through thousands of posters he’s designed over the years. It’s powerful stuff, and it would have been impossible to get that kind of insight and dialogue in a typical interview setting.

Having earned notoriety across all these endeavors, how do you respond when people try to pin you down?

I’ve kinda gotten used to shrugging it off. I had the “Flash guy” label for a long time, and that’s faded away in large part. When I was working my way into film, I had an agent that kept trying to pitch me as a platform - I could shoot a film and code it up for the web. I just kept saying no, as I have no interest in going that direction. I would much rather focus on writing and directing films. It’s important to have a direction of where you’re going for knowing where to say no.

You’ve worked with world-class creatives. Are you comfortable around them?

I still get nervous. I’m actually pretty introverted but I’m fascinated by people’s stories. If I can find the story, I can then make connections with people through the artistic endeavor. It can be brutal getting to the story though, but when it’s time to do the shoot or interview I’m never nervous. Never. A funny story along these lines concerns David [Byrne]. Even after making the Ride, Rise, Roar film, I would still feel a bit intimidated when I was around him. At one of the premieres, we were chatting afterwards and he said his daughter was attending design school in Oakland. Turns out the book they were using in class was one I wrote called MTIV: Process, Inspiration and Practice for the New Media Designer. At that point I thought, “Alright I can relax a little now.” 

What do you consider your biggest successes?

[Curtis shifts uncomfortably in his chair and glances out the window.] I feel like I’ve only had a few out and out successes. I think the MTIV book and the short films in the Artist Series I did are up there. Maybe the films “Bridge” and “Embrace” in my short dramatic work... and Ride,Rise, Roar is good... but really, only a few so far.

How did you develop this mindset of reinvention?

I was given a lot of freedom growing up. My mother was an art teacher and never put a lot of pressure on me to pursue a particular path. I originally went to school for creative writing and film. I then spent 10 years pursuing music and after failing at that I did various random jobs. I got into design out of desperation - I didn’t want to wait tables or pound nails again - without ever even having touched a computer.

So you weren’t focused from a young age?

Oh no, not at all. You know how some kids know what they want to be at 15? I wasn’t one of those kids. At times I’ve wished I was that kid, though.

How do you look back on your career so far?

I can see it a couple of ways, either as a series of detours, or I can look at as a righteous path that’s never going to end. If I see whatever I’m currently doing as just another stop along the way, then I think I’m on the right path.