From Thursday, May 8th to Saturday, May 10th, top innovators in digital media, art, design and technology will gather at Toronto’s annual Digifest. The programming promises to showcase groundbreaking digital and technological discoveries that will re-shape today’s urban challenges.

Guests include Massimo Banzi, who invented the Arduino open-source electronics platform; and Daan Roosegaarde, the designer behind the Smart Highway in north Brabant, the Netherlands. Participants can also attend a number of panel discussions, including one on wearable technology and another on gaming; as well as the Maker Showcase on Saturday, where designers, artists and hackers will display they work.

We spoke to Mark Rolston, who will take the stage as Digifest’s keynote speaker at 9am on Thursday. Rolston was chief creative officer at Palo Alto’s Frogdesign – where he created the touch screen interfaces for Microsoft and Citibank, among other seminal projects – before moving to Austin to found Argodesign, a design consultancy focused on bringing the user experience to a whole new level. Here, he reveals his thoughts on Steve Jobs, his greatest career regret, and how to effectively speak the language of design.

What is your occupation?
Designer and entrepreneur.

What projects are you working on?
We are working with several software startups in both the consumer and enterprise markets. I’m also helping several larger companies with their product design strategies. Lastly, our studio is developing several products of our own that we hope to bring to market.

What made you first go into design?
When I was young, I thought I would be an artist. But over time I realized that I did not want to produce art for myself. It seemed too trivial for my tastes. I wanted to use my passion to create for useful purposes. Really, I stumbled into the design field looking for useful things to do with my creative skills.

What was your first design job?
At age 14, which was in 1983, I wrote software for my father to track oil and gas production. On the surface it was just software programming, but really it was early software design. I learned during that process to think through a problem and design the way it should work. In high school I had a part-time job designing brochures and signage for a hospital. I was quite lucky to get that job because it gave me professional experience very early in my life. I also realized I did not want to just be a graphic designer; I wanted to design products.

What is the best part of your job?
As a designer we get to invent the future. People pay us to invent things to make other people’s lives better. How could you not love that?

What is the worst part of your job?
Designers are not uniformly understood or respected. Most of the world has either a poor understanding of the creative process or simply don’t care. I have to wade through those people to get things done.

What is the best quality in a designer?
The ability to create something from nothing, to have enough faith in one’s own imagination.

What is the worst quality in a designer?
We are insufferable egotists. By nature, creating for others requires we assume what we have to say is worth hearing. You need quite an ego for that.

What tool do you use the most?
The whiteboard.

How do you overcome creative block?
I stop and go do something else. Then what I’m looking for usually comes to me.

Who or what excites you about design at the moment?
Right now is most likely the most exciting time in history for design. The changes that technology is causing to humanity are profound.

What do you foresee as being the next game changer in design?
Machines that can think. We have been designing better levers for ages. From hand tools to computers, the march of technology has still meant only a better tool for people to operate. But today, we are closing in on machines that aren’t merely tools. They can make decisions on their own. They can sift through information in ways we could never match.

These capabilities don’t just make life better, they promise to change the very meaning of basic notions of humanity: ideas such as what it means to really “know” something if everything knowable is at your fingertips. We are not individual minds anymore. We are, by virtue of our relationship with these evolving machines, networked, matrixed. Subsequently, the role of a designer is radically changing.

Where is your ideal place to work as a designer?
In a room full of engineers.

What talent would you most like to have?
Patience.

Who is your design hero?
Steve Jobs. He brought design into the boardroom and showed the public that design should matter to them. Beyond even his impact with Apple, he has changed the product landscape forever.

Which designer do you most identify with?
I’m not sure. I try and work with the designers I most identify with so any answer sounds somewhat self serving. I still identify with my old boss, Hartmut Esslinger, even though he’s completely nuts. Yet he’s a genius. I think the designers I love the most are insufferable nuts. I really love creative people like Jan Chipchase, Robert Fabricant, and Jared Ficklin. These people are hardcore. They live their creative passion.

What word or phrase is overused in design?
Innovative. What does that really mean anymore? A word used too much is stripped of its meaning. It’s like saying “that product is so blablablah.” People can no longer actually hear the word. It’s filler. We must exercise our vocabulary to find words people will hear.

If you could change one thing about yourself, what would it be?
I would be younger.

How do you keep challenging yourself?
I quit my job as the chief creative for one of the most successful design agencies in the world. My challenge is to follow that with something interesting.

What is your greatest design achievement?
I created a wonderful agency with 20 years of really groundbreaking work. I take most pride in that over any one project.

What is your greatest career regret?
I regret not having more control over the business side of Frogdesign.

What designer or manufacturer would you most like to work with at the moment?
Tesla. They have such a cool product, fantastic leadership, and I imagine they would actually be interested in what I have to offer.

What do you value in a manufacturer?
Risk, passion and faith.

What’s your favourite app?
I am really digging a whole set of the ODBII display apps.

What are you listening to on your iPod?
Jay Reatard, PIL, Placebo, Kate Bush.

What are you wearing right now?
The designer’s uniform: T-shirt and jeans.

What is your most prized possession?
For the last 20 years I have been constantly building, racing, breaking, fixing, and building onto a 1971 240Z. Today it is likely the most recognizable 240z in the world. I’m not kidding. Look it up. I am proud of this creation and really love the time I have to work on it and race it.

Where do you see yourself in 10 years?
I don’t like to look at life that way. You end up making safe decisions.

What words of advice do you have for the younger generation?
Too many young designers job-hop looking for respect and more money. Unfortunately, given the immediate market for design, they find enough of it to keep hopping. Too often I see this stumping their careers over time because they hit an early ceiling where their lack of robust experience catches up with them. Take time to develop real depth and keep a strong sense of humility about you, even if you think you’re a badass.

What are your words to live by?
If you don’t go off the track every so often then you are not driving hard enough.

Digifest runs May 8 to 10 at the Corus Quay building in Toronto. Mark Rolston presents on Thursday, May 8th at 9 am.