Jeff Greenspan: Want to Make a Difference? Just Get Started.

When he’s not working on advertising campaigns with top agencies or freelancing as a creative director, Jeff Greenspan makes art that engages. Public art that lives online or in the real world, that captures tens of thousands of pageviews or stops people in their tracks. Projects like Hipster Traps, the tongue-in-cheek installation on the sidewalks of New York City with co-conspirator Hunter Fine. Or like Selfless Portraits, a website created with Ivan Cash that encouraged people to draw strangers’ Facebook profile photos.


Greenspan is armed with a resume that includes positions with A-list brands (he was BuzzFeed’s first Chief Creative Officer, a Creative Strategist at Facebook, and a Creative Director at BBDO NY) and a portfolio of work recognized by The One Show, Cannes, The Art Director’s Club, Webbys and Clios.

With his side projects, he injects his voice and his vision of a better world into popular culture. His aim? To get people thinking and acting in more productive and positive ways. He doesn’t mind if his work preaches to the choir — even when people agree with his point of view, they gain the confidence in their beliefs.

At HOW Design Live in Chicago, Greenspan will talk about his side projects and encourage your own, during his session Make What’s Important to You Important to Others. We recently had a rapid-fire conversation with him about how creatives can use their skills to make a difference, no matter how large or small.

Can you think of a specific project in your experience that encouraged you that, “Hey, my work can be about more than selling widgets?” Not that there’s anything wrong with selling widgets; widgets pay the bills.
The first project I ever did that saw the light of day that did that was called The Bush Booth. It was during the time of George W. Bush’s second run for office and there was so much negative, fearful rhetoric from the campaign all over the mainstream media. And I didn’t like that tone. I said to a friend, “Somebody should just shut them up.”

When I say, ‘somebody should …’ that somebody often becomes me.

We took hours of footage of George Bush, and we edited together just the parts where he was listening and not speaking to create a 7-hour loop. We put it into a soundproof booth, and people could go in and say anything to him, and he’d sit there and contemplatively listen to you. It gave people a sense of being heard, even if it was theatrical. It was about speaking up to those in power.

We built this thing and didn’t have a place to put it; it finally found a home in the lobby of an improv theater company I was involved with. They agreed to keep it for a week. The response was so great they asked to keep it a second week. And then it went to an art gallery, and then it got written about, and then an art collective in Chicago wanted to build it.

That was the first time I saw that I could do something without a brief, with my own agenda, to meet my own need to ‘do something.’ And it connected with people.

How do your side projects fuel your paying work? What’s the relationship between these two pursuits?
Well, they keep me sane!

For me, my work assignments weren’t just cutting it. I kept thinking there’d be a brief that would come along, or a client that would come along, that would allow me to do what I want to do. And that became ridiculous — no brand is going to pay for Jeff Greenspan’s personal voice. In advertising, you’re asked to speak in a number of different voices. I realized that I don’t have to wait for those projects to come along; I can create them.

I see on your website that you studied sketch comedy and improv at the Upright Citizens Brigade. What lessons do you continue to apply to your creative work?
That and being held up at gunpoint, were the most pivotal things in my life.

I was maybe 26 at the time. The Upright Citizens Brigade weren’t famous; nobody knew Amy Poehler or Tina Fey, it was a really cult thing. They had this very aggressive stance against formulaic humor, and this notion that what you think is funny has been programmed for you by the media. That your own life and your own truth are much more surprising and funny, but most people never explore that.

In long-form improv, you’re looking for patterns. We had a format called “The Harold,” where you’re essentially creating a three act play from scratch with the other members. You’re doing your scene and other members of the troupe are doing other scenes. And there’s some connective tissue among all the scenes — there may be a singular truth that ties them all together.

I became interested in trying to find the similarities in the disparate — and that’s applicable to advertising, because a lot of really great ideas are mash ups of other ideas.

Another technique that was really useful is called “A to C Thinking” — can you make what was your second thought your first thought? And can you then take your fourth thought and make it your first?

When you’re in a room of people and you’re brainstorming a campaign, can you get to your deeper ideas more quickly?

When you do improv, you do thousands and thousands of scenes, and you come to realize that ideas are infinite. That was essential to me in advertising — you don’t have to be precious about the ideas that get stolen or crushed or die. There’s another one around the corner.

Between what I was learning in advertising — how to craft a concise message, how to use different media — and what I was learning in improv — being honest, being true, not trying to write a joke but instead trying to explore the truth — those lessons came together and they became these art projects.

Given the state of the world we’re living in, creatives seem to be longing for ways to make some kind of difference with their work, but they’re unsure how. How would you advise someone to harness their talents to help create a more positive direction?
It would be a missed opportunity to answer this question without having a discussion about the current political climate we’re in. Since the election, I’ve had different days of how I feel about it — from this is what we deserve, to maybe it won’t be so bad, to this is great because it shows how broken the system is. I’m not a Trump supporter, but I understand the people who are.

I’m having a hard time processing it myself; I’ve asked myself, ‘What can I do with the talent and skills that I have?’ Maybe it’s just being a nicer person because I can see the immediate effect of that. I don’t know right now.

I used to say, ‘What’s the point of doing these projects if you’re preaching to the converted?’ But there’s something about doing things that speak to those who already agree with you:  sometimes those people live in a place where they can’t be as open in what they believe as they would like, and your project gives them a way to reinforce their beliefs in a safe and personal way. There’s a use in doing projects that corral people who agree to keep them enthused and engaged.

So, how do you start? Figure out your goal. Is it to corral those who believe with you, is it to change the system, is it to convert a thinker? That’s the first step. Then, what action do you want them to take?

And then the next step is to just … start. I find that a lot of people starting out a project are paralyzed because they can’t figure out how to get all the steps done. Trust your gut and take the step you can take, and more often than not the other steps will present themselves to you.

Jeff Greenspan will be in Chicago to help light a fire under your personal and professional work, to encourage you to just start. Come to HOW Design Live and get inspired by Greenspan and nearly 100 other wildly creative and inspirational speakers. Browse the full agenda and make plans to be there.