“In business schools and in business plans, they ask for exit strategies,” Leitner says. “I find that absurd. What I’ve learned at every stage in my career is that I learn more on the first day of doing whatever it is I’m doing than I will ever learn by planning for it.”

There have been quite a few “stages” in the winding, wending career of Leitner, founder of the Insight Labs. From military school to journalism to working on a kibbutz to working in social work and politics, his life experiences have trained him for his current passion, Insight Labs, which focuses on one thing: solving the toughest, most meaningful problems for non-profits and government agencies.

Growing up in Texas, he didn’t regard himself as a trouble-maker — or trouble-shooter — but problems always seemed to sprout up around him.

“I was the guy who never overtly did anything wrong, but things seemed to be going on. I seemed to be orchestrating them. My version of being a pain in the ass was just orchestrating larger movements that were pains in the ass.”

He was a “mostly smart kid,” played a little sports, dabbled in student government, but was mostly trying to over-achieve academically. He never grew up to be terribly tall or athletic, so “it was the only card I could play.”

After military high school, he went to the University of Texas to study government because of “my fascination in how big systems worked, like legislatures and constitutions.” He joined a fraternity and became involved in student government.

“We held the first campus-wide elections after they were banned in the 60’s due to riots. The student body, in its collective wisdom and in appreciation of the administration allowing ‘student government’ again, elected a cartoon character as its first class president.

“It was a heady time.”

AFTER COLLEGE, THE ROAD LEITNER WAS TRAVELING ON TOOK ANOTHER TURN. He ended up doing social work at a psychiatric hospital for adolescent girls for over two years. It was an introspective time for Leitner where he studied himself as much as his clients. He also saw it as his own version of the Peace Corps.

“Standing where I stand now, I start to see threads,” he said. “I seem to be going down this pretty conventional frat boy, government, law school track and then suddenly turning and being a social worker. My friends could not figure out what the hell I was doing. Nobody understood what I was doing. If you talk to people in social work or psychiatry or psychology, there is a recognition that you have to be a little nuts to do it because it helps you sort out whatever you are trying to sort out. There is a deep, deep, introspection involved in any of those jobs “

Then another life change occurred, all because of a movie:

“I saw Broadcast News, this great movie about broadcast journalism, and loved it. I decided at that moment I was going to grad school for journalism, even though I’d never taken any of the classes. So I researched and called every top school in the country. I finally got a hold of the Dean at Ohio State. I said, ‘Will you accept me?’ He said, ‘Alright.’ I hung up and realized I didn’t know where Columbus, Ohio was. But I gave notice at my job, loaded up my Jetta, and drove north until I got there.

“That’s how grad school started.”

JEFF COULDN’T TYPE, HAD NO MONEY, and had never taken a journalism class in his life. But his joy of taking on a challenge led him on. Through one of his professors he got a teacher’s assistant position that covered his tuition and then in a classic case of “you never know where life will take you,” Leitner stumbled into Broadcast Journalism through a classroom incident:

“I became a research assistant, which waived all my tuition and they gave me all my money back. They paid me $10,000 on top of tuition waiver. So I took the stipend and bought my first computer in 1988, an Apple MacIntosh. It had a little gray-green screen in the middle of a big white plastic thing. I didn’t know what to do with it and didn’t know anybody who knew what to do with it.”

“One day I’m in Journalism 101, and the teacher writes up some facts on the board and says, ‘Write a lead.’ I said, ‘May I handwrite it? I don’t know how to type.’ I was kicked out. That was alarming. I walked down the hall and I enrolled in Beginning Broadcast Journalism because they didn’t ask me if I could type.”

Then he threw himself into the most intense learning and working experience of his entire life:

“I finished in one year. I’d never experienced anything that intense. I didn’t date. I didn’t want any distractions. All I did was study because I wanted to drill down as far as I could. It was like being in a monastery. I wanted to watch myself think and push myself to see if I could do it and experience something as purely as possible.”

AFTER CLOISTERING HIMSELF IN ACADEMIA, Leitner did what everyone American does after college. That is, if by everyone you mean maybe 100 Americans a year. He joined a kibbutz in Israel, which could best be explained as taking share-cropping, socialism, and commune living ideals and mashing them into some sort of hybrid alternative lifestyle.

“I lived on a kibbutz doing chores half the day and taking classes the other half. I went because of the romance of it and I wanted to test my thoughts about socialism. I’m a do-good guy and I wanted to immerse myself in an experience where nobody owns anything and the Collective decides what you do for a living. It was amazing but it turns out I wasn’t a socialist. And neither were they. I found out that they kept sneaking things in, like TVs, which they would hide from the rest of us.”

Leitner can best sum up his experience living on the kibbutz with story about boxmaking:

“One day I am assigned to work in the factory and they ask me to assemble cardboard boxes and my supervisor says I’ll be back to get you for breakfast. Please build 10 boxes.And he doesn’t come back for a while. So I built 10 boxes and then I built 12 boxes, and then I built 15 boxes, and then I built 20 boxes, then I built 30 boxes.”

“The guy comes back to get me and he’s livid because I’ve have exceeded my goal, which throws the whole eco-system out of whack. So it really is for each according to his abilities and to each according to his needs. That’s how socialism works. You are not in America anymore, where if I had been told to make 10 boxes and I made30 boxes, I would get a scholarship. If I made 40 boxes, I would win an award.”

“There was a cultural presumptuousness to it over there. It was as if I were showing off or saying,  ‘I’m better than everybody else.’ In the States, we admire that. We admire people who at age 15 make a billion dollars; there, it was just obnoxious.”

NEVER ONE TO PASS UP AN OPPORTUNITY FOR PROBLEM SOLVING, Leitner set out on a backpacking trip through 20 countries, only to end up getting stuck in the West Bank in the middle of the night with no money. And lost in the Alps. And trapped in a Paris train station.

“I can’t remember who said it, but they said, ‘Democracy is the worst system in the world except for all the others.’ You are acutely aware of it when you’re traveling. You’re aware of what works and what doesn’t work – all of which is really important to me now in retrospect.”

“I don’t know that I could have done the things I’ve done since or been the guy I am now if I hadn’t screwed up in those places. I once got on the wrong bus and ended up alone in the West Bank in the middle of the night and no more buses were running. There is something to that. That stuff helped me a lot. There is not a lot in business that scares me now, because that was truly scary.”

“I got stuck in the Paris train station because I didn’t know the word ‘sortie’ means ‘exit.’ I got lost in the Alps with a friend who as clueless as I was. I ran into all sorts of trouble on that trip that shrunk the world for me in a profound way that, I think, influenced my worldview.”

After getting back to the US in one piece, Leitner made crazy bet with his then-girlfriend about moving to wherever one of them got his/her first job. They both ended up in Chicago because his girlfriend landed a gig at City News Bureau. The relationship ended, but Leitner’s career in journalism began.

“When I moved to Chicago in 1990, I got a job as a newspaper reporter covering local politics. I didn’t know what I was doing, so I followed good reporters around all day. They didn’t mentor me much, but they let me hang out, which trained me in how to be a reporter and ask questions.

“Reporters are fascinating because the good ones have an amazing ability to go into a situation where they know nothing, and after researching for three hours they can clearly explain the entire story to anyone. I was very serious about learning how to do that. It wasn’t about the writing; it was the process that fascinated me. After a while, I found myself teaching the people I was reporting on about how they could position their story better.

In 1996, Leitner’s reputation for knowing how to position a politician’s story preceded him because he got his first chance to run a political campaign.

“I was hooked. I joined a public affairs firm in 1997 and for the next six to seven years I managed strategy, messaging, and fundraising for candidates running for office, as well as representing corporations trying to navigate governmental waters. It was a lot of fun figuring out how to get things done in a city where I was considered an outsider and had no power or influence.”

TIRED OF WORKING FOR EVERYONE ELSE, he set out to make his own name in the Chicago political world. No small task, even for a seasoned Chicagoan, let alone a kid from Texas.

“I launched my own consulting shop in 2003. I did it for the purest reason: I wanted to do it my way. I didn’t think about the word entrepreneur,’ though I’d been around them all my life without knowing it. My best friend in college was a serial entrepreneur, though it was hard to tell since he started out by selling screen printed t-shirts out of the trunk of his car. My mom was a lawyer with her own practice, and other doctors and lawyers in my family had their own practices. But, again, I wasn’t aware that they were business owners.

“I watched several of them sell their businesses but it still didn’t compute. So when I started my own business I didn’t know I had any reference points, didn’t know what I was doing, and I had no power. But what I did know was how to solve problems.”

And that’s exactly why Clear Channel contacted him after the company failed to make any headway on an effort to put billboards on top of taxi cabs to sell national advertising.

“It was a big problem,” Leitner says. “Mayor Daley thought it was visual clutter and was strongly against it.”

Clear Channel had tried all traditional ways to get it done. They flew in the CEO to have dinner with the Mayor. They worked the commissioner. In short, they had done it exactly the way it is supposed to be done and it hadn’t worked.

“A guy I had worked with at my previous public affairs firm told [Clear Channel] they should hire me. It was very kind of him to do it and I will be eternally grateful.”

After striking a deal with the media company, Leitner had to actually figure out a way to make the mayor happy, make Clear Channel happy, and make sure everyone walked away feeling as if they had won.

“Here is how we got it done. I started poking around at something that was bothering the City a lot: taxi cab drivers would show up every few months at City Hall with placards and they would protest in favor of a rate hike because they have a pretty tough job. So I called City Hall and said I had an idea. I told them that I thought I had a way to get cab drivers more money and they said, ‘Really?’”

Leitner helped Clear Channel design a new financial model– the first one anyone had ever done that pays the drivers of the taxis who are driving around with billboards on their car.

“So, we created a model in Chicago that is now being replicated elsewhere that says when you drive around, the company who owns the taxi gets money, the City gets a lease tax, Clear Channel gets a fee, and the guy who is driving around all day gets a percentage as well.

“It solved a problem for the City. The mayor ended up championing it himself and it passed the City Council 50 to nothing.”

ALWAYS FALLING FORWARD INTO THE NEXT ENDEAVOR, Leitner finds himself with more projects than he can fulfill in a lifetime.

He and his wife launched Blanket Week, through which they collect thousands of new blankets for the millions of homeless in the US. But his biggest project, Insight Labs, was launched with colleagues at Manifest Digital.

In 2009, Leitner became friends with Jim Jacoby, founder of the creative consultancy at the now-famous 600 West Chicago building. Early conversations focused on bringing together great minds and shaking up the status quo.

“I’m a big fan of making myself the dumbest guy in the room. That’s what gets me off. That means that the longer I do something, the harder I have to make it – just to keep myself engaged.”

Insight Labs are monthly sessions, for which Leitner recruits senior corporate executives, founders and wild-cards – like artists, playwrights and physicists – for a 3-hour, full-contact strategy session to try to solve an impossible problem for a non-profit, government agency or entire industry.

“I had done work like this a few times with my first business and learned that people want to help as long as you don’t waste their time. You have to curate for talent and brains. I like to make new friends and I’m sure we do good. The whole experience is an adrenaline rush.”

There’s a waiting list for organizations that want the Insight Labs to tackle their challenges. But Leitner has strict criteria. One: The nonprofits involved have to understand that there is a value to the process. Two: They have to possess the resources to do something about it once a solution is created. And three: The problem has to be an interesting one to solve, which means it has to be interesting to Leitner, and give others a reason to get involved or “leave their desks,” as he likes to say.

“I want to solve the hairiest problems with the most interesting people. For me, the harder it is, the more exciting it is. Jim and I both say we look for opportunities that terrify us. Like the time midVentures asked if I would speak about Insight Labs at their conference, and I offered to host a lab onstage instead.”

“Or when we launched UX for Good, which is a wildly ambitious effort to come up with design-focused solutions by packing some of the most talented and creative people we can get into a room for 48 hours to solve giant social challenges.”

Leitner believes a roomful of people with different experiences and expertise in a controlled, confined space creates amazing results:

“Creativity and innovation happens when you kill politics and posturing. I also strongly believe that a single, shared vision is more powerful than an ocean of suggestions, even if the shared vision isn’t entirely right. If everyone’s rowing in the same direction, whether or not it’s a little off-course, you can win.”

When he’s not constructing and running Insight Labs, Leitner is part of a new, dedicated strategy practice at Manifest, predicated on the same ideals: very smart people, no pride in authorship and a commitment to being scared every day.

Clearly, it’s a journey without maps. Or exits.

“True,” he said. “But remember, wandering maps worlds.”

For Leitner, a lifelong sojourner, it also solves problems.