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Filmmaker Steven Montgomery Finds Fulfillment By Changing Dream

In 1980, IU alumnus Steven Montgomery seemed poised for a successful career when his first fill, the documentary "Hobie's Heroes", was met with wide acclaim.

David Dawson, Hobie Billingsley and Steven Montgomery After Screening of Hobie's Heroes


David Dawson, Hobie Billingsley, and Steven Montgomery after screening of "Hobie's Heroes"

In 1980, Steven Montgomery’s career as a filmmaker seemed to be off to a brilliant start.

The Fort Wayne native had released a documentary film about the teenage divers at Indiana University’s summer diving camp run by famed diving coach “Hobie” Billingsley, trainer of some 100 national champions and several Olympic bronze and gold medal winners.

As a teenager, Montgomery had attended the diving camp and had gone on to become a Junior Olympic diving champion. He was, as the T-shirts worn by the divers at the camp proclaimed, one of Hobie’s Heroes.

He wanted the film to inspire audiences by showing the young divers facing their fears in the potentially injurious sport.

Montgomery’s half-hour, low-budget film, Hobie’s Heroes, resonated with audiences and was met with wide acclaim. It premiered at New York’s Museum of Modern Art, was praised in the New York Times, and shown on national TV and in film festivals around the world, where it picked up numerous awards.

Montgomery had his career all planned out. He would direct and produce one more documentary, then go on the direct features. But things didn’t turn out as he planned.

On the evening of April 8th, Montgomery, who lives in New York City, gave a talk at the Indiana Memorial Union in which he described his disillusionment and his renewal. He called his talk, “Achieving Success After My Dream Failed to Come True.”

“What do you do after your dream fails to come true?” he asked the audience in the Whittenburger Auditorium. “When all your efforts are seen to be futile? When that success you’ve imagined over and over doesn’t come to pass?”

Montgomery told the audience how the success of Hobie’s Heroes had fired up his desire to inspire audiences and “change the world” through the medium of film.

“I said to myself, ‘This is what I want to do with my life as a filmmaker. To encourage people, and to even help make a better world.”

Montgomery had his filmmaking career all planned out. He would make one more documentary and then direct Hollywood features. But funding for several film projects fell through. He calls that time the most difficult period of his life.

“I was bitter and resentful that I was being prevented from doing the thing that I really loved.”

It took twelve years before Montgomery could make his second film, a documentary about a Moroccan marketplace that he hoped would change people’s stereotypes about Arabs. The years passed as he sought funding for his next project, and he grew tired of waiting for the money to come in. A comment from his mother made him take stock of his life.

“One day my mother said to me, ‘Steve, you got to get a job. So you’ll have something when you retire.’ I spent months resisting this idea. But I knew she was right.”

Montgomery got a job as a fundraiser for a small non-profit organization. He hated the job, which he found “tedious.”

“I remember one night I went out to dinner after work alone to Burger King and said to myself ‘What happened to the life I used to have, when I was so passionate about telling a story in a film? What happened to my ideals?’”

But a subsequent job as a fundraiser for the New York Philharmonic brightened his prospects. He loved hearing the Philharmonic play, and was excited to be writing proposals for their concerts and education programs.

That was five years ago. Now, Montgomery is an respected independent fundraising consultant. His specialty is helping New York City non-profits find grants in the areas of the arts, social services, and workforce development.

“And often when I’m writing a proposal, I imagine how a non-profit program will help people in the future, just as I used to visualize how a film would benefit an audience. And I write with much enthusiasm.”

Montgomery spoke with pride about the some of the programs he’s worked on. His fundraising skills have helped bring Shakespeare to poor neighborhoods, provide vocational training for dropouts, and pair caseworkers to young pregnant women in a Lower East Side housing project.

“And so, it seems that my work is helping to make a better world. And this was my goal when I left Indiana to become a filmmaker so many years ago.”

Montgomery ended his talk by offering advice to others whose dreams have failed to come true.

“Even when things are at their worst, keep the faith. Don’t fail to listen to your mother’s good advice. And then, look for an open door, and see what the world has in store for you next.”

After his talk, Montgomery was all smiles as he greeted well-wishers in the audience. He seemed happy to be inspiring people with his message of renewal.

But as he told a reporter after his talk, he has not completely reconciled his career as a fundraiser with his desire to be a Hollywood filmmaker. As he put it, “The dream just doesn’t go away overnight.”

Steven Montgomery has issued a twenty-fifth anniversary DVD of Hobie’s Heroes that includes follow-up stories on the divers. The DVD is available in some local public libraries.

Adam Schwartz

WFIU Arts and Culture Producer, Editor "Directions in Sound"

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  • Steph Geber

    What a wonderful article. It is refreshing to hear about individuals speaking about their careers and personal experiences. This article has reminded me of how important it is to stay positive, even when things may seem at their worst. Even if your dreams don’t turn out quite as anticipated, they can still come true in different ways.

    As a former IU student, I am thrilled to be returning to the beautiful campus in two weekends, when Ladies First (IU’s premier female a cappella group) will be celebrating its 10 year anniversary. The group’s spring concert will be held on Saturday, May 2nd at 8:00pm at the IU Auditorium. Tickets can be purchased via ticketmaster or at the door the night of the concert.

  • Vera Badamo

    This story is beautiful as well as moving! Montgomery should be very proud of his accomplishments, and prouder still of the way he put both his “failures” and successes into perspective. I realize, of course, that it took years for him to get to this point; I’m still waiting for my own reconciliation with my unfulfilled dreams. Reading this story is a start…….

  • John Montgomery

    The combination of this article and the audio segment captures the story and its message in a way that will have meaning to anyone with a dream. Great job!


    One time in the nineties, Steve and I were talking… “someday we would be famous” now I can see and tell of course, the that dream has became a real thing in Steve’s life with this wonderful work “Hobbie”s Heros” he had proposed with his talent as a filmmaker I know that the way he thinks about making films with a important vision and perspective to give people, hope and a different way to see our lives, like, “not to give up! In ours dreams and keep on working in our passions that we want to work on, looking for those open doors that we all need to open” to give apart of us to others, good way to go on this!!!!! Hobbie’s heroes dose it all! And we’ll be waiting for the next film/work of Montgomery”s congrats!!!!!

  • Yiming Wang

    I have a lot to relate to Steve’s career story. I liked the message of not giving up. At times in life, we just need to hold on to our dreams. I love the film “Hobbie’s heroes”, I’m not surprised at all to find out Steve was one of Hobbie’s heroes.

  • Tim Brogan

    The last film of Steve’s that I saw was back when we were in High school We were good friends and Steve had asked me to play some music for a film he was making I think about Van Gogh. He was not only good with an eight mill he was a good diver.He went off to IU and then to New York and I lost touch with him. Even though, I knew his passion was film making and that he would be consumed for life.

    I tried for sometime to find Steve and finally after he spent the thirty bucks at classmates com I got back in touch with him and I’m looking forward to seeing Hobbie’s Heros.Steve always was a hero to me

  • Gail Koelln

    What a great speech and great story. I certainly can relate, as one who has not quite reached her dream yet…

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