He confounds the stereotype of a starving artist. Formally educated and with an impressive career at just over 30, Brian Ditchfield is a dynamo in camouflage, a person whose intellectual heft is couched in a personality free from pretension or posturing. He is a quiet leader among his peers in theatre and the dramatic arts.

And now he will lead the children, as he himself was once led in the venerable Island Theatre Workshop’s Children’s Theatre program. Mr. Ditchfield takes over as head of Children’s Theatre this summer. He will be the only alumnus and the only man who has ever held the post.

And as he steps in as director of the Children’s Theatre, Mr. Ditchfield takes his place in a line that includes several of the grande dames of Island theatre. Lee Fiero, Linda Berg and the late Mary Payne, his illustrious predecessors, may cast long shadows over the mild, understated and cordial Mr. Ditchfield. And still, there is little doubt that the work of the remarkable women who preceded him will flourish in his hands.

Growing up on the Island, Mr. Ditchfield made his mark in the theatre landscape early on. The February, 1995 calendar section of the Vineyard Gazette features a photograph of Mr. Ditchfield as a beardless, breathless 17-year-old on the eve of his directorial debut, consumed by the upcoming performance of Kafka’s Metamorphosis.

Even before that he was a child star on stage during the years of Magic Fire Children’s Theatre, an energetic improvisational theatre program led by his talented parents for several years.

But Mr. Ditchfield is much more than the native son returning home to train a new generation of artists. He is also the theorist of a dramatic realignment of art, commerce and everyday life, a person who sees the possibility for artistic acts everywhere, and who wants to explode the notion that art and business are somehow incompatible.

After graduating from Boston University’s theatre program in 1999, he moved to Chicago and got a job as the assistant to the managing director at Victory Gardens, one of America’s premiere theatres. He started out as a copy boy of sorts, making photocopies of things for the theatre, and eventually worked his way up. Along the way he learned the ins and outs of financing for a cultural institution.

At the same time, he was writing his first screenplay. The Last Will and Testament of Marlborough Patch was based on a novel by his father, Michael. The young Mr. Ditchfield had undergone brain surgery the summer after graduating from college, and he said his brush with mortality provoked the realization that “you only live once, and I had always wanted to make a movie.”

He began fund-raising for the film with a zeal untarnished by the experience or expectation of failure, and his efforts were quickly rewarded. He raised enough money to finance the production, and shot the movie in 2001.

He looks back on it now with a more practiced eye. “If you watch the movie, you can tell I don’t know the first thing about making a movie,” he said. On the other hand, he calls the film testament to a certain “fortitude and youthful folly” that are essential to doing the thing that he seems to do best: make seemingly fantastical ideas come true.

Take, for example, Looptopia, Chicago and America’s only all-night arts festival. After marrying Brooke Hardman in 2004, Mr. Ditchfield took a job as business manager for a nonprofit organization dedicated to promoting downtown Chicago. He knew that arts festivals that last all night have long existed in European cities like Rome and Paris, and decided the same thing should be attempted in America. The first Looptopia, held in 2007, was a great success, and the festival is now in its third year.

Mr. Ditchfield noted that while other countries, including France and Britain, have ministers of culture, America does not.

At least not yet.

Perhaps Mr. Ditchfield ought to call in a favor from the President himself. After all, he began working on Barack Obama’s campaign when he was still a state representative from a district on the south side of Chicago. He even managed to score some publicity for Mr. Obama by installing him as the marshall for Chicago’s Memorial Day parade.

For now, the comparative lack of government support for the arts in this country has led Mr. Ditchfield to work with the private sector, developing innovative business models such as the one he created for a combination bar and art gallery in Chicago.

One of the bars he frequented in Chicago during his post-college years was owned by a Romanian artist who often had his easel set up in the bar room, his paintings hung haphazardly in an adjoining space. Mr. Ditchfield developed the scenario into an innovative business concept and then signed on as bar manager to run it.

The bar provided easels, canvas and paint for patrons, many of whom were artists, so they could paint while drinking beer and socializing. The artwork was then hung on the wall of the bar, and sold for $5 a painting. An adjoining room was converted into a gallery where artists could hold more formal shows.

Mr. Ditchfield and his wife recently launched Art Farm Enterprises, a new Island organization.

Last summer, Art Farm produced a party where guests were served red and white wine through long, spiraling tubes that descended from the branches of a tree. The hors d’oeuvres table was actually the elaborate skirt of a stationary actress.

“Theatre too often gets trapped on the stage,” Mr. Ditchfield said. This summer, Art Farm will produce two original plays; both will be set outdoors, one at the Farm Institute in Edgartown.

Last weekend Mr. Ditchfield played Duke Vincentio in a one-hour adaptation of Measure for Measure at Che’s Lounge in Vineyard Haven.

All grist that he is sure to put to good use for his Children’s Theatre productions this coming summer.