One of the paradoxes of this quixotic life is that finding success, fulfillment, or the ideal comfort level demands first subjecting ourselves to degrees of discomfort.

Without confronting our fears, to vanquish them, how can we rise to new levels of achievement and satisfaction?

For Don Quixote de la Mancha, that meant tilting heroically at giants cleverly masquerading as windmills.

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For skydiving enthusiasts, the sheer ecstasy of reaching new heights by free-falling through the air requires the death-defying act of jumping out of an airplane that’s 10,000 feet about terra firma.

For prizefighter “Iron” Mike Tyson, it means going head to head with one of the only things he is afraid to face: sharks.

BEGINNER’S MIND

For media creator Barry Diller, the excitement that envelops him when launching a landmark company or piece of entertainment escalates in inverse proportion to how little he knows about what he’s doing.

Come again? Yes, Mr. Diller says that the less knowledge he has about what he is about to build, the better he feels about his chances to succeed.

That’s called Beginner’s Mind. It’s an ancient perspective propagated by Eastern spiritual disciplines.

Under the principle of Beginner’s Mind, too much knowledge can turn into a deficit, not an asset, if it inhibits the creator from venturing into the unknown, where there await epiphanies in the fertile field of the unconscious mind.

Another expression favored by Mr. Diller is “learn to unlearn.” It applies especially to serial entrepreneurs like him. When moving on to the next startup, what worked before may not be the right formula for a new venture. The market has changed in the interim, and other variables may be in play, so the best move, he contends, is to go back to square one: unlearn what you knew and learn anew.

In the same vein, Mr. Diller also calls himself an “Infinite Learner.”

KNOW LESS

“Nobody knows anything about anything, including me,” I heard Mr. Diller tell Reid Hoffman, founder of LinkedIn, on Mr. Hoffman’s podcast Masters of Scale. “The more you know,” he adds, “the worse it is.”

For the author of that surprising statement to have had the spectacularly storied career Barry the billionaire has had is evidence enough that his philosophy of succeeding by “unlearning” is advice that more of us should heed.

Who exactly is this strange dude? Even if his name does not ring a bell, you know him by his prodigious output as one of the most successful and original media minds of the past half-century.

A partial list of the cultural touchstones on the Diller resume includes his inventing the TV movie-of-the-week and the TV mini-series in the 1970s (topped by ratings juggernaut Roots), box office blockbusters “Grease,” “Top Gun,” “Saturday Night Fever” and “Raiders of the Lost Ark,” Ticketmaster, Angie’s List, Expedia, and Tinder.

“The only things that interest me are things that haven’t been done before,” said Mr. Diller. “I learned early that you are best when you know nothing.”

He shared with Mr. Hoffman an instructive tale to buttress his assertion that “nobody knows anything.”

THE FOURTH NETWORK

In the mid-1980s, Mr. Diller casually mentioned to his boss Rupert Murdoch his idea for a fourth TV network—and was mildly shocked when the media mogul instantly said, “Let’s do it.”

Mr. Diller’s daring concept was to deliver to home viewers something completely different: the type of unorthodox, “alternative” shows the Big Three networks (ABC, CBS, NBC) never would think of airing. After all, there was no indication TV audiences wanted more of the same.

Mr. Diller recalls the time he came up with just such a quirky show and was excited about wowing the Fox executives at a screening. There was only one problem: as the sitcom was playing for the high-powered private audience, other than Mr. Diller and the show’s creator, not one of the stuffy suits was laughing. Dead silence filled the room.

CANCEL THIS DEAL!

After being told by a perplexed Mr. Diller that he already had signed a deal for Fox to buy 13 episodes of the show they hated, the executives turned apoplectic. It was ridiculed as a big mistake. “We can’t put this on the air,” one higher-up flatly stated, while another said there must be a way to cancel the contract for the 13 episodes.

Fortunately for Mr. Diller, Fox, and tens of millions of viewers, there was no way to undo the deal.

The show none of the Fox mucky-mucks thought was worth so much as a single giggle became the longest-running sitcom in the history of television: “The Simpons.”

Like the man said, nobody knows anything.

Except for Marge.

Bruce Apar is a writer, actor, consultant, and community volunteer. He can be reached at bruce@aparpr.co; 914-275-6887.