It was the night before the CS50 final project was due, and Nikhil L. Benesch ’16 was in high demand. In his first semester at Harvard, Benesch had already skipped CS50, the intro-level computer science class, and advanced to more challenging material. His freshmen friends had—predictably—come begging for help. The mood was buoyant as the adrenaline-addled group coded into the final hours before their deadline.

“Oh my god, this is going to make us rich,” Benesch, a Crimson Tech Associate, remembers kidding. This was part grandiloquent team-building, part jab at his buddies for finishing so shoddily and so close to the deadline.

They’d gotten the joke. “Guys, this is it,” someone had retorted. “We should drop out of Harvard for this.”

It was one of those jokes that is only funny because everyone knows there’s some truth beneath the absurdity. Describing the scene, Benesch breaks into a laugh and then stops, suddenly serious. “But it’s never been quite a joke for me,” he says.

Benesch is hardly alone.

Maybe it’s a fluke, or maybe it’s some secret entrepreneurial ingredient, but Harvard has a knack for churning out dropouts armed with the seeds of the Next Big Idea. First there was Bill Gates, slated to graduate in 1977, who left Harvard to found Microsoft and reinvent the cyber world. Then came Mark Zuckerberg, who dropped out in 2004 to found Facebook, reinventing computer culture all over again.

The Computer Science faculty doesn’t take that legacy lightly. Gordon McKay Professor of Computer Science Harry R. Lewis ’68, who has been at Harvard since 1964, first as an undergrad, then as a grad student, and finally as a professor, has taught Gates, Zuckerberg, and several more recent entrepreneurial dropouts.

“I always encourage students who have a burr under their saddle to take time off and deal with it,” he writes in an email. “They can come back to school any time, but they will have a lifetime to regret not seizing an opportunity that presented itself.”

In Lewis’s experience, most undergrads who drop out return to Harvard. The University makes it simple to return after taking time off, Lewis explains: Harvard allows students to take semesters off without any effect on their financial aid packages.

“It virtually never happens that people fail and never return,” he writes. “And even people who succeed tend to return.”

That’s what Meir Lakhovsky did. An Advanced Standing degree candidate in the Computer Science Department, Lakhovsky stayed at Harvard for five semesters, until he left in 2010.

“I loved the school!” Lakhovsky says. “I never thought I’d leave.” But during his junior year, Lakhovsky began working on PushPage, a social media tool that allows users to create and share question and answer sessions. His 80-hour-per-week commitment to the startup proved incompatible with a full course load. “My friends thought I should stay in school and wondered why I couldn’t work on my business later,” Lakhovsky says. “But with startups, timing is everything.”

A programmer (a.k.a. efficiency guru), Lakhovsky was frustrated by the bureaucracy that he says slows down Harvard life. But leaving Harvard required only one signature on one form. “Taking time off was the easiest thing I did at Harvard!” he quips.

This fall, Lakhovsky took three classes at Harvard—enough to earn his degree. He says he has no regrets about the decision to leave when he did.

Unlike Lakhovsky, Daniel E. Windham ’15 came to Harvard intending to drop out. The biographical blurb on Windham’s Twitter account reads, “Officially I’m #cs #neuro @harvard, but will probably have left to start a company before I make it to junior year.”

He did. During the finals week of his first semester, Windham stumbled upon an idea he says he can’t disclose yet. “I went, ‘Oh my god I have to do this!’” he recalls. “The longer you wait, the more likely it becomes that somebody else will do the same thing.”

Windham soon realized he lacked the technical skills to jump straight into his own startup and joined a different business called Athena. “The technical abilities you learn in CS50 are not the best for building distributed software,” he says. “A good metaphor is learning English grammar versus learning to write well,” he clarifies. “A class on Shakespeare is not the right place to learn predicate-noun agreement.”

Windham’s complaints about Harvard go beyond his academic experiences. He says it’s a question of the school’s mentality. “I was frequently fighting the cultural bias at Harvard that there was one correct path, one way by which one figures things out, one optimal strategy,” he says. Windham adopts a mock-heroic baritone to play-act as the institutional voice of Harvard: “‘Look, you’re going to focus on your classes.’”

“The problem is,” Windham says, “I didn’t think the most useful thing I could be spending time on was my classes.”

That’s a view to which Benesch, the not-so-facetious potential dropout, can relate.

“I’d like to get out of here,” Benesch says. “It’s weird. Classes don’t have that much real world value. There’s this ideal of a liberal arts education, but I’ve always found coding more enjoyable and meaningful. It’s the best way to create something. I can’t paint, I can’t write well, but I can sit down and solve problems.”

Does that mean that he is ready to leave New England for warmer climes and higher stakes? Not quite yet.

“I’d leave Harvard for the right idea,” Benesch says, and then catches himself. “See, there’s this signaling effect. For better or for worse, people see the Harvard degree and assume you must be great.”

If you’re looking for a job at a big company, that is. But Benesch can’t stop gushing about starting out on his own. “I’m not sure you’re getting what’s profoundly exciting about this,” he says. “Are you getting what’s so exciting about this?”

“You could literally go anywhere in the world, and all you need is your laptop,” he says, waxing lyrical. “Whether you eat depends on the code you write. Every day everything’s on the line.”

This article has been revised to reflect the following correction:

CORRECTION: March 10, 2013

An earlier version of this article misquoted Daniel E. Windham ’15 as saying he believes that the skills learned in CS50 are “not the best for building distributable software.” In fact, Windham referred to “distributed software.”