Funny or failure? It’s a fine line.

Imagine walking a tightrope. Your goal is to get to the other side without falling. Below you — certain death. Well, maybe not death. Maybe there’s a net to catch you, but it’s not a very soft net, and falling into it will certainly not feel good. That, says Will Burke, alumnus of Harvard College and nearly two-decade veteran staff writer, now director, for “Jimmy Kimmel Live!,” is what trying to be funny is like.

“The second you walk out on stage or you start to tell a joke, you’re walking a tightrope,” Burke said. “You’re betting on your timing, your point of view, and sometimes you’re putting your dignity on the line in the hopes that people will laugh.”

Making people laugh, both on stage and off, has been a lifelong pursuit for Burke ’99. His comedy career started as a class clown in the hallways of the New England prep schools where his father was a teacher, and continued on stage at Harvard with the improv group On Thin Ice and the Shakespeare troupe he helped found. Then it blossomed in Los Angeles, practicing with improv groups like The Groundlings and auditioning for acting gigs.

And while a career spent trying to be funny sounds like a dream for many, Burke said it’s actually been quite risky. There’s the risk of putting yourself out there creatively, the risk of crossing a line with a joke, and then, of course, the risk of not “making it” as a funny guy full-time.

“The biggest risk was taking my Harvard diploma in one hand and trading the ivory towers of Harvard for the dive bars of Hollywood,” Burke said. “I was turning my back on the pedigree and the connections.”

Burke knows a Harvard degree can get you far. But, he said, when he moved to Los Angeles after graduation in 1999, he also knew it wouldn’t get him on TV. He’d have to do the same open mics, auditions, and acting classes the rest of the aspiring comedians in LA were doing. And in the meantime, he’d be a bartender slash tutor slash cater-waiter slash comedian.

“I suppose in some ways, you could say for a Harvard grad it’s less risky to go try to do this thing, because if it doesn’t work out you’ve still got a Harvard diploma, and some doors will open to you in a different field. But once you’re 10 years in, 15 years in, starting over in a totally different career is risky too,” he said.

And 10 years, Burke said, would be all he gave it before accepting defeat and going back to the East Coast.

“As an actor, it took me, like, 150 auditions before I booked my first thing,” Burke said. “And at this point I had become a little jaded. I was like, ‘This is so annoying. I don’t even want this commercial. This is a terrible Taco Bell ad, who cares?’ And when you don’t care, then they’re like, ‘Oh, that guy’s great. He doesn’t care. He doesn’t need this job.’ They feel it. And so that taught me a lot.”

Besides booking some commercials, and some small roles on TV, after six years of auditioning and being rejected, Burke was offered a job back in Boston, working for a bank. He had a baby on the way, rising rent, and an income being stitched together through various odd jobs.

“I essentially, verbally accepted a job — I went down to HR and they photocopied my driver’s license and gave me the 401K package, what it would look like, and that whole thing. And I was like, ‘This feels like the most responsible thing to do. I have mouths to feed.’ And I could still scratch the itch in comedy clubs in Boston on the weekends, if I wanted. I kept trying to give myself a pep talk that I felt good about this — having a steady paycheck and a guaranteed career.”

Fate, said Burke, had other plans.

“Shortly thereafter, I flew back to LA and I got offered a job writing for ‘Jimmy Kimmel Live!’ And thank God I did. That was 19 years ago, and I’ve been there ever since.”

Since landing “Kimmel,” Burke said every day on the job, trying to be funny, is a risk.

“There were stressful days where I was convinced I was getting fired,” he said. “You’d see other writers get fired. I was like, ‘Oh, he’s not pitching stuff. Jimmy doesn’t like his stuff or her stuff,’ and then the next thing you know, that guy’s desk is empty. That’s real-world risk. There’s a lot of pressure to continue to produce stuff that lands and you’re trying to hit this moving target — the stuff that was making Jimmy laugh last week, he’s over it. Now that’s played out. Humor is like that.”

Asked about how he deals with near-constant rejection in the office, Burke said your feelings are always on the line.

“It’s impossible to not take things personally,” he said. But he added, there’s a trick to avoid getting too hurt.

“You walk into the room convinced that you are the absolute only person who could ever play this role, and you do your audition, and as soon as they say, ‘Thank you so much,’ you walk out of that room convinced you will never hear from them again and that you didn’t get it, so that you’re not disappointed. And it’s this weird game you play with yourself. Extrapolating that to the writers’ room as you’re pitching a joke, you stop caring what people think, because your nerve endings get frayed.”

In his personal life, Burke says his approach to humor errs on the risky side.

“Comedy can disarm tension. It can bridge divides. It can humanize a room, especially when you’re an underdog or an outsider,” he said. “Sometimes telling a dirty joke at a fancy dinner party is like, ‘Oh, we’re going there. Everyone loves a dirty joke, and now we’re all sharing dirty jokes, and it’s OK. This is an R-rated dinner.’”

But of course, there’s always the risk of the joke going too far. In a fictionalized scenario that definitely wasn’t him, he lays out the rule of time and place.

“Sometimes, in doing a joke, it goes too far, and you learn from it, but you have to go too far sometimes to know where the line is,” he said. “I know you thought it was super funny to come downstairs wearing a bra on your head at the party, but we’re at my friend’s house, and that’s his girlfriend’s bra, and you don’t know them.”

But overall, the chance of being funny, Burke said, well outweigh the risks of being embarrassed, or falling off the tightrope.

“It’s a dream job,” he said. “It’s what I envisioned doing when I was a little kid, and I’d see ‘Saturday Night Live,’ or even ‘The Muppet Show.’ The idea of, there’s a show going on, and there’s insanity backstage, and there’s a Stormtrooper and free chickens and Gonzo and things are crashing and the show must go on.”