Sometimes attorneys face a pre­cedent that makes it challenging to succeed. Jonathan Goldstein ’95 knows this well. In his case, the precedent was more than 30 years old but still held great influence among people he was trying to persuade. His strategy? Well, it was pretty much what he tries to do in every case.

Be funny.

Over the summer, Goldstein made his directorial debut with the movie “Vacation,” a sequel to the popular 1983 comedy “National Lampoon’s Vacation.” The new film, which he co-wrote and co-directed with his longtime writing partner, John Francis Daley, marks the most high-profile effort yet for Goldstein, who began writing comedy, initially for TV and later for films, shortly after his HLS graduation. For “Vacation,” he wanted to make a movie that stood on its own yet was respectful of the original version for the many people who have fond memories of the Griswolds’ misadventures on a family trip.

“It’s a lot of pressure. We knew that going in,” said Goldstein. “For a lot of the audience, they come in wanting to hate it. You’re so nostalgic about something from your youth and you love it so much, you feel like, ‘This can only be worse.’”

But he approached the assignment—including directing established stars like Ed Helms and Christina Applegate, and the stars of the original version, Chevy Chase and Beverly D’Angelo—with the confidence that propelled him to Hollywood in the first place. He had always loved comedy, having grown up devouring Monty Python, Woody Allen and the Marx Brothers. Yet he had no idea how to channel that interest into a career. Instead, he went to Harvard Law, which was like a life insurance policy, he said—a way to acquire a marketable skill.

That seemed to work out when he got a job with a six-figure salary at a large New York law firm. But he soon realized that his interest lay elsewhere, particularly when he heard that his friend Ted Cohen ’95, with whom he had written humorous columns for The Harvard Law Record, had landed a writing gig on the hit TV show “Friends.” So Goldstein quit his job in 1998 and ventured to Los Angeles, where he read scripts for agencies for around $400 a week with no benefits. As dubious as that career move may have appeared, he soon progressed to write for TV sitcoms, and then later sold film scripts he co-wrote with Daley, including “Horrible Bosses,” “Cloudy with a Chance of Meatballs 2,” and “The Incredible Burt Wonderstone.” Now he is in talks to write and direct a sequel to “Vacation,” as well as to write a new film in the Spider-Man franchise.

In some ways, his unconventional path helped propel him to success in the entertainment industry. His time at Harvard Law, he said, “gave me confidence to think that if I could do this, there’s no way I couldn’t do other things like working in Los Angeles in film and television.” Even his time at the law firm inspired him to write the character Kevin Spacey played in “Horrible Bosses,” loosely based on some partners at the firm.

People in comedy generally aren’t big on teaching valuable lessons. Famously, the motto for the classic sitcom “Seinfeld” was: No hugging, no learning. But when Goldstein reflects on the winding journey that eventually took him to a place he always wanted to go, he offered some advice:

“Look deep inside and forget about money for a minute and [ask] that guidance-counselor question, If you could do anything, what would it be? And then find the job that lets you do that. That’s the only path to happiness.”