For Kal Penn, the biggest risks in his career began early. From roles in cult-classic films that found their audience over time to a position under President Barack Obama, each decision came without a guarantee but with the potential to change everything.
“I tend not to think there’s any point in having regrets. You learn from decisions you’ve made that you wish had gone another way,” said Penn. “I’m very glad that I failed numerous times and continue to fail, because it helps me get better at the things that I can then succeed.”
In front of a packed Cleary Lecture Hall on April 29, Penn used his unique professional and personal experiences to frame a broader look at risk, tracing a career that led him beyond film and into public service, which he chronicled in his memoir, You Can’t Be Serious.
Hosted by President Bryan Cain, Ph.D., and sponsored by Endicott’s Center for Civic Participation, and through generous support from alumna Arlene Battistelli ’60, the event drew students, faculty, staff, and community members for an engaging evening.
“His career reflects curiosity, courage, and a willingness to step beyond traditional boundaries, values we strive to instill in our own students through the Experiential Edge,” said Jason Galui, College Fellow for Civics at the Endicott Center for Civic Participation (ECCP). “Tonight, we have the opportunity to hear from someone who has not only navigated multiple worlds, but has done so with purpose, humor, and a deep commitment to civic engagement.”
After graduating from UCLA with a degree in sociology and a concentration in theater, film, and television, he set his sights on Hollywood. In 2002, he landed a breakout role in National Lampoon’s Van Wilder alongside Ryan Reynolds.
But the role was a stereotypical portrayal of a young Indian man, and Penn wrestled with whether it was the right opportunity to take.
“It’s doing things you don’t want to do and figuring out how to professionally navigate them,” he said, explaining that because of taking the role, he was able to book his next in the Harold & Kumar franchise. “In this particular case, I made this calculated decision, taking the advice of other people to see if it would move the needle. Over a period of 10 years, it seemed like it did so in my case.”
Penn soon nabbed roles on House, Designated Survivor, How I Met Your Mother, The Namesake, and, most recently, HBO’s Industry.
But for him, the biggest lesson wasn’t about landing roles: it was about knowing when to pivot.
One day, while starring on House, Penn recalled how co-star Olivia Wilde approached him with an extra ticket to a Barack Obama campaign event. After some cajoling—and after learning there’d be an open bar—he said yes.
After speaking with President Obama directly at the event, he signed up to volunteer with his campaign. That decision coincided with the Writers’ Guild of America strike, which came with a break from his role on House, so Penn had time on his hands to join another kind of house—the White House.
“For any of you who are interested in public service—if it’s a city council race, a mayor’s race, you know, anything, it doesn't have to be a presidential race—the [roles] all start really small,” Penn said. “Especially if you’re an underdog candidate, and if you start volunteering or working for somebody, and they do well, their campaign grows in concentric circles, and you end up getting trusted to do more and more.”
From 2009 to 2011, Penn served in the Obama/Biden administration as the President’s Liaison to Young Americans, Asian Americans and Pacific Islanders, and the Arts community. He also worked on teams focused on issues including the repeal of Don’t Ask, Don’t Tell, the Affordable Care Act, expansion of Pell Grants, the DREAM Act, and rapid response to the BP Oil Spill.
Navigating public service was a risk, Penn said, because it meant stepping away from a stable career he’d worked hard to obtain.
“I just sort of said, I think it’s important for me, just my own ethics and morals, that I want to test this out,” he said.
When asked by President Cain how young people can stay engaged rather than apathetic about civic life, Penn encouraged simple yet powerful actions, such as writing a letter.
He advised students to organize collectively and create formal letters on behalf of groups or organizations. Those efforts, he noted, carry more weight—especially when backed by multiple voices—and are more likely to be seen, tracked, and taken seriously by elected officials.
“Moving the needle in your local community is still very possible,” he said. “They don’t want you to show up for a protest. They don’t want you to write the letter. That stuff actually goes a really long way, and it helps you build coalitions with people in your own community.”
While civic engagement led the conversation, another question was impossible to ignore: are Harold & Kumar due for another film?
Possibly, Penn said, noting that the studio behind Harold & Kumar has already commissioned writers to begin a fourth script.
“I hope that we get to shoot it,” he said. “We really want to make it. I’d be super excited to make a fourth movie. I have a note on my phone for cameos from people we’ve basically met over the years who have told us that they were fans of the franchise.”
Those fans? Snoop Dogg, Usher, Post Malone, and even his former boss, Barack Obama.