Kal Penn almost didn't get his White House gig because of one crucial mistake that a lot of job-seekers make, he said in an interview with Hello Monday, a podcast from LinkedIn, while promoting his new book "You Can't Be Serious."
At the time, Penn had just spent 18 months campaigning for then-Senator Barack Obama leading up to the 2008 presidential election. When it came time for the Obama-Biden administration to staff up, Penn didn't set himself up to go after a job with the White House, even though he really wanted it.
Rather than express his interest with anyone he worked with on the campaign trail, he decided to fill out an application online and see if he'd get a callback from a hiring manager.
"I'm thinking, 'well, I guess if I apply on change.gov, and if I'm actually qualified to work at the White House, then somebody will find that and they'll call me," Penn told Hello Monday. He was hesitant to leverage his connections to avoid the stereotype of being an entitled actor: "And so I filled out this very detailed form on change.gov, and hit submit."
Then, "nobody called."
While he waited, Penn felt as though he wasn't cut out for the job, even though working for the Obama campaign really inspired and motivated him, and he knew he played a part in its success. Then he heard of former campaign peers landing positions after applying online but also flagging their application to senior advisors with the transition team.
Still, it wasn't Penn's own self-advocacy that eventually landed him in the White House.
Instead, months later, Penn was invited to an inaugural event and brought along his Hollywood agent, Dan, as a guest — the only person he'd told about applying to the White House in the off chance he'd have to take a break from acting.
As Penn recalled, he got into a polite exchange with Michelle Obama, who thanked him for his work on the campaign and encouraged him to keep in touch, at which point Dan "just blurts out, well, you know, Mrs. Obama, he applied for a job."
"My face turned red," Penn continued, "and I looked at him and I was like, 'no, this is not the time to do that.' And she goes, 'What do you mean, you applied for a job? And he goes, 'Well, you're telling him to stay in touch and help out .... He applied on the website for a White House job.'"
While he can laugh about it now, Penn described Michelle Obama's reaction as "this look that unmistakably said, 'Are you really that stupid?'"
She then invited Barack Obama to join the conversation, who was also confused and poked fun that Penn would apply to the White House online but not pass along his interest to former campaign colleagues who could serve as references.
"That was the first time that clicked with me, where I thought I was doing the right thing and not shaking things up and keeping my head down," Penn told Hello Monday. In reality, Penn now sees that his lack of self-advocacy might have been perceived as a lack of interest in the job itself.
The big lesson for everyone, Penn said, is "you do need to advocate for yourself and let people know" what you want.
Given the time he already put in with the Obama campaign, "if I was serious about it, I should have made it known in a serious, professional way," Penn said. Thankfully, Penn's conversation with the Obamas, with Dan's help, opened a discussion about him finding a role in the administration.
By April 2009, Penn went on to serve in the Obama administration as the principal associate editor in the White House Office of Public Engagement. He became a co-chair of Obama's reelection campaign and in 2013 was appointed to serve on the President's Committee on the Arts and Humanities.
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