How A Former White House Press Secretary Described Working For Barack Obama

When former White House Press Secretary Jen Psaki first met then-future President Barack Obama, she was so nervous about saying her opening line that she accidentally flung the contents of her purse — think pen, lipstick, and tampons — onto his lap. In the months that immediately followed, she struggled to feel any less awkward than that initial clumsy meet-and-greet.

Psaki detailed her time with the former president in her book "Say More: Lessons from Work, the White House, and the World," released in May 2024. The MSNBC host was still in her 20s when she started working with the former Illinois senator. Her memoir offers a unique perspective of the ex-POTUS, painting a portrait of a man who's both calm and assertive, empathetic and challenging, and lighthearted and serious.

"Obama is calm and cerebral," Psaki wrote (via People). "He didn't typically shout orders at staff (which made it that much scarier when he even slightly raised his voice). And when a staffer made a mistake, Obama's reaction often reminded me of my mother, who simply says she's 'disappointed.'"

Before she had a front-facing White House position where all of her awkward moments were caught on camera, Jen Psaki experienced most of her career stumbles off-screen. Months after her first meeting with Barack Obama where her personal belongings were strewn across his lap, Psaki tried to jump over a barricade at a campaign event and tore her pants down the middle. Psaki wrote in her memoir that the then-presidential hopeful laughed off the situation by joking that her clothing was rather flashy.

While working as Obama's traveling press secretary during his 2008 presidential campaign, Psaki made a much more significant mistake. As she described in her book, she and a group of reporters missed their bus while playing a game of pick-up basketball, causing Obama and the rest of the crew to wait over an hour for them to arrive for a scheduled flight. Psaki wrote that when she apologized to Obama, he replied (via People), "You are normally an A student, so I am going to let this one slide."

And indeed, it appears that he did. Years later, Obama appointed Psaki as his new communications director in 2015. "I fully trust Jen," Obama said in a statement (via The Columbus Dispatch). "I am thrilled she's agreed to come back to the White House as communications director."

From his hilarious coffee date with Jerry Seinfeld to the time he proved he could handle Anna Kendrick's sarcasm, former President Barack Obama has never hid his sense of humor or unfazed demeanor. But former White House press secretary Jen Psaki offers an even more nuanced perspective on the ex-POTUS in her memoir. Despite all the insecurities she faced as a young, green political staffer, she was grateful for her time with Obama.

"Sometimes you can be both inspired and intimidated by someone's public persona," Psaki wrote (via People). "He's legitimately brilliant and uniquely thoughtful in how he approaches big, challenging issues. You often had the feeling he knew not only everything you were about to tell him but also everything you were supposed to be telling him but hadn't had the time or high-enough IQ to learn. He holds his cards close to his chest."

Obama's all-encompassing presence isn't lost on his family, either. His wife, Michelle Obama, described his steadfastness on an episode of Hoda Kotb's "Making Space" podcast (via YouTube). "Barack has shown me his entire life that he shows up for us, for me and our daughters, for his friends, for our families," she said. With descriptions like these, it's easy to see why Psaki would have been simultaneously unnerved and motivated by his larger-than-life persona.