Obama Reveals The Biggest Challenge Raising His Daughters (& It's Not What You'd Think)

Since Malia and Sasha Obama spent a chunk of their childhoods in the White House, Barack and Michelle Obama dealt with some uncommon challenges as parents. When their daughters were small, their main goal was to keep things normal. Some of their strategies included giving Sasha and Malia reality checks by making them do chores like setting the table and picking up after themselves. During the 2008 election campaign, Barack informed People that he was also checking in with his daughters emotionally, "monitoring whether or not they're feeling sad or neglected at all, that they're also not feeling special because their dad is running for President."

However, now that his daughters are grown up, Barack believes their efforts to keep Malia and Sasha grounded may have worked almost too well. "The challenge for us is letting us give them any help at all," Barack explained on "The Pivot Podcast" in October 2024. "They're very sensitive about this stuff. They're very stubborn about it." For example, when Malia wrote and directed "The Heart," her first film, she opted to omit her last name onscreen. While Barack told Malia that people would be aware of her identity regardless, her goal was for audiences to judge the film on its own merits. "I think our daughters go out of their way to not try to leverage [their name]," Barack added. Unfortunately, Malia did get some negative reactions, but the Obamas are well aware their adult daughters have to stand on their own decisions.    

When Malia and Sasha Obama were kids, Michelle Obama was focused on fostering their autonomy — a parenting precept she got from her own mom, Marian Robinson. Robinson forged a tight relationship with Malia and Sasha when she lived with the Obamas during their time in the White House. According to Barack Obama, Robinson didn't hesitate to intervene if she thought her granddaughters' behavior was overly self-important. "Everybody was on watch to make sure that they both had a normal childhood and that they did not feel as if they got something that they hadn't earned," Barack informed "The Pivot Podcast."

Even so, Barack sometimes had a hard time adjusting as his kids grew up and were ready to leave home. When Malia was graduating high school, he candidly admitted he would be too emotional at the event to give a speech. "She's one of my best friends, and it's going to be hard for me not to have her around all the time," Barack explained on "The Ellen DeGeneres Show" in 2016.

Now that Malia and Sasha are living on their own and making adult decisions, Michelle has also acknowledged that it can be difficult to take a step back rather than give in to an impulse to protect her daughters. "There are no guarantees that their life is going to work out and something bad may happen. That is the hardest thing about parenting, is living with that truth," Michelle divulged to NPR.