Things got a little morbid at SXSW London‘s headline Michelle Obama session on Tuesday.
The former first lady was speaking with her brother, Craig Robinson, at a live recording of their podcast, IMO with Michelle Obama and Craig Robinson. The year-old podcast usually involves a guest, but Obama kicked off the session by declaring they’d be “flipping the script” and, sans guest, would be interviewing each other.
The conversation was dappled with sibling banter, of course, as Obama teased her older brother over being a “finance bro” and his marriages, prompting audience laughter. It also featured moments of touching sincerity, such as when Robinson said his little sister “has been this personality since she was three or four years old.” They discussed how their mother’s death has made them reflect on the time they have left and what they want to do with it.
The conversation centered on Obama and Robinson’s respective professional journeys and the decisions that would shape their careers, from their parents to relationships and crucial life lessons learned along the way. On recently joining the podcast space, Obama, author of the best-selling memoir Becoming, told attendees: “It’s that courageous thing, right? The feeling that, ‘Okay, I guess we can do this, because we did all these other things.’ Bravery makes you try anything at any age. And I think, for me, I’ve just gotten used to, ‘Okay, we’re going to do this. I live in the White House!’ First Lady, that wasn’t my plan!” she declared, as the audience applauded, “but I think staying courageous and curious and open, and vulnerable and willing to share.”
She added about not fearing the career change post-politics: “I haven’t met a white man [who] talks about imposter syndrome.”
Robinson thanked their podcast team before praising his sister. “It really is a neat feeling, and every time we get together, it’s like a reunion. This has really been a pivot that’s been a whole lot of fun, and it’s really nice to hang out with my little sister,” with audience members “aww”ing. “And the most remarkable thing is I know how you guys look up to her… People get so emotional [around Obama], and I’m like, ‘Her?’”
Obama continued: “This is probably my last chapter from a career standpoint. I am 62 years old. We could be grandparents! But we are not.” She told a touching story about her mother, Marian, who died in 2024, and caring for her at the end of her life. “Even with her jaded, stoic approach to things, I was sitting with her on the couch watching TV and we had just come back from a doctor’s appointment, [we] didn’t get great news,” said Obama. “And we were watching Judge Judy, and she said, ‘Wow, that was quick.’ And I was like, ‘What are you talking about, mom?’ and she said, ‘Life.’”
“We’ve been out of the White House for 10 years, and I swear it went like that,” she added. “My daughters will be 28 and 25 this year. So, [for] this next chapter, I want to be mindful about it, so that it doesn’t just slip away. I want to be clear about how I’m spending my time, how much of it I’m giving away to others [and] what I’m choosing to do. How it makes me feel. The choices that I make now are going to be for me, not for my husband, not for my kids, not for the country, not for the world, because this is it. And at some point, it’s important for our generation to step out of the way and be prepared to step out of the way so that the next generation can really sit in these seats.”
Robinson joked that he was recently told he only has about 19 summers left in his life. “That’s a lot of summers!” said Obama. “But if I could impart any advice to you,” said her brother, “it would be: ‘Don’t sleep on this third act. Embrace the third act.’”
Obama concurred and said her biggest piece of advice for young people would be to relish the process. “Learn to enjoy the process, whatever your process is, because that’s where you develop the skills… [Getting to] the White House, it takes time. It took a level of persistence. There was a whole lot of backlash. Was I prepared for it? Was Barack prepared for it? Heck yeah — all the other things we had done, it leads up to being ready for the thing you don’t even know that you’re going to do.”
Early in the session, the siblings began by reflecting on their childhoods growing up in a working-class neighborhood in Chicago, and the experiences that led them on contrasting career paths. Obama confessed that, upon joining a corporate law firm following her time at Harvard Law School, she discovered: “Oh my god, I don’t like law. Thank you to all the lawyers, no shade,” she said, addressing the crowd, “but it just wasn’t for me.”
Robinson, a former pro basketballer and coach, lauded their parents — Fraser and Marian Robinson — for encouraging him to go to Manchester, England, to play for the Manchester Giants in the British Basketball League. “It wasn’t scary for me, because as I progressed in the sport and got better, it was the dream that, ‘Oh, okay, maybe I can play professionally,’ so I wanted to go try it,” he said. “And it’s a tribute to my parents that they never held us back because of their own fear. So, as scared as my mom was, they both were like, ‘Alright, go and do it, now’s the time to do it.’”
Obama chimed in: “I have to take a moment, just [to] give tribute to our parents. They were uniquely gifted in pushing us to do things that they wouldn’t themselves, and we’re parents now,” added Obama, who shares daughters Sasha and Malia with her husband, “and you know the hardest thing in the world to do is to let your kids try more things.”
Obama continued that their parents “did not feel like our lives were theirs to manage,” and that the hands-off approach to parenting allowed their children to figure out life on their own terms, whether it was “situations with teachers that were unfair, clashes with friends. And that’s very different from how people parent today. Everybody’s trying to curate their kids’ experiences [these days].”
Later in life, this would help Obama navigate her way through a major career “swerve” when she realized she no longer wanted to work in law. Her feeling was exacerbated by the death of her father in 1991, and as well as one of her friends, who passed suddenly from cancer. “If I were to die tomorrow, is this where I want to be?” she remembered thinking. “The 47th floor of a corporate firm — I could see the neighborhood where I came from my fancy office, but I wasn’t connected to it… And I also met Barack Obama at the time, who was the master swerver, because he did the opposite of everything he was supposed to do.”
It was at this time she learnt some life advice that Obama would go on to give to her own daughters: “Get used to living smaller than you need to, so that you can do the things you want to do when they present themselves. Living small, financially, allows you to stay free of the golden handcuffs.”
SXSW London 2026 runs June 1-6.
