In a Monday (April 28) episode of “On Purpose with Jay Shetty,” former First Lady Michelle Obama and her brother, coach and mentor Craig Robinson, opened up about the values that shaped them, the burdens of fear and the critical responsibility of investing in the next generation. Throughout their conversation, they reflected on their upbringing, the importance of family and wisdom received from their parents.
Michelle Obama and Craig Robinson on family, love and the lessons that last a lifetime
Michelle and Craig began by sharing childhood memories, including their “secret practice” of whispering to each other through a crack in the plywood wall that divided their shared bedroom. “We would spend that whole night just talking in between the walls, right? We were supposed to be asleep, but Craig could go, ‘Meesh, Meesh? Are you awake?’” Michelle recalled, laughing. Another early secret was their discovery that Santa Claus wasn’t real. After finding empty boxes in an old basement refrigerator, Michelle realized, “Mom and dad are Santa Claus,” but the siblings chose to keep the secret to avoid spoiling the magic for their parents.
Reflecting on core values, Craig emphasized the deep-rooted importance of independence and family loyalty. “There’s no one you can count on more than your siblings and your mom and your dad,” he shared. Michelle added that growing up surrounded by cousins, aunts, uncles and all four grandparents created a foundation of unconditional love and resilience. “Our house on 74th and Euclid was just brimming with love, conversation and trust,” she said.
Michelle Obama on overcoming fear, racism and why investing in the next generation is urgent
Beyond their reflections, Michelle and Craig also shared how these experiences inspired their newest project: “IMO (In My Opinion),” their own podcast where they aim to pass down life lessons and open up new conversations about resilience, empathy and growth. “We’re hoping that we can share some of these [lessons] with folks and learn some things from the people that we have on,” Craig said. “Just listening to her do that, this is the most fun I am having other than hanging with my kids and my family.”
The conversation also delved into the complex issue of unlearning fear — a mindset deeply embedded in their community during segregation-era Chicago. Michelle reflected, “Fear... kind of consumed some of our elders and stunted their growth.” She praised her parents for pushing her and Craig beyond those limitations, exposing them to new experiences to avoid the “smallness” that fear can create.
A particularly emotional moment came when Craig recounted being wrongfully accused of stealing his own bike by a Black police officer when he was just a young child. “He picks up my bike and puts it in the trunk of the car, puts me in the back of the car and says, ‘Where do you live?’” Craig recalled, later sharing how their mother’s fierce advocacy cleared his name. Michelle reflected on the what-ifs, saying, “You imagine you are just having a regular day, and your son is pulled up to your house in the back of a police car at 10 years old.”
In the present day, Michelle expressed fears not just for her daughters, but for all marginalized people navigating a world where bias can have devastating consequences. “We’re not gonna be able to count on the government — we’re not right now. It’s all on us,” she stated passionately. She urged the importance of reversing cynicism with empathy and storytelling, emphasizing that, “If they knew, they would understand.”
Above all, Michelle and Craig stressed the lifelong mission of good parenting — not for companionship or validation, but to raise compassionate, responsible adults. As Michelle powerfully concluded, “We sure as hell better be good at taking care of our kids ‘cause now we’re saying, “Well then, it’s all on us, and we can’t afford to get it wrong.’”