On the latest episode of IMO with Michelle Obama & Craig Robinson, former First Lady Michelle Obama appeared to hint that even those who seemingly “have it all” — like her husband, former President Barack Obama — may still feel unfulfilled.
The episode, which aired Tuesday, April 2, featured guest life coach Jay Shetty and centered on a heartfelt question from a 38-year-old listener named Adrian. Adrian shared that he’s single but hopes to settle down soon and start a family. His dilemma? Whether to take a career risk now or stick with stability to better support his future family.
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“When I do meet the right person at my age and knowing I do want a family one day, how should I approach this decision?” Adrian asked. “Should I prioritize my career, dreams, or financial stability and starting a family earlier in life?”
Michelle responded thoughtfully, admitting she herself hadn’t been much of a risk-taker. She followed a structured path early in life without questioning why. After a short break in the podcast, Michelle revisited Adrian’s question and offered deeper insight, telling Hello!
She encouraged listeners not to limit themselves with a “narrow view of what’s possible,” challenging them to think about their purpose rather than external markers like job titles and income.
“Don’t worry about numbers and titles because you can have all that. And I’ve seen people have it all and they’re still not happy,” Michelle said. “You know, he could have a big high-paying job, a great career, maybe he decides to get married, have kids, but then he’ll have no time for them, and then he’ll be disgruntled about that.”
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Her brother and co-host, Craig Robinson, then chimed in with a knowing, “Sounds familiar?” prompting Michelle to repeat the phrase, suggesting a possible reference to Barack Obama. While she didn’t elaborate, the moment sparked speculation.
Barack Obama served two terms as U.S. President from 2009 to 2017. The couple, married since 1992, have two daughters, Malia and Sasha.
IMO, Michelle Obama & Craig Robinson launched on March 12 and explores everyday questions about life, relationships, and the broader world. This episode offered not only advice for Adrian, but also a rare, candid glimpse into the personal trade-offs even the most successful figures might face.
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