Jay Shetty & Michelle Obama & Craig Robinson ON Breaking Generational Patterns

In this On Purpose episode, Jay Shetty sits down with Michelle Obama and her brother, Craig Robinson, a college basketball coach and executive.

They open up about their upbringing in Chicago, the family values that shaped them, and how the lessons they've learned still guide them today.

The siblings share childhood stories, from sharing bedrooms divided by plywood walls to navigating systemic racism and parental guilt. They tell Jay Shetty how resilience, humor, and deep empathy will remain an integral part of their emotional inheritance as they look ahead to the future.

Siblings Bond

Michelle Obama and Craig Robinson share with Jay Shetty one of the first secrets they ever confided in each other. For them, it wasn't just a moment, but it was a nightly ritual; they shared a single room divided by a makeshift plywood wall. At night, they would whisper through a crack near the windowsill, discussing the events of the day and many other stories, breaking bedtime rules.

The first real secret was when young Michelle Obama discovered the truth about Santa Claus. They had an unused fridge in their basement where she accidentally found empty boxes of the boxing gloves they had received the Christmas before. The discovery was their private realization that their parents were the ones who created the Christmas magic and not Santa. However, they kept the secret in order to maintain the joy for their family. This and many other shared experiences laid the foundation for their strong bond today.

Happy With Little

Michelle Obama and Craig Robinson's bond only grew stronger because they shared the room as children. Their nightly conversations about life helped them decompress and connect, even if some of the discussions were about insignificant topics. The siblings told Jay Shetty that their mother and grandfather established a nurturing home filled with love and creativity, despite having financial limitations.

The plywood wall, wood paneling, and accordion doors showcased their financial status, but at the same time also their resourcefulness and ingenuity. In spite of their constraints, there was warmth, safety, and humor that filled the house. Robinson notes that although they didn't have material wealth, they were rich in family and stability.

Independence and the Will to Move On

Michelle Obama and Craig Robinson shared with Jay Shetty the values that they acquired in their childhood home. To Robinson, it was his mother emphasizing the importance of independence. She encouraged him not to always keep an eye on his little sister, Michelle. However, he naturally took on the role of a protective older brother, which manifested in the form of walking to or from school or making long drives together.

To Michelle Obama, one value that stood out was the family ritual of constantly showing up for each other. Even during her time in the White House, she ensured that family was a priority and remained at the forefront of her life. Whether engaging in Easter egg rolls or traveling abroad, they always included extended family members. The principle that the family steps up when needed was embedded in their upbringing.

This powerful and intentional family connection played an important role in shaping identity and emotional strength.

Birthday Celebrations

An often overlooked reflection of family culture is the celebration of birthdays. Craig Robinson shares with Jay Shetty that they did celebrate birthdays, but they were not extravagant and grand. Big parties were a rarity for them. However, the occasions were celebrated with family, cards, and affection.

The former First Lady recalls the times when birthdays meant being surrounded by extended family. To them, it was their mother's seven siblings and all of their children. They often gathered at their grandfather's house, where traditions such as family dinners and singing Happy Birthday were community acts.

This approach to celebrating your birthday contrasts with the current trend of celebrating a birthday month. Michelle Obama recognizes how their mother's celebrations, surrounded by their loved ones, kept them connected to their roots.

Living in Fear

Craig Robinson and Michelle Obama opened up to Jay Shetty about the fears they've had to unlearn growing up. Robinson reveals his deeply personal fear of house fires. During the 70s, he witnessed several fires in his neighborhood, and because his father had suffered from multiple sclerosis, he would regularly practice carrying him out of the house in case of fire. Although his father felt humiliated, he let his son practice because the threat felt real.

Michelle Obama discusses a generational fear from living in an area of Chicago where black Americans were segregated. However, she explains that while overprotection from their family is understandable, it can hinder potential. Their parents actively fought against this cycle, encouraging them to step outside their comfort zones and do things their ancestors never dared to. Generational trauma can limit growth. However, their parents' approach created a space for possibility, rather than paralysis.

Racial Profiling

Craig Robinson shared with Jay Shetty how he was falsely accused of stealing a bike by a police officer when he was only 12. He had always wanted a specific bike, which he eventually received as a birthday gift. While proudly driving it around the neighborhood, a police car stopped him and confused his bike with twisted ties on the cables with a bike that was reported as stolen.

Robinson was then placed in the back of a squad car and brought home in tears, being very scared. Luckily, his mother fiercely confronted the officer, who ultimately let him go and apologized. However, this was a lucky occurrence because it was impossible to know what would have happened had the mother not been at home or advocated for him. To the police officer, it didn't matter that Craig Robinson was an articulate young man because bias still exists in society.

Today's Fears

The former First Lady shares with Jay Shetty that she no longer fears for herself, but for others, such as immigrants or people of color, or anyone viewed as not belonging. She explains that her status doesn't shield her daughters from racial bias and profiling, and her current fear stems from systemic racism rather than just individual incidents.

Similarly, Craig Robinson shares how he uses empathy to educate his teenage sons about the world. They live a privileged life in a secure suburb, which is nothing like his own experiences growing up. However, he aims to make them aware of the difficulties and challenges they may face. The siblings tell Jay Shetty that it is a heavy and emotional inheritance to pass on, one that must be handled with care rather than avoidance.

Michelle Obama and Craig Robinson cope with their ongoing fear by practicing reverse messaging, not letting fear distort the view of the world. Obama refuses to mirror the anger or judgment of others, and instead, aims to lead with compassion. The former First Lady emphasizes that effective communication is crucial. She shares stories, utilizes her platform, and encourages dialogues as methods to instigate change.

Raising Adults, Not Friends.

Michelle Obama and Craig Robinson shared with Jay Shetty the parenting philosophy instilled by their mother. She used to say, "I am not raising babies. I am raising adults." Craig Robinson clarifies that the idea of me time was not part of their parents' era. Parents focused entirely on providing their children with solid foundations for life.

The siblings agree that modern parenting often misplaces this emphasis and concentrates on making children happy rather than capable. Jay Shetty asserts that genuine love isn't about removing struggles, but about preparing children to face and overcome them. Michelle Obama explains that she allowed her daughters to fail, make mistakes, and take responsibility for their choices from an early age, and it has shaped them into independent and resilient young women.

Craig Robinson feels a sense of duty in honoring his parents and the sacrifices they made to raise him and his sister. While his coaching career is demanding, it has also helped him be a more present and engaging father. To Michelle Obama, discipline, unity, and structure are paramount in their household. They created a unified front when parenting because they believe in the importance of knowing the difference between cultivating independence and coddling.  While modern parents often equate love with control, genuine love empowers and enables a child to fail, bounce back, and thrive.

Therapy and the Survivor's Guilt

Craig Robinson admits to Jay Shetty that he was initially skeptical about going to therapy, as he saw it as not being for people like him. However, he later changed his view; now he supports his children going to therapy and sees it as vital for personal development.

Michelle Obama embraces both formal and informal therapy, from professionals to friendships to safe conversations around the kitchen table. She's currently in therapy to process her transition into the new life phase of an empty nester, and she embraces this transition season. However, she still struggles not to feel guilty when declining requests or doubting herself whether she's doing enough. She admitted to Jay Shetty that her therapist is currently helping her recalibrate her understanding of giving.

Craig Robinson opens up about experiencing survivor's guilt. Their mother used to tell them they were no different from any other children; they were just lucky to get the chance they had. He knows many kids who could have succeeded but didn't have the same support, which inspires his commitment to mentor, coach, and contribute to the community.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Michelle Obama and Craig Robinson: Break the Generational Patterns Holding You Back (How to Build Confidence, Responsibility, and Emotional Resilience)” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.