Michelle Obama: “Am I Good Enough?” Mental Health Struggles in the White House & Beyond

Here are the top 10 key takeaways from Michelle Obama and Craig Robinson's illuminating conversation with Lewis Howes on mental health, confidence, and finding purpose in both extraordinary and ordinary circumstances.

1. Parental confidence coaching

Michelle and Craig's parents practiced what they call "coaching confidence" long before it became popular. Their parents built their self-esteem by consistently reflecting back positive qualities they saw in their children. This was contrary to the prevailing parenting approach of the time, which often focused on criticizing children to "toughen them up."

Their mother would stop whatever she was doing to teach them new skills when they showed interest. She taught Craig to read at age four when he asked how it was done. Their parents celebrated their achievements, no matter how small, creating a foundation of confidence that helped them navigate challenges later in life.

2. The basketball character test

Michelle used basketball as a way to assess Barack Obama's character early in their relationship. Growing up in a basketball culture, she understood that pickup basketball reveals important aspects of someone's personality. She asked her brother Craig to invite Barack to play with him to see if Barack was as good a person as he appeared to be in social settings.

Craig observed that Barack called his own fouls fairly, took open shots but also passed when appropriate, and didn't just pass to Craig because he was Michelle's brother. These qualities showed Michelle that Barack was honest, fair, and authentic - the same person on the court as he presented himself to be off the court.

3. Finding balance in the White House

Michelle and Barack maintained their mental health in the White House by staying emotionally level. They didn't get too excited about the highs (meeting world leaders, visiting historic sites) or too devastated by the lows (comforting victims of tragedies). This emotional regulation was essential for surviving the intense scrutiny and pressure.

Their children provided grounding and normalcy amid the extraordinary circumstances. The girls' everyday concerns and activities - from school to friends to sports - reminded Barack and Michelle what was truly important. Barack even coached his daughter Sasha's basketball team, the Vipers, which became an important stress reliever and connection point with his children.

4. Overcoming impostor syndrome

Michelle experienced significant impostor syndrome when she attended Princeton. With good grades but not exceptional standardized test scores, she questioned whether she belonged there. This feeling was reinforced by others who suggested she was "aiming too high" or only admitted because of affirmative action.

Once at Princeton, she realized the myth of elitism - that many students were there for various reasons beyond pure academic merit. She saw that she could succeed at this elite institution, which helped her recognize that the messages suggesting she didn't belong were false. This experience helped prepare her for similar criticisms during her time as First Lady.

5. Managing criticism and praise

During their time in the White House, Michelle learned to filter information to avoid being affected by either extreme praise or harsh criticism. She worked with her communications team to receive only objectively important information rather than immersing herself in all coverage.

Michelle advises young people to "never read the comment section" because absorbing too much feedback - positive or negative - can cloud judgment and affect the quality of one's work. She focused instead on the effectiveness of her programs and initiatives rather than on personal commentary about herself or her family.

6. The value of small spaces

Growing up, Michelle and Craig shared a single bedroom in a small apartment until Craig went to high school. Their parents chose this modest living situation so their mother could stay home with them, prioritizing parental presence over material possessions or space.

This upbringing taught them that "home is about who's there, not where we are." This perspective helped Michelle when facing the daunting prospect of raising her family in the White House. Even in that enormous, formal building, they created closeness by gathering in small spaces, particularly the kitchen - just as most families do regardless of home size.

7. Parenting strategies for privileged kids

Both Michelle and Craig emphasize teaching their children the value of money and hard work despite their privileged positions. They maintained boundaries and discipline, avoiding giving their children everything they wanted. They gradually increased their children's independence while still providing guidance.

For Michelle's daughters in the White House, she focused on helping them maintain normalcy despite extraordinary circumstances. She gave them increasing responsibility each year to prepare them for independence. Barack attended every parent-teacher conference and coached his daughter's basketball team to stay involved in their everyday lives.

8. The importance of therapy and self-reflection

Michelle reveals that even now, at 61, she sometimes struggles with the question "Am I good enough?" She works with a therapist to address these feelings, recognizing that if she can't feel "good enough" after all her accomplishments, she likely never will without intentional healing work.

She notes that the intensity of her years in public service left little time for reflection. Only in recent years has she been able to unpack the emotional impact of her experiences in the White House. This healing work has allowed her to feel more confident in herself and her choices than at any previous point in her life.

9. Maintaining authentic relationships

Craig describes how his family tried to create moments of normalcy when visiting the White House. They brought the familiar feeling of family gatherings in Chicago into the presidential residence, providing Michelle and Barack with a connection to their pre-White House lives.

Michelle valued having her brother nearby because he maintained his joyful, authentic self regardless of the setting. She appreciates Craig's ability to approach each situation with wonder and optimism, a quality she finds especially valuable given the cynicism that can accompany high-level political work.

10. Defining greatness through impact

Both siblings define greatness in terms of positive impact rather than personal achievement. Craig describes greatness as "the ability to both have an impact on your own life and on other people's lives," emphasizing the importance of inspiring and developing others.

Michelle defines greatness as "giving more than you get," suggesting that individual accomplishments mean little without contributing to the greater good. She believes true greatness comes from putting positive energy out into the world and helping others, rather than accumulating personal success or material wealth.