
24 segments available
Michelle Obama served as the First Lady of the United States, entering the White House alongside Barack Obama. In this candid conversation, she joins Steven with her brother Craig Robinson, a former college basketball coach turned executive, to open up about everything from Trump’s inauguration to marriage challenges, grief, and rediscovering her purpose. Together, they discuss: * How their parents instilled empathy, discipline, and resilience growing up amid racial tension. * Michelle’s journey through elite schools and corporate law, driven by a need to tick society’s boxes. * The evolution of Michelle and Barack’s relationship, from colleagues to lifelong partners. * Fertility struggles, parenting tips, and what it really takes to sustain a long-term marriage. * Navigating life in the White House, grief, personal boundaries, and rediscovering her true calling. 00:00 Intro 02:01 Michelle and Craig's Childhood 04:38 Values Learned from Their Parents 08:35 Michelle Skipping Second Grade 12:06 The Role of Race in Their Childhood 15:09 What "White Flight" Means 16:50 Coping with Racism 20:45 Overcoming Being Underestimated 26:23 Michelle's Search for Identity 30:10 Meeting Barack 31:49 Introducing Barack to the Family 33:38 Why Michelle Initially Rejected Barack 37:18 Michelle's Career Change: Pursuing Joy 40:41 Relationship with Barack 44:46 Couples Counseling with Barack 49:23 Pregnancy Struggles 56:16 Hardest Moments in Their Marriage 57:20 Barack Obama Runs for Public Office 01:03:18 What I Should Have Said to Barack 01:07:00 Being the First Black First Lady and Facing Scrutiny 01:15:06 Remembering Your Mother 01:16:42 The Death of Your Mother 01:18:25 Processing the Grief 01:20:31 Not Attending Trump’s Inauguration Listen to Michelle & Craig's new podcast IMO: https://bit.ly/3YnxIUg Follow Michelle: Instagram - https://bit.ly/3Ymxs7W Twitter - https://bit.ly/4cYXiVC Follow Craig: Instagram - https://bit.ly/4lThkVB Twitter - https://bit.ly/4lTGJ1f YouTube: You can purchase Michelle’s book, ‘Overcoming: A Workbook’, here: https://amzn.to/4jTqcsi (UK) / https://amzn.to/3SbbelM (US) Think like a CEO - join the 100 CEOs newsletter: https://bit.ly/100-ceos-newsletter The 1% Diary is back - limited time only: https://rebrand.ly/r0ogao4 The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb Get email updates: https://bit.ly/diary-of-a-ceo-yt Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb Sponsors: Airalo - https://try.airalo.com/TheDiaryOfACEO with code DOAC3 Vivobarefoot - https://vivobarefoot.com/DOAC with code DIARY20 for 20% off
"People in power who haven't understood their why can lead us down some dark tunnels. We are in a really tough time right now. The one and only Michelle Obama, the former first lady, and her brother Cr..."
"know about your earliest context to understand the adults? And I use that word intentionally because I know that's what your your parents were intent on raising. The adults that are in front of me tod..."
"foundational values. Mhm. What were those foundational values that you learned in that location? And how did your parents teach you those foundational values? And I asked that with great curiosity bec..."
"not be the ones that were going to solve it. And I and this came in very handy when you're a kid in public school because you know in public school south side of Chicago teaching was kind of uneven. Y..."
"race. One of the um startling things with these two photos Mhm. mainly because I think it's this way round but um this is I believe what second grade or something that was first grade. first grade and..."
"anyone that doesn't have context on white flight, what is white? It's the sociological occurrence of what happens in communities when black people sort of start making their way up socioeconomically a..."
"moving through it. How do you stop it getting to you? One of the remarkable things I noticed even when we spent some time together yesterday was there is no apparent bitterness. And there's one would ..."
"it's a word that I saw throughout your book and it's a word you you mentioned a second ago. You knew you were going into an underestimated world, if I can call it that, a world that was going to under..."
"on is is really really remarkable for so many reasons, but it's also remarkable for the pivots along the way. And um I was reading about a bit of an identity crisis that you had when you were 27 28 ye..."
"opposite of a box checker, but somebody I describe in in my book as an ultimate swerver. He did nothing by the book, but he was brilliant and interesting. You know, he didn't go to law school right aw..."
"heard that your little sister had met a guy called Mr. Obama? Well, she called it called me up and said, "Hey, I met a guy. I want to bring him by." And my mom, my dad, and I were sitting on our front..."
"Yeah. Because he uh Barack was I I was assigned to be his advisor. And that didn't mean I was his boss, but every I was a first year associate. So they tried to pair first years sort of wi-i with new ..."
"through your story of ticking the boxes. Mhm. And then eventually it's kind of what we were talking about yesterday on your show where if you have sometimes your preconception has to fail you. Yeah, t..."
"And at that time in your life, you know those early 30s, what's what's going on with um Mr. Obama? Oh, by then he was uh he had written his book because he was the president of the Harvard Law Review...."
"Brock. What does someone like me at 32 years old who is in a relationship, who is aggressively pursuing a career because I feel like I've got to build and build and build and set my family up for the ..."
"You had some pregnancy struggles. Yes. And I I've spoken to many women on this show who have been through similar pregnancy struggles. And it's something that I've it's actually a big conversation in ..."
"Was there ever a moment where you thought, you know, there are the moments where I'm like right, but it was it real? No. No. No. There's there was never really a full moment. There were moments when I..."
"a decision that former President Barack Obama decides to make, which is to run for public office. And that is has a profound impact on both of your lives because it's the most powerful job in the worl..."
"What should you have said? Oh. Um, I should have said that I needed his team to really truly value that he had a family, you know, that I I shouldn't have just said, well, this is what it takes to get..."
"first lady in the White House, the public scrutiny that that comes with is a unique type of scrutiny. Mhm. Being the first lady anyway comes with tremendous scrutiny. Absolutely. Since stepping reluct..."
"Marian, your wonderful mother, she was a prominent figure throughout that time in the White House. Oh, yeah. What did she give you that helped you through that journey of being thrust into the very ve..."
"the family? It's 2024, so it's fairly recent. Yeah. Yeah. It's still it's still painful. Um but, you know, I'll go back to what I I said at the very beginning when you talked about the values we had. ..."
"I'm sure I have more than he does cuz he doesn't process stuff. He just keeps working through it. But yeah. Yeah. I I think I've I pro I for me um making choices for me. I feel like now I have permiss..."
"Yeah. I was watching the coverage over your decision, your decision to sort of take back some of your control and not go to Trump's inauguration. Uhhuh. Is that one of those key moments in your life w..."