Introducing Michelle Obama and Her Mentees

September 15, 2020·14 min·1 clip

What is it like to have Michelle Obama as your mentor?

The episode opens as a crossover segment from The Michelle Obama Podcast, introduced to Without Fail listeners as an exploration of mentorship. Michelle Obama welcomes three women who began their careers working with her in the White House and have remained in her life: Kristen Jones, her former research associate and assistant of seven and a half years; Chyna Clayton, who interned in 2010 and became her body person and trip director in 2015; and Yenay Damptu, her hairstylist who joined the Obama world in 2009 at age 21 and later opened her own salon and business coaching program. Michelle frames the conversation as an examination of the mentor-mentee relationship from the mentee's perspective, building on a prior episode she recorded with her own mentor, Valerie Jarrett. Each woman describes the unconventional nature of her path and the family pressures she navigated. Yenay, a first-generation Ethiopian American, explains that her immigrant parents measured success by careers in medicine, law, or engineering, and that her father did not speak to her for three months after she relocated to D.C. to do hair instead of finishing college. Her mother eventually convinced her father that Yenay was financially stable and making something of herself. Kristen Jones describes how her mother found the White House internship through a mass email chain circulated in Black communities and pushed her to apply. Her parents supported the internship but struggled when she chose to build her own venture after leaving the White House rather than taking a high-salary institutional job. Chyna Clayton recounts leaving a stable position at Disney to become Michelle Obama's body person, crediting her mother's encouragement for giving her the courage to take the leap. Michelle Obama connects these stories to a broader theme about Black families being raised to prioritize stability — college, degree, job with benefits — and asks what gave each woman the courage to deviate from that path. Kristen reflects that she has always been willing to close her eyes and jump, but that growing more comfortable with failure over time has made her risk-taking more mindful and more successful. Michelle argues that parents who shield children from failure prevent them from ever taking chances, and that stumbling is a natural and necessary part of any successful path. Chyna describes how having a tribe and community behind her makes risk feel less isolating, noting that even if she fails, someone in her orbit will support her. She also reflects on spending her 20s at Camp David discussing childbirth and college tuition with Michelle Obama's friends rather than going to clubs, and says those eight years gave her wisdom she would not have gained otherwise. Kristen recounts the moment she was offered the job as Michelle Obama's assistant while cocktail waitressing in L.A., asking White House staff whether Michelle Obama actually knew who she was before accepting. She negotiated for an extra hundred dollars in salary. Michelle recalls that Kristen walked around the White House looking terrified the entire time, and that Barack Obama would ask what they were doing to her. The episode ends as a preview, directing listeners to Spotify for the full conversation.

As heard by us

A grounded mentorship conversation about career risk, family expectations, and moving before certainty arrives.

Mentorship comes through as practical career capital: the person who can help make a next step visible when family expectations, status, unpaid work, and private fear are pulling in different directions.

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Why you'd press play

Listen if you want a preview about how mentorship can reshape the next move in a career.

Read the full recommendation in PlayNext →

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