Bozoma Saint John wears her flair on her sleeve: beads, rhinestones, gold accents; you name it, she's got it. As for the clothes, there is no color too bold, print too loud or silhouette too challenging for Uber's Chief Brand Officer to try. On traditional executive uniforms, she asks with genuine wonder in her voice, "Who made these rules, and why do we listen to them?"

But there's more to Bozoma Saint John than the impressive way in which she carries herself, the seemingly effortless confidence that she holds and espouses, the degree to which she believes in herself and wants to be the best, do the best and perpetuate the best: She is also incredibly empathetic. You almost get the sense that she's lived multiple lives, and this is why, for whatever reason, when she speaks to you, it is almost like she is speaking directly to your soul.

Please enjoy a very candid conversation in this week's episode of Monocycle. There's a bit of everything: advice for the grieving, a sound way to reconcile hardship, how she has become such an unflinching cheerleader for herself (and how, too, we can learn from this), and a little something about the persistence, reliance and beauty in the way the sun rises, day in and out. Just like, you know, we do.

Ep 62: A Conversation With Bozoma Saint John

A ten minute digest from author, humorist and creator of Man Repeller, Leandra Medine. New shows published weekly. 