In this interview, Bozoma Saint John sits down with Lewis Howes to discuss how to live a fulfilled, driven life without waiting for perfect healing or following conventional, linear advice. Bozoma shares personal anecdotes—from her early days as an assistant to Spike Lee’s agency, to a memorable car‑service ride that sparked a deep sense of satisfaction—illustrating that one can feel content while still holding big ambitions. The conversation explores the paradox of being driven during dark times, arguing that emotions like grief and joy can coexist with ambition. Bozoma challenges the “one day at a time” mantra, urging listeners to embrace messiness, unpredictability, and the freedom to be multiple things simultaneously. She emphasizes that there is no single prescribed path; individuals can heal, pursue goals, and laugh all at once, rejecting external expectations and embracing a personal, fluid mindset.
Chapters
This idea of like waiting to heal before you do the thing, that's the opposite of living the urgent life. You know, because if you're constantly waiting until you are healed, I think you.
Gotta have a dream.
The School of Greatness.
Really?
Yeah. Please welcome Lewis Howes.
I'm so excited about this because you've had such an amazing life and multiple careers in multiple industries at the highest level as, you know, head of marketing at pretty much every major company that people have ever heard of. So you've been around the block in life, you've been around the block and experiencing a lot of injustice in the world, but also injustices in relationships, heartbreak, pain, suffering, and also great success. So you've experienced a lot of great things while also dealing with dark times. And the first thing I want to ask you is how is your heart?
Wow. That's how we started out. Well, you know what? Maybe it's no coincidence, right? There's a heart on the COVID of my book.
Yes.
My heart is really good right now. It's really, really good. I feel very full in my life that there is so much that, like you said, I've accomplished. That makes me feel proud. There's so much that I have to look forward to in the future that I'm really excited about, even though it's unknown to me. I don't have a plan, you know, but I feel really excited about it. I feel satisfied with like where I am, the age I'm at, the things I've done. I feel good. I feel really, really good.
Most people never feel satisfied, right? They don't feel satisfied in their career or the relationships or even if they've been successful, how much success they've had, they don't feel that fulfillment and satisfaction. Why do you think you've come to a place of satisfied while at the same time you're not clear of what you're gonna step into next?
Yeah. You know what? You just actually said something that brought back a memory. Because I don't mean to sound corny about it, but I think I've always been satisfied with where I am. It doesn't mean that I don't have ambition. I've been very ambitious. I think you just look at my resume and you're just like, oh yeah, this ambitious person. But I've always felt very satisfied. And what you just brought up for me, the memory you just brought, is that I remember it was probably 2000, maybe 2001. I was in New York City. I was the assistant to Spike Lee at his advertising agency, Spike DDB. And I had just moved from Connecticut where I had spent an extra year after graduating from college. And I was trying to figure out what to do. I was like trying to stave off medical school 'cause that's where my dad wanted me to go and da, da, da. And I was, you know, grabbing coffee and making copies and just trying to stay out the way in the office basically, go where I needed to be. But it was such a dream to be in New York and riding the subway and like sort of independence and trying to figure it out. Didn't have money to do anything. Nothing, nothing. No money at all. and I was working late one night and that was really late, like nine or 10 o'clock, I was still in the office. And I remember the office manager said I could take a car service home instead of riding the train, 'cause I lived in Jersey City and, you know.
It'S a long night.
Yeah, I'd take the subway to the path train, cross the water, and walk home.
It was an hour, something.
Oh man, it was treacherous. And so I got a car service and it was one of those black cars. You know, and I sat in the back, and it was my first time, like, you know, having a nice car. -In a nice car like that, where I had a driver, and they were like, are you-- you- know, at that point, I was unmarried, so are you Miss Arthur? And I was like, yes. You know, and I sat down, and he's driving, and I remember rolling down the window and just like being like, God, life is really good. -Wow. -Life is really, really good, you know, and feeling very satisfied in that moment. It didn't mean that I didn't have ambitions of one day ruling the planet.
Yeah, sure, yeah.
And having car services every day, whenever I wanted. You know, but I do remember, you just reminded me of that moment feeling really satisfied. So even as I sit here today, I still have big dreams, big ambition. I don't know where it is I'm going, but I feel very, very satisfied with where I am.
That's beautiful.
Yeah.
I'm curious about you're a very driven person. You've shown that over your whole career, right? In your life, overcome a lot of different challenges and adversities and the first time in so many different ways. When someone is going through a dark time and however that looks for them, a breakup, a death, a letdown, any type of dark time in their life, is it possible to keep being driven in your career and your goals and your dreams when you're going through sadness and darkness and grief and loss without also being able to heal on the process. Can you heal and be driven at the same time? Or is it only you can be driven because you're masking the pain and the suffering and you're not actually addressing it? Is it possible to do both, be driven in the darkness.
Yeah, but that's what's so beautiful about this experience in life, right? Is that like, we don't have to be one dimensional, that all things can be true at the same time. You know, it's the reason why it's like, I remember once shortly after Peter had died, I was sitting with a friend and she was telling me a story and I started laughing hysterically, you know, it was like, yeah, it was like from my belly, you know, the kind of laugh that makes you want to fall over and slap something, you know, that kind of laugh. And then almost stopping short because I was like, oh, I'm supposed to be sad. You know, I'm not supposed to laugh like this. The truth of the matter is that life, isn't that what life is? You know, even when you're grieving, you can have belly laughs that take you out of that pain for however long that is. Maybe it's a second or maybe it's five minutes or maybe it's a few days, you know? So like, if you're in a dark place, can you still be driven? Of course you can. you know, it's not a constant either though, you know, where like being gentle with yourself and knowing that like even when you're in the darkness there will be times when you don't feel like getting up. But it's not forever, you know, or to feel badly that you're driven even though you're going through something, you know, so like even when yeah, it was.
Like.
When I decided to move from New York and take the next job, and people were like, Shouldn't you be in a cave somewhere, crying your eyes out? You know, like, why are you so ambitious? Sit down. You know? And yeah, I did question myself too. Like, why am I not sitting down somewhere? Like, why am I still out here pushing? You know, like there were, there have been many, many moments like that. And I don't think that There has to be only one definition for how we are. So like, yes, if you're in a place where you feel like the textbook expectation should be that you should take one step at a time, take it one day at a time, I hate that phrase, by the way.
Instead of taking one day at a time, what should we do?
We should take it all. Do everything all at once. Make it messy. Make it unpredictable. Defy logic. Like, why does it have to be so ordered? One day at a time for what? One step at a time for what? Sometimes I'm gonna run, sometimes I'm gonna skip, sometimes I'm gonna go backwards, sometimes I'm gonna lay down, sometimes I'm gonna sit up and look at the world. And sometimes, yes, I will take one step. But why does it have to be so ordered all the time? And so the freedom in that, I think, allows us then to be multiple things at one time. so that yes, you can be driven and in a dark place. You can be hurting and still laugh. You can be healing and still trying to figure out how to avoid the next hurt. All of those things can be true at the same time and doesn't have to mean that you're wrong or that you're doing it wrong. It's like there's no definition for how you're supposed to live your life. And I think that's also the other beautiful thing. you know, the fact that, like, no one has ever been where I am before, not a person on the planet, you know? And so it's like, why would I subscribe to the steps somebody else thinks I should be ordered for me? Right. There's no plan.
Yeah. No one fully understands your life experiences. They might be able to relate to some things, but they don't fully understand and comprehend everything.
Yeah, yeah, yeah. So there's so much freedom in there. Yeah. It's like you don't have to listen to anybody.
Right, exactly.
You know, and so it's like, yes, you can be hurt and trying to heal, maybe taking the steps to healing, you know, whether that's therapy or you're working on something that you feel like or taking a risk that you would have been fearful of before.
