Kareem Rosser has penned a searingly honest and intimate memoir in “When You’re Ready: A Love Story.” At its heart, the book tells the story of Rosser’s romantic relationship with eventer Lee Lee Jones and how he grapples with the aftermath of a horseback riding fall that caused a major traumatic brain injury for her and reshaped both their lives dramatically. But Rosser centers that story amid the encompassing tale of his own life—the struggles he faced as a young Black man from a disadvantaged background, his uncertainty about the future, and how he addressed his own mental health. 

Rosser’s first memoir, “Crossing the Line: A Fearless Team of Brothers and the Sport that Changed their Lives Forever,” detailed how the Work to Ride polo nonprofit provided a pathway for him to move beyond the poverty and violence of the inner-city West Philadelphia neighborhood he grew up in. Rosser became an accomplished polo player—the captain of the first all-Black squad to win the National Interscholastic Polo championship—went to college, and began a career in the financial world. He’s also an award-winning author and keynote speaker.

“When You’re Ready” revisits Rosser’s youth, as the Work to Ride barn was where he first met Jones. It takes the reader along as Rosser and Jones find ways to reconcile their very different worlds through their young love. After Jones’ injury, Rosser wrestles with how to honor his love for her while continuing with his own life. It’s a wrenching read but ultimately uplifting. Rosser doesn’t hold back in his brutally honest discussion of his feelings, revealing a vulnerability that makes him imminently relatable. 

We chatted with Rosser about “When You’re Ready” and his journey.

You’ve shared so much about your life and journey in “Crossing the Line” and “When You’re Ready.” Where does life find you now?

I’m actually now serving as the executive vice president of Work to Ride, the organization I grew up riding in. I’ve been doing that for last year or so. Prior to that, I was working in finance, but I transitioned to working in this capacity full-time with the charity, and, specifically, spending a lot of time on building our new indoor riding facility that we are just a couple weeks away from completing. I led a $15 million capital campaign and to raise the money for the project. Now we are in the middle of building a new facility and rehabbing our old facility. At the same time, I’m still trying to ride when I have an opportunity to, but I find myself now spending more time behind a desk than I do on top of a horse, which is almost inevitable.

I also recently joined the board of the Bryn Mawr Rehab Hospital Foundation, which was the hospital where Lee Lee was cared for. They’re getting ready to launch an endowment fund honoring Lee Lee called the Lee Lee Jones Patient Assistance Endowment Fund. So, I’m leading those efforts right now as well. And I also have my family, my wife and 3-year-old daughter. I’m just busy, spending less time riding and doing more adulting things. 

What does it mean to you to be able to bring your life full circle and give back to Work to Ride, which gave you so much?

It’s an incredible feeling. It’s very fulfilling to be in this position to use some of the professional skills I acquired over the last few years working to give back in this capacity. I’m also just really excited about the future of the organization. We’re building new infrastructure and working on a strategic plan for the next generation of kids that come through the organization. It’s a full-circle moment for me. It’s fulfilling to see the kids show up to the barn and enjoy themselves. It’s great to be in a position, both personally and professionally, to give back in the way that I’m doing it now.

You seem to have made it a goal in your life to lift others up and inspire them. How do you hope this book affects readers and inspires them? 

When I originally thought about the book, I decided that I was only going to write it if I could speak candidly and be vulnerable. I hoped it would touch other people, specifically around things like my mental health and the challenges around Lee Lee’s accident. I imagined that I was not the only person who was dealing with that, or the only person that had gone through something similar, or was even just dealt mental health challenges in general. I was hoping that I could just resonate and connect with people in a way that would, hopefully, inspire them, but also give them comfort and let them know that they’re not alone. 

As much as the book was about me trying to heal and pave a way for my new life, I also hope people can find some comfort in it, too. It was equally as important to be able to help somebody else, and I like to think that it’s doing that already. I know I’ve received a number of messages from people who were moved by the story and could relate to it. Many of the stories resonated with them, and it’s helped them in their own personal journeys.

You are very vulnerable and very honest in this book. How did you find the strength to be able to put that out into the world?

I’ve been telling my life story for such a long time now, and this was just another phase in my life that I hadn’t gotten a chance to share. So I think it was helpful that I had been sharing my story for a while, but also having my family and friends around me helped. Knowing that I had a very tight circle of people who listened and didn’t really judge made it a lot easier as well. I’ve been sharing my story for a while, so I felt like I would have been doing a disservice to myself, but more importantly, other people, if I would have kept all of this close to my chest, and not put it out there in the world.

How did the process of writing this book help you work through some of those feelings and problems?

I know some people find journaling healing as a way for them to process their thoughts and emotions. Honestly, I didn’t journal when Lee Lee’s accident happened, but I had a lot of photos and messages from people that were helpful as I started to think about the different stories and particular periods of time. I thought about how I handled those periods, especially the most painful ones, I spoke with other people who’d gone through some of those experiences with me. I spent a lot of time just looking at photos and reflecting, then sharing whatever was on my mind at that time, and eventually was able to piece that together into a book.

One of the most touching throughlines of the book is the friendship you developed with Evie Dutton, Lee Lee’s mother. What do you value about the Dutton family and the eventing community from that time in your life?

The Duttons are an incredible family; they’re just wonderful people. I honestly have learned a lot from just being around them. How selfless they are, always thinking about other people, certainly encouraged me to also act in that way. 

After Lee Lee’s accident, their lives were completely turned upside down, but I saw how they were able to keep everything together. I know it wasn’t easy, and I know it wasn’t something that just Evie or Phillip could do alone. It was incredible to see how they came together as a family to navigate the adversity and the challenges that they went through. I’ve been fortunate enough to have them in my life; I consider them as family even as I have my own family now. I continue to stay very close to them. 

As far as the eventing community, it was just incredible to see how everyone rallied behind them when the accident happened, and the support that folks have continued to to show over the years. It just speaks to who both Phillip and Evie are as people.

You write about how horses have been sort of a place you find peace and center yourself. You said it’s more difficult now, with family and professional life, but do horses still provide that for you?

Absolutely. I just pulled up to [the Work to Ride] barn right as you called, and I immediately just felt at ease seeing the barn and the horses. It’s always been my escape. I was just sharing with someone recently that I decided not to really pursue a professional polo career or any sort of riding career because I didn’t want to do something I loved like that for a living, because it might eventually stress me out and make me unhappy. I always wanted to be able to come back to horses knowing that they’re my getaway. It’s valuable to have the ability to still walk into the barn and leave all my problems behind and find peace and comfort. 

What do you think a teenage Kareem would think of the life that you’ve created? Would he be surprised where you ended up?

I think he certainly would be surprised. But I’ve always known that I wanted to do something beyond just riding horses to be a productive member of society. I didn’t know exactly what that looked like, but I am very grateful to be in the position I am now. I know, definitely, my younger self would be very proud of what I’ve what I’ve been able to accomplish and a lot of the work that I’m doing today.