Failing Up: How to Take Risks, Aim Higher, and Never Stop Learning

I really don't know how actors do it. Not the acting part (though I don't understand that either), but how they make a living out of something that's never guaranteed, doing something that is inherently risky, dealing with almost constant rejection along the way to any success should they find any, and which can be fleeting once it arrives. Those elements are, of course, a part of any professional life, but they are on the surface of every actor's life—ever present realities—and that is one reason the stories of their lives and work and perseverance can inform our own so richly.

Regardless of what industry we work in, we're all hoping to find the role of a lifetime. Leslie Odom Jr. found his as Aaron Burr in Hamilton, earning the prefix "Tony and Grammy Award Winner" in the process. But according to him, "Hamilton was the dream that almost didn't happen." He tells the story in his new book, Failing Up, of how he almost gave up the life of an actor five years earlier:

Graduating into my thirties felt significant. The instability and unpredictability of the artist's path was starting to feel like a child's way to live.

"Some things," he writes, "don't travel well from one part of your life to the next." He though that perhaps the "business of being an actor" was one of those things. The book has a lot of  lessons to teach, and the first one is about the importance of mentors. He reached out to a mentor of his, who had made the transition from actor to other roles in the industry, and who also happened to be his father-in-law, for guidance. He was taken aback when his father-in-law said that he'd support him in a career transition, but that he'd like to see him "try before he quit." For someone who landed his first role in Rent at the age of 17, and had been working hard ever since, the advice was a bit of a shock. "You know how to succeed when the phone is ringing," he told him, "But what about when the phone's not ringing?" It was a gentle admonition to take charge of his creative life, to be more proactive in pursuing his creativity—reading, writing, taking classes, practicing his craft, sending emails, proactively making calls and new connections—in the absence of calls coming in. For someone who knew the value of preparing for the roles, who writes that…

The work you put in when no one is watching will matter far more than the work you do when the cameras are rolling. The private hours of hard work you dedicate in the dark will be there own testament when you're finally standing in the light.

What he was hearing, and understanding, for the first time that he needed to step up his preparation for his ultimate role: his own creative life. "Preparation is the sign of your intention," he writes, "You can allow your preparation to speak for you in rooms you care about." It is a lesson that is universally applicable, and it alone is worth the cover price of the book, but there are so many more.

The book is simple in all the best ways—straightforward, honest, quick and easy to read—and there is wisdom embedded in it that runs deep and strikes true. It is about why being able to say no to an opportunity is just as important as actively pursuing it. It is about identity and the exploration of the American experience. It is about how he ended up in Hollywood after graduating Carnegie Mellon, and how it is similar to any competitive field—including the dangers of tokenism and placing limitations on yourself. The latter is not only about the roles we choose to take on, but in how courageously we inhabit the roles we choose, which brings us to the lesson that gives the book its title, and how, for Odom Jr.

Everything changed in an instant the first time I really gave myself the room and permission to fail spectacularly.

The moment came, again, at the insistence of a mentor, who noticed him holding back in a key musical moment that called for "passion, fervor, fire." He was certain he would fail, but he was finally convinced to abandon control and attack the moment with all the emotion he could muster:

I screamed. I flailed. I jumped. I ran. I cried. I let go. I flew. I soared. It shook me.

"In my willingness to fail," he writes, "I flew instead."

The book is also, of course, about Hamilton, which has written a new chapter the history of musical theater, and his role in it. It transcends his role as Aaron Burr, because he was a part of the process from almost the very beginning of development, years before it found its way to a Broadway stage. It is about sacrifice and defining success on your own terms; Odom Jr. turned down a guaranteed $500,000 contract on a network television series to do Hamilton, which guaranteed less than $15,000. It is about making art, and making history, and about making gratitude a daily practice. It is about giving yourself permission to fail, but also permission to succeed, permission to prosper. It is about how "Deeper creative freedom waits for you on the other side of fear."  

The path to moments of greatness in your life will be paved, in part, with your spectacular failures. Keep going.

Odom Jr. has kept going, striking out as a solo artist since his departure from the cast of Hamilton. And that role led him to a gig in Charlottesville, Virginia for the two hundredth anniversary celebration fro the University of Virginia, in the weeks after a racist white nationalist rally and the death of a counter protestor shook the city. It also leads us to the end of the book. Asked by a student why he chose to come to Charlottesville when other artists had recently cancelled the concerts in protest, he makes beautiful case for bearing witness and trying to help, about how in "Facing threats to the future of our democracy, we can't afford to fail through inaction. We have to try." 

Leslie Odom Jr.'s Failing Up is simple in all the best ways—morally clear-eyed, earnest in its affection for his craft, for preparation and for people, in its committment to active citizenship and compassion. It has a lot to teach us about how we go about our work, and a whole lot more.

We have 20 copies available.