4 Lessons I learned Reading Failing Up by Leslie Odum, Jr. (Minor Spoilers)

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For all that may not know, I am a Hamilton fanatic albeit a late bloomer. Loud and proud Hamiltrash. I remember when the buzz initially started. I was beside myself. I, also being a theater geek and history nerd, knew this play was everything I could imagine it to be plus so much more. In late 2015, I was nursing a job in Virginia I hated when the ticket prices began to soar. I couldn’t take off and started to realize my chances of seeing the show were growing slim. I do this weird thing when I can’t experience something where I blot it completely from memory. This isn’t true for everything; mostly chances where I feel it’s impossible. So I kicked out the dreams of sitting in the room where it happens and tried to avert my eyes about any Hamilton news. Three years later, I officially introduced my ears to the Soundtrack.

I am either completely obsessed with a thing or can’t be bothered. There’s rarely any in-between. I played the most feverish game of catch-up during a time in my life where literally everything was on fire. The Hamilton soundtrack served as my respite during the chaotic crescendo befalling me. I dove into interviews of the whole cast, individual interviews, projects, late-night appearances, guest hosting spots, their social media sites. I wanted to get to know the people who created such an extraordinary body of work and how they got their starts. So back in March 2018 when I learned Leslie Odum, Jr. was releasing a book about his journey, I bout ascended from my seat. I went out and bought it as soon as it hit shelves (given a week or two).

Failing Up has the bones of a self-help book but reads like a conversation. Upon opening the book I was gifted questions, which I love. What work will you put in today that will help you improve tomorrow? How do you surround yourself with people who will care about your dreams as much as you do? How do you know when to play it safe and when to risk it all for something bigger and better? They didn’t feel pointed; instead they felt like what your closest friend or mentor would ask as you contemplate everything on a couch. That’s where Leslie was when his father-in-law saw the drive, his dreams, leaving him. That’s where I was in my car waiting to walk into therapy. I was hooked from the book jacket. Onward.

1. The Truth about Saturn Return. It is thought that by the time Saturn makes its way back to the point in the sky it stood at the time of your birth - roughly 29.5 years, we have come full circle. Or at least are beginning to. We have dismissed South Node thinking and are shifting into our North Node destiny. (read up on North/South Nodes here.) 30 for me brought about rickety knees and the realization that the old me is quickly becoming dust. It was like skillfully playing a game of chess to then look up and discover I’d been playing Connect 4 this whole time. Everything I knew, loved, trusted was thrown into the air and suspended; too high for me to reach yet now so low it could be considered low-hanging fruit. Leslie was in a similar spot. The life behind him was fading while the one ahead was uncertain. His chosen path was warm, inviting and unstable. He stood backstage on deadline to get this book out with memories and reminders of his journey circling around his brain. Saturn Return will do that to you. But honestly, you’ll be better for it.

2. Believing You is Sometimes the Hardest Part. There are moments throughout this book where Leslie has to decide who he trusts more: those who love, support, believe in him or he himself. There are moments he was so sure about something to later have those with good intentions talk him out of his dream. Sometimes it was intuition, but most of the time it was fear. Their fear projected onto him. And Leslie, silencing his own instincts, honored their fear but with a caveat: they and those tactics would never be played against him again. “Through this process, I learned to say no, and it’ll be more valuable than your yes. Maybe even more so.” Being given the space to trust yourself is a gift. If it’s a new process, like it’s been for me, it’s relearning how to listen to and interpret your own voice. Leslie found his voice, literally and figuratively, when putting it to the test.

3. You’re Allowed to Fail into Place. I wince at the sense of falling. Like that moment descending in an elevator when the top of your stomach floats into your throat. I feel out-of-control and my body must move to be able to compensate for the disorientation. Afterward, I’ve regained composure, realizing I’ve landed to the ground safely. That, in sweet, relatable terms, is failing. Failing feels like falling because somewhere you’ve allowed yourself to drop without security. Failing is painful, retching, packed with lessons. It’s desiring to have all the answers without the capacity with which to hold them. It’s red eyes, torn-up plans, lost time and coin. Leslie spoke to himself during a time of potential failure. Standing in a room full of fellow actors looking to make sense of an old piece becoming new, the weight of failure was heavy. What if this doesn’t work? What if the intent is not received? What if he got it wrong? He was afraid. Safe to say so were most of those involved. But Leslie made a decision that being in the room was the bigger invite to make lasting change, granting the phrase, “you have the permission to fail”. I’ve had many business plans fails, many startups flop, many ideas blow up in my face. I fight myself internally, asking why do I keep messing up and missing the mark. I learning how to give myself the grace to fail forward. Tripping up the stairs looks different when you notice you’re higher than you were before. Try. Let’s do it together. Let’s see ourselves trying. Believe it before we see it. And let the fails be our paths to success.

4. Follow Through with the Thing Even When it Looks Shaky. There was no guarantee Hamilton would be the cultural phenomenon it is today. It started because a guy (the immeasurable Lin-Manuel Miranda) decided to bring along the biggest book he could find to read on vacation. It takes a pretty genius individual to find soul, hip-hop and showtunes in a 800+ page biography about an ill-fated founding father. Leslie got the chance to see the composers of In the Heights workshopping The Hamilton Mixtape at Powerhouse Theater. Leslie writes beautifully about receiving an open invitation to join Hamilton in its infancy, the heart of pure love he had for everything involved - the composers, the cast, the direction, the story. The dedication and sacrifice shown as seemingly better opportunities came along. Money got tight. Time grew short. But he stuck the landing and became one of the leading forces on that stage 8 times a week throughout the historic original cast run. He trusted his gut. He trusted the vision. And the rest is American history.


This book is such a beautiful read. If you’re in a space of “how?” or “where do I go now?”, I encourage you to pull up a blanket and give this your full attention. Leslie writes like he’s sending himself a letter from the future, with warm anecdotes and gut checks along the way. No one is paying me for this review - this book affected me so deeply that I wanted the world to get into it, as if they already hadn’t. Again, read it. It’ll change your life.


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