Don’t Just Wait For It (Career Lessons from Failing Up by Leslie Odom Jr)

I am not a person who sticks to reading lists. I can sign out the same book from the library over and over again, or look at the same book at my bookshelf for ages, but until it is the right time, it remains unread. A couple of years ago I bought Leslie Odom Jr.’s book “Failing Up”, loved what I read, but didn’t get very far because it was difficult to take notes while reading on the bus. This October however, after watching an episode about “Wait for It” on the Netflix show “Song Exploder”, finally watching Hamilton, listening to a lot of interviews with Lin-Manuel Miranda, and listening to the soundtrack and other Leslie Odom Jr. songs on repeat, I finally read it.

And it was brilliant. I read it twice through, took ten pages of notes and weeks later, I’m still thinking about the book. In it, Leslie Odom Jr. talks about how you must be persistent in the pursuit of your dreams, but that systemic barriers and racism cannot be superseded by a can-do attitude. That nuanced lens is too often missing from career books and books about purpose and dreaming for more, and I deeply appreciated reading something filled with hope, encouragement, honesty and humility that also acknowledges race and power and positionality. Though not an exhaustive list, here are some of the lessons I took away from the read.

  1. Your work is independent from people hiring you and, the phone ringing.

One of my favourite moments of the book is mentioned twice – firstly in the introduction to the book, and later when the moment actually happens. In that moment, tired of the financial and emotional instability of acting and performing, Leslie Odom Jr. goes to his father in law and mentor and asks him for advice in transitioning to something else. In response, his father in law says:

“Les, of course you can quit. That’s fine. And we can talk about what you might do next and how to go about it. I can support you in that. But I’d love to see you try before you quit.”  What did you do for yourself today? Did you call anyone? In what ways did you take charge of your creative life today? Did you send an email to someone who might be working on something you care about? Did you read anything? Did you write anything? Did you take a class? Did you practice? What step forward did you take for yourself today in the absence of the ringing phone?” (p.10).

This moment was a wake up call and despite being a professional actor with years of experience, Leslie Odom Jr. signs up right away for an acting class with his father in law, and resolves to never think of his work again as solely what he does when the phone rings, but rather, a commitment he has to his craft independent of his paid work.

2. Following your dreams is a spiritual journey

It requires vulnerability and a strong back and a soft heart to pursue your dreams and hopes and nurture your talents. There is so much courage in the stories shared in this book, and Leslie Odom Jr. speaks openly about how hard work is important, but you alone are not responsible for your success. There is a wider context and an attitude of surrender and acceptance needed as you walk toward your dreams. Leslie Odom Jr explains:

 “You will train and prepare to actualize your dream in countless ways. Try not to neglect spiritual fortification” (p.10). This spiritual preparation also means recognising that no’s are a step to successes and that nothing is wasted. This doesn’t mean that rejection is easy though, and part of the spiritual journey is keeping the faith in yourself even when things aren’t going your way. Leslie Odom Jr. elaborates:

“Faith will deliver the reminder that disappointment and failure don’t have to be fatal. In those times when you have done your very best and still come up short, faith fills in the gaps between your reality and your dreams. Faith is what sustains you in the wilderness” [..] You hear a lot about the Big Break from successful people. But I would challenge you to think of your Big Break as an inside job instead of something that you’ll find externally.[..] The biggest break is the one you will give yourself by choosing to believe in your vision, in what you love, and in the gifts you have to offer the waiting world” (p.54)

That spiritual journey also means keeping the faith when you have no idea about the outcomes of what you are doing. Leslie Odom Jr. describes what it was like to be developing Hamilton for years, declining other much more lucrative opportunities because of a belief in the show, and that emotional and spiritual challenge that entailed during the difficult moments, and the self-belief and self-trust needed to keep going.

3. There are no overnight successes. The conversation Leslie Odom Jr had with his father in law was in 2011. His first Broadway experience was in Rent was when he was seventeen. Before and after that first Broadway show hundreds and thousands of hours were spent learning craft. There are no shortcuts to polish one’s talents. It is a daily journey to work towards one’s goals, and Leslie Odom Jr. advises to “start now, every day, becoming, in your actions, your regular actions, what you would like to become ” (p.33).

4. A deep work ethic and critical self-reflection are necessary. Rather than looking at the work and trajectory of others, Leslie Odom Jr advises the reader to focus on their own skills.

“Reliability and craft will get you work (p.77) and when things do not go your way , celebrate the fight because coming close can be confirmation you are on the right path. Ask yourself: What can you do better the next time? What can you do to make yourself more prepared for the next time?” (p.27). Instead of comparing, have your own standards and evaluation criteria for yourself.

5. Never relinquish your ability to say no.

This is a critical point in this book. Leslie Odom Jr. explains:

“Come what may, through the fat and lean years, you must retain ownership of your yes and your no. In many respects, it is all you own in this world for a very long time. Yes can come easy. No takes a bit of practice. Your no, your willingness to walk away when something doesn’t feel right for whatever reason, will be one of your greatest assets. It will set you on a path you will own as well” (p,78).

Although work is important, not every environment and job is for you, and each job interview, or work situation or audition is as much about you investigating and assessing that environment as it is about them assessing you. Work that asks you to give up principles and pieces of yourself and crosses boundaries of your dignity and self-worth may not be work that you want to do.

6. Define space for yourself. Know your strengths, identify what you want and what you can do well, particularly because “you will meet people along the way who will be lining up to place limits on you. You don’t need to beat them to the punch” (p.96).

7. Say thank you. Make gratitude a daily practice. Throughout this book, Leslie Odom Jr. thanks people along his path by name and specifically outlines some of the ways they helped him. From his early teachers, to his wife, his father in law, this is a book that overflows with gratitude.

8. Ask yourself what success look like for you and give yourself permission to thrive. Interrogate your ideas of success and whether they resonate with you because success “looks different to each of us. The more clearly defined, the easier it will be to recognize when it shows up” (p.182).

8. Have compassion for yourself. Know that persistence through failure, grit, tenacity, does not supersede systemic racism. Your career success is not always about you understanding your skills better or articulating them, there are systems and institutions and ecosystems that can limit your success as well. Be part of building new tables.

9. We need a revolution in education, affordable post-secondary education and failure-safe spaces.  This paragraph stuck with me:

“I made plenty of mistakes in school, but I wish the environment had encouraged and provided more room for failure. My training hadn’t included any focus on audacity. Nothing in my training encouraged or spoke to the value of taking real risks and so I wasn’t in the practice of taking any. The tuition came as a particular hardship for my folks, and I racked up student loans in the shortfall of financial aid. I took the sacrifice seriously. I wanted my transcripts to reflect the seriousness with which I approached my education.

“I did really well and graduated with honors from Carnegie Mellon University.  I learned what was expected of me, and in most cases, I delivered. Because of the grading system in place and quite possibly (I say in truth and with respect) the egos of some of my professors, there’s no premium placed on risk. That meant wasted valuable time, because risk is much harder once you leave campus and stakes go up. More room should be made on our college campuses for trial and error.” (101)

From deep spirituality, to committing to yourself and your dream, being specific about your dreams, believing in your abilities, this is a book to return to again and again when you need a coach, or inspiration and a reminder to do the work. If you’ve read it, what have been some of your take-aways from the book?

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