Leslie Odom, Jr. on Failing Up

Leslie Odom, Jr.’s “Failing Up” is an autobiography written at what I hope is the midpoint of a long and successful career. He has a lot of practical advice gleaned from performing that I think is very applicable to entrepreneurs.

Leslie Odom, Jr. on Failing Up

Leslie Odom, Jr. played Aaron Burr in Hamilton, I was impressed by his performance and enjoyed the play. I read Hamilton: The Revolution by Lin Manuel Miranda and Jeremy Carter which provides context on how the show evolved over a period of several years, it also provides an annotated score that I found interesting .There are short chapters on each of the principal actors and the one the profiled Odom included this insight:

Leslie Odom Jr. says it best: “’How do you let people know what you want? You let them know through preparation. You show them’”
quoted in Hamilton: The Revolution by Lin Manuel Miranda and Jeremy Carter

That impressed me so much I decided to read his auto-biography, self-help guide “Failing Up.” Subtitled “How to Take Risks, Aim Higher, and Never Stop Learning” the book offers a wealth of practical insights for entrepreneurs

When the phone did not ring today,

what step forward did you take for yourself?

Failing Up

“He began, “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.” […]

“He said, “You know how to succeed when the phone is ringing.  I think you do extraordinarily well when you’re called upon. I think you show up and you’re confident because of your preparation. But what about when the phone’s not ringing?”

Stu went on, “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 e-mail 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?”

Excerpt from “Failing Up” by Leslie Odom, Jr. 

Stu is Stuart K. Robinson, Odom’s father-in-law, a well-respected acting coach, and a successful businessman. There are several traps that Robinson is addressing in this short bit of advice:

  • It’s great when the phone rings and someone wants to consider hiring you (or purchasing your product), but you must prepare.
  • You don’t get the day off when the phone does not ring. You have to put your time and efforts at risk to improve yourself or improve your visibility.
  • You have to see it and work to make it happen; you cannot wait for things to happen.

Walk toward the things that make you feel most alive

“Nothing can stop you from preparing for your dream opportunity. But you can’t know the day or the hour it will come to you.
You walk toward the things that make you feel most alive. You walk toward the things you love. You love them with your whole heart. Read about them. Talk about them. Find other people who love those things, too. And eventually, the thing you love most in the world will love you back. It is inevitable. Not always in the way you expect, but in exactly the way you need. The loving energy you put toward your dreams is magnified and returned to you in time.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

I like the sentiment behind this. There is something to becoming usefully obsessed in a sustainable way toward a field of endeavor. But I am not sure you can always combine opportunities to be creative with opportunities to make a living. Logan Pearsall Smith put it this way: “The test of a vocation is the love of the drudgery it involves.” If you pay attention to what energizes you and the kinds of problems and kinds that you have an affinity for, you are likely to discover opportunities that you are well-suited for. If you can pay attention to what energizes you and the kind of problems you have an affinity for, you are likely to discover opportunities you are well-suited for.

I was the worst in the class. By far.

“I was the worst in the class. By far.
I say it with a smile but I mean it completely. Being the worst is a gift in your training. I’ve pulled up the rear more times than I can count. If you can help it, you want to study in close proximity to people whom you feel you can learn from.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

It can be challenging for good students to let go of being one of the smartest people in the room. I think that’s why many entrepreneurs who succeed start out as B or C students. They are familiar with the feeling of being over your head and the need to learn from folks around them. It’s not that you have to learn from the best, but you have to compare notes with others you can learn from. I also think a certain amount of mastery involves teaching or coaching. Transmitting hard-won lessons with clear examples and explanations force you to a deeper understanding of a discipline or craft.

The luck of the beginner has a lot to do with an absence of cynicism.

“My personal feeling about the luck of the beginner is that it has a lot to do with the absence of cynicism. Beginners are too filled with optimism for cynicism to dim their light. They are too filled with joy for jadedness to dampen their enthusiasm. This magnetizes the beginner. And it isn’t about youth. It is about freshness, and openness, and love. Who wouldn’t want to be around that? Every now and then it is the job of the veteran to reconnect with the beginner inside.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

I think that “being easy to do business with” and “pleasant to be around” make it much more likely that you will succeed in business. Easy to say, hard to do. A certain amount of natural cynicism can accrue with experience that feels like wisdom but is often just fear of trusting and getting fooled again. In my case, Mother Nature has blessed me with a deep and abiding pessimism. I have to take care that I deploy it to evaluate the downside to my plans, but I don’t let it inhibit me from taking prudent risks and giving people the benefit of the doubt as my opening move. I think there can be a “constructive pessimism” but it’s like cayenne pepper, you just need a pinch to flavor the elephant stew if you still want to taste the elephant.

If you are a confirmed pessimist, team up with energetic optimists and make the effort to appreciate their ability to uncover–if not design–new possibilities that may lead to opportunity. They will value your ability to point out overlooked flaws and hidden risks, if you can do so in a way that helps them improve their plan of action.

Talent is a Gift; Hard Work and Perseverance are a Must

“Without solid vocal training, singing a rock score eight times a week can trash your voice. I remember losing my voice for the first time a few weeks into my contract. Singing training for me consisted of the choir in church, the hours I’d spent messing around on a karaoke machine that I was given one Christmas, and the hundreds of hours I’d logged with Mom and Dad’s record collection.

Having my voice gone in a moment was pretty terrifying. The powerlessness you feel is not easy to put into words. It makes you realize in the most profound way that any talent you may have is a gift.”  [..]

“Talent isn’t everything. Talent is nice. In some instances, it is a leg up, but it’s only a part of what you’ll need for success ultimately. Hard work and perseverance are almost more important.

It’s possible to marry a meager talent to enduring success with a strong work ethic. It is just as possible to squander a major talent with laziness and inaction.

Assess what you’ve got. Be honest with yourself and make the most of whatever you’ve been given.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

There are several good insights here.

    1. A lot of what looks like talent can be a matter of being early, for example, early to a market. It’s an advantage, but unless you work to improve, it’s likely to be transient as later arrivals go to school on your success.
    2. There is a risk of relying on a differentiating advantage and not developing other skills. You don’t round out your team’s capabilities and address a problem with the appropriate mix of skills, relying instead on one or two strengths that may not be the best fit.
    3. You have to protect your talents: get enough rest; l don’t strain out of panic or an unwillingness to recognize limits; keep learning and understand how to balance where you are strong with at least adequate skills in other areas.
    4. The ability to accurately assess your capabilities–at an individual, team, and firm level–and make commitments that you can keep is a superpower all of its own. Being trustworthy and diligent are two talents you can cultivate to complement other natural abilities.

When something does not feel right, walk away

“The dissolving of any fear I had left attached to the word no has been useful to me almost every day of my life since that time.

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 that you will own as well.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

I think you have to be on guard against looking for the perfect opportunity and also walking away because you won’t be perfect. You have to allow yourself to be average or adequate. Many opportunities will come your way with a very short deadline attached. This, in itself, is not a reason to walk away. Part of the value of visualizing what you are looking for in advance is that it can enable you to recognize it quickly. On the other hand, if you don’t have a good feeling about the people you will be doing business with, then “no” or a more graceful but firm demurral is the best course.

When dealing with certain customers, it’s also the case that they will unleash a purchasing agent or other skilled negotiator on you who will keep pushing until you say “no.” That’s how they know they have gotten all they can. Therefore, it’s best to calculate your limits before you sit down to negotiate so that you and your team are in agreement and can act firmly when needed. Don’t argue with each other in front of the customer.

Failing spectacularly takes a bit of practice

“Like anything worthwhile, failing spectacularly takes a bit of practice, and I had none.  […]

“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.

You should be encouraged to fall on your face, to fail in service of an ideal or a strong impulse.”

“When you find yourself on the ground after a big leap, you dust yourself off and commit to failing smarter next time. The path to moments of greatness in your life will be paved, in part, with your spectacular failures. Keep going. Get shame and fear out of your periphery as soon as you possibly can and keep going.

It is never too late to learn to risk.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

Russell Ackoff has written a similar critique of formal education. By teaching the method first and then testing you, you may never learn how to learn new techniques when you are not spoon-fed. If only the real world came with such detailed instructions. The ability to manage yourself when you are over your head is a valuable skill to master.

I think Odom regrets becoming caught up in being an “A student” and never experiencing failure. When he failed after college, he was not as prepared as he could have been.

I mastered the art of uneven performance in college–or if you prefer trying a lot of new things. Some worked out, and others did not. As a result, I have fewer–or at least different–regrets. There is an argument to be made from an information theory perspective that a 50-50 bet gives you the most information about yourself and your situation. It could be that you misassessed badly, or there are other variables that you can control, or at least influence, to increase your odds once you start to debug why are you failing.

You always have to act with integrity, but here are advantages to pursuing opportunities with a low probability of success where the real and opportunity costs are low. First, it can give you familiarity with the problem domain, perhaps dispelling some illusions you may have about yourself or the field. It may also provide evidence that you can master this discipline with more practice.

You can learn a lot sitting on the other side of the table

“When auditions began, my role shifted to that of a reader. That meant I became the scene partner for every actor who auditioned. You can learn a lot sitting on the other side of the table all day in an audition room.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

Rehearsal and practicing together as a team is an excellent way to improve performance, build teamwork and morale, and enable effective improvisation when required because everyone gains a better appreciation of each other’s role and contribution. It’s useful to practice not only things going right but also failures: prospects asking the wrong question;  your demo crashing; key team member unable to join. You perform as you train.

Preparation is the sign of your intention

“My preparation had made me fearless, and I had no expectations.  There’s nothing like preparation to make you fearless.”

“Preparation is the sign of your intention. You can allow your preparedness to speak for you in rooms you care about.”

Excerpt from “Failing Up” by Leslie Odom, Jr.

Nothing communicates a lack of interest in a business relationship like little or no preparation for a conversation. You can be surprised at a trade show booth and fall back on a prepared menu of options or approaches. Still, if you are not tailoring your outreach and presentation materials for each prospect, you limit your success chances. Familiarizing yourself with a customer and not asking basic questions that five minutes on their website could answer makes a positive impression (or avoids the negative impression that you have not done your homework). I am not arguing for a scripted or robotic conversation but one that allows you to stay in the moment because you already have a primary context that enables you to ask deeper questions early.

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