Wynton Marsalis on Humility, Self-Mastery, and Learning

Written by Sean Murphy. Posted in skmurphy

Wynton Marsalis collected ten of his letters in “To a Young Jazz Musician” in 2005. He opens the book with:

Phone conversation is one thing; a letter lasts. I love the intimacy of letters, the warm communication that flows between two people who take the time to write. It reminds me of dialogue on the bandstand. What better way to talk to a young jazz musician? Words frozen on paper like a recording.

I see a number of parallels between playing jazz and creating a new business. Both involve a need to understand “the rules” that historical success imply, the need to collaborate in an improvisational way with co-workers in real time to please customers, and the need to master a complex set of skills to compete with others who are watching and learning from your performance as you start to succeed.

Marsalis’ first letter, dated June 4, 2003 is titled “The Humble Self.” Here are some excerpts that address humility, self-mastery, and learning. Topics I believe are as relevant to entrepreneurs as they are jazz musicians.

“Humility is the doorway to truth and clarity of objectives, it’s the doorway to learning.”

Humility allows you to question what you are working on and why. It enables you to understand what it is you really want your business to accomplish. If you can codify and articulate your objectives it will enable you to connect more deeply with what energizes you and sustain the effort necessary to persevere in building a new business.

 The first level of mastery occurs over self. And the first test of mastery over one’s self is humility. True humility. [...] Do you know how you can tell when someone is truly humble? I believe there’s one simple test: because they consistently observe and listen, the humble improve. They don’t assume “I know the way.”

This is a tough challenge for any entrepreneur. Because at some level you have to assume you will find a way, and that you have a pretty good idea of where it is already. You have to have the courage of your convictions in starting a new business, but you have to be alert to what you can learn by observing and listening to prospects, customers, partners, competitors, employees, and others.

We tend to think of the powerful person as a self-confident speaker at the front of the room or being interviewed or holding forth in a small cluster at a networking event. But the most effective sales people sell with their ears, they listen carefully to diagnose and understand so that their subsequent words are effective and on target.

The effective entrepreneur is always alert to the possibility that there is a better way, not from a lack of confidence in their current approach, but because they always allow for the possibility of improvement. Even if it means having to admit to their team–and themselves–not so much that they were “wrong” before but that they have now learned a better way.

Humility engenders learning because it beats back the arrogance that puts blinders on. It leaves you open for truths to reveal themselves. You don’t stand in your own way.

Perhaps you have closed some early deals, or some large deals, or convinced investors to bet on you. It’s tempting to fall into a pure execution mode. And there is value in “working the plan” and meeting your commitments. But complex skills–and entrepreneurial expertise is a mix of complex skills–require more than the memorization of certain rules like “buy low, sell high”  or “a dollar today is worth more than a dollar tomorrow.” They require you to push yourself to the limits of what you know and are good at. To do things that don’t scale so that you can learn how to scale your business in new directions.

You have to become the center of your education. Once you accept that, you’ll  understand that learning means figuring out what you need to do to get where you want to be.

I had a terrible realization in my second computer science class. My programs were getting complex that I couldn’t show them to a friend who could immediately point out my mistake, or even in a few minutes. There was a lot of value of forcing myself to explain my approach, and in fact preparing for the explanation could often unlock my understanding of where I had made a mistake. I had stopped looking for “bugs in the compiler” and had to continually debug my assumptions and my understanding.

When I started to freelance it took me a while to realize that most of my mistakes were not in execution–the code worked fine as far as my understanding went–but in starting before I had made sure I fully understood the real results that my customers wanted and the real constraints they wanted me to observe in delivering those results. This required me to take my skills in an entirely new direction than my classes had led me: it was no longer a question of delivering a project against clear requirements, well defined deadlines, and instructor supplied test sets. Now there was considerable ambiguity in the requirements, deadlines, and how it was be tested by my customer’s customers.

It wasn’t just a shift from being given an equation or set of equations to solve to a “word problem.” It was dealing with confused narrators in a hurry who were figuring out their real needs as they went along or as their customers brought them new or even contradictory requirements.

Freelancing required almost none of the skills I had mastered to pass the standardized admissions tests for college (PSAT/SAT) or graduate school (GMAT). I had to unlearn my instincts to give an answer immediately– or commit to a date or functionality–without walking around the situation two or three times and asking some basic questions, even at the risk of appearing stupid, so that I could be relatively certain I had a fix on the customer’s problem.  These skills of discovery and diagnosis are ones that I still work at mastering today.


Here are some other blog posts that talk about the importance of humility for entrepreneurs:

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