Wynton Marsalis on Humility, Self-Mastery, and 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.

Wynton Marsalis on Humility, Self-Mastery, and Learning

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.”
Wynton Marsalis in “To a Young Jazz Musician“

I see a number of parallels between playing jazz and creating a new business. Both involve the need to:

• understand “the rules” that historical success imply;
• collaborate in an improvisational way with co-workers in real time to please customers;
• 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 that I believe are as relevant to entrepreneurs as they are jazz musicians.

Humility is the Doorway to Learning

“Humility is the doorway to truth and clarity of objectives, it’s the doorway to learning.”
Wynton Marsalis in “The Humble Self.”

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 Humble Improve

 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.”
Wynton Marsalis in “The Humble Self.”

This is a tough challenge for any entrepreneur. Because at some level you have to assume you will find a way, and that you already have a pretty good idea of where the path is. 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 Removes the Blinders Fostered By Arrogance

“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.”
Wynton Marsalis in “The Humble Self.”

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.

Learning Means Figuring Out What You Need
To Get Where You Want to Be

“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.”
Wynton Marsalis in “The Humble Self.”

I had a terrible realization in my second computer science class. My programs were getting so complex that I could no longer show them to a friend who would immediately–or even in a few minutes–point out my mistake. I learned that there was significant value of forcing myself to explain my approach, and that preparing  the explanation would 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 my work would be tested and verified 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.

Related Blog Posts

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

• Ken Imboden on Lessons From MMC, Candlestick, and NuSym
  Ken Imboden observes: “Humility is of great benefit in a software developer; hubris is of great detriment.”
• Ryan Waggoner: Maybe Startups Are So Hard Because We’re Doing Them Wrong
  Ryan Waggoner concludes, “The key seems to be patience and humility, two things a lot of 20-something founders (including myself) have in very short supply.”
• In “My Interview With Peggy Aycinena” I credit Wally Rhines of Mentor Graphics with an approach that  combines “a lot of data with humility, or the willingness to go where the data leads him.
• In “In Entrepreneurs Need a Community of Practice Not a Movement” I quote from Patrick Houston‘s (@patrickhouston) article “Lean Startup Concept No Silver Bullet”
  According to the “lean” way of life, the only prudent way to determine what the market wants is to deploy the scientific method, the very same one we learned in grade school: State an hypothesis and then do an experiment to prove or disprove it.  This inherently more humble approach to business represents a refreshing contrast to the entrepreneurial hubris that struts its stuff down the streets of Palo Alto where people live by the self-assured motto, “Go big or go home.” If only for that reason, I’m attracted to its tenets.