Three Simple Life (and Business) Lessons from Jazz Icon Miles Davis

Photo by Wim van ‘t Einde on Unsplash

Jazz, the profoundly American music that demands and celebrates improvisation, has given us such incredible live and recorded treasures. As a jazz improviser and educator, I regularly get to share the stories of some of the icons of this music, from its African-American origins in oppression, to an international music that continues to celebrate individual identity. But what I keep finding is that there’s always more to learn from jazz…

For those who already know jazz — and for those who don’t — here are some life (and business) lessons to take from one of its most important artists and improvisers.

Lessons from Miles Davis (1926–1991)

By all accounts, Miles Davis was an extremely complicated, larger-than-life figure. His contributions to jazz are seen, felt, and heard everywhere in the art form, based on decades of restless innovation, and his lineage of important sidemen who continue to perform today — many as leaders of their own groups.

But what strikes me as quite profound about the legendary Miles Davis is that he could have easily been just another trumpet player.


Miles found his own sound

When he moved to New York City and first played with saxophonist Charlie “Bird” Parker, Miles improvisations sound — on those earliest recordings — like he was a little out of his depth. He was a gifted musician apprenticing with a master, but it seemed like he was trying to — but really couldn’t — fill the virtuosic shoes of that other pioneer of bebop, namely trumpeter Dizzy Gillespie.

But over time, Miles Davis clearly stopped trying to play like Dizzy and his other trumpet idols, and found his own distinct, personal sound. It became more melodic, more intense, focused on the middle register of the horn, and always displayed his masterful use of silence.

He found his own sound and developed that.

And then for decades Miles Davis kept reinventing himself, the music, and his overall approach to jazz. (He did this, in case you’re curious, by influencing and/or leading the sub-genres of cool, post-bop, modal, jazz-rock fusion, and more.) Miles’ evolutions in his music were made often to the detriment of his growing fan base.

Often live audiences would prefer to hear some earlier version of Miles Davis, but since he was always searching for a new sound, a new way to play, a new context for his improvisations, he reinvented himself as a vanguard, a jazz pioneer. His flashy stage clothes could have easily been replaced with a lab coat and goggles to represent his constant need for experimentation.

Miles found and nurtured great talent

Miles Davis, as a bandleader (i.e. the boss), also had an incredible ear/eye for musical talent. He regularly surrounded himself with amazing young players, often whose skills were not yet widely known. In time, their performances and recordings by Miles Davis’ groups would show others — and many times the sidemen themselves — what these musicians were capable of.

Practically a ‘finishing school,’ many of those key players with Miles Davis became leaders in their own right after working in his groups. (He would sometimes let them know they were ready to lead their own groups by firing them or replacing them!)

Miles always sought out fresh sounds, new players with unique approaches to improvisation, and across all ages, demographics, or national origin. When he chose the 17-year old talented drummer from Boston, or a British-born bassist, or an unknown saxophone player, his label, his fans, club owners and others pushed back — always offering other personnel suggestions.

But Miles, in retrospect, was never wrong. These musicians he chose blossomed into widely accepted masters of their instruments and music in general. He was unwavering in his ability to spot great talent.

Miles Davis always focused on the group’s overall impact

What is apparent in hindsight is that Miles used these virtuosic sidemen, players like saxophonists John Coltrane, Dave Liebman, and Kenny Garrett, for example, to counter his more sparse, melodic playing. Miles seemed to spotlight this yin-yang approach to improvising to make his ensembles more dynamic and interesting to the listener. And it was as if each of these later bands was an echo of the young Miles standing next to the master alto saxophonist Charlie Parker.

Miles Davis is considered a world-class trumpet player, and a virtuoso improviser, but he built some astounding groups, and was able to generate creative sessions with rosters of perfectly complementary musicians, quite often yielding amazing musical results. Miles was so focused on his group interactions that later in his career he spent many performances with his back to the audience.

So here they are… three simple, but powerful lessons distilled from trumpeter Miles Davis:

  1. Always find your own path: be brave, be bold, be original because emulating others (and possibly falling short) will always lead to unfair comparisons. As an original, there are no comparisons.
  2. Don’t be afraid to leave accomplishments behind and continue your exploration, even if it means your supporters take a while to catch up.
  3. Seek out and surround yourself with incredible talent, from any age, any background. This is the key to creating something so much larger, greater, and more expansive than yourself.

For more information about Miles Davis, consider reading his uncompromising autobiography Miles: The Autobiography, written with Quincy Troupe and published in 1989, two years before Davis’ death.




Writing (fiction and non-fiction), composing music, e-commerce. Teaches higher ed music & music business. Launched:

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Andy McWain

Andy McWain

Writing (fiction and non-fiction), composing music, e-commerce. Teaches higher ed music & music business. Launched:

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