13 Aug 2026 How To Improvise A Life
“We’re all being surprised at the same time.” Seth Godin riffed on this Keith Jarrett quote (regarding jazz improvisation) a few days ago, and I thought I’d pick it up as well.
I’ve always liked the idea of jazz music as a mental model for financial planning: Rather than thinking of your life as some note-for-note transcription of a classical melody everyone already knows (work X number of years, buy the beach house when you turn 50, retire at 65, play golf and/or mahjong every day, etc.), you start with the shape of a standard (what would history and my value system say are the building blocks of a Good Life?), and you learn to play around it, bouncing off of your fellow musicians, and making something surprising and wonderful as a result. The possibilities are quite literally endless by virtue of the openness with which you began to play the music.
To put it more bluntly, most people would be happier with their lives if there was greater emphasis on learning to be improvisational rather than rote memorization and regurgitation of someone else’s music.
Is the metaphor getting too messy?
Here’s the musical version: In 1975, the aforementioned Keith Jarrett was 29-years old. He was set to play the first ever jazz concert in the Köln Opera House in the middle of an unprecedented concert tour. It was unprecedented because he was playing solo pieces that he was composing on the spot. If that wasn’t wild enough, here are some additional details:
- The concert was put on by a 17-year old German named Vera Brandes, who booked the opera house for an 11:30pm start time, as it was the only one they’d make available for a jazz artist.
- Jarrett arrived to the concert after a 350-mile drive from the previous concert in Switzerland, no sleep in the previous 24 hours, and in tremendous pain (he wore a back brace during the concert!).
- The piano that he requested—a Bösendorfer 290 Imperial concert grand piano—was promised to him, but through a series of errors, it wasn’t delivered to the concert hall. When Jarrett arrived, what was available was a Bösendorfer, just a very badly out of tune and barely playable rehearsal piano.
- After nearly backing out of the concert altogether, Jarrett agreed to go on (possibly out of kindness to the young promoter), and then proceeded to work around the tremendous limitations of the instrument to deliver what is one of the iconic performances ever given. The album made from the live recording of the concert is to this day the best-selling solo jazz album of all time and the best-selling piano album of all time.
Here is the real life version: Nothing is certain about the future. Today you have some assets and some income and many, many things you could spend money on, plus the things you must spend money on. You have interests and skills and hobbies and fears and hopes and dreams. More importantly there are other people not named “you,” some of whom you love and may have varying levels of obligation to, whether by design or otherwise.
Then life happens! Beautiful and terrible things will happen. This is the plight of everyone. When the terrible things happen, you may want to back out of the proverbial concert altogether. Don’t do that! You are needed here. But you do need to make a choice about what to do next.
And the incredible thing is that sometimes, the limitations of our lives—if we choose to play improvisationally—can turn out to become freedoms. We would never have gotten what is the best-selling piano album of all time without the dud Bösendorfer. Jarrett simply would not have played anything remotely resembling what he did in fact play, if he had gotten the piano he asked for.
The same is true for you and me.
To me, the skills required in the world of personal finance to play improvisationally and not mechanically are essentially these:
- Regular Consideration of the Good Life. What does it entail? Be careful about unexamined assumptions. Consider the wisdom traditions and the elders in your life who may have some experience to draw on. Beware the trap of status-buying and performance. Focus on being rather than seeming. A commitment to this skill is imperative.
- Margin. Of both time and cash flow. You live beneath your means so that your life can breathe a bit.
- Liquidity. Cash is inefficient until it is the only thing that will do. That “until” is not marked on anyone’s calendar, so you have to pretend a bit. Have some cash, and don’t invest in illiquid funds that may not let you get out when you need to.
- Courage. It takes courage to try stuff. Some of our best friends lived in New York City for a month with their three young kids because they thought it could be formative. And because they had margin and liquidity (and workplace flexibility), they made it happen. Other friends have made huge career changes which from the outside looking in didn’t make much sense, but which in fact were life-changing for those involved in all sorts of positive ways. Many of our friends live quiet, unassuming lives that enable them to say big “yes”es to the folks in our community who struggle to make ends meet. All of these people have courage to practice what they say is important to them, and such courage is contagious.
The idea of living improvisationally doesn’t mean you can’t play the hits. I’m not saying don’t retire at 65 or buy the beach house, or that you have to make a huge career change or do something weird. But it does mean playing those hits with your own spin and style, on purpose. It’s the autopilot-playing of sheet music you’ve been handed by someone else that we’re trying to avoid here.
So if you haven’t been practicing, working out your own playing style, now is a great time to start. Improvisation is not the same as winging it. And if we can help by having conversations around the Good Life, margin, liquidity, and courage, we’d love to do so.
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