There Are No Mistakes –
The Art of Letting Things Fall Apart

A mistake is the most beautiful thing in the world, man. It is the only way you can get to some place you never been before. I try to make as many as I can. Making a mistake is the only way that you can grow.

E.W. Waignwright, Jazz Drummer

Long before philosophy, jazz was my first love. In high school and college, you would find me camped out in front of the piano, running scales, lines, and arpeggios.

Ray McDermott, one of my first great teachers of philosophy, shared this love of jazz. When I met Ray ten years ago, he asked for my help on a question about how we think about jazz, education, and life.

The question: what does it mean to make a mistake?  We found a track of the great jazz pianist Thelonious Monk hitting a note that sounded like a clear “mistake.”  But as we listened more closely, we found that the “mistake” opened new creative possibilities.  This “wrong” note led Monk to a sequence of even more “wrong” notes that sounded so exquisitely “wrong” they became “right.”  We ended up writing an article about it called, “Plans, Takes, and Mis-Takes.”

It turned out that by letting things fall apart – by going with, rather than against, this “mistake” – Monk’s music got deeper and richer.

This week, I’m playing with the idea that just as there are no mistakes in jazz, there are no mistakes in life.

For me, this is a radical idea.  I spend much of my time avoiding mistakes.  I try to avoid screw-ups in the classroom, mistakes in my writing, and errors in my relationships and life.

All this mistake-free living can leave us clinging to perfection – gripping life like the reigns of an out of control horse.

What jazz musicians teach us, however, is that by letting things fall apart, life might just get deeper and even more beautiful.  As the famous jazz drummer E.W. Waignwright once told me, “A mistake is the most beautiful thing in the world, man.  It is the only way you can get to some place you have never been before.  I try to make as many as I can.  Making a mistake is the only way that you can grow.”

My first jazz piano teacher – a silver-haired jazz master named Keith MacDonald –agreed.  As he once told me, “Sometimes missing the note is more effective and appreciated than hitting the right note.  Playing careful is dull.  Playing with feeling is always better.  It is just more exciting to see someone on the edge – taking chances – with mistakes.”

So here’s the practice:

Step 1 Spot Your Inner Perfectionist –  As you move through each day, notice when your inner perfectionist arises – that part of you that works so hard to live a mistake-free life.   Your body is a great indicator.  Notice when tension arises.  Does your neck tense up?  Do you get headaches?  Does your back hurt?  Physical tension tends to mirror an inner state of resistance.  It indicates that in work, in relationships, or in life, you’re trying to hold everything together, trying to avoid mistakes at all cost.

Step 2Let Things Fall Apart – I’ve summited Kilimanjaro and jumped out of a plane.  But for me, the spiritual and philosophical act of letting things fall apart is one hundred times more difficult.  Climbing tall mountains requires strength and courage.  Letting go of perfection and allowing mistakes to arise in work, relationships, and life requires a deeper courage.  It requires the ability to jump headfirst into what Cornel West calls “life’s abyss.”

This may sound like a masochistic, even dangerous, practice.  What if by letting go and opening to mistakes, you lose your job, your marriage, or your life?

What we learn from the great jazz musicians is that the opposite might be just as, if not more, true.  Monk’s “mistake” didn’t ruin his career.  It didn’t lead the audience that night to walk out of the club.  His “mistake” had the opposite effect.  It opened up a new and unexpected field of possibilities.

So as you go through the week, ask your self:  “Where am I clinging to perfection and avoiding mistakes?   Is it possible that by allowing mistakes, my life might grow deeper?”

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  1. Siggi says:

    A very interesting topic. I agree about music “on the edge”. So thrilling! Easier said than done to apply this to life though, as you point out. Our fear of failure runs deep, especially if one is an “achiever” I’ll give it a shot though and try riffing on my mistakes like the great Monk.

    regards from Iceland

    P.S. Just came across your site today. Downloaded your free e-book from Really liked it! I share Thoreau’s concerns about speed and distraction. It is getting completely out of hand. The scenario you describe in the beginning of the book is real for a large part of the population. We switch between realities many times every hour, in many cases completely avoiding the NOW for days on end. The advent of “smart phones” and social media is particularly disturbing. It is never enough to just BE somewhere…you always have to “share” it or check to see if anyone else is doing something cooler. I think it is astonishing how few seem concerned with this and the potential consequences for our mental and spiritual well-being. Anyhoo….I’ll definately visit your site frequently, so keep up the good work! :-)

  2. Sean McCaffrey says:

    Hey Nate, long time, etc. Glad to see the blog continues. This one I liked. I think what you’re referring to as “allowing mistakes” is what I rather think of as just going with the flow. Not sure I’d suggest this when parachuting, for example. I certainly don’t when doing advance work for a candidate, especially if it’s, say, for a presidential event. In those instances, you really don’t allow for mistakes. But having done that sort of thing for so long, I relish the spontaneity of not planning out every little detail. Sure, in the back of my mind, there’s always a barometer of sorts that keeps track of things like time, risk, cost, etc.. But today, when half of the nation is overstressed and the other half is overmedicated, I encourage people to follow your advice in this test: turn a corner not knowing where it leads, try a new sandwich, rent a bad movie, fill up with premium, drink the worm, introduce yourself to a stranger, and so on. Like Robert Frost and his two roads… some folks take the road they know while others stand there forever, unable to make anychoice whatsoever (like whatshisname and whatshisname in Godot). Anyway, good task this week. Cheers, -Sean

    • Nate says:

      Hey Sean,

      Glad to hear that everything is going well for you! Yes, the blog continues, though at a slightly slower pace since I am currently teaching a full load. I like your advice a lot. There are certainly times where mistakes are not ideal and I’m so grateful to you for the practices you propose. I might try some of those out today!

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