How to Break Rules Effectively



“If I had observed all the rules, I would’ve never gotten anywhere.” - Marilyn Monroe

“Know the rules so well that you can break them effectively.” - Dalai Lama

Rules play an integral part of our lives. Though to push humanity forward we need rule breakers.

If we want to take part in pushing humanity forward, we must be effective rule breakers ourselves. To be at the top of any art form for decades, in investing, business, etc., necessitates constant evolution. That means we need to keep breaking the rules, others’ and our own.

We must study how the best broke rules. How they broke through comfort zones and kept doing the unexpected. How they created new rules.

Below legendary jazz pianist Herbie Hancock described his rule breaking methodology. One that has allowed him to constantly evolve and dominate the jazz scene for decades.

Note Hancock’s description of the mentor apprentice relationship - the theme of Standing on the Shoulders of Giants

Many teachers have educated and continue to train their students by placing a rule book on an imaginary pedestal and adhering to strict convention. But I believe a master teacher has the wisdom to encourage critical thinking and development outside of the anointed rule book.

Rules have no more rigidity than the stem of a sunflower. But that flower allows the blossom to bend and change in direction in order to face the sun… With this reasoning, rules need to be flexible to function within the creative aspect of living as a support for change and new development. Rules support and also encourage new possibilities.

And who are the one’s we study? Certainly not the ones who follow the rules. We study the ones who break the rules and make new rules, right?

Chris Anderson - Blind Pianist

He often used imagery when he spoke about harmony, which was interesting because he couldn’t see. He connected with nature, water going over pebbles. The whoosh of the wind. The babbling brook. The song birds. The silence of the puffy clouds.

He developed something new by taking older, overlooked ideas then restructuring and combining them with his current approach.

When I heard Chris play, I was hooked. I proceeded to copy and dissect the information and incorporate it into the harmonic expression I’ve used ever since. This beautiful mentor disciple relationship has been handed down to younger musicians through me and others and thus have incorporated Chris’s approach into the musical lexicon.

If you listen to the recording “Solitude” on the album the Joni Letters, with just me and the bassist, you hear Chris Anderson all over that tune.

An important part of the creative process and perhaps a broader interpretation of breaking the rules is taking an idea that has been edited out of the vocabulary, rediscovering, and restructuring it. An evolution of the original idea.

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@seaniddings, I really like the quotes you shared. Especially the first part about rules and the stem of a sunflower.


Yes, it’s a great analogy to remember to be flexible in your thinking.

I like to think that the sun is your inner voice (subconscious). Too many people are transfixed at looking at distant galaxies - other people - for light - ideas - when we have all the sunlight - ideas - in ourselves already.