Improv, Via Negativa

“Okay, but what is Improv really?”

In terms of creativity, it’s more useful to describe what it isn’t.

Consider a jazz saxophonist soloing over Giant Steps.

The architecture of the song is AABA. You don’t want to change that. You want it to stay the same. So that’s not where the improv lives.

The design of the playing (tone, timbre, instrument technique) is unique to the player. You don’t want to, on some notes sound like John Coltrane and on others sound like Charlie Parker. You want to maintain your sound. So the improv doesn’t live there.

What does change are the notes.

So every time you play Giant Steps, the architecture stays the same: that’s the song.

Your “sound” stays the same: that’s your style.

But the notes change. And that’s the improv.

Creativity Rhymes

An easy intro point to the creative process is rhyming.

Poetry is obvious.

Yet pretty much every creative discipline has a rhyme pattern. Here are a few:

  • contraction-release (modern dance)
  • shot-reverse shot (filmmaking)
  • high-low (fashion)
  • but-therefore (storytelling)
  • setup-punchline (standup) -call-response (jazz)
  • text-context (teaching)
  • text-subtext (drama)
  • event-interpretation (hermeneutics) -thesis-antithesis (rhetoric)
  • action-reaction (acting)
  • tension-release (architecture)
  • plant-payoff (narrative)
  • figure-ground (visual design)
  • straight man-comic (comedy)
  • real line-metaphor line (songwriting)

Even AI has picked up on this, in ways we don’t like:

  • it’s Not X, it’s Y

And sometimes, longer patterns are just back-to-back rhymes, like this 5-piece:

  1. Knock knock.
  2. Who’s there?
  3. Who?
  4. Who who?
  5. What are you, an owl?

If you want to engage your creativity, give rhyme a try.

Improv, Via Negativa

“Okay, but what is Improv really?”

In terms of creativity, it’s more useful to describe what it isn’t.

Consider a jazz saxophonist soloing over Giant Steps.

The architecture of the song is AABA. You don’t want to change that. You want it to stay the same. So that’s not where the improv lives.

The design of the playing (tone, timbre, instrument technique) is unique to the player. You don’t want to, on some notes sound like John Coltrane and on others sound like Charlie Parker. You want to maintain your sound. So the improv doesn’t live there.

What does change are the notes.

So every time you play Giant Steps, the architecture stays the same: that’s the song.

Your “sound” stays the same: that’s your style.

But the notes change. And that’s the improv.

The Art of War (and Chess and Fiction Writing)

“If you know the enemy and know yourself, you need not fear the result of a hundred battles." — Sun Tzu, The Art of War

Sun Tzu gives us two states for success:

  1. Know thyself
  2. Know thy enemy

But in chess, this is not enough.

You also need to know your openings, know your principles, and know the game you’re playing (a one-minute bullet match online is a different game than a 3 hour classical over-the-board tournament).

Which together might be something like:

  1. Know the players (psychology)
  2. Know your point (plan)
  3. Know ideas (principles)
  4. Know the parameters (sport)

Fiction writing is like chess, in that knowing your strengths and weaknesses as a writer, and the challenge of getting published before you, is not enough.

You also need to know your characters, your genre, and the audience you’re writing for.

Which together might be something like:

  1. Authorial truth (what you want to happen)
  2. Genre truth (what the conventions expect to happen)
  3. Character truth (what feels true to those experiencing the story)
  4. Audience truth (what needs to be true for the reader)

The strategy of chess is the interplay between what you know about yourself, what time control you’re playing, what opening you’re in, and which chess principles apply right now.

The strategy of fiction writing is the interplay between the story you want to tell, the story your publisher wants to promote, the story your audience wants to read, and the story that does the characters justice.

From that perspective, strategy is, indeed, an art.

Improv

Once upon a time, there was a young boy that became interested in the art of improvisation. So he played in band(s) and learned to jazz. He competed nationally in swing and learned to dance. He practiced on stage and learned to improv. And finally, he wrote a book of poetry and learned to rap.

And that young boy was me.

After those experiences, here is how I think about improv:

  1. Dance teaches the art of the move
  2. Rap teaches the art of the rhyme
  3. Jazz teaches the art of the melodic unit
  4. (Theatre improv) teaches the art of the scene

But that’s not always very useful.

For my writing community, I talk about it isomorphically:

  1. Dance is the art of the sentence. Worrying over the exact right words.
  2. Rap is the art of two sentences. Setup and punchline.
  3. Jazz is the art of the paragraph.
  4. Improv is the art of the scene.

For my computer science community, I talk about it through programming paradigms:

  1. Dance = imperative programming
  2. Rap = functional programming
  3. Jazz = procedural programming
  4. Improv = declarative programming (And 5. Combat = object-oriented programming. Put that’s another conversation).

The interesting thing is that all approaches are present in all the art forms.

You can improv in dance by thinking in terms of rhyming your moves. You can improv in jazz by thinking about the scene (motivic development). You can rap in paragraphs by focusing on storytelling instead of punchlines. And on and on.

Why should you care?

Because the foundational style of improv defines the art.

Rap starts with rhyme. If it doesn’t rhyme, its not longer rap.

Improv starts with scene. If its not a scene, but just one-liners or setup-punchline, it becomes standup comedy, not improv.

Add the others, sure. But start with the right sort of improvisation.

What’s in it for you?

Maybe 3 things.

  1. Skill: which type of improv are you most practiced in? This comes down to your parent discipline.
  2. Enjoyment: which type of improv is the most engaging, naturally, to you? This might not be what you’ve practiced, but what you enjoy watching.
  3. Impact: which type of improv gets the result you’re looking for? In fiction writing, beautiful sentences makes for great novels, rhyme makes for great sitcoms, paragraphs make for great anecdotes and short stories, scenes make for great screenplays.

But perhaps the most important question: what do you want to make?

  • Great moments?
  • Great rhymes?
  • Great units?
  • Great scenes?

There is no “right” art of improv.

Only improv that is right for your art.

A Billion Wicked Thoughts (and Five Personal Brands)

In the book “A Billion Wicked Thoughts”, a couple engineers decided to analyze internet search data to discover what we really desire.

They came up with 5 archetypes that show up in feminine fantasies:

  1. Surgeon
  2. Pirate
  3. Billionaire
  4. Vampire
  5. Werewolf

The idea is that they all represent a form of untamed masculinity.

I think they also represent 5 brand archetypes.

Consider this quote from Sahil Lavingia (founder of Gumroad): “Every job will be automated until four remain: engineer, entrepreneur, investor, artist.”

Add in the athlete, and you’ve got the modern brand version of the fantasy:

  1. Surgeon = Engineer
  2. Pirate = Entrepreneur
  3. Billionaire = Investor
  4. Vampire = Artist
  5. Werewolf = Athlete

But what makes them brands? In my head, I picture Arnold Schwarzenegger’s “come with me if you want to live, but adapted to each of these as brand promises:

  1. Engineer: “come with me if you want solutions.”
  2. Entrepreneur: “come with me if you want freedom.”
  3. Investor: “come with me if you want compounding value.”
  4. Artist: “come with me if you want beauty.”
  5. Werewolf: “come with me if you want protection.”

Leaning in to your brand promise means less process, and more product.

  1. Engineer: less tech talk, more “my product/service solves X”
  2. Entrepreneur: less hype, more new possibilities available
  3. Investor: less percentages, more legacy
  4. Werewolf: less gym sessions, more bradley.thor chopping wood

(Artists don’t need this advice, because they already get it: go to a musician’s page, and you won’t see them posting practicing with a metronome or Zoom sessions with their coach or page 23 of their music theory book. Just clips of the beauty of their finished work.)

So, what’s your brand?

Rocks and Stars

In business school, there is a framework around being a rockstar couple.

You have the rock: steady, predictable cashflow, and you have the star: high variability, but high possibility for making a lot of money.

In the entrepreneurship world we call it the Visionary and the Implementer.

But rocks and stars extend beyond business and entrepreneurship.

If you’re a rock, you won’t want to be a star, not really.

If you’re a star, you won’t be able to play the rock role for very wrong.

The real insight: accept whichever one you are.

Then, launch (your career, your relationships, your legacy) with that in mind.

Flying Solo

Hi. I’m Henry. I started my journey in entrepreneurship in 2014. Since then, I’ve had the opportunity to work with remarkable people on meaningful projects. Here is a quick timeline:

  • 2014-2016: the startup years. Started two companies with teams. Both failed. Learned 200 things not to do.

  • 2016-2020: the real estate years. Started an Airbnb company with a friend. Sold it in 2020 to move on to the next thing.

  • 2020-2024: the writing and research years. Worked for a few big startups, wrote biographies billionaires and bootstrappers, explored the world of communities and masterminds. The most lessons and insights.

  • 2024-2026: the client years. Worked one-on-one with founders as contributor, consultant, and advisor. Mainly equity partnerships and retainers. Seeking PMF, and sometimes finding it. Mainly trying to prevent the same early mistakes I made from sinking ships.

Now, I’m building my own things. I’ve always worked with teams. Turning a new leaf and working on putting out into the world the things I dream.

Stay tuned for more.