How to break rules intelligently

It’s Wednesday, April 3rd, and today we’re talking about knowing the rules before you break them.

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Break the rules intelligently

Let's start with an annoying contradiction about success:

The line between groundbreaking success and falling flat is thin. Many miss the mark because they try to reinvent the wheel before understanding why it rolls.

Also,

There are countless examples where ignorance produces greatness. Is it naive wisdom? Dumb luck?

I’ve always thought about it like this:

1. You start by breaking rules, somewhat embarrassingly.

2. Then you learn them, even respect them.

3. Next, mastery allows you to see beyond them, creating new categories.

4. But most get stuck there, too cautious to leap again.

Breaking and following rules is a skill set of its own. Dancing right on the edge of knowns and unknowns is where we break new ground.

So, why care? Because getting this cycle right is what separates the average from the mavericks.

Today, we’re going to cover:

• The four stages of competence, from clueless to master.

• A framework that’s key to big business.

• How to avoid getting stuck in the safe zone.

Let’s get into it.

In 2004, I decided to choreograph a site-specific piece as part of an arts festival.

For my non-dancer friends: "site-specific" is work you choreograph in response to a particular space, working with its constraints. For example, Blue Lapis Light's In Light, which featured aerial dancers connected by bungee cords:

If you took the same dance and put it on a standard stage, it would lose its core magic and specificity. (and if you wanna see them in action, click here)

I was still very new to dance. I chose our city library, which had multiple spaces to play with: wide steps, a large front porch, and walkways through the grass. I decided each space would belong to a different genre: jazz over here, tappers over there, a live drummer, a beatboxer, and two dancers freestyling. It was a grand vision. I decided to call it…wait for it…

Project ROA (Resurrection of Art).

I don’t know who in their right mind let me do this, but everything about this, front, back, and sideways, still gives me second-hand embarrassment. From the wildly pretentious name to the fact that I could barely dance myself, let alone have any business leading a project of that caliber.

To my surprise, I managed to recruit everyone needed and debuted our performance at the summer art festival.

I don’t recall much of it, but thank goodness digital recording was not a thing because I’m guessing it’s something that should never see the light of day.

Have you ever looked back on something you did and thought, “Where did I get the nerve?!”

It seems both harmful and helpful.

Had I known how ill-equipped I was, I would not have done it. But I was ignorant, and so naively marched forward. The project was a key experience and step forward in my journey as an artist.

But could it have done more harm than good?

Breaking the Rules Is an Earned Privilege

When leading and creating, a necessary rhythm exists: the cycle of learning, unlearning, and relearning. Breaking the rules isn't just a rite of passage but an earned privilege that carries with it the power to redefine entire categories of business and art.

The parallels between dance and entrepreneurship are striking, which is likely why I feel so deeply drawn to both. Improvisation is a happy place for me, and I often find myself pondering this cycle. Why, when watching another dancer improvise, do I find some magnetizing and others repelling?

It comes down to this cycle. When a dancer with no training and skillset performs an improv, it's clumsy, ambiguous, and lacks refinement. As a dancer masters the basics—technique, musicality, and performance—they are building a movement vocabulary and developing a body of knowledge. This foundation allows them to inform their practice and break rules effectively.

Bob Fosse did it. Martha Graham did it. But neither of them dared to ignore the rules. Rather, they mastered them, fully aware that you can only rightfully break and improve upon what you already know.

The Rookie Phase: Breaking Rules Badly

Remember your first important project? It was probably messy. Rules were bent, perhaps broken, and mistakes were made. This isn't just part of the process; it is the process. It's the business equivalent of a toddler's first steps: necessary and a hot mess.

However, there's an undeniable magic in these early blunders. They are your first, unsteady steps toward understanding the invisible boundaries that define success and failure in your world.

The Four Stages of Competence

When we start moving away from the chaos toward something more graceful, we encounter the four stages of competence.

🥴 Initially, we're blissfully unaware of how much we don't know (unconscious incompetence).

😬 Then, as we start to learn, we become painfully aware of our limitations (conscious incompetence).

🤓 This awareness drives us to acquire skills and knowledge, leading us to conscious competence, where executing our roles effectively takes deliberate effort.

😎 Finally, we reach unconscious competence, where our skills become second nature.

Through this process, we earn the right to challenge the rules we've learned.

This isn't about rebellion for rebellion's sake but innovation with intention. Companies like Netflix didn't just defy conventional wisdom on a whim; they did so after understanding the limitations of existing models and seeing the potential for something greater.

This phase of intelligent rule-breaking is what sets true trailblazers apart. It's not just that they know when to break the rules, but why those rules need to be broken in the first place.

The Exploit-Explore Continuum

The Exploit-Explore Continuum is a concept often discussed in business strategy and innovation circles. It summarizes the balance founders must strike between exploiting existing resources, capabilities, and business models (Exploit) and exploring new possibilities, innovations, and markets (Explore).

Exploit is about the stuff that already works. It’s about optimizing current assets and knowledge to ensure steady revenue and efficiency, making the most of what you already have.

Explore, on the other hand, is about venturing into uncharted territory. It involves new ways of thinking, developing new business models, researching emerging markets, and creating novel products or services. This side of the continuum is characterized by uncertainty, experimentation, and the potential for high reward, albeit at a higher risk.

The idea is to lean hard into what’s working while allowing space for lots of quick experimentation, killing what doesn’t work until you find something that does, which then moves into the exploitation category so you can find more new things.

It’s how antifragile businesses are built, and it’s a beautiful example of knowing the rules and then intelligently breaking them.

My Framework for Continuous Learning

Personally, I struggle with the tendency to gorge on information and do little with it. I devour books, podcasts, courses, and newsletters, becoming bloated with information but releasing none of it through action.

I’ve had to develop a sort of framework for this. It’s present in my own daily learning, but it’s also present in the way I work with my team, mentor founders through Techstars, and create with dancers.

I break this into four steps:

1. Embrace Curiosity: I ask “why” a lot. I also actively encourage the people I work with to do the same. Why are we doing it like this? What if we did it like that? Where are our blind spots? Why not try?

2. Just Enough Info: If I am not careful, I will spend way too long in the learning phase. Reading, researching, reading more, researching more; at some point, it becomes a clever way to hide from doing anything. The trick, I’ve found, is to learn just enough to not blow things up, and then start doing.

3. Implementation Checkpoints: Once a book, pod, or course is finished, I am forbidden from taking in another on the same topic until I implement at least one tactic. I’ve rarely struggled with a knowledge problem. I’ve struggled with an implementation problem more times than I care to admit.

4. Revise, Respect: Break the damn rules. Respect them (and respect others who choose to follow them), but when you find a “why” without a good answer, do something about it.

A small example: when I started Wondry, I decided to only take on a very small number of clients, building a waitlist instead. At the time, several friends told me this was silly and the better route was to scale and meet demand.

Why? More revenue? Build a bigger business? Why assume that these are everyone's priorities?

This didn’t work for me. A calendar with very few meetings and clients I felt a deep connection to mattered more. While most agencies value volume, I did not. Those were my rules.

I’m not saying throw away your playbook, but knowing when and how to rewrite it is the height of mastery.

With every guest on Shark Tank talking about how they’re “disrupting” and “changing the game”, few have the language for how and why it works. Now you do.

Onward,

April

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