Jordan Peele

Rewrite the Rules

Absorb what’s useful, discard what is useless, and add what is specifically your own.
— Bruce Lee

By 1964, Bruce Lee had started to gain a following. He had two martial arts schools in Oakland and Seattle, where he taught a modified version of wing chun, a martial art with foundations in kung fu. But he was growing skeptical of locking himself into a single martial arts discipline and weary of the loyalists who believed their style of combat was superior to everything else.

Lee started experimenting with minor changes in technique, testing new angles in his stances and movements. The changes weren’t dramatic—the classical wing chun style had been seared into his every movement since he began studying at thirteen years old in Hong Kong. But they were still changes. And the kung fu traditionalists took exception.

As Lee refined his approach, he would visit the Sun Sing Theater in San Francisco’s Chinatown, demonstrating his technique and voicing his perspective that unnecessary, performative, impractical movements hampered traditional martial arts. As Lee grew more vocal, the kung fu old guard in Chinatown grew more irritated. He was disrupting their ways, compromising the sacredness of kung fu, and someone needed to put him in his place.

Taking on the traditionalists

In the fall of 1964, Lee’s critics in San Francisco’s kung fu community issued a challenge. They proposed a fight between him and an opponent of their choosing. If their fighter won, Lee would have to stop teaching. And if Lee won, he could continue without opposition. Lee was 23 years old at the time and eager to prove them wrong.

The traditionalists selected a young, skilled kung-fu fighter, Wong Jack-Man, as their champion. In November, the delegation arrived in Oakland for the fight. The first order of business was laying down the rules. The traditionalists offered up one rule after another, but Lee pushed back. He wanted a street fight—anything goes—not a controlled, theatrical performance with an intricate scoring method. After some negotiation, the fight was on. Bruce Lee came out swinging.

After the initial exchange, Jack-Man sprinted away, attempting to exhaust Lee and leave him winded. Lee gave chase, trying to grab him from behind. The fight was a mess, a far cry from the combat routines each man had practiced in their gyms. Finally, Lee had Jack-Man on the ground. Lee stood over him, yelling in Cantonese, “Do you yield?” The fight was over in three minutes.

But after the victory, Lee didn’t feel victorious or vindicated. Something was still bothering him. In the weeks that followed, he realized that wing chun, even his modified version, hadn’t prepared him for an anything-goes scenario. Most of what he learned only prepared him for neatly defined scenarios or sparring in the gym. In the months and years that followed, Lee began to define his own martial art and philosophy—jeet kune do.

Bridging disciplines

Until this point, Lee used wing chun as his foundation and made slight adjustments. But as he developed jeet kune do, he emphasized formlessness and not getting trapped in a single style. He looked beyond standard martial arts for inspiration. From boxing, he took its footwork, jabs, bobs, weaves, and hooks; from fencing elements of range and the timing of the stop hit. He was open to anything that would prove useful in a real fight—practicality above all else.

Jeet kune do wasn’t about a specific style. The whole point was that it could take on any shape, style, or form. Techniques from seemingly disparate disciplines previously considered off-limits could be used at will. As long it was effective, kept your opponent off guard, and gave you an advantage, it was on the table. There wasn’t a single right way to fight—contrary to the teachings of many traditional martial arts practices, which forced students into a fixed pattern of movements and routines.

In the years following the fight in Oakland, Lee realized in its fullness what he had scratched the surface of. Most martial arts practices were built upon theories, clearly defined rules, and a neat set of movements. He referred to this type of performative fighting that protected both fighters as “dryland swimming.” These practices weren’t helpful in real fights and life-or-death scenarios where everything is unpredictable and self-defense matters most. The other person might fight dirty, have a weapon, or be an expert in any number of fighting styles. You won’t be able to pause the fight and enforce a neat set of rules.

Lee focused on adaptability and developing tools that applied to real-life scenarios. Forget style. Style is what had divided martial artists, restricting their growth by forcing them to adopt a “this or that” approach to combat. Lee’s approach was to use what worked and drop what didn’t. And this mindset is why many credit Lee as the father of mixed martial arts; because of his focus on using the most effective movement or technique based on the situation.

At some point in your own career, you will have to take the rules you learned, tear them up, and reimagine them. The whole point of learning frameworks is so you can break them in creative ways and create something of your own.

Questioning unwritten rules

Whatever industry we operate in has antiquated ways of doing things. Many of us become so accustomed to these unwritten rules or standard operating procedures that we stop observing them and accept them as truth. You must fight this urge to conform and preserve your ability to evaluate things from a fresh perspective. If you don’t, you’ll create work that’s derivative and halts any real progress or message you could help advance.

Purists don’t make progress because they’re removed from reality. They are so focused on how things should be that they become trapped by abstract rules, unable to perform in anything less than pristine conditions in their environments. They delude themselves into believing the best and right way has already been defined.

“This is the best method” or “this is how it has always been done” should set off your internal alarm. They’re a clear signal to question and challenge the status quo. The world doesn’t need another person playing it safe, afraid to go against the grain. The world needs you. And the best way you can put yourself across is by combining your disciplines, interests, and observations in a way that’s unique to you and speaks to a truth you’ve identified about the world. Even if it challenges deeply held conventions in your craft or society. Go ahead, piss some people off. It will be good for them.

When Jordan Peele made the jump to directing horror films after completing the fifth successful season of his comedy series Key & Peele, people were shocked. At first glance, comedy and horror seem to exist on opposite sides of the spectrum. But there are more similarities for Peele once you get beneath the surface. Both appeal to outsiders. Both are a means of facing our fears. The only difference is in tone. Comedy is an attempt to laugh off our fears. While horror is an attempt to master our fears by looking straight at them.

But Peele was frustrated with horror films. They were too formulaic, predictable, and revealed their cards too early, leaving little room to challenge audiences as the story unfolded. Just as Peele studied sketch comedy, learned the rules, then pushed the limits, he took the same approach in horror to challenge the confines of the genre. He was determined to reengineer the whole thing to add more depth, make the genre more accessible, and tell better stories.

Peele’s roots in comedy helped him to become a master at observation and right-sizing risks. He pushed audiences to stretch alongside him, working to understand something from someone else’s point of view—the ultimate power of storytelling. Horror was a similar way to provoke. And adapting the genre to his approach allowed him to create something new.

Just as Bruce Lee learned the craft, techniques, and discipline of wing chun, then created something of his own to improve and bridge the divide in martial arts. Peele learned the rules and combined his own experiences in a way that allowed him to push the threshold of what was typical of horror films.

Advancing your craft

With your own experiences and observations, you can push the dial further than you think. You just have to trust your perspective and break the rules when they no longer serve what you’re attempting to create.

Whether art, business, film, music, science, or technology, there are techniques, approaches, and mental models—things we believe to be true—that we will look back on in ten years and laugh about. To be part of progress, you must learn to break the rules and challenge what’s accepted without question—especially what people disguise as “best practices.”

If you want to advance the conversation, you have to stretch beyond what’s comfortable. Challenge yourself to combine ideas in new ways or test a new approach. Apply it to your life. Apply it to your discipline. By synthesizing ideas and personal observations in your own way and giving the world a fresh take, you create work that more strongly resonates with you and your audience.

If you intend to go through life as a consumer, forget this lesson. But if you want to create and leave your mark on the world, you must find ways to advance your craft and the conversation—no matter how small your first steps might appear. This is how you transcend from an operator to a trailblazer, inspiring others to create and see the world in a new way.


Call Your Own Shots

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood…
— Teddy Roosevelt

Jordan Peele, like so many other comedians, saw Saturday Night Live as the pinnacle of sketch comedy. By 2008, Peele had worked his way up the ranks through Boom Chicago, Second City, and Mad TV to hone his sketch and improv skills. Along the way, he earned a reputation for imitations. He could become anyone. 

Around this time, Senator Barack Obama was emerging as a leading candidate for the Presidency and SNL needed someone to play the part. Peele received a call from Seth Myers asking if he had an Obama impression. Peele worked on it for a week then flew out to New York to audition. This was his chance to reach the top after years of hard work.

Peele played it perfectly. SNL offered him the job. There was only one problem—he was still under contract at Mad TV. Peele figured he could negotiate his way out, but the producers at Mad TV wouldn’t budge. Despite his pleas, they refused to concede. He was required to finish out his contract. End of conversation. 

Peele was crushed. SNL was the dream he had worked so hard towards for his entire career. And just like that, with an offer in hand, it was ripped out from underneath him. What right did these network executives have to use his fate as a bargaining chip? Peele was forced to grapple with an uncertain path forward. 

In the weeks, months, and years that followed, Peele discovered a way to channel the anger and frustration from the experience. He realized that if he could become a producer, he would have more leverage and avoid trapping himself in a similar position in the future. 

Peele recognized that producers were the ones making the final decisions about art and comedy. But most of them were shit at it. They mindlessly followed what had worked in the past and were oblivious to what made good art or comedy. Peele was tired of everything having to pass through these gatekeepers to reach audiences. 

Seize creative control

In 2009, after a five-year run at Mad TV and 94 episodes, Peele’s contract finally expired. And he set out with full force to take creative control over his own comedy and content.

As Peele found his footing, he began to explore the idea of his own sketch show with Keegan-Michael Key, a fellow Mad TV alumnus. And the more they discussed the concept, the more they realized it was something they had to do. Key & Peele was born soon after. 

Over the course of thirteen weeks, Key and Peele created more than 250 sketches that showcased the breadth of their comedic skills. They would pare this down to 54 sketches for the first season. As their own executive producers, they could take bigger risks than they otherwise might have been able to. They were constantly assessing how far they could push because that’s what they believed audiences deserved.

The show would run for five seasons on Comedy Central. It is widely considered to be one of the best sketch series ever created. Key & Peele dialed into what they knew people were thinking but might not be saying, and brought it to life through comedy. The polished, bite-sized skits only increased their virality online. Skits like “Obama’s Anger Translator” and “Substitute Teacher” became staples in popular culture. But without Peele pursuing creative control, they would have never been made. 

When Peele was forced to let the SNL offer go, he could have thrown up his hands. He could have accepted that he was powerless against the weight of those who held creative control and made the executive decisions. But instead, he used this as motivation to seize creative control. To define his own work. To answer to himself.

Unveil the hidden risks

Despite what we might tell ourselves, there’s no real justification for taking a hands-off approach in our own lives. But we often do exactly this. We get comfortable operating as passengers in our own stories and console ourselves with empty anecdotes like ‘whatever happens, happens.’ The consequence is that we let mediocre leaders, peers, producers, and executives dictate our future. 

In our indifference, we allow inertia to dull the edges of our work and limit our trajectory.

Living—at least meaningfully—requires a hands-on approach. You are the only one who understands what brings you life, why that matters to you, and where you want to take your work. There are certainly things that exist beyond your control. But you damn well better pry back control of the things that are. 

You must move with conviction, direct your own life, and learn to circumvent the gatekeepers. When you subject yourself to the whims of a committee whose opinions you don’t respect, you end up compromising on too many critical aspects of your work.

There is an important difference between collaborators and gatekeepers. Gatekeepers are rent-seeking suits who justify their position through resource guarding. Collaborators are operators with skin in the game who want to help you wrestle back creative control. Collaborators pass the foxhole test.

The difference is in intention and risk tolerance. Gatekeepers aren’t looking to push things forward. They’re just trying to follow a playbook that prescribes success. Why take a risk on something new when you can make Batman for the 97th time? Never mind that it’s derivative or that in 50 years our grandkids are going to be convinced that we lacked any sort of original thought and we all had a superhero fetish to boot. 

It’s important to surround yourself with collaborators who push you and help bring your work to life. The work that’s true to you. The work that’s helping you to uncover what you believe about the world. Not a watered-down version. Collaborators will be there in the trenches helping you dig.

Create leverage

Similar to creative control, another way to think about this is by seizing the means of production. It gives you flexibility to set the tone. It creates an opportunity for you to go on the offensive, create momentum, and stop resistance in its tracks. 

By 210 B.C., Carthaginian general Hannibal had been wreaking havoc, fighting on the doorstep of Italy for sixteen years. The Roman general, Scipio Africanus grew tired of being baited into exhausting battles that they couldn’t win. Scipio then turned his attention to slowly capturing Hannibal’s means of production so he could better dictate the battles moving forward. 

Scipio’s first step was to take control of New Carthage in Spain—a regional capital where the Carthaginians stored vast amounts of wealth and supplies. Then he realized New Carthage depended on Carthage so he took the battle to modern-day Tunisia. This forced Hannibal and his army to return to their homeland and play defense for the first time in more than a decade. And finally, Scipio saw that Carthage depended on its fertile farmlands for material prosperity, so he struck the Bagradas Valley. This was a turning point in the war. Carthage sued for peace and they were all but eliminated as a threat to Rome. 

By controlling the means of production, Scipio was able to dictate his own terms. You always want to be able to set the tempo, rather than allowing yourself to be thrashed around, reacting to events happening around you. 

Maximize your upside

When you take creative control, you put yourself on the line. You assume the risk. But you also gain exposure to the upside. Both in terms of success and in what you’re learning.

You will learn far more creating your own art, training for your own race, or launching your own startup than you otherwise would optimizing the sign-up funnel at a behemoth tech company, mindlessly consuming sports, or performing sketches that have to be approved by a committee of risk-averse producers.

Far from being the thing that derailed Jordan Peele’s career, not being able to work things out at SNL allowed him to be more ambitious in his work. In five seasons at Key & Peele, he was able to hone his own writing and directing abilities which would prove invaluable later in his career. He was able to pursue more ideas, explore more worlds, and craft more characters than he would have been able to playing by someone else’s rules.

Peele leaned in, taking more creative control and risks when he could have retreated. In doing so, he created a far steeper trajectory in his own career. While it was impossible to know then how things might play out, he trusted himself and his intentions to move towards taking back creative control over his own ideas. And he acted upon that. This gave him more flexibility, room to maneuver, and eliminated dependencies that stood in the way of bringing his ideas to life. 

By taking creative control and calling our own shots, we put our ass on the line. But this demands its own level of respect. The credit belongs to the man in the arena.

When we shut the escape hatch and there’s no turning back, our commitment is what empowers us. It’s what emboldens us to face obstacles and gatekeepers head-on. In doing so, we create more opportunities to show up and take risks for what we believe in. And in those moments when we move unapologetically towards creating something that resonates with us, the universe has a tendency to answer the call.

Bet on yourself. Always.