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.

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Sources:

1. Tao of Jeet Kune Do, Bruce Lee

2. Be Water, My Friend, Shannon Lee

3. The Life Philosophy of Bruce Lee, The Art of Manliness

4. How Bruce Lee Worked, Stuff You Should Know

Seek Meaning Over Influence

“If you care too much about being praised, in the end you will not accomplish anything serious…Let the judgments of others be the consequence of your deeds, not their purpose.”

— Leo Tolstoy

Six months after reaching space aboard the Space Shuttle Endeavor, Mae Jemison announced her resignation from NASA. Her childhood dream was fulfilled. And while she wasn’t done with space exploration, she wanted to apply her knowledge, skills, and experience in new ways that would have otherwise been limited by the specialized training of the astronaut corps at NASA.

Many people considered her foolish to leave NASA—why walk away from the pinnacle of human exploration? But she trusted herself and knew it was time to focus on the next thing she found meaning in. This wasn’t the first time she made a decision that challenged the status quo in favor of an opportunity that was meaningful to her.

At 20 years old, after graduating from Stanford with a Bachelor’s in Chemical Engineering and Afro-American Studies, Jemison enrolled in medical school at Cornell. In between semesters, she traveled and found a real sense of purpose in providing primary medical care in developing countries. These experiences taught her more about herself and helped her feel more connected to the world. She immediately knew she wanted a deeper experience in this environment after finishing medical school.

Going against the grain

But the expectation at Cornell—an elite medical school—was that their graduates pursue a prestigious residency after graduation. Jemison simply wasn’t interested. She planned to complete a brief one-year internship at the Los Angeles County/University of Southern California Medical Center. She would then return to work in the developing world to help in whatever capacity she could.

The deans at Cornell weren’t thrilled about her plan. One afternoon, they called Jemison in for a meeting and asked her to reconsider. She explained her reasoning, but they interrupted and claimed she was making a mistake. They outlined the consequences—she would fall behind her peers over the next decade and feel less accomplished. She followed her decision anyway.

After completing her internship, Jemison joined the Peace Corps as a Medical Officer for Sierra Leone and Liberia. She was responsible for the health of all Peace Corps volunteers, staff members, and embassy personnel. She acted as a primary care physician and managed a medical office, laboratory, and pharmacy.

While in West Africa, she navigated environments with insufficient equipment, medication, and supplies. But she honed her resourcefulness, pulling knowledge across different disciplines to navigate challenging situations.

Early in her tenure, one of the Peace Corps volunteers became sick with what Jemison thought could be meningitis with life-threatening complications. She worked to stabilize his condition through the night. But his condition worsened, and she knew she had to act.

Jemison called the U.S. Embassy to secure a military medical evacuation. They questioned whether she had the authority to give that type of order. She calmly explained the situation and that she didn’t need anyone’s permission. The Embassy conceded. By the time Jemison and the volunteer reached the Air Force hospital in Germany, Jemison had been up for 56 hours. But she had saved his life.

These types of experiences would prove invaluable and set her apart when, on her return to the U.S. in 1987, when she applied to NASA’s astronaut training program. Out of 2,000 applicants, Jemison was one of the fifteen accepted.

Almost ten years from the day that the deans at Cornell told her that she was setting herself back in her career by taking a non-traditional approach and that she would regret it, Jemison was orbiting Earth as the first black woman in space.

What type of person are you?

Rather than prioritizing influence or prestige, Jemison was operating from a different place. She was focused on who she was and what she found meaning in. It wasn’t a position that she wanted to define her life. It was the type of person she was.

Jemison found meaning in creativity, exploration, and being helpful. She found meaning in engineering, art, dance, medicine, exploring space, exploring other countries, and exploring new ideas. Above all, she wanted to help and make a difference in the world through the skills and interests that defined her. She channeled this into her work and the opportunities she pursued at each step.

If you focus on work that matters to you and discover significance in yourself, you put yourself in a position to build something that strikes a deeper chord with others.

Influence wasn’t Jemison’s end goal. She approached it with indifference and chalked it up as nice to have but non-essential. Instead, she focused on her character, investing her time in what she found meaningful. She sought meaning over influence at each step of her life.

The desire for influence, like the desire to belong, is human nature. Many people allow this to dictate the course of their lives, often unconsciously. But acting deliberately and purposefully requires a deeper sense of awareness.

If influence acts as your guiding principle, you dull your sense of authenticity and compromise the quality of your work. How effective can your work be if you sacrifice your integrity and sense of meaning along the way?

People gravitate toward those who have discovered a sense of meaning in their work. It just hits differently.

Start with meaning

By focusing on meaning first, there’s a greater chance your life and work will resonate and make a measurable difference in the world. And even if it doesn’t, it remains valuable because it meant something to you. There’s a fundamental beauty in that.

Influence is far more likely to follow if you build something you believe in. And irrelevance is all but guaranteed if you continue to wander the path of least resistance, looking for a quick hit of attention or praise.

Your work must resonate with you before you can expect it to resonate with anyone else. You must fight like hell to ensure your work feels true before you release anything of your own into the wild.

Meaning starts with something that’s all your own. By prioritizing meaning over influence, you build the courage to speak from a place that resonates with you rather than following what other people have deemed important.

It’s a dangerous game to tie your sense of meaning and self-worth to external conditions. You introduce dependencies that can drop you into a state of anxiety, envy, or despair without warning. You allow yourself to be pulled along at the whims of others.

Regardless of the expectations or paths others had followed, Jemison made decisions that optimized for meaning over influence. She trusted her internal compass over any sort of fleeting recognition, status, or prestige.

After NASA, Jemison launched her own company. One of her first projects was to create an international science camp—The Earth We Share—that promoted critical thinking and problem-solving skills. Jemison also started teaching environmental studies at Dartmouth. Eventually, this led her to found 100 Year Starship, an initiative to establish capabilities for human interstellar travel within the next 100 years.

It’s a rare thing in this world to seek significance in yourself and build the courage to create something that resonates with you.

Seek meaning first, and authenticity and influence will follow.

Seek influence first, and you’ll risk losing yourself along the way.

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Sources:

1. Black History Bootcamp, Day 21, Mae Jemison

2. We Regret to Inform You: Rejecting Dr. Mae Jemison

3. StarTalk Radio: A Conversation with Dr. Mae Jemison

4. Jon Talks With Dr. Mae Jemison: The First Black Woman in Space

5. Find Where the Wind Goes, 2nd edition by Dr. Mae Jemison

6. Shooting Star: Former Astronaut Mae Jemison Brings her Message Down to Earth

The Outsider Advantage

“There’s no freedom quite like the freedom of being constantly underestimated.”

— Scott Lynch

At the turn of the 19th century, human flight continued to elude civilization. There were experiments, blueprints, and myths surrounding flight from Icarus to Leonardo da Vinci. But no one had figured out how to master human flight. During the late 1800s, this challenge consumed many of the era’s best scientists and engineers—Sir Hiram Maxim, Alexander Graham Bell, Thomas Edison, Samuel Langley, and the Smithsonian Institution, to name a few. 

Meanwhile, Wilbur and Orville Wright ran a bicycle shop in Dayton, Ohio, designing, repairing, and selling bicycles. But they, too, had grown fascinated with the challenge of flight. 

In 1899, Wilbur wrote to the Smithsonian Institution in Washington requesting documents on the subject of human flight. The Smithsonian passed along a stack of pamphlets on aviation, and the brothers started studying. Later that summer, above their bicycle shop on West Third Street, they began building their first aircraft—a glider with double wings spanning five feet made of split bamboo and paper.

Unlimited resources don’t equal better results

No one took the Wright brothers seriously, at least not yet. They were just two entrepreneurs building bicycles and living in the backwaters of Ohio. All the innovation was happening on the East Coast and in major European cities like Paris and London, led by well-funded scientists and engineers. But despite the resource advantage and the money being thrown at the problem, success remained elusive for those pursuing flight.

Sir Hiram Maxim, the inventor of the machine gun, spent $100,000 on a giant, steam-powered flying machine, which turned out to be a spectacular failure, crashing immediately upon take off.

But Samuel Langley was the most notable frontrunner in the race to human flight. Langley was the head of the Smithsonian, an eminent astronomer, and one of the most well-respected scientists in the United States. He was years ahead of the Wright brothers, and his experiments were backed by government funding. Langley held a tremendous advantage in his access to resources—both in terms of capital and information.

But with nearly unlimited resources, the stakes were higher and the pressure greater for Langley. After years of secretive work, he revealed what he called an “aerodome”—a steam-powered flying machine with V-shaped wings that gave it the appearance of a “monstrous dragonfly.” 

The aerodrome cost $50,000 in public money—grants from the Smithsonian and the U.S. War Department. Langley, Graham Bell, and others contributed another $20,000 of their own money. But the device could only “fly” in calm weather where the wind wasn’t a factor, which was as practical as building a boat unable to navigate waves. 

When it came time for a public demonstration, the aerodome was loaded onto the roof of a houseboat in the Potomac River near Quantico, Virginia, before being launched into the sky by catapult. Almost immediately, the wings crumbled, and the airship spun backward and plunged into the Potomac just 20 feet from where it had been launched. Langley’s efforts had taken more than eight years and failed to produce any meaningful progress. 

Resourcefulness wins out

During this same time, the Wright brothers were relentless in their efforts. Wilbur and Orville ran the bicycle shop by day and worked each night on their investigations into flight. After identifying the ideal place to test their first glider in Kitty Hawk on the desolate Outer Banks of North Carolina with windy conditions and sand hills for safe landings, they began their experiments. The first full-sized glider they brought to Kitty Hawk had a wingspan of 18 feet and cost just $15. 

Wilbur and Orville would return to Kitty Hawk every fall for the next four years to run experiments and test new iterations. As competition took notice and patrons reached out to help back the Wright brothers financially, Wilbur and Orville politely refused. They kept the bicycle shop open to help pay for their experiments and bootstrap their exploration into flight. And during frigid midwest winters in Dayton when it was too cold for cycling, they sharpened ice skates at the shop for 15 cents each to generate additional income. 

In their early, self-funded experiments, Wilbur and Orville learned that many of the widely accepted calculations and tables relating to foundational concepts in aviation, like lift and drag, prepared by authorities were fundamentally wrong and couldn’t be trusted. To improve the accuracy of their calculations, the Wright brothers built a small wind tunnel upstairs in their bicycle shop—a wooden box roughly six feet long with a fan mounted at one end. Over the next few months, they tested 38 different wing surfaces at different angles and wind speeds. 

After dialing in their own calculations, by the fall of 1902, they had completed a third iteration of their glider. And in just two months in Kitty Hawk, the Wright brothers had completed a thousand glides and solved the last remaining control problems. With relentless focus, data-driven experimentation, and thoughtful iterations, they had built a machine that could fly, and in the process, honed the skills to pilot it. The next step would be to add a motor. And by the following winter, Wilbur would complete the first powered flight in human history, covering a quarter mile in 59 seconds. 

In contrast to Langley’s $70,000 failed effort, the Wright brother’s expenses over four years, including materials and travel, totaled less than $1,000—all paid for by the proceeds from their bicycle shop in Dayton. Their competitors, with seventy times the amount of resources, couldn’t keep pace.

Despite Wilbur and Orville both lacking formal education or influential connections and living outside of the intellectual centers of the world, they were the first to solve the challenge of controlled human flight. They were both driven by and dedicated to solving the problem. Not because they were supposed to. And not because of the prestige it would garner. But because it was an inspiring challenge that they both felt a connection to. 

Less to lose

The Wright brothers were outsiders. And as outsiders, they could think for themselves while competitors imitated each other’s devices and worked from flawed formulas. The Wright brothers faced less external pressure, which crippled even the best scientists, like Langley. And this freed them to experiment and find their own way. No one was expecting anything from them, and that was just fine by them. They had less to lose. Their competitors had reputations to protect. 

It’s true that in specific industries like politics, you must be an insider to enact real change. But for the rest of us building, leading, and creating something of our own, it’s not always the advantage we believe it to be. 

As an insider in your industry, your worldview begins to narrow. And most of your energy becomes directed toward preserving your ability to think for yourself and avoid getting sucked into what everyone else is thinking. And when you have access to unlimited resources, it restricts your creativity. You’re no longer forced to effectively prioritize or consider different vantage points that allow you to do more with less. You become entrenched in what everyone else is doing, and it’s difficult to see beyond that. 

Many times, the inside track with well-funded, resource-rich, established companies, teams, and figureheads, is where the least amount of work gets done. They grow too comfortable, lack focus, or take on initiatives for the wrong reasons, like ego or fear, resulting in a fragile, reactive approach. They’re playing not to lose, which is very different from the flexibility and boldness that you play with to win. That’s why new startups come along and disrupt big companies each day. They have less to lose.

Embracing the role of an outsider can work to your advantage. You face less pressure and fewer distractions. And this helps preserve both your ability to think for yourself and the energy you can dedicate to building. If you become too enmeshed in what everyone else is doing, it can be difficult to step back and return to first principles. 

The Wright brothers leveraged available knowledge, but they questioned and validated every assumption they came across. They focused on the problem. They focused on building. They focused on their own experiments. And as outsiders, they were provided an advantage in that they didn’t have to deal with the same level of obligations or distractions someone like Samuel Langley faced. They could operate with greater flexibility and were free to do the work. 

As an outsider, you face greater odds. But those odds act as a natural filter for work you don’t find all that meaningful. If you aren’t motivated by what you’re doing and lack a deeper connection to your work, you will get absolutely crushed. There’s no faking it. Whereas on the inside, you can float by without making hard decisions or determining if you’re doing it for the right reasons. 

Bootstrap your idea into reality

This was the difference between the Wright brothers and Langley. Flight was a quest the Wright brothers found personal meaning in. They weren’t motivated by fame, reputation, or external validation. The reward was the challenge and committing themselves to a cause they cared about. And just as importantly, they embraced their role as outsiders, bootstrapping the whole thing and avoiding the obligations associated with taking on outside capital. 

You don’t need to secure a record deal, an agent, or get into Y-Combinator to create a successful album, book, or company. Andy Weir self-published The Martian, which sold 35,000 copies in its first three months and later grossed over $630 million worldwide in its film adaptation. After getting rejected by every major label in town, Jay-Z started his own label—Roc-A-Fella Records—to release his first record, Reasonable Doubt, selling more than 420,000 units. Yvon Chouinard started what would grow into Patagonia after buying a used coal-fired forge from a local junkyard, teaching himself blacksmithing, and forging climbing gear for his friends. Patagonia didn’t take a dime of outside capital for its first 20 years and has sustained success over five decades, now generating well over $1 billion in annual revenue.

We live in an era where it’s easier than ever to bootstrap our own ideas and embrace the outside track. You can launch your own startup as a side hustle and access thousands of low-cost tools to run your business without diluting your ownership. You can record your own album and distribute it independently without handing over the rights to labels and publishers. And all of this can work to your advantage. 

When you avoid taking on external resources and unnecessary obligations, you simplify decision-making and preserve the integrity of what you’re trying to build. There’s less noise influencing your work. And it helps you to avoid getting caught up in false goals and virtue signaling.

Seek accomplishment in the work, not external validation

Far too many people conflate external validation with accomplishment. But raising a Series-A, signing a book deal, or getting accepted into an Ivy League school is not the accomplishment. The accomplishment is on the other side of the blood, sweat, and tears you must pour into your work. The accomplishment is bringing something of your own to life.

The Wright brothers were just a couple of midwesterners running a bicycle shop. What did they know about aviation? Not much at first, but they were driven to learn and build. One of the few locals in Kitty Hawk, John T. Daniels, remarked, “It wasn’t luck that made them fly; it was hard work and common sense; they put their whole heart and soul and all their energy into an idea and they had the faith.”

Embrace the outside track. And once you’ve gained traction, keep a healthy distance. It’s a gift when people are unsuspecting. You free yourself to focus on creating and gain an element of surprise that keeps the competition off guard. Besides, there’s nothing more motivating than when someone has counted you out. That’s right where you want them.

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Sources:

1. The Wright Brothers by David McCullough

2. Founders Podcast, #28: The Wright Brothers

3. Founders Podcast, #239: The Wright Brothers

4. Empire State of Mind by Zach O’Malley Greenburg

5. Let My People Go Surfing by Yvon Chouinard

Find Your Flow

“The way to get out of the competition trap is to be authentic, to find the thing you know how to do better than anybody. You know how to do it better because you love it, and no one can compete with you.”

— Naval Ravikant

It was a humid summer afternoon in 1978 and Jay-Z was on his way home to the Marcy Houses in Brooklyn after a Little League game. As he wandered the maze of concrete paths, he noticed a group of kids huddled, rocking back and forth in a circle. Jay-Z shouldered his way toward the middle to see what was going on.

When he got through the crowd, he found an older kid named Slate freestyling and rhyming at the center. Slate threw out lyrics off the top of his head, rhyme after rhyme like he was possessed. He carried on like this for 30 minutes without pausing to stop. 

Jay-Z was captivated. He had never seen anything like it. And he immediately thought, I want to do that…no, I know I can do that.

As soon as Jay-Z got home, he grabbed a spiral notebook and started filling it with his own rhymes. He covered every crevice on the page with lyrics—horizontally, vertically, writing as small as he could. He pounded beats on the kitchen table. He scoured dictionaries for new words. From the time he woke up in the morning until he went to sleep, he practiced. He lived and breathed rapping, writing lyrics, and composing rhymes. 

Poetry came naturally. And he didn’t view the hours he spent practicing as painstaking work. It was something he loved to do.

Even when Jay-Z was out running around town with his friends, if a rhyme came to him, he would stop what he was doing, grab a brown paper bag from the corner store, and spread it on a mailbox to write down the idea to get it out of his head. His mind was constantly working, turning things over. Nothing was more important than writing rhymes. 

As Jay-Z got older, another rapper named Jaz-O took him under his wing to teach him the fundamentals. They locked themselves in a room to hone their craft together—trying new flows and pushing themselves to improve their speed, delivery, composition, and structure. At school, Jay-Z practiced to beats in the cafeteria during lunch. 

Eventually, Jay-Z talked his way onto the tour of a successful rapper named Big Daddy Kane. He spent four months touring with Kane, unpaid, sleeping on the bus floor. During intermissions in the show, Jay-Z would get on stage and practice his freestyle—sharpening his lyrics and delivery. 

He studied Kane on stage, watching his breath control, his wordplay, and the way he stacked rhymes. Jay-Z was a student first, enamored by the craft.

Jay-Z had found his flow—a sacred place where time seemed to melt away while focused on the task at hand. Rapping came naturally to him, and he combined this with dead-serious discipline. He could outwork anyone. Because he loved it. As he immersed himself in writing lyrics, performing, and practicing the fundamentals, he tapped into a flow state. 

Find the intersection of what you love doing and what you’re good at

Your own flow state will guide you to what you should spend more time doing. It points to the intersection of what you love doing and what you’re good at. When you identify this, you can outwork just about anyone. Because you’re immersed in something deeply rewarding to you—no matter how hard it is. It’s a competitive advantage that leads toward something you are uniquely positioned to create. 

Ask yourself, what activity are you engaged in when hours seem to pass by in the blink of an eye? What feels like work to other people that feels like play to you? What type of work invites you into a state of relaxed concentration where you feel like you’re in the zone?

You’re not going to win or create your best work by pursuing something that feels mundane or uninspiring. It’s impossible to keep up with someone who truly loves their craft—they are just willing to give more than you are capable of. When you’re not invested in what you’re doing, you give up on creating anything worthwhile. Life becomes an exercise in watching the hours pass, living for the weekend, jumping from one distraction to the next. 

When you find your flow state, it’s not that work stops being hard. It will still feel challenging. But it will feel worth it because you’re engaged in what you’re doing. When the work you’re doing resonates with you on a deeper level, you can persevere through almost anything. You can push through endless agitations and tireless hours of practice. The work is the reward. You don’t need the same level of external validation that dictates other people’s lives because the act of doing is what’s fulfilling. 

It will take years of hard work to create something meaningful—to bring the best version of your work to life. There are no shortcuts. If you want to be able to persevere long enough to create your best work, you have to find where your flow lives.

Jay-Z loved rhyming for the sake of rhyming. He immersed himself in practice—challenging himself to stack his rhymes and structure his songs in the most compelling way possible. He experimented with moving around couplets and triplets, speed rapping, and adding multiple layers of meaning. It was all he could think about. It’s what helped him make sense of the world and channel his energy. 

It takes years of honing your craft before it starts to pay dividends. And honing your craft requires thousands of hours of effort and practice. That’s why it’s paramount to identify the work that energizes you and pulls you into a flow state. Leaning into that type of work will allow you to sustain the engagement over the years and decades required to become exceptional at what you do. 

Magic is the product of relentless effort

After 14 years of practice, Jay-Z stepped into the beginning of his professional career. Clark Kent, an A&R representative at Atlantic Records, pushed Jay-Z to lay down a song with another rapper, Sauce Money. Patrick Lawrence, the producer in charge of booking studio time, set the date and brought the two rappers together to record. 

Jay-Z and Sauce sat there laughing and telling stories for the first three hours. As the night wore on, Lawrence grew agitated. Finally, he told Jay-Z that he had to record his lines. They were running out of time.

Jay-Z asked to hear the song, so Lawrence played the track. Jay-Z began mumbling to himself over the track. He picked up a notebook and seemed to write a few things. He continued pacing, muttering words, appearing to scribble on the pages. After a few minutes, he placed the notebook on a table and told Lawrence he was ready. 

Jay-Z stepped into the sound booth to record his part, and Lawrence picked up the notebook to see what he had written. The pages were completely blank. Not a single word. It was all an act. With over a decade of constant practice, Jay-Z had developed the ability to memorize all his verses instead of writing everything down. What appeared like magic to everyone else was the product of relentless effort. 

But to get to that point where it looks like magic to everyone else, it requires you first to identify what immerses you in your own state of flow. That’s the work you should invest more of yourself in. 

Your flow state is the clearest indicator you will get in this life. Whether it’s building, coding, cooking, leading, performing, writing—whatever provides your shortcut to a state of mind where time melts by and you’re completely immersed in your work is a signal worth following. 

There’s no better indicator of who you are than the work you lose yourself in

The question you must ask yourself is, what part of your life triggers this for you? You must answer this with precision. What are you focused on when you feel like you’ve stepped into a flow state? You must constantly come back to and find a way to harness this.

I have reflected on this question more times than I can count throughout my life. I use it as a checkpoint to bring myself back into focus. 

But the first time I gave it the attention it deserved, I was wandering through my mid-twenties. As I dug for my answer, I remembered how much joy writing brought me when I was growing up. It always felt natural to me and I excelled at writing assignments with less effort than my peers. I loved the puzzle of crafting and structuring a compelling story.

One afternoon I walked over to a coffee shop in Nashville near my crumbling duplex on Grandview Drive to attempt writing again. I put on my headphones, opened a word document, and started writing—whatever random thoughts came to mind. As I wrote, a great sense of relief came over me. This was my thing.

Once I found it, I was all in. I returned to that coffee shop every weeknight, like clockwork at 5:00 PM, and spent four uninterrupted hours writing. I didn’t have some grand plan to get rich off my writing. I just loved the act of writing. And I still do. That’s my craft. It’s where I go to find or lose myself. It’s how I make sense of the world. 

If you’re unsure what your thing is, experiment with as many different ideas as possible. Before I realized with precision where I found my flow state, I tried returning to academia, recording music, producing music videos, pursuing medical school, working in marketing, running triathlons, and waiting tables at a Tex-Mex restaurant. It wasn’t always pretty, but each attempt taught me something new. It allowed me to cross something else off the list. And ultimately, this discovery period led back to where I found my flow state—in writing. 

As long as you continue to spend your time somewhere where every hour feels like an eternity, you’ll be marginally effective. But once you identify and lean into what brings you into your flow state, you alter your trajectory. You shift the playing field in your favor. No one is going to outwork you. And there’s no better indicator of who you are than the work you lose yourself in. 

---

Sources:

1. Decoded by Jay-Z

2. Empire State of Mind by Zack O’Malley Greenburg

3. Three Kings by Zack O’Malley Greenburg

4. My Next Guest with David Letterman, Season 1, Jay-Z

5. Founders Podcast, #238 Jay-Z: Decoded

6. Oprah’s Master Class Podcast: Jay-Z

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.

Reveal More, Signal Less, and Why Your Stories Matter

When I picked up writing again in 2014, for the first few years I shared exactly zero personal stories. I was shielding myself. But that also meant everything I wrote felt more theoretical than practical. I didn’t think I had the level of experiences required to write from a more personal place. I would doubt myself, asking who am I to share my own stories? It’s no surprise that during this time my audience failed to grow and the ideas I wrote about failed to resonate. 

Without a willingness to reveal something about yourself, your stories will forever feel hollow. 

Good storytelling is about creating a sense of shared humanity. That means revealing more of yourself and the struggles that make you human. It’s one of the most powerful ways to connect with people, but you have to approach it from the right angle. It’s not about attention seeking, virtue signaling, or posturing—whether hero or victim. It’s about connecting with others. 

The goal isn’t to create a moat and portray yourself as some fortress devoid of a single flaw—think early Tiger Woods. Sure, people might admire you, but it’s impossible to feel connected with someone like that. 

This was a tremendous benefit to Tiger early in his career. He scared the shit out of everyone else in the field because nothing about him seemed human. And while this aura might lend itself to a highly specialized, individual sport like golf, it doesn’t translate well across the rest of life. Most jobs and challenges you face require connecting with people.

You can’t lead, communicate, trust, parent, coach, teach, or learn without first connecting with the people around you. Growth is impossible if you refuse to ever let anyone in. 

What I struggled with in my 20s, whether knowingly or not, was posturing. I was pulling a Tiger and masking any flaws—though I made a few dollars less than him in the process. I was adamant about presenting a perfect version of myself, in both my career and writing. And while it felt safe for me, it wasn’t relatable. People crave real stories of personal struggles and triumphs that they can relate to in their own lives. Flaws reveal your humanity.

Ego is what holds you back from sharing your own faults and personal stories. It’s what prevents you from making yourself vulnerable. It’s the thing that says, people are watching, don’t reveal any flaws. But the catch is that by revealing your own shortcomings and demonstrating self-awareness, you’re able to connect on a far deeper level. Honesty about the human condition is what resonates with people. Your stories matter. 

“The call to lead well is a call to be brave and to say true things”

— Jerry Colonna

Abstract models and anecdotes only go so far. Most people couldn’t care less about your theories or concepts. In her book Talk Like TED, Carmine Gallo examines the most popular TED Talks and notes that those speakers spent roughly 80% of their time telling stories. That’s what people really want to hear.

Stories are the wrappers for your ideas, lessons, principles, theories, and concepts. Stories are what draw people in to actually listen to what you have to say. 

In the past, I used shells of stories to guard myself and protect my ego. I didn’t want to reveal any faults. But as it turns out, the less seriously I take myself, the more helpful I can be. I’m able to illuminate feelings and stories that others can relate to and see themselves in. And that’s the power of good storytelling. You reveal fragments that people are able to identify with and latch onto. You give voice and clarity to things that people couldn’t quite put their finger on. 

“Becoming a writer is about becoming conscious. When you’re conscious and writing from a place of insight and simplicity and real caring about the truth, you have the ability to throw the lights on for your reader”

— Anne Lamott

Your goal in storytelling is to reveal what makes you, you. Not the carefully crafted Instagram version you’ve created. By being real, you set the depth at which your audience is able to go with you.

It’s always better to be authentic and nervous than shallow and overly rehearsed. 

There’s an initial shock that comes from opening yourself up. But when you speak from your own experiences and bring out what’s inside of you, you can sustain that indefinitely. 

“A moment a story works is usually a moment of vulnerability.”

— George Dawes Green

Where you start to run into trouble is when you exploit “vulnerability” as a guise for attention. It’s impossible to maintain a facade of something you’re not. When attention seeking or virtue signaling dictates what you reveal, sooner or later you’ll be crushed underneath the weight of trying to keep that up.

Those who overshare fail to grasp this and end up exhausting their audience in desperate attempts for another hit of short-term gratification. There are boundaries.

At its best, vulnerability helps connect you with others. At its worst, it’s an attention-seeking behavior that those who thrive on a victim mentality lose themselves in.

It takes time to learn. If you run your own experiment—whether leading teams or writing articles—sooner or later, you’ll find that people gravitate towards what’s real. Because that’s what they can relate to. That’s what strikes the deepest chord. 

Over the past couple of years, I’ve started sharing real stories—my own fears, challenges, and struggles. This shift in my approach has improved my own storytelling significantly, as measured by the number of people reached and how strongly those stories have resonated with others.

Stories are how you communicate. Not instructions. Let people interpret things for themselves. Give those around you something real to connect with.

It’s easy to feel alone in this. But remind yourself that very few of the challenges you face are unique to you. There’s someone else out there who can identify with the obstacles you’re facing. Write, speak, teach, and lead from your experiences. They matter.

“To live well is to see wisely and to see wisely is to tell stories.”

— Pádraig Ó Tuama

The Art of Drawdown Periods

Inspiration is important. Your influences matter. But you also need time to process, reflect, and create your own connections before jumping into your next project. Whether that’s a book, startup, or scientific theory, the lesson holds true for artists, entrepreneurs, and scientists, alike.

Best-selling author, Ryan Holiday, refers to these as “drawdown periods.” In the months leading up to writing a new book, Holiday guards himself against new information with the potential to clutter this mind. Instead, he seeks a period of stillness where he’s able to distill information and settle his mind before jumping off and creating something new.

““For one of my books I gave myself a January 1 start date for the writing. Two months before, in November, I entered my drawdown period. No more reading or rereading. Just thinking. Long walks. Resting. Preparing.””

— Ryan Holiday

The danger of neglecting a drawdown period is failing to create a buffer where you’re able to discover and piece together your own thoughts on the subject. Instead, you’re just regurgitating the latest idea or concept you’ve heard, as if it’s your own. To be fair, this is human nature — we’re highly impressionable, social beings.

But creating a little more distance is a good thing. It provides additional perspective that you’re able to bring back to your work. Without this, you’re just facing an onslaught of information and distraction which can be difficult to make sense of.

Is your idea worth pursuing?

Above everything else, drawdown periods help inform whether or not an idea’s worth pursuing. The original source of “drawdown periods” — where Holiday borrowed the concept from — was military strategist, John Boyd. After he encountered a breakthrough or exciting new idea, he would spend weeks examining it, assessing its originality, and stress-testing it for problems. If it survived this period, he knew it was worth investing in.

The greater the endeavor, the more vital a drawdown period becomes. It’s important to act when inspiration strikes as it relates to the little things — an article, a small experiment, a new tactic. But the mountains — new books, startups, theories — are worth reflecting on before jumping in.

This helps create a natural filter for the things you’re not completely invested in. If the idea still resonates with you tomorrow, next week, next month, you might be on to something.

Tapering before the race

Far from killing inspiration, drawdown periods promote creativity. They allow you to find your voice and the guiding principle behind your next project. Without this, it’s impossible to sort through what’s your own.

Drawdown periods are the calm before the storm. If you set off scrambling without first setting your feet, you’re putting yourself behind from the start. While everyone loses their way at some point, it’s important to have a sense of your guiding principle — this initial footing — that you can return to along the way. And the best way to establish an early version of your guiding principle is by creating room to reflect before taking the leap.

Creative work is difficult enough, as is. Don’t make it more difficult by cluttering your mind at the start. Allow yourself time to breathe before setting off on your next pursuit.

It’s similar to tapering before a race. If you’re rested, you’ll be in better condition to handle the strenuous demands of the real race and guard yourself against burnout. In endurance sports, two days before a race, your metabolic fitness level is what it will be for the upcoming race. No matter how hard you train during those final 48 hours, you won’t see any benefits to your endurance in time for the race. Rest matters.

The value of tuning out

In 1902, Albert Einstein took a job at the Swiss patent office. The years he spent there could be considered the ultimate drawdown period. It was challenging enough to keep his mind engaged, but not enough to distract him from his more important focus on comprehending and redefining physics.

Three years later, Einstein published his paper, “On the Electrodynamics of Moving Bodies,” which outlines the special theory of relativity. Its contributions to the field of physics were profound. But one of the most astonishing things about the paper was that it had exactly zero footnotes or citations. It was like he reached the conclusions through years of pure thought, without listening to outside opinion.

While Einstein is an extreme example and a profound abstract thinker, the underlying lesson holds true. For originality and creativity, sometimes you need to allow yourself to tune out.

““If you’re constantly exposed to other people’s ideas, it can be tough to think up your own.” ”

— Jake Knapp + John Zeratsky

Deliberate or impulsive?

Drawdown periods aren’t an excuse to avoid getting started. You’re never going to be as prepared as you might like. Drawdown periods are more about giving yourself a moment of calm before the grind of creating something from nothing. New startups, books, and theories can take years, if not decades, to develop.

The difference between great artists, entrepreneurs, and scientists is the difference between drawdown periods and procrastination. Drawdown periods are deliberate. Procrastination is impulsive.

At a certain point, it helps to limit exposure and turn things back to yourself. Allow yourself to mull ideas, forge connections on your own terms, and see what comes out of it. It’s impossible to find your own voice if you’re bombarding yourself with other people’s ideas without giving yourself time to breathe.

Drawdown periods offer a temporary refrain when you’re able to step back and see the terrain. This allows you a chance to appreciate the interconnected whole and create connections or bridge ideas that you might have otherwise missed. The more perspective you can build, the better you’ll be for it. And the same goes for your craft.

As a smart creative, drawdown periods are essential. Give yourself time to prepare, rest, and reflect before your next endeavor. You’ll need every ounce of energy you have if you want to get your thinking clean and bring the best version of an idea to life.

Indecision in Product: How to Avoid Becoming a Bottleneck

A few years ago, comedian Aziz Ansari released a Netflix special called “Live at Madison Square Garden”. During his set, he joked about the effort required to buy a new toothbrush. Not just any toothbrush would do, he had to have the best. He researched for hours, Googling “best toothbrush” and reading articles on the pros and cons of bristle strength. As he reflected, he questioned his indecisiveness and his desire to have the best when any toothbrush would have done the job.

For most of my twenties, I did the same thing. I researched every purchase – headphones, winter jackets, coffee grinders – in painstaking depth before making a decision. But, as I’ve learned, the quest for a perfect decision often does more harm than good.

Time is far more valuable than a marginally better solution. And if you’re leading product, the sooner you learn this lesson, the better. As a product manager, the worst position you can put yourself in is creating a bottleneck by making slow decisions.

A Case Study in What Not to Do

When I started my career, I joined a team building a web-based patient portal for healthcare providers. At the time, I was unaware “product” even existed. But I was forced to learn the space out of necessity. My first manager, Eric, was a walking case study in how you shouldn’t handle product decisions.

With something as simple as our landing page, Eric went back and forth for months. His opinion fluctuated on a daily basis. Without the autonomy to make decisions, our development team wandered without any real sense of direction or progress.

Each week followed the same pattern. The team would align on the problem, collaborate on ideas, prioritize features to build and test, then have the tables turned on them a few days later. Eric was obsessed with surveying every available option. He operated with the constant fear that we might have missed something better. As a result, we wasted months of time and energy considering alternatives with negligible differences.

And if we were unable to make decisions on something as simple as the landing page, imagine what that did to our product which was heavy on integrations with practice management and electronic health record systems. Not to mention the most important piece–the user experience of patient-facing features.

The lesson: hesitation kills creativity, morale, and momentum.

Be Wrong as Fast as You Can

Leaving your team in limbo without a sense of direction is a far worse position to be in than taking a wrong step. It’s easier to forgive a wrong decision than it is a painstakingly slow decision or the failure to make a decision.

“For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.”

— Scott Belsky

If you’re wrong, you want to be wrong as fast as possible. Andrew Stanton, director at Pixar, uses a similar model to evaluate decisions on his films. When faced with two hills and you’re unsure which to attack, the best course of action is to hurry up and choose. If you discover it’s the wrong hill, you can always turn around and attack the other. But you will fail for as long as you continue standing still or running in between the hills.

There will be things you miss and ideas you haven’t thought of. But you’re going to learn more by putting yourself and your product out there than you will trying to make the perfect decision each step of the way.

How Reversible Is This Decision?

For many product managers, faster decision making is the most significant improvement you can make. Especially when it comes to the trivial.

While somewhat elementary, the Pareto Principle should be foundational to your decision making. Which solution generates 80% of the value? Forget the other 20%. As Aziz points out in his toothbrush dilemma, perfection requires far more deliberation and research than it’s often worth. If your default position is hesitation – pausing to consider every alternative – you’ll stifle creativity and lose your team along the way.

You can also make immediate improvements by asking yourself a single question, “How reversible is this decision?” Tobi Lütke, Shopify’s founder and CEO, uses a similar strategy by asking himself, “How undoable is this decision?” Decisions that are reversible – most of the ones you make on a daily basis – deserve quick answers.

Better yet, if you have other product managers, developers, or designers coming to you with trivial decisions, empower them to make the call. Performance will improve when there’s a greater degree of autonomy and teams have more creative control over the product.

The decisions that aren’t easily reversible are the rare ones that Lütke spends his time deliberating before coming to a decision. In 2008, he had to decide whether Shopify would remain the lifestyle business he set out to build or shift towards a growth company. With venture capital implications, it warranted thoughtful consideration.[1]

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you have to make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to buying a toothbrush or choosing between two styles on a landing page.

Far too many product managers are focused on perfection from day one – an impossible task. Instead, with proper context, you should focus on making faster decisions. You’ll always be able to adapt along the way as you learn.

If you want to avoid becoming a bottleneck, just keep things moving forward. You’ll be better for it, your team will be more engaged, and you’ll be able to build better products. Decisions lead to progress because they improve the rate at which you learn.

Both life and product become much easier when toothbrush decisions aren’t monumental efforts. Learn to value your time over a marginally better solution. People appreciate decisiveness. And above all, that’s the sign of a true leader in product.

[1] Lütke still felt like he was far too slow in coming to this decision (lifestyle vs growth). To help speed up bigger decisions, he now tries to get as far ahead as he can in terms of vision and where the company is heading. In other words, being less reactive to inevitable, significant decisions that need to be made.

*This article was originally featured on Mind the Product

9 Tactics to Help You Create More, Consume Less

When it comes to remarkable leaders, artists, scientists, and entrepreneurs, each individual has their own set of principles. But there is one underlying strategy that remains constant, revealing itself in different shades across each person–creating more and consuming less.

It’s through the work you put out into the world and the way you live your life that you build a sense of meaning. Smart creatives understand this in a deep way. By creating more, you claim a larger part of yourself.

Strategies like this help build energy, establish your identity, and inform the tactics you put in place. While it takes shape in different mediums, the overall strategy is to create more and consume less. It’s the mental framework which informs smaller decisions throughout the day.

Tactics are the individual pieces that comprise the larger whole. They differ in that they require an initial investment up front. It’s what you dedicate time and energy to on a daily basis to reinforce your strategy.

Author and habit expert, James Clear, explains habits as the individual votes you cast each day for a certain identity. The same concept applies here. Tactics are the individual votes you cast each day for a certain strategy. If your strategy is to create more and consume less, you need tactics to help encourage both.

1) Make it difficult to do the easy thing (consuming)

Adding resistance can be a powerful tactic. You want to make it harder to mindlessly consume. If you struggle with Netflix, unplug the television or sign out of your account after each use. If you struggle with social media, change your passwords at the start of each week and sign out of your accounts so you can’t easily access them.

It’s amazing how impactful it can be to move things out of plain sight. Whatever’s undermining your creative energy, add more resistance so you can redirect that towards something you find greater meaning in.

2) Make it easier to do the difficult thing (creating)

This is about environment design. Building something from nothing is difficult enough as is, don’t make it any harder on yourself. Prioritize time and space for your craft to reach a deeper level of focus and creativity.

For years, my place for creativity at home–where I would sit down to write–was a couch that faced the television in my living room. And to further compound the problem, I wasn’t attempting this during quieter hours of the day. It was while people were coming and going, stopping to watch Netflix, sitting down for a meal. There were incessant distractions.

But this past year, I carved out physical space dedicated to writing. I converted one of our bedrooms to a writing studio/library and it’s made a significant difference. I also started writing first thing in the morning while my mind is fresh and I have two quiet hours before work.

Dedicating time and space where you can focus without interruption on your craft will allow you to grow exponentially faster. It’s the first step towards taking yourself and your art seriously.

Make it easier to do the right thing. This doesn’t mean sitting around waiting for ideal conditions or until you’re completely prepared, otherwise you’ll be waiting forever. It means setting yourself up for success through the things you can control in your immediate environment.

3) Pair positive reinforcements

Four years ago, when I first started taking writing seriously, I paired my writing sessions with my favorite coffee shop in Nashville. I walked over in the evenings after work to sit down and write. It’s something I looked forward to every day because of the atmosphere, the music I would listen to and, of course, the caffeine. This reinforcement helped me rediscover writing as a creative outlet.

Now I automatically associate these cues with my creative process. Coffee, coffee shops, and ambient music are shortcuts that jump me into a state of relaxed concentration that I need to do my best writing.

4) Allow yourself to get stuck

At the first sign of boredom or discomfort, most of us instinctively search for distractions and outlets for immediate gratification. And we do so without even recognizing it.

Until recently, the moment I slowed down or felt stuck in my own writing, I coped by jumping between tabs in Chrome–checking email, looking up restaurants for dinner, scrolling through Twitter.

The secret is to allow yourself to get stuck and sit with something. Once I gave myself permission to sit there without looking away, my resilience and creativity improved immediately.

Momentum is easier to come by when you don’t look away at the first challenging moment. Bouncing between distractions won’t result in some magical insight. Give yourself permission to get stuck.

“Too many people believe that everything must be pleasurable in life, which makes them constantly search for distractions and short-circuits the learning process. The pain is a kind of challenge your mind presents–will you learn how to focus and move past the boredom, or like a child will you succumb to the need for immediate pleasure and distraction.”

— Robert Greene

For writers: Tools aren’t everything but they can be helpful. I’ve found Ulysses to be one of the best investments I’ve made ($5/month). It helps facilitate each of these first four tactics. Its typewriter mode is fullscreen which makes it easier to focus, harder to jump between distractions (web, email, text messages), and the daily goals feature helps create a strong positive reinforcement.

5) Create a distraction-free phone

For most of us, myself included, our phones are our number one source of distraction. Jake Knapp and John Zeratsky outline the tactic that is a distraction-free phone in their book Focus. It’s one of the most influential tactics I’ve found in the past year. There are three main components:

1. Delete infinity-pools apps (social media) from your phone

2. Delete email accounts from your phone

3. Delete/disable the web browser on your phone

These might sound extreme, but let me explain. Last year I took step one, deleting infinity-pools apps (sources of never-ending streams of content). But the energy I wasted on social media was replaced by checking email, random websites, and Googling everything that crossed my mind.

It was only after I took steps two and three, despite my initial reservations, that I saw a measurable difference in my focus and creativity. There’s now far less clutter and distraction in my day-to-day. As a result, the clarity of my thoughts has improved and I have more opportunities to create.

I recognize this might strike terror in you. But test it out for a week and see how it goes. I no longer reach for my phone as a crutch in moments of boredom. And it taught me how many meaningless things cross my mind and how few emails (zero) require an immediate response.

6) Keep a journal instead

If you cut the time spent on your phone in half and replaced that with journaling, you’d improve your balance between creating and consuming within a matter of days. I leave a journal sitting on the table of whichever room I’m in at home. I jot down ideas as they come to me, intentions in the morning, reflections in the evening, beginnings of articles, and whatever else captures my curiosity.

The act of writing on paper allows you to explore concepts and draw connections in ways that you can’t on a screen. Your ideas take on a different dimension. Not to mention the fact that it eliminates the threat of distractions you face on a phone, tablet, or computer.

But the biggest advantage of journaling is that it helps build awareness. By reflecting, you gain insight into your own behaviors and tendencies, rather than wandering through life on autopilot. If you want to create more and consume less, you have to start by recognizing what you’re doing well and where there’s room to improve.

7) Use art as inspiration

This is not to say that you shouldn’t appreciate other people’s work. But you should use it as inspiration to create something of your own. Actively engage in the things you’re watching, reading, listening to, and consuming. Try to engage, form connections, and draw insights of your own. (Check out my book notes on 70+ titles for an example of how I approach this while reading.)

Use books, films, documentaries, paintings, research, and keynotes as inspiration to create more. If you’re a writer, weave one of the connections you made into your next article. If you’re an entrepreneur, adapt one of the stories to your current project and share it with your team to build stronger engagement.

The goal is to create an active mental landscape that’s alive with hundreds of connections. It directly benefits your creativity and craft when you’re able to combine ideas across disciplines in new and interesting ways.

8) Start small

Don’t go off the deep end and commit to twelve hours of creating each day. You’ll burn yourself out before you ever get started and make it difficult to recover. Instead, begin from a more sustainable place.

If you want to write more music, start with fifteen minutes each day then build from there. That’s how you create momentum. Develop habits that are sustainable and allow them to grow steadily over time.

Remind yourself that growth is nonlinear. Don’t expect immediate results. People tend to overestimate what they can accomplish in the short-term and underestimate what they can accomplish over the course of years. The power of small, calculated decisions and tactics grows exponentially over time. Start small and let compound interest run its course.

9) Find a medium that resonates with you

While every remarkable mind shares some sense of this strategy to create more and consume less, the medium varies. For J.K. Rowling it’s writing, Jay-Z it’s music, Scott Belsky it’s design and technology, Alexander von Humboldt it was exploration and science, Leonardo da Vinci it was art and engineering.

If you need a better starting place, consider the medium that resonates with you. Robert Greene, author of The Laws of Human Nature, suggests reflecting on three areas to help with this:

1. Inclinations in your earliest years–moments of fascination with certain subject, objects, or activities.

2. Moments when certain tasks or activities felt natural to you.

3. Particular forms of intelligence your brain is wired for.

The key is determining what’s meaningful to you and not absorbing what’s important to someone else as your own. Otherwise, you’ll miss the mark.

This is perhaps the most difficult skill of all–sorting through the noise and determining your own sense of authenticity. This requires years of exploration and reflection to determine for yourself. But it’s the only way to sustain a creative mindset and find meaning in your work.

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As a rule of thumb, it’s better to lean towards the mentality of a strategist than a tactician. Those who have the patience to expand their perspective of time and the endurance to play the long game put themselves at a significant advantage. There are multiple paths and hundreds of tactics you can use you reach the end goal.

These tactics are meant to help you find your own starting place. Use them to create momentum and discover what works best for you. Experiment and remain flexible. There’s no correct path or proper sequence of decisions. What matters is that the overall strategy to create more and consume less is held in constant focus.