Visualize the End Result

“If a man knows not which port he sails, no wind is favorable.

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— Seneca

While studying in Copenhagen during her junior term at Yale, Maya Lin lived near an area where a large cemetery, Assistens Kirkegård, was also used as a public park. Walking to and from class, she observed how death and remembrance were integrated into the daily life of the Danes, not hidden off to the side like the cemeteries she knew from her hometown in Ohio.

When she returned to Yale, she approached her architecture professor with an idea for a senior seminar to study how mortality is expressed in the structures we build for the dead. As the undergraduates immersed themselves in the study of memorial architecture, someone came across a flyer for a competition to enter the design contest for the Vietnam Veterans Memorial. Lin and her peers decided that was the perfect opportunity for their final project.

The Memorial

In the fall of 1980, Lin started working on her idea. She and her classmates visited Washington, D.C., during Thanksgiving break to look at the site. Standing on the lawn at Constitution Gardens, she started to visualize how the memorial would look within the landscape. She imagined cutting into the earth and polishing the names of the fallen and missing soldiers on its dark surface. And she contemplated the feelings she was trying to evoke in her work: to focus on the fallen and create a beautiful space within the landscape for the living and the dead to meet in as personal and evocative a way as possible. It was all about subtlety, not spectacle.

As she worked through the details, she would use two polished black granite walls that stretched out and descended gradually toward an apex, 10 feet below grade, where they converged at a V, acting as bookends to the war. From above, the walls would look like the earth had opened up. Visitors would descend into the memorial, passing the names of over 57,000 dead or missing veterans before returning to ground level. The names would be listed chronologically in order to capture the timeline of the war, allowing veterans and their families to revisit the time they served and find everyone they knew within a few panels, forging a deeper connection to their experience of the war.

Lin sent through her final submission in the spring of 1981, a soft pastel sketch with an essay explaining her concept in detail and how the experience would feel. There were over 1,400 submissions, including one from her professor and many other from professional architects. On the last day of class, Lin received a call from the Vietnam Veterans Memorial Fund, requesting to visit New Haven to ask her a few questions. Three officers arrived to meet Lin in her dorm room and delivered the news—she had won.

Standing her ground

After graduation, Lin moved to D.C. to oversee construction. By this point, word was out, and outrage was spreading over her and her design. How could a 21-year-old Asian-American woman who had just graduated from college without any experience of the war herself possibly design a proper memorial for the Vietnam veterans?

During meetings and press conferences, she faced a backlash for her Asian heritage and designing a memorial for a war fought in Southeast Asia. She received hate mail, personal insults, and racial slurs. People called her design “a black scare of shame,” an “open urinal,” and “something for New York intellectuals.” Critics wanted to make the memorial a white stone, move it above ground, and plant a flagpole or towering statue at its apex, rendering the walls as nothing more than a backdrop.

Lin faced these confrontations with admirable courage. She stood her ground and fought for the design she believed in. She had thought through the design decisions of the memorial in detail and how each contributed to the overall experience she was working to create.

In the end, Lin’s vision for the memorial was preserved, except for a bronze sculpture featuring three soldiers and an American flag added near the entrance. This addition was made without her input, and she didn’t learn about the compromise until she saw it on the news. Frederick Hart, the sculptor of the bronze monument, was paid more than $300,000 for his work, compared to Lin’s $20,000 prize money. At the dedication ceremony, Maya Lin’s name wasn’t mentioned once.

But time would be on her side. She had fought for a design she believed in, visualized what she was working to bring to life, and realized that vision. Within a year, people were clamoring for interviews with her. They finally understood her vision for the memorial because they could experience it themselves.

The Vietnam Veterans Memorial became a sacred place. Today it’s one of the most famous monuments in the world, with over five million visitors each year.

So, what are you working toward?

Visualization is the practice of considering how you want to show up in the world. Creating meaningful work isn’t going to happen by accident. It requires thoughtfulness and channeling what you believe to be true about the world into your work. But in order to do that, you must understand what you’re working toward. You have to visualize the future state and hold onto the integrity of your ideas along the way.

The reason you must understand what you’re aiming toward is because directions in life are mutually exclusive. Certain decisions and paths preclude others. Tim Urban, author and writer behind the popular blog Wait But Why, visualizes this concept in a graphic that shows all the life paths closed to you versus those that remain open. You have made decisions in your life and work that have led you to this point. You can’t go back in time and change those.

Source: Tim Urban, @waitbutwhy on X

But there are still dozens of decision points—tributaries—ahead of you that you can use to guide yourself toward realizing the best version of yourself and your work. But you must bring your vision to the forefront and understand what you’re working toward to optimize your decision-making in this moment.

The challenge is that many of us have become decision averse. We don’t want to cross any options off the table. But eliminating options isn’t restrictive: it’s empowering. This frees us to focus and bring our best ideas to life. Decisions are how we come to define our lives and our work. And deliberate, thoughtful decisions are the most powerful currency available to help you realize your vision.

Early in my career, I wanted to be everything and, as a result, was unable to commit to anything. I wanted to be an author, entrepreneur, director, photographer, musician, and that’s just a fraction of the list. I convinced myself that I could balance dozens of unrelated goals. But progress proved impossible because I was unwilling to prioritize and had no idea what I was aiming toward.

In his book, Four Thousand Weeks, Oliver Burkeman explains, “Since every real-world choice about how to live entails the loss of countless alternative ways of living, there’s no reason to procrastinate, or to resist making commitments, in the anxious hope that you might somehow be able to avoid those losses. Loss is a given. That ship has sailed—and what a relief.”

Visualization forces us to realize that we can’t be everything. We have to understand, at our core, what we can’t live without. Then we must sacrifice and optimize decisions for what matters most.

Realizing your vision

Maya Lin faced many of these decisions in her architecture. What type of experience was she trying to create? What was she trying to say about death? How would the memorial pay its heartfelt respect to the fallen soldiers, veterans, and their families? How would she make it feel like a private, personal experience? What tradeoffs would she make with how visitors moved through the memorial? All of these decision points required a holistic understanding of the vision she was working toward to ensure all elements of the memorial worked together.

Visualization works in both the immediate and long-term. It’s helpful to visualize both your next move and your ultimate goal. What does it look like if you project ten years into the future on your current path? Is that the life you envision for yourself? What feels right? What needs to be different? The same exercise can be applied to your current work on a shorter timeframe. Do you understand and know what you’re working toward? Have you built conviction around that direction? Once you know this, you can track the optimal path and fine-tune your near-term tactics to give you the best chance at making progress against your longer-term vision.

Remember: you are the architect of your own life and work. But you must understand the shape of what you’re building to create anything worthwhile. When you know what you’re working toward, you empower yourself to make tough decisions and navigate challenging tradeoffs in favor of your ultimate goal. But it will always require some sort of sacrifice. It’s your job to determine where you’re willing to make those sacrifices and which elements of your work take precedence, demanding an unyielding approach.

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Sources:

[1] Branch, Mark Alden. "Maya Lin: after the wall." Progressive Architecture, vol. 75, no. 8, Aug. 1994, pp. 60+. Gale General OneFile, link.gale.com/apps/doc/A15739154/GPS?u=denver&sid=bookmark-GPS&xid=2d91b918.

 [2] Burkeman, Oliver. Four Thousand Weeks: Time Management for Mortals. Farrar, Straus and Giroux, 2021.

[3] Clinton, Chelsea, and Grace Lin. She Persisted: Maya Lin. Philomel Books, 2022.

[4] Lin, Maya. Boundaries. Simon & Schuster; Reprint edition, 2006.

[5] Menand, Louis. "The Reluctant Memorialist.” The New Yorker, vol. 78, no. 18, 8 July 2002. Gale General OneFile, link.gale.com/apps/doc/A88605695/GPS?u=denver&sid=bookmark-GPS&xid=969bd096.

[6] Mock, Freida Lee, director. Maya Lin: A Strong Clear Vision. Ocean Releasing, 1994.

[7] "Thinking With Her Hands." Whole Earth, winter 2000, p. 72. Gale General OneFile, link.gale.com/apps/doc/A68617397/GPS?u=denver&sid=bookmark-GPS&xid=0aa391a1.

[8] Urban, Tim, @waitbutwhy. “We think a lot about those black lines, forgetting that it’s all still in our hands.” 5 March 2021, 10:14 AM, https://twitter.com/waitbutwhy/status/1367871165319049221?lang=en.

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. 

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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

Run Your Own Race

“What is my job on the planet? What is it that needs doing, that I know something about, that probably won’t happen unless I take responsibility for it?”

— Buckminster Fuller

In the mid-1990s, whether you were an investor or entrepreneur, everyone in technology was flocking to internet startups. Companies like eBay, Amazon, and Yahoo were gearing up for monstrous initial public offerings. It was a frenzy.

Meanwhile, Tony Fadell went to work for Philips building consumer electronics and handheld computing devices. Everyone told him he was out of his mind. Philips was a dinosaur. The Internet was where all the innovation was happening and fortunes were being made. No one needed another handheld device. But while everyone else chased lucrative internet startups, Fadell continued building hardware. 

Prior to Philips, Fadell spent five years working at General Magic—a failed company that lives on in the lore of Silicon Valley because of its alumni who went on to play pivotal roles at Adobe, Android, Apple, Google, and Nest, among others. 

At General Magic, the team worked to create a mobile computing device for personal communications and entertainment. It was released as the Sony Magic Link and had a phone, touchscreen, email, apps, games, a way to buy plane tickets, and animated emojis. The problem was that the technology wasn’t reliable and it was built for an audience that didn’t yet exist. 

The product was clunky—its processors weren’t fast enough, the touch screens weren’t great, and the battery life was too short. The team at General Magic built almost everything from scratch which was incredibly time consuming and expensive. And in 1995, the Internet was still in its infancy—email had yet to reach widespread adoption. The device became an exercise in innovation to impress other engineers at the company. The team failed to start with a problem that real people experienced and could relate to. They were ten years too early.

As the product floundered, Fadell created a plan to pivot away from making a communications and entertainment device for the general public, instead focusing exclusively on businesspeople. He pitched the idea to Philips since they were already a partner, making semiconductors and processing parts for General Magic.

Explore a different angle

Fadell held to his conviction that there was room for something amazing between desktop computers and cell phones. After pitching the mobile computing device for businesspeople on the go, he joined Philips full-time and got to work. It remained a niche market, but they successfully launched the Philips Velo in 1997 and the Philips Nino in 1998.

In 1999, after a successful run at Philips, Fadell left to start his own company. His vision at Fuse Systems was to build a better digital music player. People were starting to ship MP3 players but they were all clunky and difficult to use. And Fadell was tired of hauling around his collection of CDs everywhere he went. 

Again, he was cautioned by peers that he was continuing to compound his own mistakes by remaining in consumer electronics while the next big wave in tech passed him by. In 1999, internet startups were reaching their pinnacle of hysteria. Fadell continued to stick with personal electronics because that’s what he loved and that’s what he wanted to learn—bridging hardware and software, atoms and electrons.

The dot-com bubble finally burst in 2000—markets crashed and venture capital funding dried up with it. Fadell pitched his company to 80 different VCs and was rejected by every single one. Risk off. No one was interested in investing—even if it wasn’t internet related.

The team at Fuse was barely hanging on when Fadell received a call from Apple in late 2000. Apple had recently purchased iTunes and the application was starting to take off. Steve Jobs wanted iTunes to work with MP3 players and realized Apple needed its own device.

Jobs asked Fadell to join Apple as a consultant on an initiative to create a digital music device, codenamed Project Dulcimer. Fadell agreed, hoping he could use that money to continue paying his team or parlay it into a buyout for Fuse. 

As conversations developed, Fadell joined Apple full-time in January 2001 and brought over his team from Fuse. Jobs signed off on the concept for the device proposed by Fadell and his team in March. And the first iPod was shipped in November.

Fadell led the team that created the first 18 generations of the iPod and the first three generations of the soon-to-be iPhone. 

While people thought he was a fool to stick with hardware and personal electronics for a decade across five companies, by the time Apple called him to make the iPod, he knew exactly how to do it. Every job he held had given him a different vantage point on the same problem. He built a more complete view of the challenge and knew with precision what to work backward from. 

In retrospect, Fadell’s decision to stick with personal electronics seems obvious. But to hang in there for a decade while everyone around you is clamoring after the next big thing—internet startups—and constantly in your ear about missing out while they make nauseating amounts of money is no small feat. That takes serious discipline and trust in yourself. 

Chase problems you care about solving, not trends

Fadell was never optimizing for money. His primary focus was aligning to problems he wanted to learn more about and a space he was passionate about driving forward. That meant building devices and working at the intersection of hardware and software. It’s what he loved doing and that was enough justification for him. 

The most difficult challenge we face in life is to avoid getting pulled into races we aren’t willing to run. It’s why we end up chasing trends or grow insatiable in our quest for more. We’re perpetually consumed with a bigger title, a larger paycheck, the next milestone in life. We don’t want to miss out on anything. But this comes at the cost of sacrificing ourselves along the way. 

Oftentimes we allow ourselves to be carried away by the herd because it gives us a convenient excuse to cling to throughout life. By not committing to our own personal direction, we tell ourselves what could have been. “If I wanted to, I could have written a book, built my own company, led this team.” But you didn’t. The fear of actually dedicating yourself to becoming, grinding it out, and putting your ass on the line left you cowering in fear. So you chased after everyone else. 

To combat this, you must determine what is your own. You must slow down to clarify what you’re after, hone in on the problems you want to spend your time thinking about, and ignore everything else that gets in the way.

If you allow yourself to get caught up in the status quo—what everyone else around you is doing—it’s easy to end up in a dead-end career. You trap yourself into solving problems you don’t find meaning in and in doing so, diminish the impact you could have otherwise had. 

You’re not going to make a dent in this world or create anything meaningful by jumping ship every two years and chasing the next big thing. If you’re deeply interested in a problem and care about solving it, you have to stick with it, regardless of who thinks it matters. Over a long enough time horizon things will work out in your favor.

Staying true to yourself will be the hardest, loneliest thing you will ever do. You’re going to be standing in the wilderness wondering what you’re doing while other people get rich and seem to have it all together. But authenticity is about playing the long game—what can you sustain indefinitely? What were you meant to bring to life? That’s where your best work is born from. 

And while those same people who got rich overnight lose it just as fast and get written off as one-hit wonders, you will have slowly built an empire. Because you ran your own race. 

Ready yourself to face distractions

You’re still going to receive calls that entice you—opportunities to make more money, follow your friends, work on something trendy. But these are distractions that will only pull you away from the work you find real meaning in. That’s why you must determine what you’re after and hold to that with all your might. 

You must be able to navigate these distractions without losing yourself along the way. Do you have the willpower to stand up for yourself? Are you prepared to do the hard thing and turn down opportunities that don’t align with where you want to go? Do you have the endurance to stick with a problem you care about while everyone else jumps ship and tells you it’s a waste of time?

In 1973, Ed Catmull, the founder of Pixar Animation Studios, visited Disney to pitch a new computer rendering technology for animation. Disney laughed him off and instead tried to tempt him into a job designing theme parks with the Imagineering team. Holy shit, what a cool job. Since childhood, Catmull had been fascinated with Disney. But he turned it down without hesitation. He knew it was a diversion. He wanted to animate. And he trusted that. 

Life will throw everything it can at you—attempting to distract or tempt you along the way. That’s the test you must face. When things get tough are you going to give up on the work you care about? When the easy money or the comfortable job comes knocking are you going to sell out on your own priorities? Or are you going to stand steadfast in what matters most to you—the work you are meant to do?

If authenticity is what you’re after, you have to find and stick with what you believe in. You have to trust yourself enough to run your own race. And if you do, it’s just a matter of time before you come out ahead. 

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Sources:

1. Build by Tony Fadell

2. General Magic by Sarah Kerruish and Matt Maude

3. Masters of Scale with Tony Fadell

4. The Tim Ferriss Show: On Building the iPod, iPhone, Nest, and a Life of Curiosity

5. Creativity, Inc. by Ed Catmull

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.

Subtract To Get To Your Truth

“Knowledge is subtractive, not additive—what we subtract (reduction by what does not work, what not to do), not what we add (what to do).”

— Nassim Taleb

On August 6th, 1986, Bob Dylan walked off the stage at Paso Robles State Fairgrounds alongside Tom Petty and The Heartbreakers and he knew he was done. Dylan had one more stretch of shows lined up with Petty the following year—The Temples in Flames Tour—but after that, it was time to hang it up.

It had been 25 years since an unassuming kid from Hibbing, Minnesota showed up in Greenwich Village to immerse himself alongside his heroes in the folk-music community. And it was a legendary run. But Dylan acknowledged the reality of what his fans, critics, and peers had already voiced, his best days were behind him.

Dylan could no longer fill stadiums on his own and had to rely on big names like Tom Petty and The Heartbreakers or The Grateful Dead to draw crowds. He struggled to write new material—not that he had much desire to do so. And despite the hundreds of songs he had written over the course of his career, there were only a handful he would consider playing. 

During the Summer tour in 1986, Benmont Tench, the keyboardist in Tom Petty and The Heartbreakers, often pleaded with Dylan to include different songs in the set, like “Spanish Harlem Incident” or “Chimes of Freedom.” Dylan would muster up some excuse or play it off until he was able to divert the attention away from himself. 

The reality is that he could no longer remember where most of the songs he wrote came from. He couldn’t relate to or understand how he might even attempt to bring those songs back to life. They were a mystery lost to the past. 

Dylan’s plan was to coast through the final tour with the same 20 songs and try to come out unscathed before he went into hiding. That was the deal he made with himself to get through one more run.

The next year before kicking off his final tour with Petty, Dylan was scheduled to play a few shows with The Grateful Dead. He traveled to San Rafael, California to rehearse with The Dead at their studio. After an hour of rehearsal, it was clear that the strategy he used with Petty wasn’t going to work. The Dead were adamant about playing different songs from the depths of Dylan’s catalog. Material he could barely recall. 

He sat panicked and knew he had to get out. The Dead were asking for someone he felt no longer existed. During a lull in the rehearsal, Dylan falsely claimed he left something at the hotel. He stepped out of the studio and onto Front Street to plan his escape.

After wandering for a few blocks, Dylan heard music coming from the door of a small bar and figured that was as good of a place to hide out as any. Only a few patrons stood inside and the walls were baked in cigarette smoke. Towards the back of the bar, a jazz quartet rattled off old ballads like “Time On My Hands.” Dylan ordered a drink and studied the singer—an older man in a suit and tie. As the singer navigated the songs, it was relaxed, not forceful. He eased into them with natural power and instinct. 

As Dylan listened on, there was something familiar in the way the old jazz singer approached the songs. It wasn’t in his voice, it was in the song itself. Suddenly, it brought Dylan back to himself and something he once knew but had lost over the years—a way back to his songs. 

Earlier in his career, Dylan wasn’t worried about the image that others projected upon him, the expectations, or the fame. All he cared about was connecting with the song and doing it the justice it deserved. He was there to bring the words to life—a conduit of sorts. The old jazz singer had reminded him of this simple truth and where to pull from.

Returning to The Grateful Dead’s rehearsal hall, Dylan picked up where he left off like nothing happened. He was rusty and it would take years for him to truly get back to form, but he settled back into a state of relaxed concentration by returning to his principles that were buried underneath all the success, failure, praise, and criticism.

As he continued the final tour with Tom Petty and The Heartbreakers, over the first four shows Dylan played 80 different songs, never repeating a single one, just to see if he could do it. It wasn’t perfect. It wasn’t always pretty. But he was starting to tap back into himself and knew how to reach the music again. 

Where am I?

In our own lives, we inevitably reach moments where we feel like we’ve lost ourselves along the way. Where am I? How did I get here? What am I even trying to do? We feel like fragments of our former selves. Exhausted rather than energized by the challenges we face. 

Dylan is not alone in his experience. When we lose the connection to ourselves, our work, careers, and lives grow stagnant. We can’t create anything meaningful if we’re absently going through the motions. Gradually, then suddenly we become strangers to ourselves. 

As the emptiness creeps in, there’s a temptation to go into hiding. We fixate on our faults and let that feeling wash over us. We lose ourselves in the darkness. And when we get stuck here, we compromise our own integrity and the integrity of our work.

Life is deceptive in this way. We overcomplicate things. We inflate the importance of things that don’t really matter. We lose track of what brings us to life—the things we find deeper meaning in. We let our guiding principles fall out of focus. 

In the messiness of life, we make small compromises that add up over time. We say yes to the wrong things and no to the right ones. Things start to pile up. And the more we stack on top of ourselves, the deeper we bury our own priorities. Eventually, the weight of it all drags us down and obscures our vision. 

At this point, we can continue adding more, doing more, always saying yes, never saying no, breaking ourselves to meet the expectations cast upon us. We can continue floundering and creating more distance from ourselves. Or we can step back and ask, is this still serving me? What do I need to shed to come back to myself? What’s at my foundation?

Finding our way back

Sometimes the way back to yourself is through subtraction. 

This starts with peeling back the layers that have built up over the years.

What’s hidden underneath it all? 
What was your original motivation in your work? 
What got you here in the first place? 
What did you know then that you’ve since forgotten? 
What about this once brought you joy?

Finding a way to return to the simple truths we once knew can help us realign ourselves. Our foundation reminds us of what we set out for.

Far too often we attribute our identities to things that are beyond our control. We get caught up chasing what’s external to us because we trick ourselves into believing that’s what makes us who we are. But we are not our jobs, companies, titles, or paychecks. We are not the criticism, praise, accolades, or rejection we face. We exist beyond that. 

When we are just starting out, we instinctively understand this. We focus on internals and creating from what we know to be true about ourselves. We build from what inspires us. And that is enough. Because that’s all we really know. 

As Dylan faced this struggle, inspiration from an unlikely source brought him back to a beginner’s mindset and the principles he understood early in his career before everything got so carried away. Performing was about reaching for the truth within the song and putting that front and center. 

This mindset allowed him to tap back into himself. He was able to once again find meaning in his songs and remember why he was doing what he was doing. He embraced his responsibility to perform each song to the best of his ability. 

From this point on, Dylan focused on playing smaller theaters and more intimate shows—drawing songs from every stage of his career, reinterpretations, new songs, and rarities. Returning to the basic truths he lost along the way led to his resurgence as an artist. Rather than signaling the end of his career, The Temples in Flames Tour helped Dylan uncover the start of something new.

Letting go to remember

Connecting back to yourself starts with cutting away the nonessentials and reminding yourself how you found your way here in the first place. Subtract to get to the truth of things. 

In the process of letting go, you start to remember who you are and what you find meaning in. 

This doesn’t mean you should try to recreate the past. You can’t go back in time. Dylan wasn’t trying to bring a younger version of himself back to life. He was just returning to the principles that set everything in motion and rebuilding from there.

A beginner’s mindset can help you distill the real parts of yourself—the anchors that give you substance and depth. By paring down to what’s real and what’s within your control, you tap back into what sustains you. And as you sift through the rock, dirt, and debris, you free yourself to move with conviction towards bringing your best work to life. 

A Call to Arms: Guarding Yourself from Despair in an Ocean of Layoffs

Let’s be honest about the current environment in tech. The past decade made us soft. We got caught up in the hysteria of unicorn valuations. Companies succeeded despite mediocre execution. And along the way, we tricked ourselves into believing things would always be up and to the right. 

But we all have to learn this lesson sooner or later—never allow yourself to be caught off guard. To combat this, resourcefulness and self-sufficiency are critical—the ability to think for yourself, adapt, and focus on what’s within your control.

When you get caught up in it and lose your sense of self along the way, these lines become blurry. Your company and your job consume your identity. And over-identifying with a job or a company strips your ability to think for yourself and hands over your peace of mind to something beyond your control.

It’s difficult to guard yourself against this as you get further into your career or if you’ve idealized working at a certain company as your ‘dream job.’ The definition between you and your job begins to blur. You get wrapped up in your work because you care, you see your recent valuation as a lottery ticket, and you tell yourself that your Metafam will always take care of you. Then a downturn hits, your job is cut, and you’re facing an identity crisis. 

“No one is crushed by Fortune, unless they are first deceived by her.”

— Seneca

It’s easy to feel like it’s all over when the winds of fortune shift, as they can and will for all of us. Because too many of us have trapped ourselves into focusing on externals and things beyond ourselves to define who we are and fuel our sense of self-worth. And too often we fail to recognize that conditions of the recent past won’t extend indefinitely into the future. 

To combat this you must first untangle yourself. You are not your company. You are not your job. If you were impacted by a layoff and feel blindsided, you are not alone. Now is the time to build the muscle so you’re never caught off guard again.

This starts with a focus on the mental models and resources you need to establish a greater degree of self-sufficiency and resourcefulness. With these, you can build resilience, flexibility, and independence. That way, when the unexpected strikes, you are able to avoid catastrophe, instead using that as a catalyst for growth. 

Hold your identity lightly

“You are not your work” sounds catchy. People throw it around, but what does it actually mean? When you tell yourself you are a ‘Head of Product’ or your identity is constructed around the fact that you were an early employee at Stripe, and then you’re pushed out, things crumble. Because titles and companies are externals that fall beyond your complete control. Over-indexing here can make you rigid and fragile. 

“When you cling too tightly to one identity, you become brittle. Lose that one thing and you lose yourself.”

— James Clear

The reframe this, you must go back to why you do what you do. Who are you as a person? Forget the bullshit, forget the vanity, forget the ego. Who are you at your core? Are you the type of person who loves building and creating? Are you a storyteller?

When you base your identity in who you are rather than what you are or where you are, you create room for flexibility and resilience. Holding your identity lightly allows you to adapt. It allows you to find harmony in the motion that is life.

Assign things their proper value

Inherent to this focus on who you are rather than your title or your company, is a shift back to what’s within your control. Self-sufficiency begins with identifying what’s within your control, what’s beyond, and what falls in between. By going through this exercise, you can start to map out and assign things their proper value. 

You can control how you show up. You can control your focus on your craft. You can control the boundaries you set between your job and your identity so they’re not blurred beyond all recognition. You cannot control economic conditions. You cannot control every decision made at a company. 

Focusing on what’s within your control is about reducing the dependencies you create between external conditions and your internal well-being. The less reliant you are on others to provide the things that only you’re able to give yourself—meaning, character, integrity—the more resilient you become to the whims of market conditions and executives. 

“There is only one road to happiness—let this rule be at hand morning, noon, and night: stay detached from things that are not up to you.”

— Epictetus

Live below your means

If you’re working in tech, you have been in an extreme position of privilege in terms of compensation. But inflating your lifestyle to match your income is one of the most dangerous things you can do. And while you might be able to get away with this in good times, should economic conditions turn south, this mistake will crush you.

“Independence, at any income level, is driven by your savings rate. And past a certain level of income your savings rate is driven by your ability to keep your lifestyle expectations from running away.”

— Morgan Housel

If you’re in this position currently, write this on your mirror and stare at it every day: build a safety net. When you’re employed, you should be stashing away as much of your paycheck as humanly possible. While inflating your lifestyle to match your income makes you fragile and dependent. A safety net creates flexibility, independence, and peace of mind so you’re never buried in desperation. 

You always want to have options. This is about taking back your life from those who have you strung out on an addiction to your biweekly paycheck or annual bonus. 

Getting laid off from a job can be a catalyst to come back to yourself, find alignment, and focus on more meaningful work. But without a contingency plan—emergency funds and a modest lifestyle—you’ll throw yourself into a state of panic. This state of desperation forces you either jump at the next opportunity rather than the right opportunity or get stuck in jobs you hate. 

The mania will return one day, do not allow yourself to get caught up in it. Begin building a buffer to protect yourself against ruin. You always want to have the power to walk away or bounce back if difficult times come your way. Work your ass off to create a safety net that puts you back in control of your own life. 

The good times won’t last forever, but neither will the bad.
 

Take back your identity

If you want to take back control of your life and build resilience, focus on eliminating dependencies. Disentangle your identity, your sense of self-worth, and your well-being from your current job and company. Assign things their proper value by focusing on what’s within your control.

You are not invincible. You are not immune to the winds of the market. The best way to guard yourself against the waves of mania and panic that define the human condition is a relentless drive toward self-sufficiency and resourcefulness. 

With these skills, you can take your happiness, your well-being, and your life back into your own hands. No one else can do that for you. Not your partner. Not your job. And certainly not your company. This allows you to build resilience, flexibility, and independence which guard you against despair when all hope seems lost. 

It all starts with creating the space for yourself and sitting in that. No matter how uncomfortable it might be or how much easier it is to lose yourself in the busyness of work. You must sort through the noise and determine what is your own. 

Now is the opportunity to find your way back to yourself. Now is the opportunity to create your own momentum in life.

Build Up Your People to Build Up Your Customers

The most successful product-driven companies are customer obsessed. Teams at these companies work relentlessly to get close to customers and represent the voice of the customer. This mindset allows your teams to develop a deeper understanding of the problems worth solving and build greater empathy for the people who face those problems.

Most leaders are able to acknowledge the importance of this. But too many leaders believe they can jump in, put a mandate in place, and see immediate results without having to put in the work themselves. If you want to build up your customers, you must first build up your people. 

Empathy gives rise to empathy. Trust gives rise to trust. 

You can’t expect your team to connect with and care deeply about your customers if you don’t demonstrate the same for your team. Attempting to build from a place of “do as I say, not as I do” is delusional and ineffective. But if you create this connection first within your team, it creates the foundation for a deeper connection with your customers.

“Operations occur at the speed of trust.”

— Jim Mattis

As a leader, this doesn’t mean you need to be in the weeds leading discovery efforts and research interviews with customers. But if you want your team to show up and care about your customers, you need to build that same empathy and trust within your immediate team. 

This can be as simple as using 1/1s to talk through challenges your team might be facing. You don’t always have to fix things or offer up solutions. Listen, make them feel heard, and connect to what they’re feeling about an experience. Then you can think about problem-solving together.

Retros are also a great way to build trust. But you need to lead by example, put something out there that you’re struggling with, and create a sense of safety for the team. When the team feels this, they’ll lean in together to lift each other up.

I’ve also found that providing actionable, thoughtful feedback after a big meeting or presentation can go a long way. Recognizing the specifics of what someone did well and what could be improved fosters a growth mindset. And reflecting on how to get even better as a team—what to double down on, what to work on—shows you’re working in the same direction.

Each day you have an opportunity to make people feel heard and to help the team push each other. Sprint planning, standups, quarterly planning, career conversations, engagement surveys, product reviews—every single touchpoint is an opportunity to lean in with your team.

Where this can break down is when we trick ourselves into believing top performers don’t care as much about these things. We tell ourselves they have their own work ethic and hold themselves accountable. We just need to focus on providing the right incentives and meaningful problems—which is certainly true in some capacity. But it’s a shortcut our minds take to avoid putting in the work and having real conversations. Staying in the shallow can feel easier in certain moments. But the truth is that top performers are also motivated by empathetic leaders who give a shit about their people. This connection is critical to their success and your team’s success.

“Understanding a person’s hunger and responding to it is one of the most potent tools you’ll ever discover for getting through to anyone you meet in business or your personal life.”

— Mark Goulston

By glossing over building a deeper connection with your team, you might end up with a marginally effective band of mercenaries who can keep the lights on. But you’ll struggle to connect with customers or achieve any sort of meaningful impact. It starts from the inside out.

And this is true at every level of your career. If you’re a product manager leading a squad, you must care about your team and building them up before you can think about delivering meaningful impact for customers. If you’re a middle manager, the same holds true of your direct reports—you must create a connection built upon empathy and trust. This provides your people the confidence to mirror this approach across both their teams and the customers they interact with.

If you want to increase your leverage and maximize your impact as a leader, start here. It’s a simple lesson but one that’s easy to lose sight of. By building up your team—showing up, listening, and instilling trust—you unlock your people to do their best work and show up at their best with customers.