Visualize the End Result

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

”

— 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.

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

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.

The Barbell Strategy for Your Timeframes in Life

If you follow the self-help genre, you’ve likely been bombarded with waves of conflicting advice:

Stay present, but make sure you spend time thinking deeply about what you want out of life, setting goals, and creating checkpoints to measure progress.

Find a flow state in your work, but expand your perspective of time so you’re assigning things their proper weight.

Drive results today, but sharpen your strategic mind by thinking multiple steps ahead and considering higher-order consequences to outmaneuver your opponents.

All of this advice on what timeframe to orient towards becomes exhausting. Am I over-indexing on the future and paying too little attention to today? Am I making shallow decisions and not thinking far enough ahead? Am I setting goals that match the optimal timeframes?

Each piece of advice on its own seems intoxicating. But when you try to reconcile these ideas against each other, it’s easy to get stuck. No one tells you how to achieve balance or what that looks like. 

The reality is there aren’t just two timeframes in life—present-oriented or future-oriented. These are just the bookends, there are other timeframes that sit in between. But the bookends are the most powerful timeframes to operate in. And the middle proves to be the most dangerous. 

A few weeks back, I came across a post on Twitter from @john_j_brown that provided me with a framework that created clarity…

While this post is geared towards investors, a similar model can be applied to the timeframes in our lives.

There are four timeframes in life…
1) Immediate = today
2) Short = days/weeks
3) Mid-term = months
4) Long-term = years/decades

The most rewarding life is found by pursuing a balance of 1 and 4 and avoiding too much time in 2 and 3. The most dangerous timeframes in life are the short and mid-term.

What’s the barbell strategy?

The optimal balance for these timeframes can be framed similarly to Nassim Taleb’s barbell investment strategy which proposes that you be as hyperconservative and hyperagressive as you can be, instead of being mildly aggressive or conservative.

In life, the parallels are the immediate and long-term. Using the barbell strategy, we should spend 40% of our time focused on the immediate term, 40% on the long term, and only 20% of our time in the middle thinking about short or mid-term. Of course, this is just a mental model. No one is going to sit around and calculate how much time they spend in each category. But as a rule of thumb, it’s an effective way to keep yourself in check and balance the most effective timeframes to operate in. 

Why optimize for the immediate and long-term? 

1 and 4 are where I find fulfillment in the work itself and a connection to a more meaningful vision I’m working towards. 2 and 3 are where I become impatient, anxious, and scattered—anticipating that presentation next week which distracts me from putting in the work today, fueling unrealistic expectations before reaching sustainable growth, or making shallow decisions that optimize for comfort.

The immediate-term (1) allows you to be fully present and immersed in your work. It helps you remain focused instead of anticipating any sort of future payoff or conflict. This is what allows you to achieve a relaxed state of concentration. The gratification is in the work itself. 

While longer timeframes (4) allow for calmness, perspective, and compounding. Thinking in terms of years or decades connects you back to the bigger picture. It also combats the tendency to exaggerate the magnitude of conflicts we face on a shorter time horizon and guards you against deceiving yourself into short-sighted moves that favor comfort and predictability. The long term is what smooths out the anxiety and steadies the waves that can break your knees.

It’s when you become consumed by the short and mid-term (2 and 3)—the days, weeks, and months ahead—that patience and focus give way to restlessness and anxiety. In this timeframe, you’re anchored to unrealistic expectations of linear, short-term growth which compromises strategic thinking and your connection to your ultimate goal.

When you’re focused on the moment in front of you, you’re not anticipating. You’re absorbed in your work. When you’re focused on the longer term, you connect to something larger than yourself and expand your perspective of time. Ego is what operates in the mid-term. It breaks your flow state by anticipating rewards, results, and external validation. It’s what scares you into seeking predictability and comfort to protect yourself—limiting your available upside.

The allure of the short and mid-term is so strong because it’s easy. People who are better at talking than doing thrive in these timeframes. It allows them to create the illusion of progress through seemingly intelligent observations without putting in the work or holding themselves accountable to the long-term results. These are the politicians, the academics, the suits, and the startup flakes who prove unable to stick it out.

Many people live their entire lives here. They’re simultaneously distracted and not thinking long-term enough. They’re living for the weekend, their next vacation, or the comfort of their annual bonus. It’s the most comfortable place to operate, but the least rewarding because the short and mid-term are the most shallow timeframes.

Real depth is found in the immediate and distant—putting in the work today and building up the endurance to sustain for years. 

Certainly, you need some balance of the short (2) and mid-term (3) as checkpoints and it’s important to have things to look forward to. And of course, there are obvious exceptions. But sustainable results don’t appear over the course of weeks or months. They appear through years and decades of hard work and a constant connection to what you find meaning in. 

Growth is nonlinear

Remember, growth is nonlinear. People tend to overestimate what they can accomplish in the short term and underestimate what they can accomplish over the course of years. The power of small, calculated decisions grows exponentially over time. Especially if you have a clear vision that you’re working towards. Start small and let compound interest run its course.

Focus on the short and mid-term is what interrupts this. Because growth is not always observable in comparison to the previous week or month. When you expect linear results equivalent to the effort you’re putting in, you’re bound to give up too early or make short-sighted decisions that create the illusion of progress at the expense of sustainable long-term growth.

If you’re playing the long game, 1 and 4 are where you build up the resilience and endurance required to contribute your best work. This is what allows you to continue showing up or making difficult decisions that sacrifice comfort for growth. 

Optimizing for this balance of immediate and long-term timeframes allows you to persevere. To find meaning in the moment and the work in front of your face, while continuing to come back to your underlying strategy. One that extends beyond the weeks and months, but that you can advance in the moment. Dedicating more of your energy to 1 and 4 allows you to bring your best work to life by ignoring the distractions and noise that sit in between.

What’s in it for you?

When you adopt the barbell strategy for investing your time, you’re able to accelerate your trajectory and outpace those operating in the mid-term. Those who spend 80% of their time focused on the short and mid-term often end up stuck in dead-end careers. They’re prisoners seeking comfort and predictability in the weeks and months ahead. Their trajectory and growth are limited as a result.

The barbell approach encourages a deeper connection to your work and an understanding of what kind of life you want to live. If you know what you want out of life and you’re willing to put in the work, the competition crumbles. It becomes a race against yourself.

But you must never trick yourself into believing you are above the work. The work is where you find solace. Pairing this with the long term and what you’ve defined to be a meaningful life is what allows you to create enduring work and transform yourself. In both the moments you have today and in the decades ahead.

“As one achieves focus, the mind quiets. As the mind is kept in the present, it becomes calm. Focus means keeping the mind now and here. Relaxed concentration is the supreme art because no art can be achieved without it.”

— W. Timothy Gallwey, The Inner Game of Tennis

Immediate, distant, but avoid the in-between

When you’re focused on the moment in front of you, that’s where you begin to hone your craft and unlock a flow state so you’re able to do your best work.

When you’re immersed in a longer time horizon, that’s when you’re connected to something bigger than yourself and tap into your strategic mind, allowing you to drive towards your vision. 

But when you’re stuck in the middle, that’s where anxiety, anticipation, and ego take hold. Because it’s too soon for most results, distracts you from putting in the actual work, and leads you to cling to the comfort of the familiar in order to avoid the discomfort of introspection—who you are, what you want, the challenges you’ll face, and the work you need to do today to get there. 

The sweet spot is found by immersing yourself in your work, achieving a state of flow, and appreciating the moment. But also remaining connected to a greater sense of meaning you find in your life and harnessing the power of your strategic mind. 

The best endurance athletes in the world demonstrate this. Consider your strategy, focus on the mile in front of you, and dig deep to stay connected to the reason that keeps you going. The mid-term serves as a hydration station on your path, a place to refuel. But it’s nothing more than that—a brief checkpoint. Then it’s back to putting in the miles and honing your strategy. Leave nothing on the table.

3 Questions to Help You Rise to the Level of Mastery

“To rise to the level of mastery requires intense dedication. You have to really want it. What would make you have such commitment and dedication?”

— Robert Greene

At the start of my career, I wondered what I was doing wrong. I wanted to dedicate myself to my career, but I didn’t trust myself to know which potential directions were worth going all in on. I was terrified of making the wrong decision. And my early 20s, ego gave me a false sense of confidence and deluded me into believing I could be anything I set my mind to. Rather than eliminating options and accepting that directions in life are mutually exclusive, I sat in indecision. 

But the truth is that you can’t be anything in this life. There are things you are uniquely suited to do based on your skill set, interests, and experiences. And the sooner you accept this reality and cross options off the list, the more time you give yourself to dedicate to the things you’re uniquely good at. But this demands reflection—you have to allow yourself to reflect on the skills you’ve excelled at, the subject areas you’re naturally drawn towards, and where you find meaning. 

What are you naturally good at?

At 24, I was living in Nashville with no idea what I wanted to do in my life. One weekend, I forced myself to go to a coffee shop around the corner, put my headphones on, and write. It was the first time since I was eight years old that I was writing for fun.

Over previous months of reflection, I asked myself what I was naturally drawn towards in childhood and what skills I excelled at without trying as hard as other kids. I remembered that writing was one of those things so I pushed myself to reconnect with this. The connection was immediate and the state of flow I was able to achieve in writing was addicting. That’s how I knew I was on the right track. 

As I used writing to reflect on who I was, I also started to recall how industrious I was as a kid, working to generate extra money. From as early as I can remember, I was working my way through the neighborhood mowing yards, shoveling snow, or starting a mobile snow-cone operation on the back of a wagon that I’d roll door to door during the summer. I loved testing new ideas.

And finally, as I searched for how to fit the pieces together and what to focus on, I began reading for enjoyment again—another thing I loved as a kid and lost through school over the years. This allowed me to hone my sense of focus. I also began to develop stronger strategic thinking skills and stack mental models from different disciplines against each other to improve my decision-making.

All of this led me to a career in product management that I’m deeply invested in. Product demands an elite level of resourcefulness, focus, and communication skills. You have to be driven to create, take risks, and articulate stories in a way that resonates with different audiences. And you have to be able to quickly evaluate directions from multiple perspectives. These were all things I showed aptitude in from an early age. I just had to reconnect with those things and forget all the shit that happened between age 8 and 24 to get back there and align myself to that. 

Perhaps the most important aspect of this is that when you leverage skills that come naturally to you, you can outwork everyone else around you because the work itself is deeply rewarding and where you find your flow state. Your validation comes from the craft itself—internal, not external.

If your goal is mastery, the first step is reconnecting with your childhood interests and skills that come naturally to you. These are the places you must invest in.

To achieve alignment and build from a place of authenticity, you must first remember who you are.

What subject matter are you drawn towards?

During the early part of my career, I bounced between different industries—music, film, healthcare, and insurance. And what I learned through exploration was that those weren’t the things I cared deeply about. After a year or two in each, I was bored and struggled to sustain a connection with the problems we were tackling.

When I started my career in film production working on set for major music videos, I was barely able to sustain two summers in that line of work. It seemed glamorous from the outside looking in. But the inefficiency of working 22 hours for a three-minute music video drove me insane. And most importantly, I wasn’t willing to struggle for the end result because I didn’t connect with many aspects of the work that I was exposed to—whether finance, set design, project management, or cinematography.

I also found I didn’t have a natural interest in the entertainment industry or the value we were providing. And if you don’t care about the subject you’re focused on, it’s going to be tough to stick it out.

But early on, finding something that doesn’t resonate with you can be just as valuable as finding something that does. Because it helps you eliminate a direction and move on. The goal is to learn and refine to better align yourself with each move. 

Through trial and error, the subject areas that I’ve found a deeper interest in are philosophy, education, and finance. After close to a decade of exploration, before I applied to my current job, I knew I was going to stick with edtech and fintech as the sectors I wanted to work in. And it worked. Snapdocs is in the broader fintech category and I find the work endlessly fascinating. So I can stick it out despite the challenges and obstacles in the way of achieving our vision.

There are subjects you’re naturally drawn towards. Consider what you enjoy reading and learning about right now. That’s your starting place. The more you invest in these things, the better. Because it’s very difficult to sustain interest in a field or subject that you aren’t pulling from a deeper sense of curiosity about.

Mastery requires a relentless level of focus and effort.

Where do you find meaning?

And finally, you must also search for meaning. Because no matter how naturally talented you are and how interested you are in a field, you have to find meaning in the work or you’ll forever lack the persistence that mastery requires. 

This can show up in different ways but once unlocked it’s the force multiplier that allows you to endure. Whether it comes from the group of people you’re building alongside or the end result you’re driving towards or the brokenness you’re working to fix. There will be weeks and months that test your limits. If you lack meaning, it will be impossible to continue showing up. Mastery demands endurance. 

“Almost nothing in the world can resist persistent human energy. Things will yield if we strike enough blows with enough force.”

— Robert Greene

I find meaning in accelerating personal growth and pushing the confines of my current limits. I find meaning through the people I’m collaborating with on a daily basis to solve challenging problems. And I also find meaning in solving problems that translate directly to human outcomes. That’s one of the reasons I love my current position, I’m motivated to make the disaster that is the home buying experience less shitty. I want it to be accessible and more transparent for everyone involved. And it’s incredibly challenging. But worth it, because the end result we’re working towards is meaningful to me and I’m able to test myself along the way. 

Another way to think of this is asking yourself, what are you willing to suffer for? You’re going to struggle regardless of the line of work you enter. It’s going to be hard. There will be moments that piss you off or lead you to question what you’re doing. To get through these moments, you have to recognize and reconnect with a deeper reason that keeps you going.

Where do you find meaning? You can endure anything if there’s a deeper connection to your craft and the problem you’re focused on. Keep this front and center and you will be able to persevere when the inevitable obstacles stand in your way. Endurance is foundational in the pursuit of mastery. So what are you willing to show up for every single day?

Rising to the level of mastery

Once you’ve achieved alignment with the answers to these three questions, you’re on your way. But you still have to put in the work. You still have to show up. There is no path towards mastery without having skin in the game. 

As tempting as it might be to distance yourself from the work and make it easier on yourself, this works in opposition to mastering your craft. You can never be above the work. This also helps ensure your incentives are aligned and you have a vested interest in the outcome. Because even when you come up short, you can always take solace in the fact that the credit belongs to the man in the arena. 

When you’ve aligned yourself to skills that differentiate you, subjects you’re naturally drawn towards, and focused on where you find meaning, this all acts as a force multiplier for your work. 

You are uniquely positioned to bring certain things to life. You can’t be everything. And if you want to maximize what you’re giving back to this world, the sooner you focus on mastering what you’re uniquely positioned to contribute, the more fulfillment you will find.

10 Lessons on the Road to 33

Birthdays and New Years serve as two natural checkpoints for me. Birthdays act as a time to reflect on what I’ve learned and consider lessons that have resonated strongest over that year of my life. Whereas New Years signal it’s time to set five primary goals and assess how well I did against the previous year’s goals. Most years I publish these reflections, the following are 10 lessons that stood out most over the past year. 

1) Show up, even when it’s inconvenient 

Fighting through canceled flights, delays, and traffic jams to show up for someone when they need it most, even if you’re only there for an hour, matters. Regardless of what plans you might have made for your evening or weekend. The timing of events beyond your control might be inconvenient. But the universe isn’t on your agenda. And there isn’t some perfect version of the future where your life is free of challenges. The challenges and obstacles are what give life meaning. You can point to those as your excuse, or you can show up anyway when it matters most. 

2) Commitment adds meaning

Just as obstacles add meaning, so too does commitment—whether your relationships, career, hobbies, you name it. Directions in life are mutually exclusive. In my early 20s, I optimized for optionality and never committed to anything. Many of these things were unfulfilling and left me restless. But once I started to cross options off my list and double down on the people and things I cared about most, life became far more rewarding.

Getting married to my favorite person in the world this summer after six years together has continued to deepen our relationship. The same goes for my career and the way it has been accelerated by committing to problems I care about solving and the vision we’ve crafted around solving those. 

3) You don’t have to agree with the entirety of someone’s opinions

Almost everyone has good ideas and bad ideas. And you don’t have to agree with the entirety of them. One good idea doesn’t mean every idea that a person has is worthwhile. Just as one bad idea doesn’t mean the entirety of that person’s ideas are garbage. This lesson shows up frequently for me in books. When I was younger, I would take the entirety of an author’s ideas in a book as truth. Now I find myself more often disagreeing with certain aspects, and that’s fine. This ability to balance multiple opposing views and perspectives is what leads to improved critical thinking. This also speaks to the danger of ideologies and blindly accepting a docket of opinions without thinking for yourself. Guard yourself against this at all costs. 

4) More music, less everything else

During the pandemic, this got away from me. I didn’t have my regular outlets at coffee shops or commutes to let go and listen to music. It was all work, all the time. And in the brief moments when I wasn’t working, we were watching Netflix. But music is the thing that allows me to reach a state of relaxed concentration where I do my best work. Making more time for this, creating focus blocks throughout my day to tune everything else out, and starting my day with music while reading or writing in the morning makes me happier. And the same goes for evenings at home. Just turning on music instead of the TV feels more rewarding than whatever show we might be watching. 

5) Focus on what’s within your control

As long as I’m around, I don’t think I’ll ever shut up about this. Focus more on yourself. Every second you spend projecting or losing yourself in imaginary conversations consumed by others’ opinions is truly wasted. Focus back on yourself. Most people waste away consumed by distractions without ever searching within. If there’s any sort of secret in this life, it’s figuring out what you want out of life, reframing that as an internal goal you can actually influence, and pursuing it with everything you’ve got. 

6) Happiness is knowing less about what’s going on in most people’s lives, not more

Comparison is the death of joy. Most people are far too connected and could use more distance. I can only speak to my life, but I am far happier when I know less about people outside of my closest group of friends and family. And that’s a group of about 10 people. Beyond that, it’s just noise. 

Certainly, you must care for your community. But your capacity to give a shit is limited. You have to pick your battles. Anyone who claims they can keep up with everyone and every cause is virtue signaling. Instead, focus on yourself and your family, fight for your cause, and ignore the bullshit. There’s only one way out of the noise most people find themselves consumed by—distance yourself.

7) In-person interactions hold company’s together

I’ve worked fully remote at different points in my career. I’ve never actively sought it out, it’s just worked out that way and I was rather indifferent to it. But over the course of the pandemic, I’ve changed my stance entirely. If your intention is to create an enduring company of top performers who band together to overcome challenging moments, co-located teams will crush remote teams. Fully remote teams sacrifice camaraderie, morale, and meaning in the name of short-term productivity. My expectation is that most fully remote teams will self-destruct over the next few years because they won’t be able to absorb the higher turnover caused by a lack of human connection. 

8) Appeal to Your audience’s self-interest

Whether it’s a presentation, email, article, you name it, most people start by focusing on what they want to say. That’s exactly the wrong path if you’re hoping to land your message. Instead, ALWAYS start by putting yourself in your audience’s position and emphasizing the benefit from their perspective. Addressing the ‘What’s in it for me?’ question within the first 30 seconds is the only way to capture attention, disarm, and influence.

9) your first responsibility is to shut up and listen

I’m surprised at how common this problem is. A new hire joins the company, insecure and eager to prove their value, they immediately jump to providing feedback and solutions without having any context of the business, the product, or the team. And in doing so, they immediately erode any semblance of trust and have to work twice as hard to rebuild that over months. Seems like a fun way to start. This seems especially rampant in senior leaders who come into companies and should know this lesson better than anyone else, but they turn out to be the worst offenders. 

During your first 30 days at any company, just shut up and listen. Regardless of what level you’re coming in at. True confidence can look like keeping your mouth shut and simply listening. This will help you build deep relationships that will serve you far better than attempting to offer up empty feedback that lacks context and only draws attention to your attempts to overcompensate.

10) to command respect, be fearless

Timidity kills careers. Jump into the deep end. Raise your hand. Aspire to always have skin in the game and never act like you’re above the work. Regardless if you’re a middle manager, executive, or individual contributor, the work matters. You certainly have to know how to delegate. Otherwise, you’ll drown. But there will be occasional points where you must go deep on the subject and fight alongside your team in the trenches. If you avoid this second piece, you will never command respect from your team. 

The Danger in Projecting Your Most Important Thing

After graduating from college, I poured most of my time and energy into triathlons. That was my most important thing. And it stayed that way for most of my 20s. I optimized my days for training across each discipline—swimming, cycling, and running. 

When I went out on my bike, I’d ride with a group of cyclists twice a week. For years they would throw shade my way for not showing up to as many rides as they did. They couldn’t understand why their most important thing wasn’t mine. Their attitude towards me was dismissive—triathletes were just flaky, wannabe cyclists who couldn’t commit to one sport. And if we’re being honest, I harbored a similar sentiment in return. 

There’s a certain level of arrogance most of us hold with our own priorities. We believe, to varying degrees, that our most important thing is often the right thing for everyone. Our priorities take precedence.

But while it’s important to build confidence in your own path, presuming you know best and projecting that same path upon everyone else is hubris. To avoid spiraling past this golden mean, it requires humility. Without this, you become rigid and inflexible. You squander your limited time and energy on things beyond your control. And your relationships are worse for it. 

You are only responsible for yourself, your path, and identifying your most important things. Every second you spend consumed by what you believe other people should want is truly wasted. You are never going to change or help someone by prescribing what they should do with their life. You’re just going to piss them off. And in doing so, you’ll begin to stagnate as your focus drifts from your own life. 

The counterbalance to losing alignment with this golden mean—the place where you build confidence and trust in your own direction while respecting other’s differences—is reminding yourself that not everyone will share the same goal as you. Not everyone is your competition. Different people will have different priorities, and that’s okay as long as it isn’t harmful to society. All you can hope for is that everyone is thoughtful in their own approach. 

This manifests itself in different ways depending on your priorities. Consider your career and lifestyle. You might think someone is crazy to leave (or stay with) your company based on the opportunities available and the company’s trajectory. But that’s based on your vantage point, your level of engagement, and your aspirations. Rather than judging their decision—something beyond your control—all you can do is hope that they were thoughtful and made the best decision for themselves. What’s right for you right now will not be the same for everyone else you work with. And the same holds true for your lifestyle. 

When I was younger, it used to shock me that people would stay and raise their kids in the same town they grew up in. Weren’t they missing the opportunity to discover themselves and wreck their comfort zones by moving somewhere new? But my judgment assumed their priorities and mindset were identical to mine, which is exactly wrong. If someone’s most important thing is deepening their roots in the community they grew up in, all that matters is that they’ve aligned themselves to that. And while I will never have this experience, it’s something I’ve grown to appreciate as equally valuable.

Not everyone needs to see the world the same way as you. You don’t need to convince people you are right. The best you can hope for is to achieve a sense of alignment and authenticity within yourself. And respect when other people are trying to do the same. Besides, the world would be rather uninspiring if everyone held identical values and pursued the same paths. 

Your perspective and the principles you live by are what define you, your art, and your life. Trust that. Find solace in your direction. But don’t presume it’s for everyone. And don’t allow others to throw you off your game. 

The Greeks had a term for this—euthymia, which Seneca defined as “believing in yourself and trusting you are on the right path, and not being in doubt by following the myriad of footpaths of those wandering in every direction.” The key is that this starts and ends with yourself. 

Until I worked this out, I’d waste a soul-crushing amount of time judging and dismissing other people because of my own insecurities. It wasn’t malicious or all-consuming, but it was decidedly unproductive. When I developed the awareness to recognize this, I was able to better hone my own focus. In turn, this unlocked all the time and energy I wasted worrying about other people and allowed me to channel that towards my own growth. And that’s when I was able to define a stronger direction for my own life. There was nowhere to run when I faced uncomfortable conversations with myself. I couldn’t point to other people as a distraction to avoid self-reflection.

In my own life, self-sufficiency (within reason) is my guiding principle. I want to have skin in the game and make my own way, rather than spectating and criticizing from a distance. I believe voluntary hardship and forgoing too much convenience are key to living a fulfilled life. In moments that force me to choose between comfort and growth, I almost always choose growth. No matter how painful that is. But I no longer pretend to believe it’s for everyone. Directions in life are mutually exclusive. And it’s important to respect divergent paths because those differences are what make life interesting. 

Building confidence in your own path is a critical skill if you want to live a meaningful life. It’s the golden mean between self-doubt and hubris. Find your thing. Trust in your path. Figure out what you’re after in your own life and double down on that, knowing your priorities are unique to you. 

When you stop worrying about what everyone else is focused on and play your own game, you can better navigate distractions and channel that energy towards the things that matter most—actually listening to those around you and making meaningful progress towards your own priorities. 

“There are hundreds of paths up the mountain, all leading in the same direction, so it doesn’t matter which path you take. The only one wasting time is the one who runs around and around the mountain, telling everyone that his or her path is wrong.”

— Hindu proverb

15 Lessons I Learned Before Turning 31

31 feels slightly less monumental than 30. Last year, I reflected on the most important lessons learned over the course of my 20s. But there are no off-years in life. If you’re doing it right, each one offers new experiences and opportunities to grow.

Every year I create checkpoints to consider lessons learned, challenges I’ve faced, and progress I’ve made. Birthdays are one of those triggers to step back and administer a healthy dose of perspective. 

I’ve found that the true test of how much I’ve learned in the previous year is considering myself at that same point in time 365 days ago. If I laugh at how stupid I was, that’s a good sign. Investor, Ray Dalio, shares a similar sentiment, “It seems to me that if you look back on yourself a year ago and aren't shocked by how stupid you were, you haven't learned much.”

The years I’ve been able to look back and contemplate how much I’ve learned, despite laughing at the expense of my younger self, have been the most rewarding.

This year was an important one for me. Although it’s not as big of a milestone as 30, this year was full of little victories, failures, and lessons. I’ve learned as much as I ever have in a single year. Here are some of the most important lessons that have stuck with me.

1) What matters most is the ability to bounce back

There will be times you fail to rise to the occasion. What matters most is the ability to bounce back. It’s one of the most critical skills you can build in life.

I’ve learned this time and time again in my career. You can’t expect perfect conditions each step of the way. Things are going to break, you’re going to run into ignorant people, and there will be times that you face an onslaught of obstacles with no end in sight. What matters is that you find a way to come back with a fresh perspective each day, ready to try again. 

The best teams I know embrace imperfections beyond their control and contribute something meaningful anyway. The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

2) Experiences can still surprise you

I’ve been fortunate enough to have traveled to dozens of beautiful places across the world. I believe the more you travel, the more perspective you build – an invaluable gift in life. But the catch is that the more you travel, the more you seem to lose the novelty of first-time experiences. 

I will never have the same feeling that I did the first time I went dogsledding in the arctic circle, kayaking in the Milford Sound, or camping in the Vietnamese jungle inside Hang En cave.

But this year, I went to South Africa and was surprised to discover that elusive feeling in the raw experience of a safari and in the bliss of the beautiful countryside of Babylonstoren, one of the oldest Cape Dutch farms. If you keep an open mind and maintain an appreciation for life in all its forms, experiences will never cease to amaze you.

3) Convenience is worth paying for

Five years ago, “frugal” would have been one of the best adjectives to describe me. Over the past few years I’ve let that go in favor of convenience. And this comes from learning to value my time properly. 

My routine for years has been to write at a coffee shop on Saturday afternoons. But I would always cut that short to head across town to pick up groceries, an absolute nightmare on weekends. This year, instead of interrupting myself during this time, I’ve started using a grocery delivery service. 

On average, I save two hours of uninterrupted focus time. And it only costs me five extra dollars. At a certain point, you have to learn that time is the most valuable thing you have. 

4) Reversibility matters more than certainty in your decisions 

Time is far more valuable than a marginally better solution. To help make faster decisions, I’ve started asking myself, “How reversible is this decision?” If it’s easily reversible, I make it right there. Assessing decisions based on reversibility, rather than certainty of the potential outcome, has improved my decision making significantly. 

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to picking a restaurant for dinner or testing a new layout for the landing page of your website. 

5) Success doesn’t come from preventing things from falling through the cracks

This is about building a systems mentality. In other words, developing the ability to step back and consider the interconnected whole – the structures, patterns, and cycles – instead of being blinded by a single event or moment in time. This frees you to focus your limited time and energy on what matters most. Success doesn’t come from being better at preventing things from falling through the cracks. It comes from knowing what to let fall through. 

You can identify those who have failed to build a systems mentality by how overwhelmed they get by minutiae – especially when the stakes are at their highest. They become fixated on insignificant things, gripping for control in their foolish quest for perfection. They’re unable to let the little things go.

6) Four things separate you from the top of your field

When I started my career in product, those above me seemed almost lightyears ahead in terms of their intelligence and abilities. I wouldn’t put myself anywhere close to the same category. But the more interactions I have with executives and senior leaders, the more I’m convinced that they aren’t infinitely smarter. The real difference is in their risk-taking, network, growth mindset, and a healthy dose of luck. It’s a good reminder that you’re not that far off. 

7) Don’t get pulled into races that you’re not willing to run

If I don’t create room for reflection, I often find myself getting pulled into other people’s aspirations and playing stupid games for stupid prizes – struggling to position myself on the corporate ladder, equating meetings with productivity, or seeking validation through arbitrary certifications and recognition. 

This is one of the most difficult skills to develop, sorting through the noise and determining what’s your own. As a human being, you are highly impressionable. This is great when it comes to social cohesion, but terrible when it comes to realizing your own aspirations. It’s okay if you don’t want the same things as everyone else. Just make sure you aren’t getting pulled into races that you’re not willing to run.

8) People are amazingly consistent in their behaviors

Another way of saying this is that everyone gets what’s coming to them – for better or worse. It’s just a matter of time. Habits and behaviors projected over the course of years dictate future conditions and outcomes. The trouble is that when you’re young and could use this advice the most, your perspective of time is too shallow to really grasp the lesson.

I see examples of talented, hardworking people catching breaks every month. I also see examples of grown adults clinging to the same identity they had in college who are paying dearly for short-sighted decisions in their careers, health, and relationships.

Use this as motivation to focus on getting the conditions right, developing better habits, and playing the long game. With this mindset, it’s just a matter of time before you start catching breaks. 

9) Compound interest from reading is no joke

After five years of reading 50+ nonfiction books each year, it’s only within the past few months that I’ve felt like I’ve been able to make seamless connections and pull relevant stories on demand. Once you form these connections, you propel yourself forward with a wealth of vicarious experience. 

This is critical to so many areas of life – mastering a multidisciplinary approach, identifying your guiding principles, outthinking misguided people. Without reading, you have to learn this all from direct experience. But books provide you with lifetimes of experience and perspective that you can call upon at will. 

10) Stories > instructions

Stop telling people what to do. Unless you’re running a laboratory, people don’t give a shit about instructions. Stories are the best way to communicate. If you let people interpret things for themselves, you get better results. Especially in fields that demand creative thinking. 

Of course, there are obvious exceptions and integrity matters. But you see the power of this in presentations. Speakers who use stories are able to capture the imagination of their audience. That’s what resonates with people. The same thing goes for brainstorming, design sprints, whiteboarding, and every meeting you have.

Everyone craves stories because that’s how we make sense of the world and piece together our own ideas.

11) Improv makes you a better human

I signed up for improv classes to help improve my public speaking skills. I wasn’t sure what to expect but I wanted to take a non-traditional approach. Fortunately, this has been one of the most profound experiences of my entire year. There are so many positive takeaways and important lessons that I’m planning to write a full article on the experience. 

The short version is that improv will get you out of your own head, train you to be a better listener, and wreck your comfort zone. 

If you aren’t listening with every ounce of your being, you will fail. You can’t fall back on normal cognitive patterns and predictions that you use in everyday conversations. And the constant discomfort during class forces you to embrace and accept the fact that you’re going to look like a dumbass on stage. There’s no way around it. It’s an empowering realization. I’ve since given up my attempts at perfection during presentations, which has helped me relax and improve my delivery.

12) Routine is essential to creativity

The more automatic my habits and routine become, the more energy I can pour into being creative. Ever since I carved out dedicated time and space for writing, my craft has improved significantly. Most mornings I start writing at 6:30 AM. Since I’ve built this habit over years, when I sit down at my desk in the morning I’m able to shift into a creative mindset without a colossal effort.

I often think of this quote from Gustav Flaubert, “Be regular and orderly in your life, so that you may be violent and original in your work.” With that being said, there is a golden mean. I have to challenge this routine on occasion to make sure it’s still working for me and I’m not becoming too rigid in my approach.

13) Drawdown periods matter

I’m excited to release my first e-book next month. But it was no small undertaking. It required five months of sustained effort. Before jumping off I had to make room for a drawdown period where I was able to prepare, rest, and reflect before starting. I knew I would need every ounce of energy I had if I wanted to get my thinking clean and bring the best version of the idea to life. 

This drawdown period was essential in helping me create a buffer where I was able to piece together and discover my own thoughts on the subject. It was an escape from being bombarded by influences and outside noise. The bigger the project, the more important it has been for me to settle my mind leading up to it. 

14) Time your vacations to avoid burnout

Over the past few years, I’ve kept track of when I start to feel like I'm burning out in a given year. And I've noticed it always occurs around the same time. So this year, I planned vacations and weekend getaways to avoid falling into the same pattern – February, May, July, August, and November.

As ridiculous as it sounds, one of my New Year’s resolutions was to take five vacations. It was a way to self enforce breaks when I would otherwise attempt to be a hero and power through things. This has made a huge difference in my wellbeing, the quality of my work, and overcoming the burnout I’ve faced in recent years. 

15) Purpose starts with meaning

Over the past year, I’ve had conversations with many people struggling with purpose. I love being able to share these deep conversations and I sympathize. That was the first ten years of my adult life – forever tiptoeing on the edge of an existential crisis. Some days I still wonder what the hell I’m doing. Purpose is such an overwhelming thing. 

But what I’ve learned, and what I try to share in these conversations, is that purpose is just the series of pieces you find meaning in. Look for where you find meaning in your day to day. By doing more of those things, you move purpose within reach. And if the quest for purpose ever becomes too much, settle for doing meaningful things instead.