Creativity

Indecision in Product: How to Avoid Becoming a Bottleneck

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

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

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

A Case Study in What Not to Do

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

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

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

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

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

Be Wrong as Fast as You Can

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

For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.
— Scott Belsky

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

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

How Reversible Is This Decision?

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

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

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

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

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

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

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

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

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

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

*This article was originally featured on Mind the Product

Why Your First Bet Is Always Wrong

Why Your First Bet Is Always Wrong

Far too often we fixate on optimizing the first idea we come across. We become emotionally attached to a single design, storyline, or hypothesis. The end result is a slow crawl towards incremental improvement. Our work becomes a shell of how good it could be if it were allowed to evolve.

9 Tactics to Help You Create More, Consume Less

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

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

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

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

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

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

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

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

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

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

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

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

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

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

3) Pair positive reinforcements

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

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

4) Allow yourself to get stuck

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

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

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

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

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

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

5) Create a distraction-free phone

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

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

  2. Delete email accounts from your phone

  3. Delete/disable the web browser on your phone

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

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

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

6) Keep a journal instead

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

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

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

7) Use art as inspiration

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

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

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

8) Start small

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

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

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

9) Find a medium that resonates with you

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

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

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

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

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

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

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


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

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

The Philosophy of Remarkable Minds

Each of us has the capacity to face difficult work. In many ways, this defines life. The struggle to create something of our own is where we find meaning.

Our modern era of comfort and convenience can be a double-edged sword. It’s allowed us to eliminate the daily struggle for survival and afforded us the privilege of having this discussion. But when taken to an extreme, it leads to a deep anxiety and restlessness. Emptiness can be a fiercer foe than hardship.

Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary.
— Sebastian Junger

It’s easy to sit by as a passive consumer and allow someone else to assume the risk. On a surface level, it might even appear that you’re reaping all the benefits. But if you fail to establish a creative outlet where you can build something of your own, you sacrifice your primary source of meaning along with it.

It’s through the work you put out into the world and the way you live that you instill your life with a sense of meaning. By creating more and consuming less you claim a larger part of yourself.

Those who have lived remarkable lives hold this philosophy in constant focus.

Into the Venezuelan Jungle

When Alexander von Humboldt was born in 1769 to a family of wealthy Prussian aristocrats, by all standards of the day, he had it made. His father was an army officer and advisor to King Friedrich Wilhelm II, and his mother was the daughter of a rich manufacturer. If he wanted a comfortable existence, all he had to do was sit back and stay the course.

But despite these advantages, he was anxious and unhappy for most of his early years. His adventurous spirit was never satisfied by the confines of a classroom or the promise of a lucrative career as a civil servant. His dream was to explore the natural world.

As a child, Humboldt was fascinated with the journals of Captain James Cook and his accounts of distant countries and cultures. Humboldt wandered the Berlin countryside to recreate adventures of his own, stuffing his pockets full of plants, rocks, and insects, earning the nickname ‘the little apothecary.’

But after his father died at the age of nine, his financial dependence on his emotionally distant mother allowed her to dictate much of the early, unfulfilling course of his life. Despite his objections, she demanded that he work his way up the ranks of the Prussian administration.

Humboldt found creative ways to channel his deep interest in science, geology, and languages at different universities and academies along the way. He poured over the work of various artists, botanists, explorers, and thinkers. And while each provided inspiration, it was not enough to fill the void he faced for the first twenty-seven years of his life.

Humboldt was torn between the expectations of his family and his insatiable desire to set sail, experience the world firsthand, and contribute something of his own to the scientific community. He lacked an outlet to discover and create in a way that resonated with him. Without this, an emptiness continued to build.

It was only after his mother’s death in 1796 that he felt in control of his own destiny. Longing to escape his tiny corner of the world, he began planning a voyage to South America.

At age thirty, Humboldt set off on the expedition which altered the course of his life. He would explore treacherous landscapes that no scientist had set foot in before. The driving force was his desire to piecing together a more cohesive understanding of the natural world. Most scientists of his day were focused on isolated disciplines. Humboldt was interested in bridging the divide and the interconnected whole.

After arriving in Venezuela, Humboldt trekked for two months across the tropical grasslands of Los Llanos, facing temperatures near 120 degrees Fahrenheit. He followed this with seventy-five days of grueling river travel down the Orinoco, covering 1400 miles to reach the Casiquiare canal–a natural tributary between the Orinoco and Amazon rivers. Along the way, he faced torrential rains, incessant mosquitos, the occasional jaguar, and bouts with fevers and dysentery.

This would seem disheartening to most, but Humboldt came alive with boundless energy and enthusiasm during these explorations. No matter the conditions, he insisted on measuring the height of mountains, determining longitude and latitude, taking temperatures of the air and water, making astronomical observations, collecting new species of plants, and documenting it all with detailed notes. Each new environment brought him closer to understanding how the natural world fit together.

The pinnacle of his experience in South America came during a 2,500-mile journey from Cartagena to Lima to explore the Andean Mountains. During this trip, he attempted to summit Chimborazo, an inactive volcano standing at 21,000 feet.

At 15,600 feet, the porters refused to go on. But Humboldt continued his ascent, fighting through freezing conditions, deep fields of snow, and altitude sickness. Without fail, every few hundred feet he stopped and fumbled with freezing hands to set up his instruments to measure temperature, humidity, altitude, and boiling points. He reached 19,286 feet–a world record at the time–before he was forced to turn around due to impassable conditions.

This experience inspired Humboldt to sketch ‘Naturgemälde,’ a depiction of Chimborazo’s cross sections with the distribution of vegetation, temperature, humidity, and atmospheric pressure according to altitude. Humboldt showed for the first time that nature was a global force with corresponding climate zones across continents. And he presented it in an unprecedented infographic style, allowing those without a scientific background to understand the concept.

Naturgemälde – Alexander von Humboldt’s first depiction of nature as an interconnected whole

Naturgemälde – Alexander von Humboldt’s first depiction of nature as an interconnected whole

Upon his return to Europe, Humboldt’s exploration of South America inspired him to write thousands of letters, essays, publications, and lectures. By making connections and framing nature as a unified whole, his work revolutionized the way we view the natural world. As an interesting aside, he was also the first to observe and describe human-induced climate change.

Humboldt inspired generations of scientists and writers including Charles Darwin, Henry David Thoreau, and John Muir. But his greatest contribution was making science more accessible and exciting to a broader audience.

In Berlin, his series of free lectures packed music and university halls with royal family, students, servants, women, and children. He took his audience on a journey that ignited their imagination–combining exact observation with painterly descriptions. He brought distant landscapes to life through poetry, geology, and astronomy, bridging the divide between art and science.

Humboldt continued exploration into his sixties with a 10,000 mile, six-month journey through Russia. He was invigorated by each expedition, showing the same youthful energy and endurance that he had thirty years earlier. He shared his learnings in publications and letters up until his final moments when he died in 1859 at the age of eighty-nine.

The Struggle to Create

Humboldt could have settled into his early existence, lived a comfortable life, and allowed others to assume the risk in their own research and exploration. But this shallow life wasn’t enough for him. Instead, he set out with an insatiable curiosity to better understand the natural world and contribute what he learned along the way.

His adventures were his outlet for creativity, discovery, and meaning. There’s nothing easy about a 2,500-mile trek through the Andes. But the struggle to study and create something that resonated with him at a deeper level brought him to life. Without this, he would have never found his own sense of authenticity and fulfillment.

Creativity is about finding something worth struggling for.

We live in a unique time. Most of us, like Humboldt, could coast through life without facing any significant hardship if we so chose. That’s a wonderful thing. But it collapses into its opposite when we allow our entire lives to be dictated by comfort and immediate gratification. We must not forget the importance of meaning, which is found through the struggle to create something of our own.

Spending the evening watching four episodes of your favorite show on Netflix or scrolling through Instagram might be the path of least resistance, but it’s mostly empty. There’s little opportunity to create meaning of your own. More often than not it’s a distraction that pulls you away from the things that actually matter.

Your unique identifiers are the work you put out into the world and the way you live your life. These are what add depth to your voice. Not the things you consume–fashion, film, food, music, research, sports, technology.

This is not to say that you shouldn’t appreciate other people’s original work. But you should use it as inspiration. It should serve as a catalyst for you to create more and find alignment in your own sense of authenticity. It’s the height of selfishness to expect other people to create meaningful work for your personal benefit without contributing anything of your own.

Creating begins with making yourself an essential part of the process. Not standing by as a passive consumer and allowing someone else to take the risk.

But don’t let anyone fool you, creating is challenging, uncomfortable, and a slow grind. There’s no way around it. That’s why most people fail to sustain the habit. You have to trust your capacity to suffer. But it’s where all the upside is found.

Endurance, Imagination, and Depth

When you prioritize creating something of your own, you give yourself more opportunities for peak experiences and claim a larger part of yourself–just as Humboldt did at the age of twenty-seven when he shifted the course of his life. This is infinitely more satisfying than the temporary highs of a consumer.

By creating more and consuming less, you add an unusual depth to your voice that draws people in. Your creative outlet is where you are able to channel the questions and struggles you’ve faced into something that offers profound insight. And that’s what life is all about.

Whether you forgo a life of privilege to trek through the Venezuelan jungle or you set aside Instagram so you can focus on your art, science, startup, or relationship with the person right in front of you, what matters is that you provide yourself an opportunity to create.

Those who make a measurable difference in the world are inspired to contribute something of their own. Instead of taking the easy route–opting for comfort and immediate gratification–they push themselves further into the unknown.

Human nature has given us remarkable endurance to face difficult work and the imagination to build something from nothing. It’s through this struggle to create that we instill our lives with a sense of meaning.

To find your sense of authenticity and fulfillment, you must fight to create more.

 

*If you want to learn more about Alexander von Humboldt, check out The Invention of Nature: Alexander von Humboldt’s New World by Andrea Wulf. It’s a tremendous read and the source of many details in this article.

Quit Killing Your Team

Most people recognize the importance of hiring. Building something from nothing requires a core team of smart creatives with a deep well of curiosity. These are the innovators who are able to connect ideas between multiple disciplines and offer new ways of looking at the world.

But what’s valued in the hiring process–freethinking, curiosity, creativity–is often forgotten in the day-to-day. And it’s your job to preserve this, for both yourself and your team.

If you want to drive results, you need a better strategy than tightening your grip.

Not everything needs to be about efficiency, productivity, and deliverables. Breathing room helps nurture creativity and curiosity. Those who fail to grasp this nuance end up stuck in a one-track managerial mindset, unable to effectively lead.

Progress comes from having the autonomy to stray into the expanse of your mind and connect ideas in new and interesting ways. Focus on getting the conditions right so everyone has the opportunity to create these connections and find fulfillment in their work.

Without this, you’ll face a barrage of apathy, burnout, and unrealized potential. And once you lose engagement, meaningful progress becomes impossible or short lived.

This is not to say that you shouldn’t set deadlines or establish goals. You need this, too. But if you want to sustain engagement and encourage innovation, allow the people you invested the time to hire to do what set them apart in the first place. Let curiosity and creativity lead the way. This puts your team in a far better position to create something worthwhile.

Leaders fight for a balance between deadlines and exploration.

Designers need freedom to explore creative directions.
Developers need freedom to explore new technologies.
Product managers need freedom to explore different visions.

There’s a sense of artistic expression to each. Creating this space helps build morale by pushing each person to find a deeper sense of satisfaction and meaning in their daily work. It also lays the groundwork for innovation by encouraging people to bridge disciplines, offer new ideas, and test different angles.

This mindset is foundational to every high-performing, rewarding team that I’ve been on. Most recently at Asurion, during a recent year-long effort to drive messaging volume, my team reached a place where we were slowing down and struggling to sustain engagement. To rebuild momentum, we created space to explore how we might leverage a few of our ideas in the smart home–a new space we were all interested in.

We balanced this with our primary initiative, as it wasn’t immediately evident how it would fit in or what was technically feasible. But a few weeks later, we finished building out an Alexa skill which allowed customers to speak with our messaging experts asynchronously via text to speech.

We were able to create something entirely new with the capacity to change how our customers interacted with us. But even if we failed and came out with nothing to show for it, the change of pace held value of its own. It allowed us to reenergize and refocus.

What mattered most was that we gave ourselves space to explore.

There won't always be a one-to-one translation between what you’re exploring and the objective you’re working towards. Sometimes pursuing an idea out of a sense of wonder, is reason enough.

Engaging your curiosity and creativity will help expand your perspective and build momentum. Allow yourself to be distracted from time to time and follow the random ideas that strike your interest, regardless of where they lead.

The most brilliant minds throughout history infused their work with a wandering sense of curiosity.

Leonardo da Vinci embodied this better than anyone else. His entire life followed a series of digressions from his career as an artist.

Leonardo allowed himself to be distracted and seek knowledge for its own sake. This led him to study human anatomy, conduct dozens of dissections, create schemes to divert rivers, choreograph pageants, investigate the flight of birds, and create diagrams of technical innovations such as human flight machines.

Some consider this to be a lack of discipline, which only served to pull him away from more important work. But when you study his life in its entirety, you begin to see how these detours helped shape and inform his art. His obsession with human anatomy, for instance, helped him breathe life into the finest details of his paintings, as he worked from the inside out.

As for the more fantastical detours, such as schematics for flying machines or giant crossbows, I doubt Leonardo would consider this wasted time. It was a channel for his relentless curiosity and creativity–the very things that made him who he was, and a source of pure fulfillment.

Creativity and curiosity are the building blocks of engagement.

Everyone needs space to wander, much like Leonardo, and explore new technology, ideas, and interests. Otherwise, you’ll miss the opportunity to piece together your own insights.

Do you want a team of lemmings going through the motions? Or would you rather have a team that’s imaginative, engaged, and curious?

That’s the difference between driving your team into the ground with a relentless focus on productivity and allowing them breathing room to channel their own creativity.

Your first responsibility is to the people immediately surrounding you–not the product, goals, or traditional measures of productivity. You’ll achieve more in the long run when you have morale, engagement, and innovation on your side.

Authenticity Is Your Now

Authenticity is not a fixed point on a map. It’s fluid, much like your identity, and shifts over the course of your life.

It’s easier to trick yourself into believing the feel-good advice that your voice comes from a sudden revelation. You just have to wait for that moment. And once you’ve found it, the entire picture comes into focus and remains that way for life.

But authenticity is found through fragments. It evolves over time. It’s a moving target that falls out of focus and can be lost to the chaos of life.

Authenticity is less about identifying a singular purpose and voice that should define your entire life. It’s about finding and trusting your voice today. In other words, embracing the impermanence of your identity, knowing that it can and will change.

How you live your life–your interests, principles, and priorities–will evolve over time. As you grow, you’ll add depth to your voice. If you remain the same for too long, that’s when you know you’ve stopped learning or are clinging to an expired version of yourself.

It’s easy to get caught up in the expectations you hold for yourself or that others project upon you– who you should be, where you have been. If you fuel these doubts, you can opt out of the unknown and find comfort in your plateau. But you won’t grow through the familiar, and you won’t find alignment.

Your sense of authenticity–your now–is something that’s all your own. It’s discovered, developed, and deepened, by the obstacles you face, the uncertainties you navigate, and the inspiration you find along the way.

If you want to create something that matters–to both yourself and others–you have to create from where you currently are in your life. That’s how you build momentum and depth. Trust yourself.

It’s the difference between artists and entrepreneurs who get lucky once and those who sustain success over decades. If you cling to what got you there in the first place, you’ll fail to evolve and render yourself irrelevant.

Artists who reinvent themselves fight for projects that allow them to grow, stretch their abilities, and discover new things. In doing so, they create from a place that resonates with them at a single point in time.

Over the course of years, a series of single brush strokes reveals an evolving sense of authenticity.

Bob Dylan, one of history’s great songwriters, has reinvented himself time and time again throughout his career. He’s altered his voice and bridged various genres, beginning in folk, shifting towards rock, and experimenting with country and Christian albums along the way.

Five decades later we can step back and admire his trajectory–how he’s pushed himself to grow, defy expectations, and channel that into his art. Time makes this seem inevitable, as if all he had to do was fall in line with destiny. But that fails to take into account the years of criticism, outrage, and uncertainty Dylan faced.

Authenticity–creating from who you are today, despite expectations tearing you in different directions–is not for the faint of heart.

Dylan threw the folk community into a fit of rage when he “went electric.” He could have stuck with what was working and fallen in line with their expectations, but validation was never his primary motivation. He sought meaning over influence at each step of his career. As a result, he achieved exactly that–lifelong influence.

Dylan resonates with people because his songwriting tracks his own development as a human being. His songs reflect who he was–his observations, experiences, and imagination–and who he refused to be at each point in time. Dylan’s career is a master class in embracing the impermanence of identity and authenticity. The fragments of himself that he brought to life shows he understands this in a deep way.

There were a lot of better singers and better musicians around these places but there wasn’t anybody close in nature to what I was doing. Folk songs were the way I explored the universe...
— Bob Dylan

There’s no single template for finding your voice as it exists today. It’s different for each person. Legendary director, Steven Spielberg, was quite different from Dylan. Dylan had unusual depth which he developed at an early age. Spielberg developed his own sense of depth over decades.

Spielberg’s progression from Jaws (1975) to Schindler’s List (1993) demonstrates this. In those eighteen years, he grew by finding projects that spoke to him at a specific point in time. What felt authentic to him in 1965 was entirely different than 1993. That doesn’t negate his early work, he was just creating from a different place.

Spielberg’s voice evolved through his films, just as Dylan’s did through his albums. That’s why they’ve remained relevant for so many years. They’ve changed, adapted, and grown. But most importantly, both have had the courage to speak from where they were in each present moment.

Both faced criticism along the way for unpopular decisions, but that’s the irony of the whole thing. People are enraged by change, but if you stay the same you guarantee failure. You lose touch with yourself, a sense of fulfillment in your work, and a deeper connection to your audience.

Before you release your work into the wild, fight like hell to make sure it first resonates with you.

No one gets it right each time. There will be times you lose your sense of authenticity. Not even Dylan and Spielberg are immune to the chaos of life. But when the intention and awareness are there, it’s easier to rebuild and rediscover a sense of momentum.

Life is motion. Authenticity is about finding harmony in that motion.

It’s not always easy, but it’s meaningful. Allow yourself to evolve through uncertainty. When you find the courage to speak from this place, you add unusual depth and clarity to your voice. That’s what draws people in.

Start by reflecting on what resonates with you at this point in your life–experiences, interests, observations, values. Authenticity is your now. No matter where you are, trust yourself to create from who you are today.

The Four Elements of Becoming a Better Writer

There's nothing that writers love more than reading about writing (although, reading about reading comes in at a close second). Everyone's looking for a universal secret that sets apart the best writers or makes the writing process easier. Unfortunately, that secret doesn't exist.

The only consistency I have found across all great writers is that they show up. They define themselves by an insatiable desire to write–it's a core part of their routine and they put in the work every single day. 

While you might not self-identify as a "writer," that's okay. Journaling for reflection, working on your communication skills, and piecing together a 300-page novel are each valid objectives. But if you want to improve your writing–the foundational skill to each of these–you have to consistently show up, work at it, and make it part of your routine.

Over the past year, quite a few people have reached out asking for details on my own writing process. While I consider my writing skills to be a work in progress, this is my attempt to detail what my current system looks like. I don't pretend to have all the answers, but my hope is to provide you with a few tactics that you might leverage on your own.

Takeaways:

  1. Reading, writing and learning fuel each other. Channel your intellectual curiosity and you'll never face a shortage of ideas.

  2. Timing is important but it's not everything. Determine what's sustainable for you and stick with that.

  3. Writing is about momentum and a relaxed state of concentration. Don't interrupt this unnecessarily.

  4. Editing demands grit. It's here where the great writers set themselves apart.


How do you come up with ideas?

Reading, writing, and learning fuel each other. Anytime I've struggled to come up with new ideas, it's almost always because I'm not reading enough or challenging myself to learn anything new. If you channel your intellectual curiosity, this problem takes care of itself. 

Read, listen to podcasts, make sure you're learning something new in every environment you're in. This is how you begin building a network of mental models which allows you to uncover new ideas and connect concepts in interesting ways.

When you commit time to pursue knowledge and exercise your own curiosity–in whatever form that takes–you'll never face a shortage of new material and ideas to choose from. 

I keep a running list of all my ideas, potential topics, and relevant thoughts in Notes (iOS) and Ulysses. This way I don't lose track of anything that comes to me throughout the day. 

When do you write?

Timing is important, but it's not everything. It can either be an excuse to avoid putting in the work, or it can be turned to your advantage. While many great writers have tended to write early in the morning, you shouldn't obsess over replicating their routines. Find what works and is sustainable, for you. The most important thing is getting started.

Once you're in the habit of writing, if you want to fine-tune your process, consider your internal clock. Writing is an intensive, creative process that demands significant focus. If at all possible, pick a time of the day when you're at your peak level of concentration. Otherwise, it will be tough to sustain.

I'm a morning person–my most productive hours are between 6:30 and 10:30 AM. Each morning I wake up at 6:00 AM and write for at least a couple hours before heading into work. I guard this time seven days a week, as it's the most important part of the day for me. Weekends are slightly different, with a few hours of writing in the morning, and a second shorter session at a coffee shop in the afternoon. 

This will inevitably change over time as your position in life changes. Five years ago, I was the exact opposite and only wrote at night. Allow yourself to adapt, but make sure you don't lose the habit.

What does your writing process look like?

Sometimes I begin writing an article because I have a general idea of what I want to say. Other times, I'm trying to figure something out for myself. Either way, for me, writing is about momentum.

When I sit down to work through a new idea, I'm not writing for structure or format. I'm not writing to assemble a cohesive argument. And I'm not writing from an outline. I'm writing to get every relevant thought I have on that topic down on paper. For a single article, this can take anywhere from an hour to a few days.

The motivation during this initial phase is to get to a place where I'm not thinking about the act of writing. If I start thinking too much about what I'm doing, I can't achieve a state of relaxed concentration where I am at my most creative and coming up with my best work.

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

Other than my initial approach, I've found a couple of tactics that help facilitate this momentum, flow, relaxed concentration–whatever you want to call it. 

The first is that I'll listen to the same song for hours on end to help induce a deeper state of creativity. I've found that listening to one song on repeat often helps jumpstart things and push me towards the proper state of mind. I'm not the first one to discover this, it seems quite popular among writers and software developers.

The second tactic I use is to help steal some sense of momentum when things have stalled. To overcome inevitable lulls, I'll double back and rewrite the previous sentence or two. It's a mental thing where I feel like I can carry that energy through better if I'm able to create some type of forward motion.

Think of it as riding your bike up a hill. If you mount your bike in the middle of a hill, it can be difficult to make your way to the top based on the immediate level of resistance. Whereas if you start at the bottom (less resistance) and build some momentum going into the climb, you'll be able to better carry that through to the top. It's amazing how often this gets me back on track heading into a new section. 


How do you edit/refine your articles?

This is where the attention to detail comes into play. My rough drafts are very rough drafts. As a result, I spend a significant amount of time editing, rewriting, and refining.

After I have all my thoughts down, I go back through the material to identify common themes and distill the most important ideas. Certain insights may (or may not) appear, and I'll draw from those as I begin to organize the article. 

I'm never finished writing at this point. Often, there's quite a bit of work to be done. After I've arranged the article and developed some sense of structure, I'll go back and immerse myself in certain sections so I'm able to simplify ideas. Again, if I get stuck I'll use the tactics mentioned above to capture the same sense of flow I had during the initial writing process. 

This part of the creative process often feels similar to a puzzle. You're piecing together fragments and determining how they best fit together. And it's in the process of uncovering and assembling those fragments that you find yourself and your best ideas in.

From the outside, writing appears romantic. You just pour your ideas onto a page then call it a day. But those who live it know the grit it entails. The editing process demands the greatest persistence of all. And it's never something you can rush through.

Grit entails working strenuously toward challenges, maintaining effort and interest over years despite failure, adversity, and plateaus in progress. The gritty individual approaches achievement as a marathon, his or her advantage is stamina. Whereas disappointment or boredom signals to others that it is time to change trajectory and cut losses, the gritty individual stays the course.
— Angela Duckworth

No one is above this final piece of the writing process–not even the greats. Ernest Hemingway rewrote the ending of A Farewell to Arms 47 times. Harper Lee spent two years working with her editor, Tay Hohoff, reworking the entire plot and cast of characters in what would become To Kill A Mockingbird

It's foolish to expect perfection each time you sit down to write. If you get to the point where you've stared at what you've written for too long and begin to hate it, step away for a few days. Time and distance are often the true tests of quality.

But regardless of your objective, the most important part is sitting down to practice the craft.

Writing is not about some stroke of genius and it’s not pretty. It’s about grit, showing up, writing, editing, rewriting, and refining.

The Secret to Developing Thick Skin

If there’s a defining feature that sets apart smart creatives who are able to sustain themselves at a high level of performance, it’s thick skin. They’re persistent in their work and resilient to outside opinion and rejection. They’re able to put themselves out there, time and time again, and deliver. And while this might appear to be a natural talent, it’s far from it. It’s a skill that takes years to develop, and it begins with renegotiating expectations.

Many talented people struggle with this–entrepreneurs, artists, athletes, writers. While they might be brilliant in their work, when it comes to putting themselves out there, they end up demoralized or enraged by the slightest hint of criticism.

This becomes a downward spiral that throws off the entire creative process. Even if you are able to correct course, it’s an unnecessary distraction that disrupts your focus and pulls you away from more meaningful work.

Internal vs. External Expectations

To offset this and develop the thick skin required to put yourself out there, you must first differentiate between internal and external expectations, assigning each their proper weight. Internal expectations–the expectations you hold for yourself and your creative process–should always take precedence.

How your work is interpreted, received, or recognized, is beyond your immediate influence. It’s not that this is completely irrelevant, but it should matter far less because it’s an unreliable metric against which to measure yourself. The greater the importance you assign to external expectations, the more dependencies you introduce, and the higher the likelihood that you’ll end up pissed off, burned out, or distracted from the work that matters most.

Self-sufficiency is the path towards effectively managing expectations. In the opposite direction are dependencies–evidence of placing a premium on things you can’t affect.

When you prioritize the internal expectations you hold for yourself, you naturally develop the thick skin required to put yourself out there and consistently produce at a high level. Instead of seeking value in the recognition, you begin seeking value in the creative process itself. And this is the only sustainable path forward.

The tranquility that comes when you stop caring what they say. Or think, or do. Only what you do.
— Marcus Aurelius

Turn your attention back to what’s within your control. Put in the work. Focus on your craft. Create something that resonates with you. When you limit the external dependencies and surrounding noise, the more relaxed, concentrated, and effective you will be.

Feedback vs. Criticism

This is not to say that you shouldn’t seek feedback–which is critical to further developing and growing your skills. But feedback is to criticism as internal expectations are to external expectations.

In other words, the source is fundamentally different. Feedback comes from fellow creatives with skin in the game–the doers–who are taking risks by putting themselves and their work out there. These are the people whose opinions and judgment you should respect most. Criticism comes from insecure bystanders, shouting from a distance, who are incapable of creating anything meaningful of their own.

The intention behind feedback is also different. Criticism is often shallow and malicious in nature–focused on breaking you down. True feedback, from an inner circle whom you respect, is diligent, constructive, and objective. Its purpose is to challenge you to improve yourself and your craft.

In short, it’s about growth–which is a painstaking process in its own right–not about praise, telling you what you want to hear, or making things easier. It’s up to you to draw the line and determine who has your best interest in mind.


Create Your Own Momentum

When the inevitable criticism does come, use it as motivation and redirect that energy to create momentum of your own. With the right perspective, it becomes almost laughable.

Consider how much time and energy it took that person to criticize you–it consumed them. Nothing is a more sad, ineffective use of time–so let the childish tantrums end there. Refuse to allow yourself to be distracted by those without skin in the game. Their opinion holds no validity.

An opportunist in life sees all hindrances as instruments for power. The reason is simple: negative energy that comes at you in some form is energy that can be turned around–to defeat an opponent and lift you up.
— Robert Greene

For most talented, hardworking people, it’s just a matter of time. Which means you need to find the energy to keep going–to continue creating. The more dialed into yourself that you are, the less outside opinion should matter, and the more resilient you’ll be in your creative process. If you rely on external validation to keep you going, you’re going to have a short career.

A meaningful, fulfilling creative life demands hard work and tough decisions. Those who aren’t cut out for it will lean towards the path of least resistance, as defined by mindless consumption or shallow criticism. It’s easy to live that life.

If easy is what you want out of life, feel free to join the ranks of the unremarkable.

But those who make a difference show up, bust their ass, and sustain themselves at that level by having their expectations in order. They’re able to differentiate between internal and external expectations, valuing self-sufficiency over dependencies and feedback over criticism.

If you take the time to develop these skills–resilience, persistence, and mental toughness–outside opinion will lose its grip and you’ll be able to better carry your own momentum forward.