Creativity

The Art of Drawdown Periods

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

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

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

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

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

Is your idea worth pursuing?

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

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

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

Tapering before the race

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

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

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

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

The value of tuning out

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

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

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

“If you’re constantly exposed to other people’s ideas, it can be tough to think up your own.”
— Jake Knapp + John Zeratsky

Deliberate or impulsive?

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

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

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

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

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

Inverting the Distraction of Social Media

There are plenty of articles out there that rail against social media. The trouble is not that they’re inaccurate–most hold valid points. It’s that they’re often a laundry list of complaints without any real takeaways, other than “social media sucks” or “regulate Facebook.” At best, you get a call for moderation. 

A more effective approach is to invert the problem. How does the ever-present distraction that is social media present an advantage for you?

Most people aren’t going to dedicate their time to reading, writing, creating, training, or reflecting. Each of these are difficult things to do. It’s much easier to turn to Snapchat or Instagram as a crutch to waste away the hours. 

If you train yourself to do the difficult work that others avoid and ignore the distractions that others can’t resist, you put yourself years ahead. 

But this requires mental toughness and an ability to suffer. Most people panic at the first sign of discomfort. You’re sacrificing immediate for delayed gratification. If you’re able to master this impulse and embrace discomfort, you provide yourself more opportunities for growth. 

We distinguished the excellent man from the common man by saying that the former is one who makes great demands on himself, and the latter the one who makes no demands on himself…
— José Ortega y Gasset

In the age of distraction, there’s no greater differentiator than establishing yourself as a stalwart of focus and creativity. 

This comes from allowing yourself to sit with something, even if it means getting stuck. Nail Gaiman, author, uses a similar technique when he sits down to write. He gives himself permission to either write or do nothing. But everything else is off the table. Sooner or later, staring off into the distance gets boring and the only alternative is to write. 

In many ways, distractions are a training ground. Social media is just the latest culprit. If you’re able to resist the easy thing within reach and focus instead on the more challenging task, that translates across every aspect of your life. 

Most people think they can wait around for the big moments to turn it on. But if you don’t cultivate ‘turning it on’ as a way of life in the little moments – and there are hundreds of times more little moments than big – then there’s no chance in the big moments.
— Josh Waitzkin

You can either complain about the distraction that is social media or you can use that energy to turn in to your advantage. And it’s a tremendous advantage for those able to ignore the noise and create more

Are you going to sit down and do the work? Or are you going to be a sucker for another quick hit of empty recognition that comes from someone mindlessly scrolling through their feed and tapping on your status? 

Let other people wander towards distraction. Social media should be just another test to hone your focus and practice tuning out the noise. 

The more time you spend creating, the more fulfilled you are going to be. History belongs to those able to overcome the incessant distractions of their time. 

Why the Worst Product Managers Expect the Best

With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.

Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.

It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way. 

The best teams embrace imperfections beyond their control and create great products anyway.

The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.

Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.

Creativity and resilience

At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched. 

There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.

Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience. 

The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits. 

Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life. 

Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you. 

This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.

Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.

Opportunities for reflection

In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t. 

This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.

Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work. 

Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life. 

Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you. 

Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”



*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.

The 5 Best Books to Help You Create More

Perennial Seller – Ryan Holiday

A useful starting place to understand the entire creative journey–from sitting down to create, through positioning, marketing, and building a platform. Holiday pulls dozens of examples from creative minds throughout history to uncover tactics and best practices. But the underlying strategy consistent throughout the book can be summed up as playing the long game. If you want to create something of lasting value, there are no shortcuts or paths to immediate gratification. Dedicate yourself to your creative process and put in the work.

To create something is a daring, beautiful act. The architect, the author, the artist–are all building something where nothing was before.
— Ryan Holiday

Grit – Angela Duckworth

In any creative endeavor, you’ll need both direction and determination–what Duckworth defines as “grit”– if you want to make meaningful progress. The book emphasizes the importance of deliberate practice, purpose, and stamina over intensity. The best thing about Duckworth’s writing is that she makes it real. It’s not about a magical experience that leads you to your passion, purpose, or life’s work. Instead, this comes through a discovery period–often messy, serendipitous, and inefficient–followed by years of refinement, and a lifetime of deepening.

Passion for your work is a little bit discovery, followed by a lot of development, and then a lifetime of deepening.
— Angela Duckworth

Atomic Habits – James Clear

Once you have a sense of direction, you need to build the creative habits to put things into action. The concept behind Atomic Habits is that by stacking tiny habits over time you can achieve compounding, remarkable results. Your creative results, as Clear suggests, are the lagging measure of your habits. He offers great insight into nonlinear growth (breakthrough moments), identity, discipline, and environmental design. The importance of building better systems is hard to overvalue. There’s room for everyone to improve in this capacity, and if nothing else it’s a refreshing reminder: “Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?"

It is only by making the fundamentals in life easier that you can create the mental space needed for free thinking and creativity.
— James Clear

Creativity, Inc. – Ed Catmull

One of the best modern examples of the impact that comes from harnessing creativity and building a culture where the creative process can thrive. Catmull discusses the evolution of Pixar Animation, including the philosophies and strategies that have established them as creative force. Most notably, the team at Pixar embraces the years of ambiguity inherent to the creative process as a story evolves into its own. Instead of becoming attached to a single storyline or character, they seek out a deep truth at the core of the film–the guiding principle–and craft the story around that. Catmull also emphasizes the role of leadership in cultivating creativity. It starts with loosening your grip, accepting risk, trusting your people, and giving them space to do what they do best.

There is a sweet spot between the known and the unknown where originality happens; the key is to be able to linger there without panicking.”
— Ed Catmull

Leonardo da Vinci – Walter Isaacson

Throughout history there have been more profound, practical thinkers than Leonardo. But there’s never been anyone as creative as he was across so many different fields–art, science, engineering, technology, the humanities. If you’re hoping to improve your own creativity, you can do worse than studying the life and work of the person who became history’s archetype of the Renaissance Man. The depth of his curiosity and imagination are something to behold. What makes Leonardo such a powerful influence is that he was relatable and not some distant, untouchable figure. His creative genius was self-made, built from personal experience, experiments, and dedication to his craft.

Be open to mystery. Not everything needs sharp lines.
— Walter Isaacson

And One More…

If five books isn’t enough, check out Mastery by Robert Greene. It’s a comprehensive guide to living a creative life, and one of my favorites. Greene starts with the essentials–discovering your art and immersing yourself in the mindset of an apprentice–and tracks the journey through building creative strategies and, ultimately, mastery.

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.

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.

7 Lessons from Life as a Product Manager

Six years ago, I found my way into product management out of necessity. I was beginning my career at a healthcare technology startup in what was supposed to be a marketing/communications position. But during my third month on the job, I was thrown on-site at a regional hospital to help facilitate a go-live with our software. As it turns out, job titles don’t always predict the scope of your work in startups.

That day, it became obvious that there was a significant gap between key stakeholders, customers, and our development team. It was impossible to prioritize or build the right thing because we weren’t close enough to the end user. As a result, we ended up working exclusively on client requests–perhaps the least effective way to develop a product. We needed someone to step in, close the gap, and work alongside our small team of five developers. Cue my newfound career path.

As companies learn the importance of evolving into product-driven organizations, there are increasingly greater opportunities for those with a specific skill set — see below — to explore product management. Over the past few years, I’ve put together some of the key lessons I’ve learned from leading product at my own startup, as well as from the innovative, hardworking teams that I’ve had the privilege to be a part of.

1. Develop a multidisciplinary approach

Broad exposure to a range of subjects enables you to leverage the most useful knowledge from each and make better decisions. Specialization gets a lot of attention these days, but it doesn’t fly here. Product requires seeing things from multiple angles and being able to quickly navigate a latticework of mental models. On any given day, you need to be able to evaluate the user experience, assess the feasibility from a development perspective, identify and sort relevant data, communicate key experiment results, and determine how a feature aligns with the overall vision.

Developing a multidisciplinary approach should also help to set you apart, as most who work in technology are focused exclusively on concepts and trends native to the industry. The majority will miss the important lessons and models from other fields of study that can be applied more broadly.

But the ultimate reward is that by positioning yourself at the intersection of multiple disciplines, you develop the ability to connect seemingly unrelated ideas in a way that the vast majority are otherwise incapable of discovering. It’s here where true creativity and the most innovative solutions are found.

2. Establish three skills in the top 25%

The best companies look for diversity on their teams in terms of background and experience, as well as hard and soft skills. This range of skills includes analytics, communication, design, development, research, strategy, synthesis, and user empathy, to name a few. Figure out which you’re good at and commit to developing those skills further.

That’s not to say you shouldn’t listen to feedback about where to improve. But you distinguish yourself by becoming very good (top 25%) at two or three skills.

Reaching this level demands years of dedication to your craft and the discipline to continue learning. You’ll only be able to sustain this effort if you allocate more energy to the skills that you’re naturally drawn to and enjoy immersing yourself in for indefinite periods of time.

You make yourself rare by combining two or more ‘pretty goods’ until no one else has your mix.
— Scott Adams

3. Manage product, not people

Any job with “manager” in the title carries an immediate connotation that you’re overseeing people. There’s no worse approach to product or faster way to alienate your team. Your sole focus should be on building the best product and user experience. This means collaboration with your team, not management. And if you’ve developed at least a few skills in the top 25%, you should be a true contributor.

Those who resort to managing people often do so because they lack the willingness or ability to contribute to the experience being built. Make yourself an indispensable part of the process.

4. Help your team answer their own questions

You can’t possibly have the answer to every question, nor should you pretend to. The most intelligent, respected leaders are always aware of the limitations in their knowledge. But you can help your team clearly articulate questions and begin to uncover answers through conversation.

If you’re able to help others think more rationally and find their own answers just by talking it through, you’re naturally going to get more buy-in than you would by telling someone what to do. It’s human instinct to feel more invested in answers and solutions you’ve helped come up with.

When everyone on your team is engaged, contributing, and learning from one another, the quality of work improves significantly. This skill demands exceptional listening and learning how to ask better questions. If you do it right, you will be able to promote transparency, self-awareness, and better orchestrate the perpetual moving pieces.

5. Consider second and third-order consequences

First-order consequences are those that are immediately evident and often end up in contradiction to long-term gains. Failing to think beyond first-order effects often results in poor decision making. For example, most of us might not enjoy the rain. But we wouldn’t wish away rainy days because the subsequent-order consequences–drought, wildfires, famine–are in direct opposition to our best interests.

While product is slightly lower stakes than climate, tunnel vision is a common struggle when building out a feature that’s intended to drive a key metric. You might be focused on retention, but how is that affecting the bigger picture? What if you’re compromising the experience for customers who are your strongest advocates? What if the strategy contradicts the identity you’re working to create?

It’s important to move fast, but it’s also important to navigate between these different levels so you have fewer headaches down the line. You’re not always going to have a definitive answer, but this thought exercise should help you consider the future implications of your decisions.

6. Value feedback over intuition

This is one of the biggest struggles I see from entrepreneurs across the board. Everyone wants to pour money into their project because they’re convinced it’s a million-dollar idea. But very few have the humility to prototype a product, put it out there, and seek honest feedback. And unless your risk tolerance borders on insanity, this is the cheapest, most effective way to assess the viability and potential market for your idea.

As a product manager, the story remains the same. You want to figure out the fastest, cheapest way to test your concept. This often requires hacking something together, getting it in the hands of your users, and actually listening to what they have to say. Great product managers find creative ways to gather customer feedback at the earliest stage possible.

Human beings are complex and fickle, so it’s impossible to predict how they’ll react to a brand-new solution. When our new ideas fail, it’s usually because we were overconfident about how well customers would understand and how much they would care.
— Jake Knapp + John Zeratsky

The momentary discomfort that comes from seeking brutally honest feedback is far less of a risk than taking off in a blind sprint based on intuition. You want to limit the potential downside and wasted effort whenever possible. The earlier you’re able to correct potential flaws in your product or assumptions, the greater your likelihood of success.

7. Be open with your failures

Most people never venture past the surface level of the “fail fast” mentality. We acknowledge that failure comes with the territory when working on disruptive ideas, but we forget to consider the underlying importance of this sentiment.

The goal should never be to force an idea to work, no matter the cost. It should be to assess if there’s a “there” there, as quickly as possible. There’s a fine line between sharing an overall vision and becoming emotionally entrenched in the success of a specific feature. The latter blinds you from objectively assessing outcomes and often leads to bad practices, i.e. “massaging” the data.

As a product manager, your job is to take chances and determine which opportunities show promise. When one of those efforts doesn’t result in the next big thing, there are still positive takeaways. You definitively know that it’s better to allocate energy elsewhere, which is valuable knowledge that will help shape your company’s direction. With the right approach, failure is a sign that you’re committed to pushing the realm of current possibilities–a necessity if you want to evolve your product and position yourself for long-term success.