Creativity

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 (1965) 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.