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 Essential Question for Every Entrepreneur

Sometimes the best question you can ask yourself is, "Am I building something I would want?"

As an entrepreneur, this should precede every other question. If the answer is no, there's a fundamental disconnect. You're going to have a difficult time sustaining the necessary effort over the long run. Momentum comes from engagement.

The real secret to product development is creating something that you would want to use.

I evaluate every new product, opportunity, and startup that I consider pursuing with this filter. Success demands years of hard work. If I'm not engaged or I don't find purpose in the work, it's a nonstarter. Otherwise, I know I'll be at a disadvantage facing off against someone solving for their own point of need.

I use the same filter when considering partnerships or investments. I look for founders and teams who are building things they've demonstrated a deep interest in for years.

Consider those who have sustained success over decades–Bill Gates, Sergey Brin, Larry Page, J.K. Rowling, Oprah Winfrey, Bob Dylan, Walt Disney, Albert Einstein, Thomas Edison, Benjamin Franklin. Each person created things they wanted in the world around them. They pursued fields of work they found engaging and compelled to contribute to. That's what kept them going.

And that's the difference between people who burn out or get lucky once and people who sustain success–regardless of industry.

But despite this simple truth, many entrepreneurs insist on building things or addressing problems that they have no real interest in themselves. Most often this is due to inexperience or a lack of integrity.

Inexperience reveals itself in early entrepreneurs who believe that their first decent idea is their only shot at making it. Instead of practicing patience, they force the issue.

But the real currency of successful startups is in execution. You can have the best idea in the world, but if it doesn't resonate with you as an individual, it's going to be difficult to get through the necessary struggles. Creating something from nothing is hard work.

The notion that ideas are a multiplier of execution is empowering. It frees you to be more selective about the startups and projects you get involved with. Instead of looking for a single brilliant idea, look for a strong idea that resonates with you and that you are uniquely suited to bring to life.

There’s no shortage of ideas out there. You might as well take on something you're aligned with and invested in so you feel like you're working towards something worthwhile.

Entrepreneurs with integrity don't involve themselves in projects that aren't aligned with their values and interests. They don't allow themselves to be distracted–even by the allure of easy money. And they don't allow envy to dictate their direction in life.

If you're building something you wouldn't actually want and that you're not proud of, you're sacrificing integrity. And integrity is far harder to come by than money, recognition, or an inflated sense of self-importance. Never mind the ensuing search for lost time.

“Your goal in life is to find out the people who need you the most, to find out the business that needs you the most, to find the project and the art that needs you the most. There is something out there just for you. What you don’t want to do is be building checklists and decision frameworks built on what other people are doing. You’re never going to be that. You’ll never be good at being somebody else.”

— Naval Ravikant

The world needs more people creating real value–building things that resonate with them and pursuing work that reflects their deepest interests and principles. That's what it takes to build something great and sustain the effort that it takes to overcome inevitable obstacles.

For most hard-working, talented people it’s just a matter of time. Years of consistently showing up, learning, and dedicating time to your craft pays dividends. The power of small, calculated decisions, habits, and behaviors grows exponentially over time.

But first, you must find alignment.

Are you building something because you think someone else might want it?

Or are you creating something that you would actually want to use? This reflects a deeper interest and resilience. It's an immediate advantage that puts you in a far better position to succeed. This is where you want to be.

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.

30 Lessons for Living at Your Best by 30

Behind almost everything I’ve done in my 20s there’s been a single motivating factor–discovering what it means to live well. By living well I don’t mean extravagantly. I mean determining what I want out of life, living in a way that aligns with those values and principles, and learning in everything I do. In other words, striving to be the best version of myself.

While there will be inevitable ups and downs, no matter where you are, you want to be able to step back and see a clear upward trajectory which tracks the course of your life.

The best way to ensure this is by learning from your failures, putting in the work, and aspiring to be at your best. There will be days, weeks, even months, when things might seem to stagnate or head in the opposite direction, but you need the mental toughness to adapt and push yourself towards progress, as defined by you.

With my 30th birthday in sight, I’ve narrowed in on a few hard-fought, as well as mind-numbingly simple lessons, which have helped me establish a sense of this trajectory. I don’t presume to have all the answers. These are just the lessons that have resonated strongest with me over the past decade. Remember, there’s no “right” path, but I hope these prove useful as you find your own way.

1. Get the essentials down first

If you expect to feel good and achieve anything in your life, you need to prioritize sleep, exercise and eating well. These are the non-negotiables. You can’t neglect yourself and expect to function at a high level. This is foundational to everything else on this list.

2. Limit the number of do-overs

Don’t underestimate the power of avoiding dumb decisions. Most of the trouble that people run into is self-inflicted. There are enough obstacles ahead of you as is, don’t create extra work for yourself. This doesn’t mean you have to be brilliant in every decision you make, just avoid the big mistakes. Focus on making well-rounded, rational decisions each day, and allow compound interest to run its course.

3. There is no way things are “supposed to be”

The sooner you give up an imagined reality, the better you’ll be able to negotiate the way forward. Close the gap by differentiating between internal and external expectations and assigning each their proper weight. Prioritizing internal expectations is the path towards gratitude and self-sufficiency. External expectations introduce dependencies. Don’t place a premium on things you can’t affect.

4. Create more, consume less

What you consume doesn’t make you unique. The fact that you’re a fan of the Golden State Warriors, listen to Ed Sheeran, watch Game of Thrones, and only buy Apple products, are not unique identifiers. What you create and what you’re putting out into the world is what defines you.

5. Life is a single player game

You can’t expect to retain your sanity if you insist on comparing yourself to people heading in an entirely different direction. Measure you against you.

6. There is no substitute for true resourcefulness

One of the biggest obstacles I faced when I took my first job out of college was my inability to handle ambiguity and uncertainty. The predictability of the curriculum and instruction in school won’t do you any favors here. As it turns out, life is far more about resourcefulness than a checklist of prescribed actions. You must learn to adapt, teach yourself, and create your own momentum. There is no blueprint to walk you through every step of your life.

7. Put in the self-work

It’s not going to be easy, but it’s going to be worth it. Your 20s should be a decade primarily dedicated to yourself so you can figure your shit out. Before you enter into any relationship or realize any of your aspirations–if you don’t want them to go up in flames–you need to be self-aware and self-sufficient.

8. Directions in life are mutually exclusive

For the first half of my 20s I wanted to be everything, so I was unable to commit to anything. But the earlier you cross the irrelevant off your list, the faster you’ll be able to make meaningful progress and give your complete attention to the things you can’t live without. If you’re unsure where to start, try this exercise from Warren Buffett and double down on those things.

9. JOMO (joy of missing out) > FOMO (fear of missing out)

“FOMO” is another way of saying you’re incapable of prioritizing–you want to be everything and everywhere, which is an impossibility. Once you’ve figured out what’s important to you, passing on unnecessary obligations or engagements which you’re not invested in will be a source of great satisfaction.

10. What you walk away from defines you as much as the things you stick out

Whenever you encounter a moment of self-doubt or the urge to quit, ask yourself, do you feel like quitting because it’s difficult? Or do you feel like quitting because it contradicts your character, values, or priorities? The former means you should stick it out, the latter means it’s time to call it quits.

11. Growth is nonlinear

As Nassim Taleb explains in Fooled by Randomness, nonlinear relationships are the rule, not the exception. We mistakingly believe that if two variables are causally linked, a steady input in one should result in a positive linear progression in the other. Life doesn’t work that way. You can’t always expect visible progress when comparing one day to the next. You might have to dedicate years to your craft before something clicks. Remember, it’s your overall trajectory that matters, not the noise you encounter on a daily basis. The shorter the time frame, the more variance there will be–focus on the big picture.

12. Figure out what you can sustain indefinitely

That’s what it’s going take to set yourself apart. Most people drop off at the first sign of adversity or boredom, outlast them.

13. Leverage compound interest

The power of compound interest applies to almost everything in life, not just financial investments. For most hard-working, talented people it’s just a matter of time. Years of consistently showing up, learning, and dedicating time to your craft will pay dividends. The power of small, calculated decisions, habits, and behaviors grows exponentially over time.

14. Physical endurance builds mental endurance

Most people live in fear of the slightest discomfort or inconvenience. If you’re able to practice consistently pushing yourself to the point of discomfort and sustaining at that level, you begin to build resilience. In this regard, physical endurance translates into mental toughness.

15. Lasting comfort is found by embracing discomfort

Intermittent periods of discomfort prepare you to handle a wider range of potential scenarios. This helps you expand the confines of your current comfort zone and, ultimately, experience less discomfort than those who cling to convenience and familiarity. The latter find themselves in positions of considerable vulnerability–rigid and unable to adapt. This is the paradox of comfort.

16. Stillness is the best lesson traveling will teach you

I was an insatiable traveler for most of my 20s, visiting 25 countries and four continents. The only thing I’ve found more fulfilling than travel is learning to be still and content at home. Travel, go see the world, live somewhere new–otherwise, you’ll regret it later on. But this should lay the foundation for you to find peace in your future immediate surroundings. And this is the real value of experiences gained from travel–they help you build a broader perspective and a stronger sense of identity and appreciation at home. There’s nothing more fulfilling than the sense of gratitude that comes from moments when you’re content right with being right where you are.

17. Get a dog

Very few things have had a more profound, positive impact on my life. Presence, patience, empathy, joy–a dog will remind you of these values every single day.

18. Read like your life depends on it

To quote Naval Ravikant, once, “The genuine love for reading itself, when cultivated, is a superpower. The means of learning are abundant–it’s the desire to learn that is scarce. Cultivate that desire by reading what you want.” And twice, “Reading science, math, and philosophy one hour per day will likely put you at the upper echelon of human success within seven years.” The power of compound interest applies as much to reading and building better mental models as anything else.

19. No one alive has all the right answers

Avoid the urge to overidentify and reach for absolutes. Learn to live in the gray area. That’s what separates lifelong learners from pretenders.

20. General advice > specific advice

You will encounter mentors who want to prescribe specific advice. For the most part, it’s ineffective, because there is no single path to success. You will never be able to replicate the lives of those you admire. But you can examine the systems and mental models that give them their edge. This is where you’ll find the truly valuable lessons that you can apply to your own life, direction, and decision making.

21. Avoid ideologies at all costs

As Charlie Munger suggests, “Heavy ideology is one of the most extreme distorters of human cognition.” There’s no better way to impair your own rationality and decision making. Ideologies will drive you towards confirmation bias and close-mindedness.

22. Legacy is a mirage

If you have any sense of historical perspective, you’ll realize that you won’t be remembered. The desire for legacy is narcissism in disguise. This realization should be empowering, not disheartening. It will allow you to go out and make a difference now, instead of attempting to preserve some future image of yourself when you won’t be around to reap any of its benefits.

23. “In victory, learn when to stop.”

Drifting expectations are dangerous. This is one of Robert Greene’s 48 Laws of Power. You have to allow yourself time to reflect on what you have and how far you’ve come. Those who refuse to come to terms with this lesson find themselves as textbook examples of hubris, brought down by the same insatiability and arrogance that led them on an accelerated, unsustainable path towards the top. This is the reason people lose fortunes, families crumble, companies self-destruct, empires fall. More is not always the answer. Know when you’ve won.

24. Money matters

In The Geometry of Wealth, Brian Portnoy explains that wealth and investing are about funding contentment and underwriting a meaningful life, as defined by you. Not about getting rich, having “more,” and losing yourself on the hedonic treadmill. There is a point of diminishing returns when it comes to the impact of income on experiential happiness (around $75,000), but there is no cap on reflective happiness. Wealth is a tool to achieve freedom, self-sufficiency, and spend your time exactly how you want to.

25. You can’t have it all, but you can have what you prioritize

Don’t try to keep up with those living an extravagant lifestyle. If your goal is to fund your own contentment and underwrite a meaningful life, you need to figure out what’s most important to you. Spend money on those things, without hesitation, and invest in yourself. Live frugally and cut costs everywhere else.

26. Moderation is king

This is the single most important value no one has told you about. Avoid excess. As a society, we pride ourselves on extremes. But even our virtues, when taken too far, collapse into their opposite–crippling flaws in character. Find the golden mean.

27. Everyone is facing their own adversity

I’m reminded of this on an almost weekly basis. The carefully curated versions people project of themselves on social media don’t reflect what’s actually going on in their lives. You never know what someone’s going through or what they’ve been through. Be kind.

28. Commit to the people who share your most important values

I can’t say it better than Ray Dalio, “When you have alignment, cherish it. While there is nobody in the world who will share your point of view on everything, there are people who will share your most important values and the ways in which you choose to live them out. Make sure you end up with those people.”

29. Build a philosophy of life that works for you

Philosophy is about the art of living. It will make these lessons easier if you have a reference point that reflects your most important values and principles. For me, this is a version of Stoicism. Go out there and find one that works for you, or create your own. Whatever you do, establish one, because this adds purpose, direction, and serves as a constant reminder of what’s worth attaining in life.

30. There’s no secret to happiness, other than gratitude

The single trait that the happiest people all have in common is a profound sense of gratitude. They wake up in the morning and feel lucky, with an appreciation for life and their current position. I achieve this by reflecting on all the good things I have, worst-case scenarios, and the finer details in my immediate surroundings.

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The only true failures in life are moments of apathy or defiance, when you’re unwilling to learn. Knowledge and experience count for little if you’re unable to commit them as life lessons.

Determine what you want out of life, live in a way that aligns with those values, and never stop learning. That’s what it takes if you want to discover what it means to live well and maintain an upward trajectory over the course of your life. Go out and find the lessons that resonate strongest with you.

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.

Top 6 Books for Better Mental Models (<200 pages)

Many of the smartest minds throughout history–those who have demonstrated mastery in their respective fields and contributed something meaningful to the world–have favored a multidisciplinary approach over specialization. They’ve recognized that the more flexible and wide-ranging your mental models, the stronger your cognitive abilities, and the less rigid your thinking. At an individual level, it’s not only more effective but also more fulfilling.

A multidisciplinary approach leads to resourcefulness, ingenuity, and resilience. It better prepares you to develop each of these skills, navigate inevitable obstacles, and build your own momentum. It’s the antithesis of confining yourself to a single discipline with a shallow skill-set and isolated mental models.

In fact, the defining feature of a multidisciplinary approach is its dynamic latticework of mental models. This is achieved by broad exposure to a range of subjects, which allows you to leverage and connect the most relevant knowledge from each. By positioning yourself at the intersection of multiple disciplines, you cultivate the ability to tie together seemingly unrelated concepts in a way the vast majority are incapable of. It’s here where the most creative, innovative ideas are discovered.

Last year I wrote an article on the beginner’s guide to a multidisciplinary approach and recommended four books for building better mental models. It resonated with quite a few people who were looking for an introduction to this concept. In revisiting this theme, I’ve wanted to provide a new reading list that’s even more accessible–each book is under 200 pages.

While this is in no way comprehensive, it is my hope that this will help you begin building your own framework across multiple disciplines. If you’re up for a short read, dig in.

1) The Obstacle Is the Way — by Ryan Holiday

One of the most accessible modern introductions to Stoic philosophy. Holiday examines the inevitable obstacles we all face in life, how to better frame them as opportunities to practice virtue and harness them to create momentum of our own. He structures the book around the three interconnected disciplines required to overcome any obstacle: perception, action, and will. There’s an incredible amount of knowledge packed into these 200 pages. No matter what challenges you face or where you’re trying to go, it’s a great resource for fine tuning your attitude, strategy, and mental toughness. Inspired by Marcus Aurelius, “The impediment to action advances action. What stands in the way becomes the way.”

“Talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.”

— Ryan Holiday

2) The Geometry of Wealth—by Brian Portnoy

A look into the relationship between money and meaning. Portnoy suggests that wealth and investing are about funding contentment and underwriting a meaningful life, as defined by you. Not about getting rich, having “more,” and losing yourself on the hedonic treadmill. He explains that simplification is the path towards effectively managing expectations in money and life–and the trajectory of a happy life is shaped by expectations. The Geometry of Wealth is as practical as it is philosophical. À la Charlie Munger, Portnoy emphasizes individual behavior, mainly self-control and self-awareness, as the most important factor in investment success. He suggests we focus on being “less wrong” over being “more right,” in the sense that asset allocation is far more important than security selection and market timing. But on the path towards adaptive simplicity in investing, he also digs deeper into its importance in our broader lives, offering an enlightened discussion of experienced vs. reflective happiness, expectations, and human nature.

“The ‘good life’ is not the tweak of ephemeral pleasure, but the engagement with more meaningful, virtuous pursuits. Momentary pleasures are distinct from the enduring gravity of meaningful experience.”

— Brian Portnoy

3) The Bed of Procrustes — by Nassim Taleb

Great introduction to Taleb’s ideas on uncertainty, which he discusses in detail in his other books that make up the Incerto series: Antifragile, Fooled by Randomness, and The Black Swan. This book offers a succinct look into how we deal with what we don’t know. Taleb considers our tendency to package and reduce ideas into neat narratives that fit within the constraints of our limited knowledge. I would argue that he’s one of the most original, brilliant minds of our time.

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

— Nassim Taleb

4) Real Artists Don’t Starve — by Jeff Goins

Practical and refreshing resource for smart creatives and entrepreneurs. Goins picks apart the myths surrounding the Starving Artist and offers an improved alternative of the Thriving Artist. There are dozens of useful rules of thumb you can apply to your own position, no matter where you are. Thriving Artists build their creative dreams step by step (not overnight). They focus on rearrangement and building upon the work of those who have influenced them (not obsessing over originality). They leverage their existing jobs for resources (not quitting too early and without reason). They recognize the value of a multidisciplinary approach and multiple revenue streams (not mastering a single skill and risking it all on a single bet). Goins follows this same pattern throughout the book, detailing the difference in mindsets, how to position yourself in the market, and how to make a living. It’s a modern-day guide for living a better, more creative life, without struggling for the sake of struggling.

“Thriving Artists don’t just live off their art. Like good investors, they keep diverse portfolios, relying on multiple income streams to make a living. Rarely do they go all in on any single area of work. The challenge, then, is knowing what investments to make and when.”

— Jeff Goins

5) The Inner Game of Tennis — by W. Timothy Gallwey

I’m usually skeptical of anything that remotely resembles sports as a metaphor for life, but this a tremendous read. It’s less a book about tennis (although there are a few sections) and more about the art of relaxed concentration. It’s a simple but profound concept that suggests the secret to performing your best is in developing a quiet confidence, and most importantly, not trying too hard. Gallwey draws a line between Self 1–the conscious teller, and Self 2–the doer. He advocates developing greater trust in Self 2, which helps to cultivate effortless concentration (flow), instead of a more tense, overly controlled approach which creates an unnecessary obstacle. Gallwey also offers an insightful perspective as he digs deeper into concepts including judgment, awareness, ego, and mindfulness, which adds another dimension to the book.

“The player of the inner game comes to value the art of relaxed concentration above all other skills; he discovers a true basis for self-confidence; and he learns that the secret to winning any game lies in not trying too hard.”

— W. Timothy Gallwey

6) Tribe — by Sebastian Junger

Clear, concise, and thought-provoking read that examines the struggle to find loyalty, belonging, and meaning in modern society. Junger spotlights military veterans and the growing rates of post-traumatic stress disorder, but he also takes a step back to examine the human condition at large. He discusses hardship, raw experiences, social bonds, community, mental health, and what we can learn from tribal societies. Tribe explains that there are three essential needs that must be met if we wish to feel content–the need to feel competent at what we do, the need to feel authentic in our lives, and the need to feel connected to others. Junger considers the effects of their absence and makes a compelling case that we should strive to rediscover and prioritize their importance.

“Human beings need three basic things in order to be content: they need to feel competent at what they do; they need to feel authentic in their lives; and they need to feel connected to others.”

— Sebastian Junger

The Myth of Losing Your Edge

One of the biggest fears that many hardworking, talented people have is that if they ease up in any facet of their lives, they’ll lose their edge. It’s a myth that’s fueled by a failure to differentiate between internal and external expectations. If you want to be at your best, it’s important to make this distinction and assign each their proper weight.

If you’ve convinced yourself that your edge comes from orchestrating external factors–things that are by nature beyond your control–that’s your ego taking over. This mindset is what pushes people to high strung, compulsive, and rigid behavior. Attempting to inflict your will with brute force and control every variable will drive you to exhaustion.

What keeps you ahead is not a state of constant dissatisfaction and the excessive demands you place upon the world. And while you might be quick to dismiss this as the ‘slackers credo’ of aiming low, take a closer look. Renegotiating expectations has nothing to do with the trajectory of your aim. It’s about prioritization.

You do not control the actions of others, how your work is interpreted, the recognition you receive, the specific obstacles you face, or whether the perfect sequence of events unfolds immediately before you.

It’s not that these things don’t matter. But they should matter less. Because they aren’t what define your edge and they aren’t reliable metrics against which to measure yourself.

The greater importance you assign to these types of external expectations, the more dependencies you introduce, and the higher the likelihood that you’ll end up pissed off, burned out, and distracted from the work that matters most. While you might be able to influence these to an extent, any significant control you believe you possess over them is illusory.

Your real edge is in your persistence and your own abilities. Your inner drive is independent of external expectations–the two are not inextricably linked. You have to be able to separate these from one another, as the resourceful and antifragile know well.

Rather than compromising your edge, redefining internal and external expectations puts you at a significant advantage. You free yourself to focus back on the things you can actually affect–mainly, your actions, dedicating time to your craft, discovering meaning in your work, living in accordance with your principles, developing your own resourcefulness, navigating inevitable obstacles. This is the most accurate way to measure your own progress.

When you become reliant on someone or something else to determine a successful outcome or your personal sense of self-worth, you’re putting yourself in an impossible position. Dependencies introduce anxiety and envy.

The mentality of “if only X, Y, Z happened for me, that would solve everything” is more of a liability than it is an asset. And it doesn’t say much for your ability to prioritize. Why place a premium on things you can’t directly affect? You’re wasting your limited time and energy, which could be better allocated elsewhere.

What you should prioritize is a state of relaxed concentration. It’s here where your best work gets done.

When you turn your attention back to your own abilities and immerse yourself in the task at hand, the anxiety subsides. There’s something calming about putting in the work when it’s down to just you and your craft. It brings things back to self-discipline, self-expression, and the pursuit of meaning in your work, all of which are within your immediate grasp.

Most top performers, who once believed their insatiable, demanding tendencies to be their edge, will concede this with age. What you achieve in life is not conditional on your external expectations. They don’t make you better and they don’t guarantee success. There will always be other factors in play beyond your control, and that’s okay. What actually matters is your internal focus, the work you’re putting in, and the expectations you hold for yourself.

Renegotiating expectations doesn’t mean sacrificing personal aspirations or expecting less from yourself. And it doesn’t mean aiming low. It means aiming higher and demanding more–of yourself–and prioritizing that. Define yourself by substance. Not by luck or futile attempts to bend the world to your will.

When you differentiate between internal and external expectations–assigning each their proper weight–it’s not your edge that you’ll lose, it’s your angst. In its place, you’ll build gratitude and a greater capacity to focus on the work that resonates strongest with you. It’s here where you can make a real difference and develop the quiet confidence that it takes to create something meaningful.

Your First Responsibility in Any Job

Many smart creatives have lofty ambitions — a desire to create something meaningful, make a difference, improve the world. But it’s easy to get caught up in these aspirations and overlook your most important responsibility.

Each of us has the capacity to directly impact (and improve) a handful of people’s lives on a daily basis through our work. This is our obligation to each other — no matter how high our position or perceived impact.

When you come into work each morning, your first job should be to improve the quality of life for your immediate team. It doesn’t matter if you’re an engineer, analyst, designer, manager, or intern. Everything starts with the people around you. Take your ego out of it. Only then will you be able you branch out and improve, as a group and individuals.

Building the morale of your team is what precedes creating anything of lasting value. If you don’t get it right at this immediate level, it’s impossible to sustain at higher levels of performance with multiple moving pieces. 

This can be better understood as a five-tier model, similar to a rather famous hierarchy of needs.

Levels:

1. Improve the lives of those on your immediate team

2. Elevate the quality of individual and group contributions

3. Establish and grow the culture

4. Advance the overall mission and purpose

5. Contribute something meaningful to the world and improve people’s lives

The people around you come first. Before the customer. Before the experience. Before the achievements.

Improving the lives of those around you doesn’t mean making things easier, and it doesn’t mean people pleasing. What it does mean is engaging, challenging, collaborating, and empathizing. And it all must be authentic —everyone’s different, it takes time to build trust and develop your own cadence and rapport. 

Environments where people care and know how to push each other, produce better outcomes. This is where the seeds of cultured are sown.

While it’s an individual attitude at its core, you can also structure teams in a way that facilitate this type of growth and interaction. Small empowered teams — what we refer to as journey teams — encourage people to check their egos and focus on coming together. It’s the same mentality in startups — lean, resourceful teams who care about each other, their values, and their mission.

Those who are only in it for themselves will struggle to survive in this type of an environment. 

There’s less room to hide behind personal brand — or whatever garbage they disguise it as. While this might work in a more rigid, corporate hierarchy, true motivations become glaringly obvious on self-sufficient teams. Pretending to care about the people around you because you’re supposed to, is not the same as actually being invested. You can’t fake that. At least not for long without breeding resentment and disengagement.

Authenticity, purpose, and challenge are each important if you want to keep smart creatives engaged and contributing their best work. This is one of the most significant obstacles that companies face in today’s business world. That’s why so many people are on the two-year plan, bouncing from one opportunity to the next. It’s difficult to sustain a high level of engagement for years on end.

The best way to combat this is by building a community of people who not only challenge, but care deeply about each other. It’s a true competitive advantage that’s not easily replicated. It’s hard work, that’s why it’s so rare. But few things have a more powerful, direct contribution to your overall wellbeing than this type of work environment. 

If you want to make a difference, start by making a difference in the people’s lives immediately surrounding you, then build from there. This remains true regardless of what aspirations you hold.

Show compassion and interest towards the people you work with. Discover meaning in your work, together. Enjoy your time together, struggle together, and strive to improve each other’s lives.

If you want to achieve what you’ve set out to, you’re going to need people who care about and challenge each other. That’s what it takes to bring an idea to life and contribute something meaningful to the world. When you make this your first responsibility, everyone will come out better for it. 

The Difference Between Lifelong Learners and Pretenders

There’s an underlying difference between lifelong learners — smart, intellectually curious thinkers — and those who use obscure knowledge as social collateral. Often it’s the first visible symptom of misplaced motivation and a shallow foundation of ideas — overidentification.

We all know someone who overidentifies with each book, documentary, or source of information they come across. They regurgitate the ideas and arguments presented, ad nauseam. There’s no room for personal interpretation. They seek a source that fits neatly into their existing worldview and repeat it for weeks as if it’s their own.

In contrast, the smartest minds allow themselves to sit in the gray area. They don’t overidentify with any single source of knowledge. Instead, they give themselves time to distill information and ideas into their most useful components.

The pretenders take the opposite approach. It’s all or nothing. They fail to grasp that you don’t have to adopt 100% of the arguments presented by a public voice — author, filmmaker, thought leader, etc. But a single idea you don’t identify with doesn’t negate the overall value of their work.

At its core, this mindset is often rooted in the promise of some external reward. When your desire to learn is fueled by ego, approval, attention, or recognition, overidentification is the obvious end result. You’re not truly committed to learning. You’ll stop when you come across the first idea that appears satisfactory, perpetuating your own confirmation bias.

Although, it’s not always a conscious decision. It’s easy to overidentify, especially early in life with limited perspective. You have fewer reference points. As a result, when you find an influencer who you admire, you naturally gravitate towards all of their ideas.

But the more you read and the more you learn, the more aware you become of just how wide the spectrum of opinions is.

It’s a strange feeling. We’ve all experienced a strong desire to identify with the entirety of the views from those we respect. It would certainly make things easier and eliminate most of the painstaking introspection required on our part. Who wouldn’t want a definitive, personal guide to entrust with navigating life’s uncertainties on our behalf?

Unfortunately, there’s no neatly packaged manual for our individual lives.

“Have the moral courage to live in the gray, sit with uncertainty but not in a passive way. Live the questions so that, one day, you will live yourself into the answers.”

— Jacqueline Novogratz

Part of a self-sufficient mind is being able to sift through facts, opinions, and interpretations to piece together your own cohesive worldview. You’re allowed to, and should, borrow ideas from multiple sources. But that means you’re going to have to put in the work.

There’s not a single person who has been right about everything. And there’s not an intelligent, enlightened thinker who has gone their entire life without changing their mind about something.

There are many people committed to learning and developing the most informed view on a specific subject. But that doesn’t mean they have every right answer. Most people are just doing their best to figure things out.

You should still maintain a zero-tolerance policy for deception or pure ignorance. If someone is unable to accept empirical facts or universal laws, it’s probably not worth investing the time to consider their ideas further. By refusing to operate with any sort of foundation in science or reason, it shows an unwillingness to enter a neutral arena. It’s the easiest way to distort reality and manipulate the field.

No one said it was going to be easy. The true litmus test of your critical thinking skills is how well you hold, assess, and incorporate new ideas into your own worldview. Is it a free for all? Or is it a careful examination and contemplation of the ideas that check out and resonate strongest with you?

Lifelong learners embrace ambiguity. They resist the urge to immediately adopt or discredit someone’s point of view based on a single interpretation or opinion. The deeper your well of knowledge, the better you’re able to balance multiple viewpoints, and the more rational your perspective.

Allow yourself to live and learn in the gray area.