Stoicism

How the Stoics Mastered the Art of Influence

Desire for influence is human nature. Many people allow this to dictate the course of their lives, often unaware. But the Stoic philosophers developed a deeper sense of awareness and took the opposite approach.

Influence wasn’t their end goal. They approached it with indifference and chalked it up to fortune–nice to have but nonessential. Instead, they offered a more effective strategy–seek meaning over influence.

If you focus on work that matters to you and discover significance in yourself, you put yourself in a position to build something that strikes a deeper chord with others.

Find significance within yourself. Within your own sphere of power–that is where you have the greatest consequence.
— Epictetus

But if influence acts as your guiding principle, you dull your sense of authenticity and depth. You might get lucky and hit the target a few times. But you’ll always be guessing. And it’s difficult to sustain when you’re creating from outside of yourself and dependent on things beyond your control.

It’s a dangerous game to tie your sense of meaning and self-worth to external conditions. You introduce dependencies that can drop you into a state of anxiety, envy or despair, without warning.

Sooner or later your voice begins to waiver. By allowing influence to dictate your decisions, you compromise the quality of your work and your character. And how much good can you do if you sacrifice your integrity and a sense of meaning in your work along the way?

What you’re building must first resonate with you before you can expect it to resonate with anyone else.

But if you lose your honor in striving for greater (perceived) significance, you become useless.
— Epictetus

People gravitate towards those who have discovered a deeper sense of meaning in their work. That’s why the Stoics remain relevant to this day. They created from a place of meaning and valued their internal compass over recognition.

When you seek meaning over influence, you add an unusual depth to your voice that draws people in.

Epictetus, Marcus, and Seneca knew this well. They channeled their own sense of authenticity into their work and they way they lived their lives.

As their influence grew, they leveraged it to contribute something worthwhile. But they weren’t dependent on it. Despite the obstacles faced and privileges afforded, they remained focused on what was within their realm of control–living a meaningful life to the best of their ability.

Meaning starts with something that’s all your own. By prioritizing meaning over influence, you build the courage to speak from a place that resonates with you.

You would be foolish to ignore your audience entirely. But that’s a secondary consideration because there’s no guarantee. You’re the one who has to live with the work you put out into the world and the way you live your life.

Influence is far more likely to follow if you build something you believe in.

Keep your principles in order. When influence tilts your way, you’ll be prepared to lead with a steady hand like a Stoic. You’ll position yourself as the antithesis of the paranoid, corrupt leaders scattered throughout history.

But if you fail to assign things their proper value, you’ll risk losing yourself to an obsession with influence and power.

Focus instead on the things that are your own and create from there. There’s more fulfillment in this work and it often leads to better outcomes.

When you focus on your own authenticity, there’s a far greater chance it will resonate and make a measurable difference in someone else’s life. And even if it doesn’t, it remains valuable because it meant something to you. There’s a fundamental beauty in that.

Beautiful things of any kind are beautiful in themselves and sufficient to themselves. Praise is extraneous...Are any of those improved by being praised? Or damaged by contempt?
— Marcus Aurelius

It’s a rare thing in this world to first seek significance in yourself and build the courage to create something that resonates with you. Trust yourself. The world is drawn to authenticity.

When you value meaning over influence you’ll achieve a state of relaxed concentration to do the work that matters. The work you find meaning in. And it’s through this work that you build character and a sense of authenticity.

Seek meaning first, authenticity and influence will follow.
Seek influence first and you’ll risk losing yourself along the way.

*My original post appeared on Daily Stoic – a great resource for all things Stoicism. Check out their daily email for thought-provoking morning meditations.

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.


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 Stoic Guide to Winning the War of Reality vs. Expectations

Fortune falls heavily on those for whom she’s unexpected. The one always on the lookout easily endures.
— Seneca

Most of us are torn between the duality of what’s playing out in our minds and what’s actually taking place around us.

We all have certain expectations that things should go a specific way. For some of us, it’s holding fixed expectations that our relationships should be exactly as we’ve imagined—perfect partner, kids, family, friends. For others, it’s the expectation that we should have it all figured out by now, that our careers should follow a carefully plotted path, or that some special event—wedding, birthday, vacation abroad—should live up to the hype.

The trouble with this line of thinking is that higher expectations do not equate to higher levels of happiness, gratitude, or performance. Additionally, projecting fixed expectations is in fundamental opposition to the impermanence and ambiguity that define life. Expecting things to go a set way is to reject the fabric of life. You cannot and will not eliminate all uncertainty from your life, no matter how hard you try.

In reality, there’s no such thing as the way it should be. Everything is in a state of constant motion.

The harder you work to eliminate uncertainty and ambiguity from life, the smaller the confines of your comfort zone become. True comfort is found through embracing discomfort, not shielding yourself from uncertainty—and this is the paradox of comfort. The wider the range of potential scenarios that you’ve trained yourself to handle, the better things will turn out.

It’s not that expectations are inherently dangerous. But they become exactly that as we fixate on a single outcome that’s outside of what the Stoics deemed as our ‘reasoned choice’—one which we have little to no control over. Positive visualization—setting expectations sky high and fixating on the best-case scenario–is not so much a strategy, as it is a recipe for failure. Sooner or later you’ll end up wrecked by something beyond your control.

Expectations outside of your reasoned choice leave you fragile, rigid, and reactive. Focusing your limited energy on trying to control every variable and getting from A to B like you’ve dreamed it in your head is restrictive and ineffective. It limits what you will learn, what you can achieve, and the person you will be.

Who then is invincible? The one who cannot be upset by anything outside their reasoned choice.
— Epictetus

Negative visualization—contemplating the range of potential outcomes, including the unfavorable and worst-case—is a far more effective technique offered by the Stoics (also known as premeditatio malorum). The greatest minds don’t sit around thinking of a fanciful alternate reality where everything plays out according to plan. They develop the resourcefulness to navigate inevitable obstacles and turn them to their advantage.

The only expectation worth holding is that you take advantage of opportunities to act in accordance with your own values and principles. You should expect to leverage your own resourcefulness and resilience to better yourself, regardless of current circumstances or obstacles. Create your own momentum.

Just as nature takes every obstacle, every impediment, and works around it – turns it to its purposes, incorporates it into itself – so, too, a rational being can turn each setback into raw material and use it to achieve its goal.
— Marcus Aurelius

It all comes down to your perspective. Prepare yourself to handle a range of potential outcomes, develop confidence in that ability, and limit any expectations beyond your reasoned choice. When you adopt this mindset, you strip setbacks and external circumstances of their power to catch you off guard and dictate your life.

Reality rewards resilience. Projecting fixed expectations in life blinds you to everything but the one-track, imaginary path you’ve predicted.

At the foundation of each of these Stoic lessons is the negotiation of reality and expectations.

Acknowledging this inner war allows you to bridge the gap and begin developing the mindfulness, focus, and resilience that it takes to make meaningful progress of your own. Otherwise, you run the risk of becoming disconnected and discontent with the only life you have.

8 Stoic Secrets to Help You Build Mental Toughness

What distinguishes the greats is the will to keep going when others start dropping off and to see through what they believe in when it’s at its bleakest moment. And this persistence requires developing mental toughness—the ability to embrace uncertainty and discomfort while negotiating the way forward.

Greatness is not always synonymous with the common indicators of success. As Seneca explains, “Success comes to the lowly and to the poorly talented, but the special characteristic of a great person is to triumph over the disasters and panics of human life.” You can be lucky or born into advantageous circumstances and appear “successful” to most of society without making any meaningful progress of your own.

But if you want to be more than a shell and develop the substance that sets apart the greats, you need the endurance to stick it out, handle rejection, and embrace prolonged periods of intense learning. There are no shortcuts.

At the end of the day, the only real way to develop mental toughness is by putting yourself out there and learning how to effectively deal with whatever that comes your way.

For most, including myself, mental toughness is hard won. But once you cultivate this ability, the playing field shifts in your favor. You just have to determine what’s sustainable and what’s worth seeing through. Over the years I’ve found a few effective strategies with their roots in Stoicism that have helped me to begin developing greater resilience.

1. Life Is About Resourcefulness

In this way you must understand how laughable it is to say, ‘Tell me what to do!’ What advice could I possibly give? No, a far better request is, ‘Train my mind to adapt to any circumstance.’…In this way, if circumstances take you off script…you won’t be desperate for a new prompting.
— Epictetus

The modern education system, with its rigid structure and syllabus for every course, does its best to train this out of us. One of the biggest obstacles I faced when I took my first job out of college was my inability to handle ambiguity. If I wasn’t assigned specific tasks and provided explicit instruction, I crumbled.

As it turns out, life is far more about resourcefulness than a checklist of prescribed actions. There is no single blueprint to walk you through every step of your life. You must learn to adapt and create your own momentum–even when you encounter setbacks.

Each day is an opportunity to practice making things happen–regardless of your current environment or circumstances–and to leverage the experience you’ve gained along the way. There is no substitute in life for true resourcefulness.

2. Spend Time in Solitude

Nothing, to my way of thinking, it better proof of a well-ordered mind than a man’s ability to stop just where he is and pass some time in his own company.
— Seneca

Learn to be content spending more time in your own company. Introspection is the only way you can determine what matters most and what you want out of life. The earlier you learn to do this, the more focused you will be. It’s also a tool to help you reach a deeper state of concentration and flow. Those who bounce from one distraction to another are incapable of developing the resilience required to set themselves apart.

You have to establish a place in your mind that you can step back into, quiet the surrounding noise, and immerse yourself in your craft or remind yourself to show back up tomorrow. Prioritizing focused time alone is a sign of stability–a core component of mental toughness.

3. Create More, Consume Less

We too could have some or all of that power by a patient immersion in any field of study. Many people cannot handle the boredom this might entail; they fear starting out on such an arduous process. They prefer their distractions, dreams, and illusions, never aware of the higher pleasures that are there for those who choose to master themselves and a craft.
— Robert Greene

If you’re putting yourself out there and contributing your own original work to the world, it requires an inherent degree of mental toughness. It’s far easier to opt out, but is there anything more selfish than relying on other people to create art, value, and meaning, so you don’t have to risk putting yourself out there?

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 Veep, 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. And creating something from nothing is no small task, it demands and helps grow resiliency.

4. Show Up, Every Day

You must build up your life action by action, and be content if each one achieves its goal as far as possible–and no one can keep you from this. But there will be some external obstacle! Perhaps, but no obstacle to acting with justice, self-control, and wisdom. But what if some other area of my action is thwarted? Well, gladly accept the obstacle for what it is and shift your attention to what is given, and another action will immediately take its place, one that better fits the life you are building.
— Marcus Aurelius

Show up, every day, and put in the work. The simple act of showing up and immersing yourself in your craft does wonders for mental endurance. You build focus and come to terms with the arduous process that it takes to achieve anything great.

It’s not easy and the rewards are nonlinear. You have to put in countless hours of work before you reap any of the benefits. But there are no shortcuts if you want to build your life on a foundation of substance. You must first determine what you can sustain at a high level for an indefinite period of time, because that’s what it’s going to take.

Overnight “success” is unsustainable because it comes to those who are unprepared, often destroying their character in the process. Make sure you earn it, action by action, and dedicate uninterrupted time to your craft each day.

5. Measure You Against You

I will keep constant watch over myself and–most usefully–will put each day up for review. For this is what makes us evil–that none of us looks back upon our own lives. We reflect upon only that which we are about to do. And yet our plans for the future descend from the past.
— Seneca

There’s no faster way to undermine yourself and your efforts than comparing yourself to someone focused on a completely different objective. Hold yourself accountable to you. As uncomfortable as it might be, you have to be willing to stare yourself in the face.

While reflecting on each day, consider whether you made rational decisions and acted in accordance with your values at every opportunity. You’re not always going to make the right decisions each step of the way–and that’s okay. But you should always be willing to reflect on your actions so you can learn and grow.

The more in tune you are with your current progress, the better decisions you will be able to make and the easier it will be to keep things in perspective.

6. Keep out the Critics

If a person gave away your body to some passerby, you’d be furious. Yet you hand over your mind to anyone who comes along, so they may abuse you, leaving it disturbed and troubled–have you no shame in that?”
— Epictetus

The cornerstone of Stoicism is identifying externals and what is beyond your influence. There is no better example than outside opinion. Allowing yourself to be upset by the opinion of someone you don’t know or don’t respect is as foolish as getting upset about the weather. It’s a waste of energy.

That’s not to say that you should live in denial. You should actively seek honest feedback from those you respect. But above all, you should strive to make something that resonates with your spirit. And if you create from that place, it’s bound to inspire others. Just don’t expect everyone to get it.

You will get overlooked at some point in your life and brutally criticized by those without skin the game. Don’t hand over your peace of mind to outsiders to disrupt as they please. Recognize the noise for what it is and it will become almost laughable.

7. Never Play the Victim

If you consider yourself a victim, you are not going to have a good life; if, however, you refuse to think of yourself as a victim–if you refuse to let your inner self be conquered by your external circumstances–you are likely to have a good life.
— William B. Irvine

Always assume responsibility. The “why me?” mentality is an enemy to mental toughness. You might not be at fault, but your life depends on you determining what’s within your control and taking those things into your own hands. You must train yourself to frame things this way instead of immediately resorting to self pity.

It’s certainly easier to pawn off blame on others when something goes wrong. But only those with a degree of mental fortitude are able to step up–even when it’s not their fault–and right the ship.

Be that person who steps in to take action, not the one who looks the other way and casts blame. When you victimize yourself or your current position, you relinquish control and absolve yourself of personal responsibility. And without a sense of ownership, meaningful progress becomes an impossible task.

8. Practice Voluntary Hardship

Here’s a lesson to test your mind’s mettle: take part of a week in which you have only the most meager and cheap food, dress scantly in shabby clothes, and ask yourself if this is really the worst that you feared. It is when times are good that you should gird yourself for tougher times ahead, for when fortune is kind the soul can build defenses against her ravages. So it is that soldiers practice maneuvers in peacetime, erecting bunkers with no enemies in sight and exhausting themselves under no attack so that when it comes they won’t grow tired.
— Seneca

The easiest way is rarely the most fulfilling. Voluntary hardship challenges us to propel ourselves forward under our own power and embrace discomfort. While it contradicts society’s obsession with immediate gratification, that’s precisely the reason it’s a more effective strategy.

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 resiliency. For this same reason, physical endurance translates well into mental endurance.

If you’re more prepared to handle a wider range of potential scenarios, the everyday annoyances and inconveniences begin to feel less disruptive. And if the worst case scenario prevails—which it rarely does—it won’t leave you completely wrecked.


If you’re content with stumbling through life and relying on your position of privilege, you might still find success. But the inevitable fall will leave you in ruins—as your rise wasn’t built on anything of substance, just dumb luck and smoke in mirrors.

Only those who develop resilience and dedicate painstaking time to their craft are able to sustain themselves at the pinnacle. And when they do face setbacks, they have the mental fortitude to rebuild without crumbling. There is no single path to greatness, but there is one common element that every great person shares–mental toughness.

Top 4 Books for Better Mental Models

In a world of specialization, mental models are the most powerful argument for adopting a multidisciplinary approach. The concept behind mental models is that broad exposure to a range of subjects enables you to leverage the most useful knowledge from each and make better decisions.

When you position yourself at the intersection of multiple disciplines, you develop the ability to connect seemingly unrelated dots 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.

Charlie Munger coined the term “latticework” of mental models–which is exactly what you’re aiming for. The models you pick up should be intertwined with one another, as well as with your personal and vicarious experience. The more connections, the faster you’ll be able to navigate the latticework of your mind, and the stronger your cognitive ability.

You can begin building better models by going straight to the source. If you read and study those who have demonstrated mastery over their specific fields–regardless of industry–you can improve your decision-making ability considerably.

Over the past year, I’ve read (and reread) over 70 books in search for the best systems. These have served as the foundation for improving my own mental models. I’ve distilled what I’ve found to be the most important methods and strategies down to just four books. Each documents real models from some of the most intelligent, imaginative minds in history.

While these are in no way comprehensive, it is my hope is that they will provide a useful starting place to build your own latticework.

1) Mastery — by Robert Greene

You would be hard-pressed to find a more profound, relevant book, no matter your position in life. If I had to recommend a single book of Greene’s to get you started, this would be it. He begins by defining mastery as the sensation we experience when we feel that we have a greater command of reality, other people, and ourselves. The book offers a deep dive into every element of mastery–including insight for those just starting out and searching for their life’s task. True to form, Greene also provides detailed accounts and models from some of the greatest masters in history–Leonardo da Vinci, Benjamin Franklin, Charles Darwin, Albert Einstein, Paul Graham, and dozens more.

“The pain and boredom we experience in the initial stage of learning a skill toughens our minds, much like physical exercise. 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

2) Tools of Titans — by Tim Ferriss

A collection of interviews with hundreds of the most talented entrepreneurs and thought leaders consolidated into their most useful sound bites. It follows the same format as his popular podcast. Ferriss lays the framework for building better, more productive mental models. Rather than suggesting a checklist of X-Y-Z required to set yourself apart, he emphasizes strategies and tactics which can be applied more broadly. A few of my favorite sections feature Naval Ravikant (entrepreneur/investor), Josh Waitzkin (chess prodigy), and Alain de Botton (philosopher). There are sure to be a handful of ideas that will resonate with you and help improve your own mental models. It’s a book I revisit with regularity–especially when I’m in need of a new perspective.

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

3) Antifragile — by Nassim Taleb

Taleb introduces his concept of antifragility, which explains that certain things–including us–benefit from a degree of randomness, chaos, and disorder. While comfort, convenience, and predictability, breed the opposite–fragility. He presents this as part of what he calls ‘the central triad’ which ranges from fragile to robust to antifragile–the key to personal growth. As he explains antifragility, he discusses the value systems that hold us prisoner, ancestral vs. modern life, and Seneca’s version of Stoicism. It’s a dense read, but worth it for a glimpse into the originality of Taleb’s models.

With randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind.
— Nassim Taleb

4) The Daily Stoic — by Ryan Holiday and Stephen Hanselman

I’ve found Stoicism to be the most effective philosophy for modern life. If you’re unfamiliar with Stoicism, you’re probably operating under the misconception that it’s synonymous with a lack of emotion. In actuality, it’s a school of philosophy focused on cultivating an unwavering sense of focus, appreciation, and rationality. The Daily Stoic is a great introduction to some of the most memorable Stoic philosophers and their models for living a better life, including Epictetus, Seneca the Younger, and Marcus Aurelius. The book offers daily wisdom–366 short sections–focused on the most important Stoic themes. This is not a philosophy textbook filled with abstract concepts. It’s an accessible overview of Stoicism and its emphasis on the art of living.

Take a good hard look at people’s ruling principle, especially of the wise, what they run away from and what they seek out.
— Marcus Aurelius

In Defense of Moderation: The Stoic Range of Virtue

As a society we pride ourselves on extremes. We flaunt how few hours of sleep we maintain, how insatiable we are in our careers, and how comfortable our lives are thanks to an excess of luxury goods. But the problem is that when we aspire to extremes, we also run the risk of taking our virtues too far, which collapse into their opposite–crippling flaws in character.

Qualities and virtues are not something you either have or you don’t. There are varying degrees of intensity. A dualistic attitude in this context proves dangerous, as two categories fail to capture the ambiguity that defines life. We should ignore the impulse to designate personal qualities as good or bad with no in-between.

Instead, it’s far more reliable to frame qualities in context of a spectrum using Aristotle’s “golden mean,” which explains that the range of virtue is found firmly in the middle, between excess and deficiency. Seneca offers a similar perspective when he observes that, “So-called pleasures, when they go beyond a certain limit, are but punishments…”

The idea is that on one end of the spectrum, we see those who lack a specific quality and interpret it as a flaw. But virtues in their excess are just as prominent signs of weakness. You can in fact be too ambitious (insatiable), too empathetic (codependent), and too disciplined (repressed). Only those who embody moderation are able to identify this golden mean, guard themselves from the downside of the extremes, and establish an equilibrium in the delicate range of virtue.

Moderation (the range of virtue): Between deficiency and excess

Ambition: Between Lazy and Insatiable
Empathy: Cold and Codependent
Endurance: Fragile and Depleted
Self-confidence: Insecure and Arrogant
Adaptability: Rigid and Soft
Self-sufficiency: Dependent and Isolated
Discipline: Impetuous and Repressed
Composure: Frenzied and Stagnant
Calculated: Reckless and Timid
Euthymia: Nihilism and Grand Narrative

Ambition: Between Lazy and Insatiable

Laziness is an obvious enemy and sign of weakness. But the spectrum stretches further in the opposite direction than ambition. Calculated ambition is a virtue. It’s important to have goals, aspirations, and a purpose that you’re working towards. But when taken too far, we cross into the realm of insatiability.

It’s here where we burn out–unable to reconnect with the present and appreciate what we already have in our lives. Insatiability is a flaw in equal proportion to laziness. Without moderation in our ambitions, retaining personal sanity becomes an impossible task.

Do not go past the mark you aimed for; in victory learn when to stop.
— Robert Greene

Empathy: Between Cold and Codependent

Empathy is more advantageous than coldness or indifference. If you’re in tune with those around you, the stronger your relationships will be and the better you’ll be able to navigate specific situations. However, if left unchecked, empathy can lead to codependence and deriving your self-worth from meeting the emotional needs of others while neglecting your own.

It’s critical to keep these extremes in mind so you can use them as a checkpoint to operate within the range of virtue. If you find yourself in situations where people are exploiting your empathetic nature, check yourself, but also make an effort to distance yourself from those relationships.

Avoid those who are gloomy and always lamenting, and who grasp at every pretext for complaint…a companion who is agitated and groaning about everything is an enemy to peace of mind.
— Seneca

Endurance: Between Fragile and Depleted

Endurance is a common virtue among top performers. In this context, it’s interchangeable with mental and physical endurance. Those who lack the endurance to overcome life’s obstacles are fragile and will fail to demonstrate the persistence required to set themselves apart. However, there comes a breaking point at the opposite end–total exhaustion–when you have nothing left to give.

It’s important to prepare and build endurance. But in your preparation, know your breaking point and guard yourself from burnout. You have a limited amount of energy. It should be allocated only to things that fall in line with your personal aspirations and goals. Don’t run yourself into the ground.

We must undergo a hard winter training and not rush into things for which we haven’t prepared.
— Epictetus

All Good Things Come in Moderation

We often hear people speak of wisdom, justice, and courage, but rarely do we hear people praise moderation. Moderation is the best kept secret and perhaps the most underrated value in modern society. It might not be the most exciting principle, but locating this middle ground—the golden mean—has the capacity to make the largest difference.

Consider your strengths and what you believe gives you a competitive advantage. You should leverage these as you learn and grow, but remember that there also comes a point where your best qualities should be kept in check. Don’t allow them to inflate your ego and grow into unnecessary liabilities. All good things come in moderation.

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