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.

Where Advice from Successful Entrepreneurs Falls Short

As we acquire experience it’s natural to wonder what we would change or tell our younger selves. It’s all the more intriguing when the question is posed to the entrepreneurs we admire.

The one consistency I’ve found is that few advocate altering the course of their lives. The entrepreneurs we consider successful don’t wish away past events or decisions they’ve made. When asked if there’s anything they would do differently in their careers or lives, they reject the question entirely. They’re comfortable with the decisions they’ve made and the obstacles they’ve faced because it has led to where they are today.

At an individual level, this a productive, if not essential, behavior. But some of the most brilliant minds also have a tendency to prescribe their past decisions as a blueprint for others to follow–advice that’s in direct contradiction to their emphasis on the importance of making it their own way.

The reality is that there is no single path to success and it’s impossible to make the optimal decision every step of the way. But you stand a far better chance if you leverage your unique abilities and embrace the direction you find for yourself, instead of attempting to replicate the decisions of those who have experienced past success.

The Greeks defined this as euthymia. Seneca explained it best as, “believing in yourself and trusting you are on the right path, and not being in doubt by following the myriad of footpaths of those wandering in every direction.” Some will call this fate. Seneca referred to it as tranquility.

Once you trust in the direction you’re heading, you’re able to better negotiate one the most formidable obstacles you face–yourself. As you move out of your own way and out of your own head, you free yourself to make meaningful progress instead of second guessing.

It should come as no surprise that most successful entrepreneurs embody this lesson. But their unequivocal belief in themselves and their ideas often makes it difficult for them to refrain from projecting their path upon those with open ears.

Queue the contradiction–advocating the importance of your individual path and choices, then turning around and prescribing specific actions to others attempting to reach similar goals. It’s something I encounter on a weekly basis, with advisors directing early-stage startups to emulate a specific set of actions because it worked for them once upon a time.

To be fair, this seems to be a human tendency–regardless of the degree of success experienced. But pay careful attention to the next podcast you listen to when the inevitable, “What advice would you give your 20-year-old self?” comes up. Is the line drawn after relevant insight and a useful aphorism, or does it digress into advice for listeners to follow an exact sequence of events?

This is a useful way to identify the smartest entrepreneurs in the room–those who understand that their choices are their own and could never be replicated by anyone else. They accept that there is no standardized path for getting from A to B.

While it’s important to trust in your own direction, pretending like every decision you’ve made has been the optimal choice and that others might follow your exact path, is ego at its finest.

The belief that your route and your decisions were the only possible combination to get to where you are today is just not true. At best, it’s a foolish narrative we tell ourselves that takes the concept of fate too far. At worst, it’s pure arrogance. The concept of euthymia is only relevant at an individual level.

The likelihood that anyone has made the correct decision every step of the way–or that there is even a “right” decision to begin with–is an impossibility. Each one of us, including the most successful, have made the wrong move at certain points in time. And that’s okay. Some decisions carry greater weight than others, obviously you want to avoid the fatal errors. But more often than not, it’s about what you do next. What’s your next move? How can you use this decision as leverage to get closer to where you want to be and better yourself?

Success, as defined by you, is far more about resourcefulness than a checklist of prescribed actions.

There are dozens of ways to get to any single point. What’s important is your strategy for dealing with obstacles and learning from failures, not your attempts to replicate someone else’s career or life progression. The likelihood of the latter working is infinitely small and would require far more energy in attempts to exert control over random events.

The more productive route is to harness the energy from random encounters, breaks, and obstacles that are unique to your own life, and turn them into momentum.

There are routes to success that are nonrandom, but few, very few people have the mental stamina to follow them.
— Nassim Taleb

This is not to say that you shouldn’t learn from the mistakes and lessons others have faced, whenever possible. But to a much greater extent, the course of your life will be determined by your resourcefulness and willingness to learn when you come up short. Sustainable success is built by having skin in the game–as Taleb advocates–and learning as you go.

Advice to follow a template of decisions should be approached with caution. The individual path and environment that worked for someone else, no matter how successful, is irrelevant to your current position.

You will never be able to replicate the lives of the entrepreneurs that you admire. But you can examine the systems and mental models that give them their competitive advantage. This is where you’ll find the truly valuable lessons that you can apply to your own life, direction, and decision making.

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