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.

A Quitter's Guide to the Galaxy

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

There are those who pride themselves on persistence, regardless of the cost. And there are serial quitters who seem incapable of sustaining a single effort. Somewhere in the middle is a delicate balance of knowing when to keep going and when to quit. This balance allows you to dedicate your limited energy to the things that matter most.

As far as big decisions go, no decade seems to demand more or carry such monumental consequences as that of your 20s. Part of this is born out of naiveté in terms of experience — fewer years equals a shallower perspective and an inflated sense of self-importance. But this mindset also holds some validity in that it’s setting the trajectory for your later years, which is why quitting is such a valuable skill.

The importance of quitting grows in proportion to the number of new things you explore.

The trouble is that there is rarely ever a clear-cut “right” and “wrong” decision. The vast majority of life plays out in a gray area. Although, I’ve found that by pursuing almost everything that has piqued my interest throughout my 20s, I’ve been able to develop my own strategy to navigate this perpetual in-between and make more effective decisions.

Whenever I encounter a moment of self doubt or the urge to quit, I ask myself, do I feel like quitting because this is difficult? Or do I feel like quitting because it contradicts my character, values, or priorities?

Everything I’ve stuck with, despite the urge to quit because it was purely difficulty or challenged the confines of my comfort zone — new careers, meaningful relationships, deep personal interests — has always been worth it.But I must often first work my way through an initial period of insecurity to discover what’s sustainable, then I allow the power of compound interest to run its course.

Everything I’ve quit because it was in contrast to my character, values, or priorities has always proven, over time, to be the best available decision. This includes jobs that have run their course, relationships that lack reciprocity, undergrad majors that have bored me to tears, organizations that demand blind obedience, and even hobbies that I haven’t been all in on.

In other words, whenever I’ve doubled down and completely committed to the things that truly matter to me, they’ve paid significant dividends. Whenever I’ve cut ties with the things I’m supposed to want or that have made me question my own value system, it has allowed me to better allocate energy elsewhere.

The only disclaimer is that it’s often more difficult than simply asking yourself where the desire to quit is coming from. Most of us are in the habit of reacting to initial emotions and rationalizing our subsequent decisions beyond all recognition. To improve your decision making, you need to examine your true motivations, which demands a level of mindfulness and introspection.

Don’t take everything you feel at face value.

If you start a new job and feel like quitting, is it because you’re feeling insecure, overwhelmed, and haven’t given yourself enough time to learn? Or is it because the culture isn’t a great fit, you don’t enjoy the work, or you were misled in the interview process?

It demands greater courage to act independently and in your own best interest, than it does to sit back and allow inertia to take you down the path of least resistance. It’s easy to grow comfortable with current circumstances. That’s what makes quitting so difficult — by definition, it is change. But being able to quit something you’re not invested in is the mark of a self-sufficient mind.

If you invest more in the things that resonate with you and bail on the things that don’t, you’ll begin to develop a stronger sense of self and identity. This is the only sustainable source of gratitude in life — an awareness of what matters most to you and the persistence to adapt and see it through.

You can’t sustain something that’s in fundamental opposition to you and your priorities and expect to come out better for it.

“You always have three choices: You can change it, you can accept it, or you can leave it.”

— Naval Ravikant

Struggling to Find Direction in Life? Try This

Few things cause more angst in your 20s than struggling to come to terms with what you want out of life. But the best insight often reveals itself the moment you accept that you cannot be anything you want. In a world that loves empty sentiments and the delusional advice that you will be great at whatever you set your mind to, it’s an empowering realization.

I recently received a LinkedIn request from someone fresh out of college whose headline read: “Experienced Project Manager, Thoughtful Leader, Aspiring Musician and World Traveler.” My immediate impulse was to send out the word that, at long last, we’ve found the next Leonardo da Vinci. But empathy set in soon after, as I realized I was this exact person for most of the past decade.

When you trick yourself into believing you can be anything it often leads to paralysis. You become unwilling to make a single move out of fear of closing the door on a potentially rewarding alternative. But the reality is that many directions in life are mutually exclusive. Only once you check your inflated sense of self, are you free to focus on a single direction and begin creating momentum.

“Picking a lane isn’t limiting. It’s the first act of empowerment.”

— Ryan Holiday

To say I struggled to determine what to dedicate my time to during most of my 20s would be an understatement. It wasn’t that I had a shortage of interests, but the opposite–I felt like I had far too many. I wanted to be everything and as a result ended up unable to commit to anything. I convinced myself that I could balance dozens of unrelated goals. But meaningful progress proved impossible because I was unwilling to prioritize.

As I came to this realization, I discovered a thought exercise from Warren Buffett which he refers to as his “not to do” list. Rather than approaching my lack of direction and focus in the same way that I had for years, Buffett uses inversion to reframe the problem. And for me, this made a world of difference. It was only after I used this model that I was able to refocus and commit to the right things.

Here’s how to do it:

1) Write down your top 25 aspirations

List out 25 things that you want out of your life. 25 is general rule of thumb, go crazy. No matter how ridiculous you think they might be, get them on the page. My original list was all over the place and included things like publish a book, become a travel photographer, join/start a forward-thinking technology company, study Stoicism, and live near the mountains. Side note: There were far more ridiculous goals, but I’ve omitted those to avoid public humiliation.

2) Circle your top five

Ask yourself, which five aspirations are essential to having a good life. Which can you not live without? Which leverage your natural talents and allow you pursue more of what you enjoy? Remember, most of these are aspirations and goals for a reason. You’ll have to put in years of dedication and hard work to achieve them. Figure out which include a process you’re able to immerse yourself in and sustain for indefinite periods of time, because that’s what it takes.

There are certain goals that you should be able to cross off with relative ease, while others might require additional soul searching. “Become a travel photographer” was an easy one for me. That’s a dismal idea for someone who is average at photography and has no natural curiosity to further my skills in this area. All it took was a simple reminder to look beyond the romanticized end result and consider the process involved.

3) Avoid the other 20 at all costs

Once you’ve narrowed it down to your top five, bury the other 20. Buffett refers to these as goals to ‘avoid at all costs.’ They’re particularly dangerous because as long as you allow them to, they’ll linger in the back of your mind, distracting you from making progress where it matters. This can be difficult to come to terms with, but it’s essential if you want to contribute your best work to the world. You only have a small window of opportunity. Your focus must be dialed in to your top five if you have any hopes of accomplishing them.

This exercise demands a deep level of honesty and introspection, but can be done in a single afternoon if you’re dialed in. Don’t get too caught up in the specifics, you can adapt it however you see fit. But no matter how you approach the exercise, it proves to be one of the most valuable frameworks to help you negotiate your priorities and reflect on life’s more difficult decision.

My personal approach is to use the top five for larger aspirations which encompass dozens of smaller goals. One example that made my final list is publishing a book. I’ve broken this down further into its individual components, which I view as necessary to the success of the greater objective. These include growing my newsletter to 10,000 subscribers, writing shorter articles that cover a range of subjects to see which gain the most traction, and partnering with online publications that match my style to generate additional exposure.

There’s great value in using your 20s to try as many new things as possible and allowing your work to teach you as you go. In this trial by fire, you often learn as much about what’s worth sticking out by discovering what you don’t enjoy and what you’re not good at.

But you have to be realistic. 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.

Remind yourself that you don’t have to be everything. There will be things you suck at, and that’s okay. The only true responsibility you have in this life is to give something back to the world based on what resonates with you as an individual.

7 Lessons from Life as a Product Manager

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

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

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

1. Develop a multidisciplinary approach

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

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

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

2. Establish three skills in the top 25%

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

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

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

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

— Scott Adams

3. Manage product, not people

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

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

4. Help your team answer their own questions

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

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

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

5. Consider second and third-order consequences

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

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

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

6. Value feedback over intuition

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

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

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

— Jake Knapp + John Zeratsky

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

7. Be open with your failures

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

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

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

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.

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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.