Why the Worst Product Managers Expect the Best

With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.

Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.

It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way. 

The best teams embrace imperfections beyond their control and create great products anyway.

The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.

Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.

Creativity and resilience

At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched. 

There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.

Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience. 

The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits. 

Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life. 

Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you. 

This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.

Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.

Opportunities for reflection

In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t. 

This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.

Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work. 

Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life. 

Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you. 

Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”

*This article was originally featured on Mind the Product.

Why Your First Bet Is Always Wrong

Why Your First Bet Is Always Wrong

Far too often we fixate on optimizing the first idea we come across. We become emotionally attached to a single design, storyline, or hypothesis. The end result is a slow crawl towards incremental improvement. Our work becomes a shell of how good it could be if it were allowed to evolve.

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.

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.

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.

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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