30 Lessons for Living at Your Best by 30

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

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

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

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

1. Get the essentials down first

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

2. Limit the number of do-overs

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

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

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

4. Create more, consume less

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

5. Life is a single player game

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

6. There is no substitute for true resourcefulness

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

7. Put in the self-work

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

8. Directions in life are mutually exclusive

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

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

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

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

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

11. Growth is nonlinear

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

12. Figure out what you can sustain indefinitely

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

13. Leverage compound interest

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

14. Physical endurance builds mental endurance

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

15. Lasting comfort is found by embracing discomfort

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

16. Stillness is the best lesson traveling will teach you

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

17. Get a dog

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

18. Read like your life depends on it

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

19. No one alive has all the right answers

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

20. General advice > specific advice

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

21. Avoid ideologies at all costs

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

22. Legacy is a mirage

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

23. “In victory, learn when to stop.”

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

24. Money matters

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

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

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

26. Moderation is king

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

27. Everyone is facing their own adversity

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

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

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

29. Build a philosophy of life that works for you

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

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

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

---

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

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

The Secret to Developing Thick Skin

If there’s a defining feature that sets apart smart creatives who are able to sustain themselves at a high level of performance, it’s thick skin. They’re persistent in their work and resilient to outside opinion and rejection. They’re able to put themselves out there, time and time again, and deliver. And while this might appear to be a natural talent, it’s far from it. It’s a skill that takes years to develop, and it begins with renegotiating expectations.

Many talented people struggle with this–entrepreneurs, artists, athletes, writers. While they might be brilliant in their work, when it comes to putting themselves out there, they end up demoralized or enraged by the slightest hint of criticism.

This becomes a downward spiral that throws off the entire creative process. Even if you are able to correct course, it’s an unnecessary distraction that disrupts your focus and pulls you away from more meaningful work.

Internal vs. External Expectations

To offset this and develop the thick skin required to put yourself out there, you must first differentiate between internal and external expectations, assigning each their proper weight. Internal expectations–the expectations you hold for yourself and your creative process–should always take precedence.

How your work is interpreted, received, or recognized, is beyond your immediate influence. It’s not that this is completely irrelevant, but it should matter far less because it’s an unreliable metric against which to measure yourself. The greater the importance you assign to external expectations, the more dependencies you introduce, and the higher the likelihood that you’ll end up pissed off, burned out, or distracted from the work that matters most.

Self-sufficiency is the path towards effectively managing expectations. In the opposite direction are dependencies–evidence of placing a premium on things you can’t affect.

When you prioritize the internal expectations you hold for yourself, you naturally develop the thick skin required to put yourself out there and consistently produce at a high level. Instead of seeking value in the recognition, you begin seeking value in the creative process itself. And this is the only sustainable path forward.

“The tranquility that comes when you stop caring what they say. Or think, or do. Only what you do.”

— Marcus Aurelius

Turn your attention back to what’s within your control. Put in the work. Focus on your craft. Create something that resonates with you. When you limit the external dependencies and surrounding noise, the more relaxed, concentrated, and effective you will be.

Feedback vs. Criticism

This is not to say that you shouldn’t seek feedback–which is critical to further developing and growing your skills. But feedback is to criticism as internal expectations are to external expectations.

In other words, the source is fundamentally different. Feedback comes from fellow creatives with skin in the game–the doers–who are taking risks by putting themselves and their work out there. These are the people whose opinions and judgment you should respect most. Criticism comes from insecure bystanders, shouting from a distance, who are incapable of creating anything meaningful of their own.

The intention behind feedback is also different. Criticism is often shallow and malicious in nature–focused on breaking you down. True feedback, from an inner circle whom you respect, is diligent, constructive, and objective. Its purpose is to challenge you to improve yourself and your craft.

In short, it’s about growth–which is a painstaking process in its own right–not about praise, telling you what you want to hear, or making things easier. It’s up to you to draw the line and determine who has your best interest in mind.

Create Your Own Momentum

When the inevitable criticism does come, use it as motivation and redirect that energy to create momentum of your own. With the right perspective, it becomes almost laughable.

Consider how much time and energy it took that person to criticize you–it consumed them. Nothing is a more sad, ineffective use of time–so let the childish tantrums end there. Refuse to allow yourself to be distracted by those without skin in the game. Their opinion holds no validity.

“An opportunist in life sees all hindrances as instruments for power. The reason is simple: negative energy that comes at you in some form is energy that can be turned around–to defeat an opponent and lift you up.”

— Robert Greene

For most talented, hardworking people, it’s just a matter of time. Which means you need to find the energy to keep going–to continue creating. The more dialed into yourself that you are, the less outside opinion should matter, and the more resilient you’ll be in your creative process. If you rely on external validation to keep you going, you’re going to have a short career.

A meaningful, fulfilling creative life demands hard work and tough decisions. Those who aren’t cut out for it will lean towards the path of least resistance, as defined by mindless consumption or shallow criticism. It’s easy to live that life.

If easy is what you want out of life, feel free to join the ranks of the unremarkable.

But those who make a difference show up, bust their ass, and sustain themselves at that level by having their expectations in order. They’re able to differentiate between internal and external expectations, valuing self-sufficiency over dependencies and feedback over criticism.

If you take the time to develop these skills–resilience, persistence, and mental toughness–outside opinion will lose its grip and you’ll be able to better carry your own momentum forward.

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

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

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

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

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

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

1) The Obstacle Is the Way — by Ryan Holiday

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

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

— Ryan Holiday

2) The Geometry of Wealth—by Brian Portnoy

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

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

— Brian Portnoy

3) The Bed of Procrustes — by Nassim Taleb

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

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

— Nassim Taleb

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

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

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

— Jeff Goins

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

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

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

— W. Timothy Gallwey

6) Tribe — by Sebastian Junger

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

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

— Sebastian Junger

The Myth of Losing Your Edge

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Your First Responsibility in Any Job

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

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

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

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

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

Levels:

1. Improve the lives of those on your immediate team

2. Elevate the quality of individual and group contributions

3. Establish and grow the culture

4. Advance the overall mission and purpose

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

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

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

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

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

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

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

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

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

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

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

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

The Difference Between Lifelong Learners and Pretenders

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

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

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

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

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

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

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

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

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

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

— Jacqueline Novogratz

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

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

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

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

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

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

Allow yourself to live and learn in the gray area.

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.