Personal Development

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 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 andantifragile 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.

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.