Focus

The Essential Question for Every Entrepreneur

Sometimes the best question you can ask yourself is, "Am I building something I would want?"

As an entrepreneur, this should precede every other question. If the answer is no, there's a fundamental disconnect. You're going to have a difficult time sustaining the necessary effort over the long run. Momentum comes from engagement.

The real secret to product development is creating something that you would want to use.

I evaluate every new product, opportunity, and startup that I consider pursuing with this filter. Success demands years of hard work. If I'm not engaged or I don't find purpose in the work, it's a nonstarter. Otherwise, I know I'll be at a disadvantage facing off against someone solving for their own point of need.

I use the same filter when considering partnerships or investments. I look for founders and teams who are building things they've demonstrated a deep interest in for years.

Consider those who have sustained success over decades–Bill Gates, Sergey Brin, Larry Page, J.K. Rowling, Oprah Winfrey, Bob Dylan, Walt Disney, Albert Einstein, Thomas Edison, Benjamin Franklin. Each person created things they wanted in the world around them. They pursued fields of work they found engaging and compelled to contribute to. That's what kept them going.

And that's the difference between people who burn out or get lucky once and people who sustain success–regardless of industry.

But despite this simple truth, many entrepreneurs insist on building things or addressing problems that they have no real interest in themselves. Most often this is due to inexperience or a lack of integrity.

Inexperience reveals itself in early entrepreneurs who believe that their first decent idea is their only shot at making it. Instead of practicing patience, they force the issue.

But the real currency of successful startups is in execution. You can have the best idea in the world, but if it doesn't resonate with you as an individual, it's going to be difficult to get through the necessary struggles. Creating something from nothing is hard work.

The notion that ideas are a multiplier of execution is empowering. It frees you to be more selective about the startups and projects you get involved with. Instead of looking for a single brilliant idea, look for a strong idea that resonates with you and that you are uniquely suited to bring to life.

There’s no shortage of ideas out there. You might as well take on something you're aligned with and invested in so you feel like you're working towards something worthwhile.

Entrepreneurs with integrity don't involve themselves in projects that aren't aligned with their values and interests. They don't allow themselves to be distracted–even by the allure of easy money. And they don't allow envy to dictate their direction in life.

If you're building something you wouldn't actually want and that you're not proud of, you're sacrificing integrity. And integrity is far harder to come by than money, recognition, or an inflated sense of self-importance. Never mind the ensuing search for lost time.

Your goal in life is to find out the people who need you the most, to find out the business that needs you the most, to find the project and the art that needs you the most. There is something out there just for you. What you don’t want to do is be building checklists and decision frameworks built on what other people are doing. You’re never going to be that. You’ll never be good at being somebody else.
— Naval Ravikant

The world needs more people creating real value–building things that resonate with them and pursuing work that reflects their deepest interests and principles. That's what it takes to build something great and sustain the effort that it takes to overcome inevitable obstacles.

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 pays dividends. The power of small, calculated decisions, habits, and behaviors grows exponentially over time.

But first, you must find alignment.

Are you building something because you think someone else might want it?

Or are you creating something that you would actually want to use? This reflects a deeper interest and resilience. It's an immediate advantage that puts you in a far better position to succeed. This is where you want to be.

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.

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 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.

Life Is a Single Player Game, Measure Accordingly

Life Is a Single Player Game, Measure Accordingly

“I wish I only cared about the things that everyone else seems to.” I’ve had this conversation with my closest friends dozens of times. It was especially common in the less triumphant moments of our early 20s. But every now and then, when paths are at their most ambiguous, this thought resurfaces.