Learn without Limits
How embracing uncertainty will revive your love for learning
By Damodar Roe
What is The Purpose of Education?
Have you ever have an experience in school where it felt like learning had been replaced by nitpicking? Have you ever felt like many of the classes you had to take were totally irrelevant for the rest of your life? Whether it was making sure you memorized the right facts to pass an exam, or taking a class simply because it was required—it can start to feel like the real purpose of education gets lost in the details, reducing it to a series of hoops you have to jump through to get a prize.
But now, imagine the modern education system becoming a person, and traveling back in time to have a conversation with the legendary Greek philosopher, Socrates. Together, they explore one of life’s most essential questions:
What is the purpose of education? What is the purpose of knowledge?
Modern education personified might say:
“The purpose of education is to achieve financial success and be the best.”
But Socrates might reply something like this:
“A stable job offers security, but are money and status really the only purpose of education? If so, then everyone would be pressured to become a lawyer, a doctor, or whatever other profession has the highest income and social regard. But just imagine if every animal aspired to be a lion. Wouldn’t they be giving up their natural roles just to look good in the eyes of others? Similarly, it’s natural for every individual to have a different role in society, according to his own abilities. The purpose of education is to help you discover your own calling, and not to become a perfect version of someone else.
The purpose of education might sound like a theoretical subject. But at each moment, life is challenging you to make decisions. You can only answer by the choices you make. Without first knowing who you are, and what you’re meant to do, how will you make wise choices? I say that education is a lifelong process, and it’s meant to support the individual to live an authentic and virtuous life. Wealth and status are also important, but they should only take a supportive role to the pursuit of truth and integrity.”
We can’t be sure exactly what Socrates would say. But let’s get practical. What would you say is the purpose of your education? If you ever wish you had an easier time thinking outside the box, asking questions, facing the possibility of failure, and finishing what you start, it’s time to reconsider your idea of what education means. In this chapter, we will explore how you can reclaim a deeper, more meaningful approach to learning that is based on a deep appreciation of your own nature and purpose, and which thrives on imperfect, but continual movement forward.
Know Yourself
The foundation for all forms of education is understanding of your own nature and life purpose. Without this, success alone doesn’t necessarily lead to knowing who you are, and without that, whatever you achieve will feel empty. You find yourself chasing after the approval of other people to fill the void, trying to embody the image of perfection, whatever that might be. But when you lose yourself in the process, it raises a crucial question: how do you know who you are? On one hand, there’s nothing more natural than assuming you know who you are. But on the other hand, what happens when someone asks you directly, “who are you?” It can trigger feelings of awkwardness, confusion, and insecurity. Why is that? Well, first of all, there are so many different elements to who you are — from your career, roles, affiliations, and experiences, to your beliefs. It’s hard to choose which elements to define yourself with. How do you know which ones are masks and which ones are authentic? Even if you know some of the answers, the fear of judgment can hold you back frombeing yourself. So while you might think you should be able to clearly articulate who you are, actually trying can bring you to a counterintuitive realization: you might not even fully know yourself.
The missing link that will give you confidence in who you are is a strong sense of purpose. Purpose gives your life a focal point, helping you to organize the many elements of your identity into something coherent and meaningful. When you know what drives you at a foundational level, all the complexities of your identity start to fall into place. Your career, relationship roles, and beliefs aren’t just scattered pieces; they become part of a bigger picture guided by your sense of purpose. It’s this clarity of purpose that allows you to confidently answer the question “who are you” with more than just a list of tentative possibilities—you can answer with conviction about what you stand for and why it matters.
Of course, when you begin to ask yourself deep questions like, “Who am I?” or “What is my purpose?” you might not have a lot of certainty about your answers, and this can feel unsettling. At the same time, as counterintuitive as it is, acknowledging what you don’t know is the first step towards figuring it out. It opens up new windows for exploration and opportunity. You can consider lots of different possibilities before you have to narrow them down. Therefore, keep asking yourself meaningful questions like, ‘What am I good at? What difference do I want to make in the world? What do I really want?’ By giving time and attention to these kinds of questions, your understanding will evolve over time.
Whatever answers you come up with to the big questions of life, you need to put them to the test. Otherwise, you can think very highly or very lowly of yourself, but it’s all just theoretical. For this reason, you can’t fully know yourself without taking action, trying new things, and facing challenging situations. Each new experience, whether it seems to be a success or a failure, reveals something deeper about your nature. Sometimes it’s a character flaw you need to work on. Sometimes it’s a strength you never knew you had. But most importantly, with each experience you will gain some inner sense about whether what you’re doing is closer or farther away from what you ultimately want to do. You only gain these insights through hands-on, practical experience.
Knowing who you are isn’t about being perfect or having all the answers. It’s not about impulsively doing whatever you feel like. It’s something you discover by facing challenges and uncertainty with courage. Every experience—good or bad—becomes an opportunity to grow and align with what truly matters to you. The key is to remember that you can’t control everything, but you can control how you respond. Failures, uncertainty, and change provide opportunities for growth. Admitting what you don’t know, asking deeper questions, and learning from others takes humility, but it also empowers in your uniquely human role of finding meaning in the universe. Self-knowledge is an elusive treasure, but it comes looking for you when you stand up to face the challenges of life with purpose and courage. Just like a job sustains you financially, a strong sense of purpose sustains you spiritually, transforming even the most difficult moments into stepping stones toward deeper fulfillment and satisfaction.
In the meantime, you don’t need perfect certainty to develop a sense of purpose. Just like you can use a placeholder when you can’t think of the exact word you want in a sentence, you can adopt different responsibilities to fill in the blanks of doubt and uncertainty. These responsibilities will act like a bridge that gradually connects you to more and more confidence about your true calling. So start today by asking yourself deep questions and finding something you can take more responsibility for. It might be your schooling, job, or community service. But just get started investing more time and energy into something that’s actually important to you. Your life purpose will always involve other people, but no one else can ever decide what it is for you. Even though school might be an important part of your journey, you can’t depend on the institution to give you a sense of purpose in life. It’s something you have to discover inside yourself through reflection and taking action. Therefore, stop waiting for the “perfect answer” to come to you, and instead, face the challenges of life.
Wisdom Begins with Wonder
Once I had a friend who was driven from a young age with a desire excel in school. He got straight As all the way through junior high because he was very good at memorizing answers. One day, he was accepted into a prestigious school and his family was ecstatic about it. The halls were lined with plaques and trophies of all the alumni and he dreamed of also having his name there one day.
But a lot of the work wasn’t about memorization anymore. Along with the immense pressure he put on himself, his family and teachers pushed him to rank just as highly as he did at the less advanced school. as he struggled to understand some subjects, he wanted to ask questions. But each time he thought about raising his hand, a voice in his head whispered, ‘What if they think you’re stupid?’ He decided to find the answers in the textbook, where there wasn’t the risk of being exposed, but even then he was having a hard time focusing. His grades were slipping fast and his family was not happy about it.
When he realized he couldn’t be a “perfect student” anymore, he didn’t see any point in continuing to try at all. It felt safer to give up completely and pretend not to care anymore. This way he could avoid the pain of trying his best but failing anyway. But unfortunately, he never questioned his own assumptions that he needed to seem to know all the answers already, and that asking questions was an admission of inadequacy. This pattern continued for decades, as he neglected to find a sense of purpose in life while doing the bare minimum with whatever responsibilities were required of him. Last I heard from him, he was heavily addicted to pornography and avoiding real women who were interested in him. Despite his dissatisfaction with his life, he was unwilling to do the hard work required to get his life together.
In our modern, perfectionistic culture, we often believe that competence is measured by knowing all the answers, rather than embracing the process of learning by continually asking better questions. My friend’s story show how this belief can lead to very unfortunate results on a personal level, but let’s also consider the potential risks on a international scale. In 2003, George Bush made the decision to invade Iraq. Despite many important considerations that were yet to be explored, the President pushed forward with the invasion. He was afraid that people would think he was weak if he didn’t do something decisive in the aftermath of the 9/11 terrorist attacks. So he disregarded information and voices that went against his desire, and fully committed to selling lies that Iraq had “weapons of mass destruction.” This decision that led to the unnecessary deaths of millions of people, and no weapons of mass destruction were ever found. It goes to show the dangers of pretending to know all the answers and rushing to action.
Socrates, on the other hand, spent his entire life asking questions. He made a point to profess his ignorance for the sake of keeping conversations open to all possibilities. In fact, when people told Socrates that an Oracle had declared him the wisest man in Athens, he didn’t believe it. He searched the entire city to find someone wiser than himself. But after questioning politicians, poets, craftsmen, and others, Socrates realized that his wisdom was only superior in one way. While others falsely believed or pretended they had all the answers, he was more than willing to admit what he didn’t know.
Embracing a mindset of curiosity can be a transformative experience for perfectionists. Instead of seeing uncertainty as a threat to our self-image, we can embrace it as an opportunity for discovery and growth. By remaining open to new information and perspectives, we can develop a resilience in the face of change and uncertainty. We can also avoid the embarrassing consequences that come from settling for superficial knowledge, jumping to conclusions, or egotistically pretending to know more than we actually do.
Socrates never produced a conclusive and systematic explanation of everything. But he is still admired to this day because he revolutionized the world of philosophy. He did this by surcharging the philosophical process with a spirit of relentless curiosity. The process of learning only begins after you give yourself permission to acknowledge what you don’t know and then ask questions. And who knows? Maybe other people are wondering the same things as you, but are also afraid to raise their hands. By taking the chance yourself, you might not be judged but appreciated.
Think outside the box
The drive to prove yourself is a good thing that leads to impressive achievements — like good grades or a successful career. But it can also turn into a golden cage when your underlying motive is to gain approval. The cost of seeking success according societal expectations is that you might never take the time to consider how much of it aligns with your own beliefs, values, and desires. When it’s time to follow your own path, the fear of being different can trap you, keeping you from spreading your wings when you most need to fly. Therefore, before you chase “perfection” or “success”, it’s important to ask yourself what these words mean to you personally. Are ideals that are aligned with your true self, or are they borrowed from a desire to fit in and feel “good enough”?
Once my friend Matt traveled to Taiwan to film part of a documentary. The field producer of their crew was a great planner and had every filming location, interview, and shot predefined. Matt wanted to fit in and meet expectations, so he found comfort in the structure and worked hard to keep everything on track. If they followed the plan that would ensure the project’s success. But as they navigated unfamiliar streets and language barriers, the plan began to unravel. Matt was working day and night to stick to the original vision, but the travel and long hours were taking a toll on his health. Another producer eventually contacted the director with a more flexible plan, and the project finished on time. Matt was surprised when the director praised his colleague’s ability to think outside the box.
Matt’s story shows how perfectionists rigidly cling to rules and expectations because they see them as a path to gain approval from others. But the real world doesn’t always conform to our expectations, and individuals in every group have their own relationship with the rules. Following them is usually helpful, but it doesn’t guarantee acceptance in the crew or success on the project.
While perfectionism is based on fear, authenticity encourages us to act from a place of inner alignment. Here are some of the essential differences between perfectionism and authenticity:
Signs of Perfectionism:
You adopt popular values and try to excel at them out of an anxiety to fit in.
You place more importance on how tasks are perceived by others than what you learn from them yourself.
You place so much pressure on yourself that you compromise your own well-being.
Signs of Integrity:
You make decisions aligned with your core values, even if they aren’t popular.
You accept responsibility for tasks, even those you dislike, when they serve a larger purpose.
You are comfortable saying “no” to requests that don’t align with your priorities.
Socrates was an expert at noticing opinions disguised as facts. He took great personal risks in bringing assumptions to light, making no distinction whether those opinions were held by friends and neighbors, or powerful authorities in the government and military. He never assumed he was doing something wrong based on people’s reactions, even if they were visibly annoyed with him. Instead of making decisions out of fear of conflict or a desire to please others, he held himself and others to the same standards of rationality and the pursuit of moral goodness. By doing so, he was able to navigate life with boldness, free from neediness for external validation. You also have the right to consider different perspectives and choose for yourself how you want to see things. Some of the cultural values around you might be based on a solid moral compass that’s worth holding on to. But other ideas or practices might not be serving you anymore. To stay true to what’s personally important to you, it’s essential to have the courage to think outside the box, and risk unpopularity sometimes.
Do Your best, however imperfectly
When perfectionists are advised to relax their standards, they often ask, ‘Why would I strive for anything less than perfection? I don’t want to be lazy and complacent.’
To answer this question, it’s crucial to understand the difference between two things:
Expecting to get perfect results all the time.
Embracing the outcome of your best efforts, taking the circumstances into consideration.
Over 2,000 years ago, Cicero explained this distinction by using the analogy of archery. When you’re shooting arrows at a target, it’s best to aim for the bullseye. The target is there to give you feedback so you can adjust your throw. But it’s not possible to hit the bullseye every time, especially when you’re trying harder shots. The key is to measure your success by the effort you put in to the art, and how much you improve over time. When you define success in a way that focuses on what you can actually control, you’re always giving yourself a chance to succeed. You might come in 3rd place, but still feel proud of what you’ve done. In fact, you’re more likely to do well when you focus on the process instead of worrying too much about the result.
Doing your best doesn’t mean laziness or complacency. It means redefining what success in a way that acknowledges realistic limitations. It’s not about always being perfect or beating others, but becoming better than you were yesterday. If you treat results and status as the only things that matter, you risk discouraging yourself and burning out. Instead of overestimating yourself, set realistic goals and celebrate the small victories along the way. Acknowledge the progress you make and remind yourself that everyone starts as a beginner. Success doesn’t come from perfection, but from continually focusing on the next step, letting the results naturally follow from your consistent effort.
Fortune favors the bold
Once I had a friend in 10th grade named Jake. For some reason, he didn’t care at all about embarrassing himself in French class. While the rest of us were too nervous to get laughed at if we made a mistake — Jake just went for it. Every day, he’d raise his hand, mispronounce words, mix up sentences, and sure enough, people made fun of him. But he kept practicing, speaking up even when it was awkward, and by the end of the third year, he was actually speaking French pretty well. Years later, I found out that he ended up moving to Paris, where he met his wife. All of us who were too worried about looking dumb never got past “bonjour.” Jake, on the other hand, learned a second language and fell in love halfway across the world.
Successful people learn from their failures rather than trying to avoid them. Leonardo da Vinci, for example, designed intricate flying machines that were far too heavy to ever take off. Centuries later, Alexander Graham Bell built an experimental aircraft which flew for just seven minutes before crashing into the water. The Wright brothers, too, faced countless setbacks and crashes before achieving the first successful flight in 1903. These daring individuals didn’t see “failure” as a defining event or endpoint, but as a feedback mechanism, narrowing down the possible avenues to eventual success.
It’s true that perfection can be objectively measured in subjects like math, science, or logic. But even then, you don’t have to take it personally when things don’t work the way you hoped. For example, Thomas Edison didn’t invent the lightbulb on his first try. Rather, he famously said he found 10,000 ways that didn’t work, viewing each experiment as a step toward eventual success. And in most areas of life, what constitutes perfection is only a matter of opinion. Socrates made people question their assumptions about success, and even though he often left many philosophical conversations without a final answer, he inspired people to take a more thoughtful approach to life. When perfection is subjective, out of your immediate reach, or straight-up impossible, you’re faced with a choice: stay in your comfort zone and hardly grow at all, or embrace the possibility of failure, try anyway, and learn from your mistakes. Fortune favors the people who are bold enough to pursue their dreams even when the possibility of failure is part of the journey.
Finish important tasks
I’ve got to be honest—I’m face-deep writing this long article and it feels like I’m drowning. Despite a lot of time and effort I’ve put into it, I’m not sure how it will turn out. It’s that uncomfortable feeling when I find myself beginning major revisions and half-way through, doubting whether I’m actually making it better or worse. I’m worried that at the end of all this effort, the outcome won’t be worth keeping anyway.
Part of the struggle with writing—and really any kind of knowledge work—is that it forces you to think at a higher level than you’re capable of on the first attempt. You want your ideas to flow perfectly, but the reality is far more chaotic. Writing is messy, full of uncertainty, and packed with self-doubt. You’re reaching for clarity, but early drafts feel like you're drowning in information and options, unsure which direction is right. And that’s because, unlike simple tasks, knowledge work doesn’t come with a clear path. There’s no one there to tell you exactly which choice is correct, no definitive right or wrong—just an overwhelming flood of possibilities.
The truth is, it’s not possible to do high-level work without feeling that sense of drowning at some point. It’s part of the process and what makes breakthroughs possible. It’s in the discomfort, when you’re unsure and swimming in options, that real clarity starts to emerge from the blurriness. Each draft, each revision, refines your thinking. It’s messy, yes—but that’s how progress happens. The key is to keep going, to trust that the more you wrestle with the chaos, the closer you get to something meaningful.
As I push forward with this project, I’m inspired by the courage that Socrates showed when he completed the one thing that’s harder than anything else to finish: life itself. After years of challenging conventional wisdom and pushing people to think critically, Socrates was tried and convicted for corrupting the youth and denying the gods of Athens. Offered the choice between the death sentence or giving up his teachings, Socrates chose death rather than compromising his philosophical integrity. In this way, he exemplified his ultimate teaching and became a legend that has inspired countless people, from Ancient Greece to the French Revolution, to today.
It takes courage to finish what you start. The more ambitious the project, the more complicated it gets and the more likely it is to remain incomplete. In fact, I have tons of unfinished writings just sitting around because I struggle with perfectionism myself. I begin working on a new idea with excitement, but at some point, I’m faced with the uncertainty and resistance I feel to do the work required to finish.
You have to be willing to accept the vulnerability of putting a lot of effort into something without knowing for sure how it will come out in the end. You have to be willing to trust the process and keep moving when the path is dark, uncertain, and you can only afford to take baby steps. It’s a fight with a formidable adversary, where you can’t predict the outcome upfront, and there are many moments when you feel close to defeat. Courage is an amazing paradox contained in one term. You have to have the desire to win along with the willingness to risk losing.
Perfectionism makes us think that we must get everything right, or else we’ve failed. This keeps us stuck in a golden cage where we try to be perfect in other people’s eyes, but we feel anxious and insecure on the inside. Your education, career, and relationships become about looking good rather than learning and growing as a person. Yet, if we look to the spirit of Socrates, we see a different path — one where meaning and growth come from the journey itself, and not from exuding perfection at every step. Finding yourself begins by facing uncertainty and moving forward anyway, not by pretending to have all the answers. Ultimately, you will find the there is one thing above all which empowers you to take this noble and Socratic path: the courage to be imperfect.
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