A monthly newsletter on mastery and creativity Subscribe


Learn The Timeless Art of Turning Obstacles Into Opportunities

At the start of my self-education journey, I came across an interview of a young writer who was both smart and inspiring. His story of dropping out of college at 19, apprenticing under a great author, and getting a six-figure book deal was something unheard of. When I went to his blog, the first post I read was about why we need to study philosophy. Looking at my bookshelf, I realized I didn’t have any books of that nature.

This is how Meditations by Marcus Aurelius became my bible, and in turn, changed my life forever. That is not an understatement.

Ryan Holiday, author of The Obstacle Is The Way, writes about a timeless spiritual practice of flipping obstacles into opportunities. In short, learning from failure, adversity, uncertainty, and realizing that whatever obstacle is in front of us can become fuel to our endeavors. Even the most severe adversity can become an advantage, only if you choose to see it that way. The book isn’t about Stoicism per say, but about histories’ icons using Stoic principles to overcome hardship and roadblocks. This practice isn’t just for the greats—it’s for everyone.

The one invaluable lesson that we don’t learn in traditional education is flipping failure. School, for the most part, is all about avoiding failure—avoiding being laughed at, avoiding the F. We may come across it from time to time depending on who our teachers are, but it isn’t a staple in education. We don’t spend enough time teaching upcoming generations about managing their perception, realizing that what they’re feeling is based on what they tell themselves. We are failing to teach some of the most important lessons and practices in succeeding and thriving as a human being. Which is why, in the words of Seneca, “We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application—not far far-fetched or archaic expressions or extravagant metaphors and figures of speech—and learn them so well that words become works.”

This art of seeing objectively, keeping a cool head, and realizing that nothing can truly hurt us is the backbone to success and accomplishing great feats. You will get hurt. You will be lied to, cheated, bullied, taken advantage, undervalued, forgotten, and much more. Someone will cut you off on the road and not care. Your car will break down, the pipe in your house will explode, your bank will mess something up. How will you deal with it? Emotionally? Throwing a rant, posting worthless statuses on Facebook? Or will you save yourself the stress and energy and focus on a more mindful solution instead? All of this is up to us—how we respond, how we act, and how we persist. Holiday does a masterful job of making this book simple but significant; succinct but deeply insightful and practical.

There are two quotes that are the lifeblood of this book, a quote from the Roman Emperor Marcus Aurelius, two of my favorite quotes indeed:

“Objective judgement, now at this very moment.
Unselfish action, now at this very moment.
Willing acceptance—now at this very moment—of all external events.
That’s all you need.”

“The impediment to action advances action. What stands in the way becomes the way.”

Is anything more boom?

Whenever I can catch myself in the vice of entitlement and boiled emotions, I repeat these quotes to myself, among many others. It’s a practice that allows me to settle my emotions, to focus on why I specifically feel this way, and more importantly, what to do next. It helps me live better.

Obstacles are indeed part of life. Call it God or fate or karma, there will be moments of turbulence in our lives, many of them unexpected and happening at the wrong times. But these moments can strengthen or weaken us, and that all depends on how we respond to it. Holiday shares the fundamentals of how we deal with obstacles:

“Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty. It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

What’s fascinating is this practice and mindset was written about thousands of years ago. As Holiday says:

“It turns out that the wisdom of that short passage from Marcus Aurelius can be found in others as well, men and women who followed it like he did. In fact, it is a remarkable constant down through the ages.

One can trace the thread from those days in the decline and fall of the Roman Empire to the creative outpouring of the Renaissance to the breakthroughs of the Enlightenment. It’s seen starkly in the pioneer spirit of the American West, the perseverance of the Union cause during the Civil War, and in the bustle of the Industrial Revolution. It appeared again in the bravery of the leaders of the civil rights movement and stood tall int he prison camps of Vietnam. And today it surges in the DNA of the entrepreneurs of Silicon Valley.”

I wrote about how Stoicism is the ideal philosophical system to embrace for life and work.

As mentioned before, the book is divided into three main parts: perception, action, and will. Each element is worth deeply studying. If you study any psychology, a lot of this should sound familiar. Let’s start with the first:

“WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean. Our perception can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives. It takes skill and discipline to bat away the pests of bad perception, to separate reliable signals from deceptive ones, to filter our prejudice, expectation, and fear. But it’s worth it, for what’s left is truth. While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredibly advantage for us in the fight against obstacles.”

“WHAT IS ACTION? Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals. Action requires courage, not brashness—creative application and not brute force. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action. Nothing else—not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.”

“WHAT IS WILL? Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared. Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. But that needs to be cultivated. We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness in dark times. Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength. Try ‘God willing’ over the ‘will to win’ or ‘willing it into existence,’ for even those attributes can be broken. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.”

Like anything worthwhile, it’s a practice. When we recognize adversity or a failure, we need to pause, think over these principles, and then act accordingly. And when I say a practice I mean every possible moment in your life—standing on the DMV line, waiting in traffic, dealing with a rude customer. These are small pockets of opportunity to exercise your philosophy, to see how it helps you or how it changes your attitude.

A good place to start is failure, something that we deal with on a regular basis.

We should listen to our failures. Holiday says:

“It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen.

Lessons come hard only if you’re deaf to them. Don’t be. Being able to see and understand the world this way is part and parcel of overturning obstacles. Here, a negative becomes a positive. We turn what would otherwise be disappointment into opportunity. Failure shows us the way—by showing us what isn’t the way.”

To continue this train of thought, Holiday explains why we become so easily emotional, and why outward appearances must be challenged:

“Outward appearances are deceptive. What’s within them, beneath them, is what matters.

We can learn to perceive things differently, to cut through the illusions that others believe or fear. We can stop seeing the ‘problems’ in front of us as problems. We can learn to focus on what things really are.

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things. Unhelpful perception can invade our minds—that sacred place of reason, action and will—and throw off our compass.”

How easy it is to automatically act emotionally, as if that were our default setting. Someone cuts us off and we immediately flip them the finger and honk the horn, instead of saying, whatever, it happens.

The other day while playing basketball, I lost my cool. Losing my cool made me play stupid. And playing stupid made me furious. But I didn’t take it out on myself, I took it out on my opponent, which of course almost broke out into a fist fight. After calming down, I realized how foolish I behaved, and how easily I lost control of my perception. My actions reflected weakness and entitlement. I let the opponent’s words get under my skin. The ride home I felt angry at my opponent for playing the way he did. “Because he fouled me I started playing rough,” I would tell myself. But I realized how wrong I was for thinking that way. I was the perpetrator, not him. He didn’t make me mad, I made myself mad.

As Marcus Aurelius once said, “Today I escaped anxiety. Or no, I discarded it, because it was within me, in my own perceptions — not outside.” When I first came across that quote, it made me think about how I lead my life. How quickly I placed blame on external elements rather than investigate what’s going inside me—my thinking, my perception, my desires. As a student of Stoicism after all these years, the principles have helped me become a better person and lead a better life. It has humbled me, taught me to accept things that I cannot control, and to be attentive to the things that I am in full control of—my perception, action, and will. Failure, adversity, hardship, random hassles, assholes, are all part of life. Learning to deal with them in a positive, helpful way is a skill set worthy of learning and mastering. It defines who we become and what we’re capable of achieving. Ryan Holiday does a fantastic job taking the practices of Stoicism and revealing them in the behaviors and mindsets of history’s greats, as well as giving us a guidebook on overcoming our own obstacles.

Always remember that there is a solution to every problem. Along the way you may encounter a huge boulder obstructing your journey. Will you run away from it while cursing under your breathe? Or will you use this obstruction and learn something from it?