“Life is not about one obstacle, but many.” Author Ryan Holiday writes in his book, The Obstacle is the Way. Holiday looks at life as a series of challenges and views our success as being measured by how we respond to the road blocks and obstacles we face along our journey. In this view, the measure of success is not wealth, or career titles, or any of the other myriad of ideas of success we have gained from popular media, but instead, it is how well you adapt and adjust along the way. Popular visions of success may be byproducts of overcoming obstacles, but rarely are they a true measure of our success as Holiday sees it. Successfully navigating a sea of obstacles and challenges should be our focus because we never reach a place where difficulties subside and life becomes simple. Our attention should constantly be on self-improvement and self-reflection to guide us through the difficult times. Holiday writes,
“We will overcome every obstacle,—and there will be many in life—until we get there. Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.”
By expecting that life will not be easy and that we will not reach a place of simplicity, we can prepare ourselves for what we will actually face while we grow. Aligning our actions to match our expectations and directing actions toward obstacles will help us reach success. We will not be judging ourselves against a ruler built by someone else, but instead we will judge ourselves based measures of our own efforts. This measure will be calibrated by the impediments, adversity, and luck of our own lives. Our actions build to become the rings on the ladder lifting us further against our ruler.
To continue our path requires constant focus and motivation. The perseverance that Holiday discusses comes after we have studied our challenges and identified the best path forward. The path is rarely the path of least resistance, but rather a path filled with questions that will challenge, push back, and ultimately help us grow as we learn and climb. The quick energy needed to surge forward with new ideas and perspectives can only come if we have a strong level of endurance to support our efforts over the long haul.
Author Ryan Holiday provides an in depth exploration of human will in his book, The Obstacle is the Way. Giving us an in depth view, Holiday writes, “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.” Holiday sees our will as something deeper than what we typically understand as will power, and by building a more profound meaning of will, he gives us a new dimension of fortitude and strength. This vision that can be cultivated and built into who we are, the goals we have, and how we press forward to overcome the obstacles we face.
Will is our ability to relentlessly approach the world in a way where we can benefit and grow. Holidays continues in his writing to explain that will is not just the idea of perseverance to win, but a deeper strength of mind that stays with us even when we have lost everything else. Our mind is the only thing we can ever have the possibility of controlling, and our will is derived from our habits of thinking, our actions, and our perceptions. It is our ability to take a situation in which action appears impossible and in which all seems lost, and find a way to move forward in a positive direction. Will builds from our ability to recognize our situation, choose our reaction, and continue to pursue our goals.
Holiday explains that typical forms and ideas of will fall short of the view he puts forth. Rather than thinking of will as the degree to which we want something, it is better to see will as our inner strength that does not waver when we face an obstacle. Holiday explains that this type of will is stronger than the will that pushes us to act and charge forward, because a will built on calmness and inner power will guide us ahead evenly, regardless of whether the world is surging around us or falling down.
There are three parts to overcoming our obstacles that Ryan Holiday lays out in his book The Obstacle is the Way. In a single short quote he gives us a quick roadmap for developing ourselves and facing our challenges.
“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.”
His approach breaks down the barriers that we face and looks at each part of an obstacle to help us see how we can take small steps to face what limits us. It also builds a framework for looking at our problems that can become a committed part of who we are, and a habit that we adopt for thinking about the world. The process is not intended to be a tool that we pull out when needed for a specific job, but rather a mental scaffolding built around our decision making and thought processes.
I think it is very fitting that Holiday calls this process a discipline. It requires self-awareness and self-control to stand back and methodically pick through our obstacles to find creative solutions to bridge the gap between where we are and the success we desire. Even once we have imagined a creative solution we must put forth great effort for that solution to manifest in the real world. Holiday is honest in the quote about about the challenges of applying this discipline. Each of his three steps require taking action that runs counter to the easy path away from our obstacles. Facing and using our obstacles to build new opportunity requires not just determination and strong will-power on our end, but the ability to overcome the negative voices in our head which tell us to turn away from our challenges in search of an easier rout. It requires that we change the way we think about that which limits us, and demands that we find new solutions to the problems we face.
Our new perceptions and novel solutions don’t just help us overcome any single obstacle, but they literally change who we are. The growth we find on our path results from our new ways of looking at the world, and from the practice of building greater will-power to reach our goals. The solutions we develop become a playbook for facing obstacles, and serve as proof of our accomplishments.