If it comes as a constant surprise each and every time something

Hear the words of the modern Stoic, Ryan Holiday, who speaks with clarity about the path of struggle and achievement: “If it comes as a constant surprise each and every time something unexpected occurs, you're not only going to be miserable whenever you attempt something big, you're going to have a much harder time accepting it and moving on to attempts two, three, and four.” These words are carved from the same stone as the wisdom of the ancients, for they remind us that adversity is not an accident but a certainty, and that the wise do not stumble at its arrival, but prepare their hearts to endure.

The meaning is this: whenever we attempt something great, we will face obstacles, setbacks, and defeats. To be surprised by this truth, to expect the road to be smooth, is to condemn oneself to misery. But to embrace the expectation of the unexpected is to be free. For then, when difficulties arise, they do not strike us as betrayal, but as part of the natural order. In this way, we are not paralyzed by them, but strengthened, ready to rise again for the second, third, or even fourth attempt.

The ancients themselves taught this wisdom. The Stoic philosopher Epictetus said: “When you embark on a voyage, prepare your mind not only for fair weather but for storms.” He knew that surprise at misfortune is the mark of the untrained soul. The sailor who is shocked by waves should never have left the harbor; the warrior who is stunned by arrows should never have walked to battle. Holiday echoes this eternal truth: those who undertake anything great must expect hardship, and in expecting it, they rob it of its power to shock.

Consider the story of Thomas Edison, who sought to create the electric light. He failed not once, not ten times, but thousands. If he had been shocked each time at the “unexpected” failure, his spirit would have collapsed long before success arrived. But Edison saw each setback not as betrayal, but as part of the process. “I have not failed,” he said, “I have found ten thousand ways that do not work.” Because he did not waste his soul on surprise, he endured, and in enduring, he triumphed. His strength was not brilliance alone, but resilience born of expectation.

History also gives us the tale of Abraham Lincoln, who lost election after election, endured personal tragedy, and stumbled many times in public life. Yet he was not undone by these misfortunes. He did not greet each failure as something unthinkable, but as a stepping-stone toward growth. In time, because he endured through repeated attempts, he rose to the presidency and carried his nation through its darkest hour. His greatness was not in never falling, but in never being destroyed by the fall.

The lesson is clear: the one who seeks greatness must make peace with hardship. If you are astonished each time you fall, you will soon lose the will to rise. But if you expect the fall, you will rise more swiftly, and each rise will make you stronger. Life is not a path of unbroken victories; it is a series of defeats met with resilience, until at last victory is earned. Surprise is the enemy of endurance; expectation is the ally of perseverance.

Practical actions must follow. When you begin any endeavor, remind yourself: “Obstacles will come, and I will not be surprised.” When you face failure, record what you have learned, so that the next attempt carries the wisdom of the last. Prepare your spirit daily, through meditation, reflection, and discipline, to expect difficulty as part of the natural order. Teach yourself to see setbacks not as insults, but as teachers. In this way, you will have the courage not only to try once, but to rise again for the second, the third, the fourth attempt—and beyond.

For remember this eternal truth: strength is not found in the first success, but in the refusal to be broken by failure. The world belongs not to those who are shocked by obstacles, but to those who expect them and keep walking forward. As Holiday teaches, prepare your heart for hardship, and you will find within yourself a power that cannot be conquered.