The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph

“They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions. Which is to say, we are never completely powerless.”

Holiday encourages the reader to recognize that they always have some personal agency that they can employ, no matter how hopeless the situation seems. Holiday advances his theme about the importance of recognizing and acting on what one can control in a challenging situation.

“Regardless of how much actual danger we’re in, stress puts us at the potential whim of our baser—fearful—instinctual reactions.”

Holiday explores The Importance of Emotional Regulation in shaping useful perceptions and actions. He argues that managing one’s stress is an important aspect of forming perceptions of a problem. He suggests that developing mental resilience or “nerve” helps to quell fear, which makes people more prone to rash decisions rather than strategically sound plans.

“The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind. Don’t let the negativity in, don’t let those emotions even get started. Just say, No, thank you. I can’t afford to panic.”

Holiday advises the reader to identify which of their emotional reactions could be more “harmful” than helpful and learn to tame these feelings. This ties in with his argument that emotions may be reactive, rather than a constructive approach to solving a problem.

“Objectivity means removing ‘you’—the subjective part—from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious […] With other people we can be objective.”

Holiday argues that evaluating a situation objectively can help people identify solutions more easily. He tells the reader that their personal involvement in a situation can obscure, rather than clarify, the issue, and advises them to try to be more objective about their problem.

“When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t.”

Holiday summarizes the Stoic approach to problems, which teaches people to focus only on the things that they can control in a situation. Holiday argues that for perceptions to inform helpful actions, one has to first assess what is in one’s power to change.

“The implications of our obstacle are theoretical—they exist in the past and the future. We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.”

Holiday contends that focusing on the small picture of the present, rather than constructing grand narratives or judgments about a situation which may or may not reflect reality, will encourage people to direct their energy toward practical actions. This argument ties in with his instruction to pragmatically observe, rather than emotionally perceive, one’s problems.

“In the surging counteroffensive, Eisenhower was able to see the tactical solution that had been in front of them the entire time: the Nazi strategy carried its own destruction within itself. Only then were the Allies able to see the opportunity inside the obstacle rather than simply the obstacle that threatened them.”

Holiday points to Eisenhower’s “tactical solution” to Blitzkrieg to demonstrate how shifting one’s perception can lead to problem-solving success. Rather than focusing on the Allies’ vulnerability to German maneuvers, Eisenhower insisted that the Germans’ strategy must be exploitable in some way.

“He had channeled his rage and pain into his training, and then later into his speeches, fueling it all with a kind of fierceness and power that could be neither matched nor resisted.”

Holiday lauds ancient Greek orator Demosthenes as an example of how a person can harness resentment into productive action. He encourages the reader to put their own problems into perspective against the obstacles Demosthenes faced, which included being orphaned, enduring an illness, and a speech disability.

“We may be able to articulate a problem, even potential solutions, but then weeks, months, or sometimes years later, the problem is still there.”

Holiday laments that many people can conceive of reasonable actions to take but lack the motivation and will to carry them out. He argues that procrastination is futile, as obstacles simply remain unaddressed.

“We talk a lot about courage as a society, but we forget that at its most basic level it’s really just taking action—whether that’s approaching someone you’re intimidated by or deciding to finally crack a book on a subject you need to learn.”

Holiday connects bravery to the decision to act, even when it comes to something as seemingly minor as reading a new book. He sees the cultivation of courage as concrete, rather than an abstract process honed through thought alone.

“Edison once explained that in inventing, ‘the first step is an intuition—and comes with a burst—then difficulties arise.’ What set Edison apart from other inventors is tolerance for these difficulties, and the steady dedication with which he applied himself toward solving them.”

Holiday points to Edison as an inspiration for his persistence in the face of constant failure. Though the reader should expect to encounter difficulties in their projects, they should not feel discouraged by them. By quoting Edison, Holiday emphasizes that obstacles are a normal and expected part of new endeavors. He also suggests that genius is only one part of invention—most is accomplished through persistence.

“This is why stories of great success are often preceded by epic failure—because the people in them went back to the drawing board. They weren’t ashamed to fail, but spurred on, piqued by it.”

Holiday argues that failure can be a learning tool if people are willing to examine and build on their experience. He develops his message about reframing negative experiences as opportunities for growth.

“When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync.”

Holiday explains that one gains an advantage by breaking down larger problems into smaller tasks. By completing these tasks to a high standard, people can gradually work toward resolving larger problems or meeting goals.

“Right action—unselfish, dedicated, masterful, creative—that is the answer to that question. That’s one way to find the meaning of life. And how to turn every obstacle into an opportunity.”

Holiday defines “right action” as performing obligations and duties with dedication and excellence. He encourages the reader to create their life’s meaning by dedicating themselves to their work and embracing whatever role they may have to play at different times in their lives.

“Pragmatism is not so much realism as flexibility […] But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.”

Holiday urges the reader to consider how they might have to work around rules or conventions in order to reach their goal. This passage affirms that thinking creatively and being flexible is an important aspect of overcoming obstacles.

“The art of the side-door strategy is a vast, creative space. And it is by no means limited to war, business, or sales.”

Holiday encourages the reader to consider how they could defeat their problems by approaching them in a new way, rather than assuming they must confront them head on. He uses George Washington’s evasive military tactics as an example of how people can overcome a stronger enemy through a “side-door strategy.” He emphasizes the benefits of thinking creatively and strategically.

“So instead of fighting obstacles, find a means of making them defeat themselves.”

Holiday points to Gandhi as an example of someone who understood how to turn the enemy’s use of force against them, in his case through peaceful protest. In Holiday’s view, Gandhi furthered his cause by embracing his weaker position. This forced the military to either not enforce its rules and admit that their policies were flawed, or take violent action against the activists and lose the sympathy and support of the public. Holiday contends that the British defeated themselves, and that Gandhi’s cause prevailed.

“If you look at history, some of our greatest leaders used shocking or negative events to push through much-needed reforms that otherwise would have had little chance of passing. We can apply that in our own lives.”

Holiday urges the reader to look at negative events as opportunities to try something differently or explore a new option in life. While it is easy to focus on the negatives, Holiday claims that setbacks such as illness or job loss can present a chance to pursue a new path which may prove rewarding.

“Some actions are rendered impossible, some paths impassable, some things are bigger than us. This is not necessarily a bad thing. Because we can turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even if it is just learning to accept that bad things happen, or practicing humility.”

Holiday further explores his key theme, Turning Obstacles Into Opportunity. He argues that some obstacles are unbeatable and beyond one’s control. However, it is still possible to gain something from them, such as the chance to grow personally. 

“It came to be that every quality produced from Lincoln’s personal journey was exactly what was required to lead the nation through its own journey and trial […] His own experience with suffering drove his compassion to allay it in others. He was patient because he knew that difficult things took time. Above all, he found purpose and relief in a cause bigger than himself and his personal struggles.”

Holiday argues that Abraham Lincoln’s difficult personal life and struggles with mental health were an advantage, as they helped him develop the skills and attributes he would later use as president. He suggests that challenges can hold benefits by helping one become mentally stronger and develop useful traits.

“The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard.”

Holiday argues that anticipation and planning are essential to overcoming obstacles. By predicting challenges, people will be better prepared, and will overcome them with less effort and emotional distress. This passage ties in with Holiday’s overarching argument that obstacles are inherent to life and should be expected and embraced.

“Let’s be clear, that is not the same thing as giving up. This has nothing to do with action—this is for the things that are immune to action. It is far easier to talk about the way things should be. It takes toughness, humility, and will to accept them for what they actually are. It takes a real man or woman to face necessity.”

Holiday argues that acceptance is a sign of maturity and strength, and that it demonstrates an awareness of what is and isn’t in our control. According to Holiday, acceptance is a healthy reaction to an obstacle one cannot change. It’s a sign of strength, not weakness.

“Our actions can be constrained, but our will can’t be. Our plans—even our bodies—can be broken. But belief in ourselves? No matter how many times we are thrown back we alone retain the power to decide to go once more. Or to try another route. Or, at the very least, to accept this reality and decide upon a new aim.”

Holiday argues that people are always in control of their will, and that they can direct it toward problem solving. He emphasizes the importance of personal agency and the role of people’s actions and will when facing obstacles. He encourages the reader to develop a strong belief in themselves.