Entrepreneurs are no strangers to obstacles. Whether or not a business launches, how well it performs, and whether or not it ultimately succeeds depends on the obstacles along the entrepreneurial journey and how well they are managed.

But how should we, as entrepreneurs, approach obstacles? How do we turn obstacles on their head? How do we capitalize on obstacles, transforming them into opportunities and, in the process, use them as a means of self-improvement?

This is a book review of Ryan Holiday’s bestselling The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph, in which I’ve plumbed the book’s major concepts and excerpts and presented them for your edification. Please enjoy Holiday’s insights on entrepreneurship, adversity, and turning trials into triumphs.

So, how do entrepreneurs most effectively manage obstacles? The answer lies in ceaseless creativity. And opportunism. And a host of principles rooted in 2nd century stoic philosophy. Let us turn to a brief parable for illustration. Holiday writes …

“There is an old Zen story about a king whose people had grown soft and entitled. Dissatisfied with this state of affairs, he hoped to teach them a lesson. His plan was simple: He would place alarge boulder in the middle of the main road, completely blocking entry into the city. He would then hide nearby and observe their reactions.

            “How would they respond? Would they band together to remove it? Or would they get discouraged, quit, and return home?

            “With growing disappointment, the king watched as subject after subject came to this impediment and turned away. Or, at best, tried halfheartedly before giving up. Many openly complained or cursed the king or fortune or bemoaned the inconvenience, but none managed to do anything about it.

            “After several days, a lone peasant came along on his way into town. He did not turn away. Instead he strained and strained, trying to push it out of the way. Then an idea came to him: He scrambled into the nearby woods to find something he could use for leverage. Finally, he returned with a large branch he had crafted into alever and deployed it to dislodge the massive rock from the road.

            “Beneath the rock were a purse of gold coins and a note from the king, which said: ‘The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity improve our condition.’”

Indeed, the obstacle becomes the path. To avoid obstacles is foolish. Instead, one must understand the obstacle for what it is, employ creative analysis of solutions, and look for weakness or opportunity to begin taking action. As Benjamin Franklin put it, “The things which hurts, instructs.”

Holiday recommends keeping six key principles in mind when confronted with an obstacle. These principles lay the foundation for the whole of Holiday’s book.

      Be objective

      Control emotions and keep an even keel

      Choose to see the good in a situation

      Ignore what disturbs or limits others

      Revert to the present moment

      Focus on what can be controlled

Be objective: Separate fear and anxiety from the obstacle. Your subjective appraisal of the obstacle - “These emails will be a nightmare to read and respond to!” - must be separated from what the obstacle is - an inbox of 20 or 30 unread messages. You have the power to decide how to react to obstacles in your path. There is no good or bad without our thinking it so. Just because your mind tells you that something is negative doesn’t mean that you have to agree with your mind. After all, it is your mind. Objectivity means removing “you” and seeing an obstacle for what it truly is, not how it feels.

Control emotions and keep an even keel: Despite popular belief, talent is not the most important characteristic a person should have. Grace and poise are. Without grace and poise, Holiday argues, no other skill can be used to its fullest potential. The bottom line: when people panic, they make mistakes. The Greeks had a word for anti-panic: apatheia, a calm equanimity that comes with the absence of irrational or extreme emotions. The cool-headed entrepreneur practices apatheia before making big decisions, entering into critical meetings, or responding to important emails.

Choose to see the good in a situation: When you break apart a problem, it loses its power over you. By breaking problems into pieces, obstacles become opportunities, chances for growth, moments for reflection, iteration, and improvement. In the words of English serial entrepreneur Richard Branson, “Business opportunities are like buses; there’s always another coming around.” You missed a business opportunity? You failed to capitalize on an important meeting? Good, because failure is a chance to improve. Stories of great success are often preceded by epic failure - because the people in them went back to the drawing board. They didn’t harbor bitter feelings toward the obstacle. They didn’t sulk. They didn’t fear. They learned from the obstacle, created an alternative solution, and put it into action.

Ignore what disturbs or limits others: We shouldn’t listen too closely to what other people say about our product or service, nor should we listen too carefully to the voice in our head. If we do, we’ll find ourselves erring on the side of caution and accomplishing nothing. Entrepreneurs, Holiday writes, are people with faith in their ability to make something where there was nothing before. And our best ideas come where obstacles create new, unforeseen options. After all, how can innovation - the hallmark of entrepreneurial products or services - be achieved if we, as entrepreneurs, limit ourselves to thoughts and ideas that are already ‘out there?’ You’ve got something original. Pursue it and don’t let the opinions of others diminish your creativity.

Revert to the present moment: Those who most successfully use obstacles as opportunities do so because they took things day by day, even minute by minute. By focusing on the moment, not the monsters that may or may not be up ahead, we can learn to be content with what happens as it happens, a critical skill for entrepreneurs who oftentimes get caught up in the “big picture” and the “meaning” of everything. You don’t know for certain that your worst possible business outcome will happen. All things considered, it likely won’t. So get busy! Take the next step in designing or taking to market your product or service.

Focus on what can be controlled: What is up to us? Our emotions, our judgments, our creativity, our attitude, our perspective, our desires, our decisions, and our determination. Perhaps most importantly, action is within our control. We can act. And we can direct our action toward the service of our main goal as a way to solve our problems, advance our product/service, and find fulfilment in our work. If history is any indicator, those who attack problems and life with the most initiative and energy almost always win.

Throughout his short, bedside-table book, Holiday peppers in characterizations of the most successful entrepreneurs. He writes that great entrepreneurs are:

      Never wedded to a position

      Never afraid to lose a little of their investment

      Never bitter or embarrassed

      Never out of the game for long

He claims that one of the biggest problems facing entrepreneurs is impatience. The “all at once” mentality inhibits entrepreneurs from taking action. Or, the bigger the dream, the more paralysis by analysis may take place. Paralysis by analysis is the state of over-analyzing (or over-thinking) a situation so that a decision or action is never taken, in effect paralyzing the outcome. “We are A-to-Z thinkers,” writes Holiday, “fretting about A, obsessing over Z, yet forgetting all about B through Y.”

In the end, The Obstacle Is The Way deconstructs intimidating obstacles, revealing them oftentimes to be opportunities for business or personal growth and success. So, the next time you’re confronted with an obstacle, wonder - What do I stand to gain? How can I break this unmanageable object into manageable pieces and actionable steps? And lastly - Might I be better off for working through this now than putting it off until the obstacle grows even larger?

Let’s say it once again, just to remind ourselves:

“See things for what they are.

Do what we can.

Endure and bear what we must.

What blocked the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.”


ABOUT THE AUTHOR

PETE FREEMAN IS A STUDENT-RESEARCHER FROM THE UNIVERSITY OF NOTRE DAME IN THE UNITED STATES. MR FREEMAN IS CURRENTLY ENGAGED IN A RESEARCH PROJECT MEASURING GENDER DISPARITIES IN SWISS ENTREPRENEURSHIP AND POLICIES AFFECTING THESE DISPARITIES. HIS RESEARCH WILL BE USED TO SUGGEST INITIATIVES FOR GREATER GENDER PARITY IN THE SWISS ENTREPRENEURSHIP SPACE. IF YOU ARE AN ENTREPRENEUR INTERESTED IN DEVOTING 15 MINUTES TOWARD THIS STUDY, PLEASE COMPLETE THIS BRIEF, ANONYMOUS SURVEY. SHOULD YOU HAVE ANY QUESTIONS MR FREEMAN CAN BE REACHED AT THE FOLLOWING ADDRESS PETEFREEMAN14@GMAIL.COM.

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