In business, obstacles tend to appear when we least expect them. We can allow ourselves to be inconvenienced by these unforeseen events, or we can choose to rise to the challenge instead. Turning obstacles into opportunities is a crucial skill for any business owner. Often, our most significant disadvantages have the potential to become our greatest strengths.

Overcoming Difficulties 
by Shifting Your Perspective

Can any obstacle or disadvantage be turned into something good? In his book The Obstacle is the Way, author and marketer Ryan Holiday provides a three-part solution for turning obstacles into opportunities: perception, action, and will. By mastering these three disciplines, we can transform any setback into success by turning failure into triumph.

Perception

The first pillar of Holiday’s framework for turning obstacles into opportunities
is perception: not just what happens to us, but how we choose to interpret what happens to us. This isn’t about rose-colored glasses or forced optimism. It’s about developing the mental discipline to see situations objectively and recognize the hidden opportunities within every challenge.

As an example of the power of perception, Holiday writes about John D. Rockefeller and the Panic of 1857. While others faced ruin and despair during this economic downturn, Rockefeller saw an opportunity to develop the strategic thinking skills that would eventually make him one of history’s wealthiest men.

The secret to turning obstacles into opportunities lies in asking the right questions when an obstacle occurs: “What can this teach me? How might this encourage me to take a better path? What skills might I develop that I otherwise never would have learned?”

Action

The second pillar of Holiday’s framework emphasizes that perception without action is nothing more than an intellectual exercise. Once you’ve shifted your perspective to see the opportunity within the obstacle, you must then act with discipline, persistence, and strategic thinking.

As an example of decisive action, Holiday describes the Greek statesman Demosthenes and his seemingly insurmountable challenges: a speech impediment, physical weakness, and no lack of formal education.

Rather than accepting his lot in life, Demosthenes developed a systematic approach to overcome each of his obstacles. He practiced speeches while running with pebbles in his mouth, built an underground study chamber, and even shaved half his head to eliminate distractions. His disciplined action transformed each of his disadvantages into a strength.

The lesson is clear: sometimes our obstacles force us to discover methods we never would have considered initially, leading to solutions far better than anything we could have planned on our own.

Will

Holiday’s third and final pillar in turning obstacles into opportunities
is will, not merely wanting something, but developing the inner strength to persevere regardless of circumstances. Drawing from Stoic philosophy, Holiday describes this as building an “Inner Citadel”—a mental fortress that is impervious to external events.

Holiday illustrates this principle with Rubin “Hurricane” Carter, a boxer who spent nineteen years of his life wrongfully imprisoned for murder. Although he couldn’t control his circumstances, he did have control over his thoughts, words, and deeds. He utilized his time in prison to study history, philosophy, and law, ultimately contributing to the overturning of his conviction.

Similarly, Holiday writes about Theodore Roosevelt. Born with debilitating asthma, Roosevelt could have resigned himself to his physical limitations. Instead, he built up his strength through exercise, gradually overcoming his weakness through persistent willpower.

The Power of Disadvantage

Malcolm Gladwell has also written at length on the potential power of disadvantage. In his book David and Goliath, Gladwell demonstrates that what we conventionally consider advantages, such as size, strength, and superior resources, aren’t always beneficial. Sometimes our perceived weaknesses force us to develop strategies that advantages never could.

Gladwell terms this concept “asymmetric warfare,” exemplified by the titular David’s victory over Goliath. David didn’t attempt to match Goliath’s conventional strengths. Instead, he identified his unique advantages—speed, agility, and ranged weapons—and developed an unconventional strategy that turned the giant’s size from an asset into a liability.

As part of his research, Gladwell studied entrepreneurs with dyslexia. Their learning disability, traditionally viewed as a severe handicap, actually fostered unusual creativity, enhanced listening skills, and remarkable resilience. They developed alternative approaches to processing information that often proved better than traditional methods.

This principle applies across countless contexts. For example, small schools, despite having fewer resources, often provide more personalized attention and opportunities than large institutions. The supposed “disadvantage” of limited resources forces innovation and creates stronger community bonds, turning obstacles into opportunities
.

The key insight is context: what constitutes an advantage or disadvantage depends entirely on the specific situation and how we choose to navigate it.

Obstacles are Opportunities

Obstacles invite us to develop capabilities we never knew we possessed, discover strengths that only emerge under pressure, and create solutions that benefit not only ourselves but our entire organization. As Holiday and Gladwell demonstrate, embracing challenges can teach us more about leadership than smooth sailing ever could.

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Coach Dave