Progress Demands Risk: Lessons from the Baseball Diamond
Created at: August 2, 2025

Progress always involves risks. You can’t steal second base and keep your foot on first. — Frederick B. Wilcox
The Essential Link Between Risk and Progress
Wilcox’s metaphor highlights a universal truth: moving forward inherently requires leaving something behind. Just as a baserunner cannot safely reach second base without letting go of first, individuals and organizations cannot achieve growth while clinging to comfort zones. This principle applies broadly, illustrating how calculated risks underpin nearly every significant advancement.
Historical Examples of Bold Advancement
History is replete with innovators who risked old certainties for new possibilities. Take the Wright brothers, who, in pursuit of powered flight in 1903, wagered their reputations and resources on a dream few believed possible. Their leap from the familiar ground of bicycles to the uncharted skies underscores Wilcox’s point: bold steps are prerequisites to progress.
The Paralysis of Playing It Safe
Continuing from this, an overemphasis on safety can breed stagnation. Organizations that avoid experimentation for fear of failure often miss out on transformative opportunities. This is reminiscent of Kodak’s reluctance to fully embrace digital photography in the 1990s—by keeping their 'foot on first,' they ultimately lost their lead in the industry.
Risk Management Versus Recklessness
Nevertheless, Wilcox’s baseball analogy isn’t a call for impulsive action. In baseball, successful steals require timing, skill, and awareness—not mere bravado. Similarly, meaningful progress involves thoughtful risk-taking, balancing boldness with prudence. Literary strategist Sun Tzu in 'The Art of War' (5th century BC) advocates for calculated moves, underscoring that strategy must guide every risk.
Embracing Uncertainty for Personal Growth
Zooming in to the individual level, personal development often means stepping into uncertainty. Whether changing careers or pursuing higher education, advancement rarely unfolds in comfort. Like the baserunner, we must trust in our preparation, seize the right moment, and be willing to let go of familiar ground. In doing so, we discover new capabilities and horizons that playing it safe would render forever out of reach.