Leaders Who Rewrite Rules Define the Future of Markets.
Rule-Breaking Leadership Transforms Resistance into Renewal and Long-Term Advantage.
The Leadership Paradox
Leadership has always balanced the pull of continuity against the urgency of change. Rules safeguard stability and provide organizations with predictable structures. They codify decades of accumulated experience. But when followed unquestioningly, they become anchors rather than compasses. History shows that rules work, until they don’t.
Berkshire Hathaway, under Warren Buffett, is often seen as the archetype of disciplined rule-following. His principle of “purchasing at a rational price” produced one of the most successful investment runs in history, with
Apple alone now accounting for more than $150 billion of its portfolio value. Yet even Buffett has had to break with convention: abandoning textiles, embracing insurance, and later pivoting into technology.
The lesson for leaders is stark, long-term impact depends on knowing not just which rules to respect, but when to step outside them.
Breaking the Rules Brings in the New
The biggest shifts in markets and societies come when entrenched rules are broken. For more than two millennia, the Gordian Knot symbolized an unsolvable problem, until Alexander the Great ignored the puzzle’s logic and sliced through it. This act remains a metaphor for the decisive leadership needed to unlock complex challenges. Modern equivalents abound.
In 2007, Apple launched the iPhone not by refining the mobile phone as it was, but by abandoning the physical keyboard entirely. At the time, experts doubted consumers would embrace touchscreens. Within a decade, Apple had sold over a billion units, redefining not just a product but an entire ecosystem of communication, entertainment, and commerce.
Rule-breaking, in this context, was not rebellion for its own sake; it was the only way to leap from incremental to exponential.
Sticking to the Rules Has Limits
At times, rules act as stabilizers, until they trap leaders in decline. Nestlé’s first attempt to push Nespresso in the 1980s failed, because management tried to fit it into the existing B2B sales system. Office managers and hospitality clients resisted, and the idea languished. Only when Nestlé broke with its own system, creating Nespresso as a standalone unit targeting consumers directly, did the concept flourish. Netflix provides another lesson: while it rewrote the video rental rulebook by pioneering streaming,
Blockbuster clung to its in-store model and late fees. Despite once commanding over 9,000 outlets worldwide, Blockbuster declared bankruptcy in 2010. Leaders who cling to rules confuse continuity with resilience. Those who adapt rules with foresight transform them into launchpads for growth.
Re-Entrepreneur-ing the Organization
Entrepreneurial thinking is too often confined to the startup phase. As Charles-Edouard Bouée argues, organizations must continually “re-entrepreneur” themselves if they are to endure. This means treating legacy not as a burden but as raw material for renewal. The Dutch Kidney Foundation illustrates this principle. Rather than lobbying for incremental reform in dialysis treatment, it reframed the challenge: could a dialysis machine be reduced to the size of a shoe box, freeing patients from clinic dependency? By insisting on a wearable device, the foundation challenged both manufacturers and insurers. The process required reimagining not just technology, but the economics and regulations surrounding care.
Re-entrepreneuring, in this case, turned a stagnant system into a source of innovation, shifting risk tolerance and redefining market incentives. Leaders who fail to inject this entrepreneurial lens into established institutions preside over slow decline.
Asserting Position Amid Resistance
Impactful leadership also requires asserting position when rules collide with values. Colin Kaepernick’s decision to kneel during the U.S. national anthem was not a market play; it was an act of principle that catalyzed global conversation about racial justice. The cost was immense, Kaepernick has not played in the NFL since 2016, but the cultural and corporate impact was undeniable. Nike’s 2018 campaign featuring him triggered both backlash and loyalty, ultimately boosting sales and stock performance.
The case shows that leadership impact is measured not only in quarterly returns but in the ability to shape culture. Resistance is inevitable when rules are challenged, yet leadership is defined by the willingness to bear that resistance to achieve outcomes larger than oneself.
Building New Rules for the Future
Rule-breaking without reconstruction is reckless. True leadership impact lies in building new rules that enable organizations and markets to function more effectively. The Challenger disaster in 1986 underscored how broken communication rules could cost lives. NASA’s subsequent overhaul of reporting and engineering protocols set new standards for safety and accountability.
Similarly, companies that survive disruption are those that create durable replacements for the rules they’ve overturned. Customer friction, outdated legacy processes, and collapsing middleman models are three areas most ripe for profitable rule-breaking today. Leaders who rewrite these rules with clarity don’t just survive, they institutionalize resilience for the next cycle of turbulence.
For Leaders
Break rules decisively when they block transformation: delay only compounds irrelevance.
Re-entrepreneur continuously, treat heritage as a starting point, not a museum.
Assert cultural positions, silence in contested arenas is itself a choice with consequences.
Build rules that endure volatility, absence of new rules leaves organizations fragile.
Bottom Line: Leadership Means Breaking Rules to Create Impact
Impactful leadership is neither blind compliance nor reckless disruption. It is the discipline of knowing which rules to abandon, which to rewrite, and which to create anew.
Leaders who master this cycle transform resistance into momentum, stagnation into renewal, and organizations into institutions capable of bending history in their favor.
