The Rewards—and Risks—of Breaking the Rules

Jane Genova

From the get-go, America has been about breaking the rules. With big rewards.

That kicked off with the Puritans. They left behind the standard rules of business in the old country and created the most powerful economy in the world.

In public relations at Mobil, Herb Schmertz did the unthinkable in 1970: paying to place op-eds in the New York Times. His legacy is as one of the most prominent players in that sector.

In tech, Marc Zuckerberg’s MO has been “Move fast and break things.” Currently his corporation Meta is the darling of investors.

Verge describes Elon Musk as having “an uncanny ability to sort out which of America’s rules are real.” His wealth, influence and power are unprecedented.

But rule-breaking also brings risks. Big ones.

Break-the-rules creator of high-yield bonds Michael Milken wound up in prison.

After violating social norms through his friendship with Jeffrey Epstein, Leon Black resigned as Apollo’s CEO and Chairman. He also stepped down from heading the board of the Museum of Modern Art.

Some watchers of the Musk phenomenon are betting that he’s breaking too many rules with too much bravado and is on the way to crashing.

Rules about breaking the rules

In American business rules are a funny thing.

On the one hand, those policies and procedures exist to ensure that investors can bet on predictability, a strong culture, consistency in internal processes, ethical branding and compliance with the law. On the other hand, as David Freedman hammers in LinkedIn, leaders are paid to “challenge the status quo, rewrite the playbook and break the rules that no longer serve the organization.” That’s exactly what Richard Edelman is doing at the Edelman agency.

Best practices about breaking the rules

What if you’re an ambitious professional during this era of employment insecurity and fewer promotions? A way to differentiate yourself is to break the rules. Here are the fundamentals of how to go about that.

Have the rules down cold. It was Picasso who observed: “Learn the rules like a pro, so you can break them like an artist.” Those rules, of course, are both formal and informal. The latter can be tricky. To gain insight into what really counts you probably have to penetrate the corridors of power. Find out what the very top layers really think.

Take advantage of chaos. Stanford University researchers found that there’s a tendency in organizations in turmoil for players to aim at “keeping the ship on course.” They expect to be rewarded for holding things together. Yet, the timing is right—and timing is almost everything—to stand back and determine what needs to be broken.

Appear powerful. To be perceived as having power, Science Times reports, you might have to become known as a bit of a rule-breaker in daily office routines. For example, don’t be so deferential when interacting with higher-ups. Proceed with minor changes without permission. That aura of power opens the door to being taken seriously when presenting the proposal for disruption.

Focus on what’s achievable. Carefully structure the situation to embed hefty odds of success. Start out with minor wins, using them as a platform to build strategies for major disruptions. Currently the buzz phrase for those who get things done is “high agency.”

Find a champion or champions. Success has many mothers. Those in the organization who can move the dial for you on what you need can be motivated by sharing in the glory. You have to size up who could be that champion.

Another way to lure support is through FOMO – that is, fear of missing out. At Apple, John Sculley, reports SiliconValley, followed a “straight and narrow path.” He was incapable of angst about what Steve Jobs could accomplish and missing out on sharing in the success. Eventually Sculley lost that job and permanently tarnished his brand.

So much risk

However, the corridors of failure—personal and organizational—are cluttered with rule-breaking gone very wrong. They include:

Job loss. Walmart hired marketing whiz Julie Roehm to push the envelope. The way she went about breaking away from the stodgy branding included a family-unfriendly commercial for lingerie. Within 10 months of the hire Walmart fired Roehm.

In criminal hot water. Breaking the law is all too common in an effort to get ahead in a job. According to the World Bank Group, those at one-third of businesses do that through paying kickbacks. That builds their accounts. When caught the penalties are severe.

Not up to it. You sold the business on the disruption you could pull off. But you might have lacked the experience in refining the strategy and organizing for implementation. The historic Chrysler turnaround could have gone that way. Those brought in for the Iacocca team were primarily buttoned-down rule-observing corporate types. They had no background in breaking the rules such as borrowing a lot from the US government, purging middle management and investing heavily in new products. Some contend that luck, such as the bounce-back of the US auto industry, that explains why they succeeded. Otherwise, they could have gone down in corporate history as losers.

Burning Bridges. Going for it can involve sharp-elbowing those who are supposedly in the way. You’re a very confident player in a hurry. It doesn’t seem to matter that you’re alienating many. But it always does. From there on in, it could be the nights and days of the long knives. Musk might be in this exact pickle.

Collapse of support. The champion, sensing the project is going nowhere, backs away. Resources dwindle. You’re isolated within the organization. An option is to retrofit the venture. Another is to resign. Quick wins are necessary, with early signs of progress.

A flop. Most disruptions fail, documents Forbes. Classic was the inability of Marissa Mayer and her glam hires to innovate Yahoo back to its former glory. The team was hailed as game-changers. The critical error in judgment was to assume they could do that after a number of other teams had tried without success.

Here you are

In this era of disruption, breaking the rules is expected. As always, it can be the path to stardom for both organizations and individual professionals. But American capitalism is binary: win or lose. If the rule-breaking doesn’t pan out constituencies, ranging from investors to the board of directors, can be unforgiving.

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As an intuitive career coach, Jane Genova uncovers the opportunities/obstacles in your earning power that others miss. Free confidential consultation. Fees are custom-made for your budget. For an appointment: contact Jane Genova (text/phone 203-468-8579, [email protected]). In-person and remote.