EDITION #15: UNCONVENTIONAL WISDOM: WHEN BREAKING THE RULES LEADS TO SUCCESS.

As leaders, we’re often taught that success follows a clear, well-worn path.

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We're encouraged to stick to the proven methods, follow best practices, and avoid unnecessary risks.

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But what if the very thing holding us back is our adherence to these "rules"?

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What if breaking the rules—within reason—could unlock new success levels?

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Dear TRANSFORMATIONAL LEADER, you are welcome to the 15TH EDITION of my newsletter. Thanks for consistently reading and engaging.

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In today's rapidly changing world, sticking to the status quo isn't always a recipe for growth.

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Some of the most successful leaders and innovators didn’t follow conventional wisdom. Instead, they CHALLENGED it.

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They saw rules as guidelines, not barriers.

They recognized when rules were outdated, limiting, or simply didn’t apply to their unique vision.

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RULE BREAKERS WHO CHANGED THE GAME

Think about some of the biggest names in business:

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STEVE JOBS famously defied market research, insisting that customers didn’t know what they wanted until they saw it. The result? Revolutionary products like the iPhone and iPad that redefined technology.?

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SARA BLAKELY, founder of Spanx, ignored traditional advice and launched her billion-dollar company without a business plan. Her relentless belief in her vision broke all the typical startup rules—and it paid off.?

ELON MUSK, with his bold goals and unconventional approach to industries like space exploration and electric vehicles, consistently challenges the limits of what’s considered possible.

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These leaders weren't reckless—they were calculated in their rule-breaking.

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They didn’t ignore all advice or recklessly abandon structure.

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Instead, they knew which rules to follow and which to bend to meet the moment. They saw opportunities where others saw boundaries.

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WHEN TO BREAK THE RULES

As leaders, how do we know when it’s time to challenge convention and take a more daring path?

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Here are a few signs that breaking the rules might be the best strategy for you:

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??Innovation Is Stalling.

If your team is stuck in a rut and innovation has slowed, it may be time to shake things up.

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Sometimes adhering too closely to established processes can stifle creativity.

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Question the rules, experiment, and explore new ways of doing things.

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??The "Rules" No Longer Serve the Future.

Just because something worked in the past doesn’t mean it will lead to future success.

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Industries are changing faster than ever.

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If the rules you're following were made for a different era, it might be time to rewrite them.

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??You’re Chasing True Differentiation.

In crowded markets, following the same playbook as everyone else can lead to blending in, rather than standing out.

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Breaking away from industry norms might be the key to positioning your business as unique and innovative.

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??Fear Is the Only Reason You're Following the Rules.

Sometimes we follow the rules out of fear—fear of failure, fear of judgment, or fear of the unknown.

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If you find yourself clinging to convention because it feels safe, that might be a sign you need to challenge it.

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Growth doesn’t happen in comfort zones.

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HOW TO BREAK THE RULES - RESPONSIBLY

Breaking the rules doesn't mean ignoring good advice or abandoning structure entirely.

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It means having the wisdom to recognize when a different path is needed and the courage to follow it.

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Here's how to do it RESPONSIBLY:

1) Start Small

You don’t have to overturn your entire operation to see results.

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Start by breaking small rules in non-essential areas.

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Test new processes, challenge long-standing assumptions, and see what works.?

2) Use Data to Back Your Moves

Even unconventional decisions should be based on solid insights.

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Make sure you have data or a well-founded rationale behind your decision to break a particular rule.

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3) Align with Your Vision

Don’t break the rules just for the sake of rebellion.

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Make sure any unconventional decisions are aligned with your overall vision and purpose.

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Ask yourself: Will this help move the needle toward our bigger goals?

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4) Prepare for Pushback

Anytime you break from the norm, there will be resistance.

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Be ready to face questions or skepticism.

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Use these moments as opportunities to refine your vision and communicate why the rule-breaking is necessary.

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5) Encourage Rule-Breaking in Your Team

As a leader, creating an environment where people feel empowered to challenge the status quo is important.

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Encourage your team to bring up new ideas and question outdated processes.

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Reward innovation and creative problem-solving, even if it means stepping outside of traditional boundaries.

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Fostering a culture of thoughtful rule-breaking can lead to breakthrough innovations, higher engagement, and a dynamic, forward-thinking organization.?

Conclusion

The key to success isn't always found in following the rules—sometimes, it's in breaking them.

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The leaders who make the most significant impact are often those willing to take a step into the unknown, guided by vision, purpose, and an understanding of when convention no longer serves progress.

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So, the next time you find yourself at a crossroads, ask yourself: Am I following this rule because it’s the best course of action? Or am I following it because it feels safe?

The answer may determine whether you’re leading—or simply maintaining the status quo.

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Your unconventional success story could be one bold decision away.

What are some "rules" in your industry or role that no longer serve you? Have you ever taken a risk that paid off? I'd love to hear your stories in the comments.

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