S9: E2

How to Break the Rules (Strategically) and Get Ahead at Work

In this episode of the Trill MBA Show, Felicia dives into Rule #2 from Dr. Jeffrey Pfeffer’s book Seven Rules of Power: Break the Rules (but do it strategically).

If you’ve been working twice as hard, following all the rules, and still feel stuck, it’s time to shake things up. The reality? Power doesn’t reward compliance, it rewards confidence. The people who rise in their careers don’t just follow the book; they strategically bend and break the rules to their advantage.

Felicia shares real-world examples, including how one woman finessed her way into a VIP event at Sundance by taking bold action and how breaking the “no direct access” rule with senior leadership can make you visible and indispensable.

She also gives actionable steps on how to break unspoken workplace rules, from challenging the idea that junior employees should stay silent in meetings to directly connecting with high-level decision-makers.

Key Takeaways from This Episode:

Power Rewards Confidence, Not Compliance – The assumption? If you broke a rule, you must have the power to do so. Instead of asking for permission, take bold action and let the results speak for themselves.

Break Small Rules First to Test the Waters – Challenge unwritten norms in your workplace by speaking up in meetings, emailing the CEO, or setting up a coffee chat with senior leadership. Small, strategic rule-breaking builds credibility and influence.

Surprise Gives You Power – People are wired to follow the rules. When you break them strategically, you shift power dynamics in your favor because people don’t know how to react—and they’re forced to take you seriously.

Understand the Rules Before You Break Them – Read your employee handbook (yes, for real). Know both the written and unwritten rules so that when you break them, you do it with purpose and precision.

Your Challenge This Week: Break One Rule – Identify one workplace rule holding you back and challenge it this week. Whether it’s speaking up in a meeting or reaching out to a high-level executive, take the leap.

Resources & Next Steps:

Seven Rules of Power Book by Dr. Jeffrey Pfeffer – If you want to buy this book you can get it here. (As an Amazon Associate, I earn from qualifying purchases.)

Download Your Free Guide – Get the worksheet for this episode to help you identify which rules to break and how to do it strategically. Click here.

Live Q&A Session – Listeners who download the guide will get exclusive access to a live Q&A with Felicia to discuss workplace rule-breaking strategies.

Career Consulting with Felicia – Facing challenges at work? Book a career strategy session to get personalized strategies for navigating your career.

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Editing and Sound Design by Chris Mann of Podshaper

Until next time, keep it trill!