S6 Ep197: When to Break Your Own Rules

Hey y’all — welcome back to the Design for the Creative Mind podcast! Today we’re talking about something that might surprise you… when it’s actually smart to break your own rules.

Your rules exist for a reason — they protect your time, your profit, and your sanity. But sometimes, breaking one intentionally can lead to big opportunities. In my case, one rule I broke turned into hundreds of thousands of dollars in profit — no joke.

So in this episode, I’m pulling back the curtain on:

Why your business rules and boundaries matter

When they turn from protection to a cage

How to know the difference between a strategic exception and a fear-based compromise

Because business doesn’t live in absolutes — it lives in the messy middle.

IN THIS EPISODE, I SHARE:

Why boundaries and rules eliminate decision fatigue (and chaos!)

The difference between bending a rule for strategy vs. breaking it out of fear

Real-life stories from my firm — the good, the bad, and the “what was I thinking?” moments

The $100K+ example of breaking my “no weekend work” rule the right way

The painful lessons I learned from breaking rules for the wrong reasons — like discounting from fear or saying yes to a client who wasn’t a fit

My personal framework for deciding: Am I doing this for strategy or for fear?

You’ll walk away knowing exactly when to hold firm — and when to give yourself permission to flex.

Rules protect you — but they can also box you in. The real power comes from discernment: knowing when a little flexibility can actually strengthen your business.

If you’ve ever wrestled with questions like “Should I make this exception?” or “Am I being too rigid?” — this episode will help you decide with clarity and confidence.

Remember: flexibility isn’t weakness — it’s wisdom. Or as Kenny Rogers said, you gotta know when to hold ’em and know when to fold ’em.



RESOURCES:



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