Stop Leading Like a Fool: Break the Cycles That Are Holding You Back

Dear Business Leader,

Let’s be brutally honest. You are too smart to keep making the same mistakes. And yet, here you are—repeating patterns that have already cost you time, money, trust, and energy. You tell yourself, “This time will be different.” But will it? Or are you just dressing up old foolishness in a fresh excuse?

I care too much to stay silent while you return to your own vomit, like Proverbs 26:11 warns. A dog doesn’t know any better. But you do. You’ve read the books, attended the conferences, hired the consultants. You know exactly where your blind spots are. And yet, you circle back to the same destructive behaviors as if hoping for a different outcome.

Maybe it’s time to stop chasing new strategies and start facing the patterns you refuse to break.

Where Are You Fooling Yourself?

Let’s get specific. Where have you convinced yourself that you’re “learning” when you’re actually just rehearsing the same failure in a different context? Where do you see the pattern—but refuse to break it?

Here are some of the common ones I see in business leaders who should know better:

1. Hiring the Same Mistakes – You keep hiring the wrong people, even when the red flags are there. You convince yourself that “this time, they’ve changed” or “this time, I’ll manage them differently.” But the truth? You are ignoring reality. Your hiring process is flawed, or you are leading with sentiment instead of strategy.
2. Ignoring the Right Advice (Until It’s Too Late) – You surround yourself with sharp, experienced people—but you only take their advice after everything falls apart. You wait until there’s no other choice instead of making the hard call upfront.
3. Overcommitting and Under-Delivering – You keep saying yes to things you don’t have the capacity for, believing you’ll “figure it out.” But then you under-deliver, lose credibility, and damage relationships. When will you start respecting your own limits?
4. Chasing Quick Wins Instead of Building Sustainable Success – You go after immediate revenue spikes rather than long-term stability. You jump into trends without a real strategy, thinking, “We need to move fast.” And then you pay the price when those rushed decisions cost you integrity, brand trust, or stability.
5. Leading From Ego, Not Wisdom – You say you value feedback, but deep down, you resent being challenged. You avoid admitting when you’re wrong, and you make decisions based on how they make you look rather than what’s actually right for the business.

Sound familiar? If any of these sting, good. That means we’re getting to the real issue.

Why Do You Keep Returning to the Same Mistakes?

This isn’t just about behavior. It’s about mindset. The reason you return to foolishness isn’t because you don’t know better—it’s because you haven’t confronted the real reason behind the cycle.

Ask yourself:

• Are you making decisions based on fear of loss instead of wisdom for growth?
• Are you addicted to being busy because it makes you feel important—even if it’s leading you nowhere?
• Do you refuse to trust others, and so you keep overextending yourself instead of delegating?
• Is your need for validation pushing you to take on things that aren’t aligned with your mission?
• Are you so desperate to prove yourself that you’re making reckless, impulsive moves?

Be honest. If you don’t answer these now, your circumstances will force the answers out of you later—usually through failure.

What Will It Take for You to Change?

Here’s the truth: If you don’t actively break the pattern, it will break you.

At some point, the cost of repeating the same foolishness will outweigh your ability to recover from it. And then what? You will sit there, shaking your head, wondering how you got here—again.

So let’s do something different this time.

How to Break the Cycle of Leadership Foolishness

1. Own the Pattern. No more excuses. No more justifications. Name the cycle. Call it out. Say it out loud: “I keep trusting the wrong people.” “I keep making decisions based on short-term panic.” “I keep avoiding the hard conversations.”
2. Install Real Accountability. Not passive accountability. Not “I’ll check in with my mentor when I have time.” No. I mean a system that actively calls you out when you’re about to repeat the pattern. A board member, a coach, a trusted advisor—someone who will say, “You’re doing it again.” And you have to listen.
3. Create a Hard Stop for Future Mistakes. Decide now what you will NEVER do again. Make it a written rule: “I will never hire based on desperation again.” “I will never take on a new initiative until the last one is fully executed.” Treat it as a line you refuse to cross.
4. Choose Wisdom Over Comfort. Change is uncomfortable. Breaking cycles is painful. You might have to fire someone you should’ve never hired. You might have to let go of a revenue stream that’s not worth the ethical cost. You might have to admit you were wrong. Do it anyway.
5. Stop Expecting Change Without Making Change. You don’t get different results from the same behavior. You know this. So what will you actually DO differently? Today. Not next quarter. Not after the next big deal. Today.

Final Word: Don’t Let This Be Another Moment You Ignore

Right now, you have a choice. You can read this, nod, and go back to business as usual. Or you can stop. Really stop. And face the uncomfortable truth: If you don’t change, you will repeat this cycle until it destroys the things that matter most.

Your business deserves better. Your employees deserve better. Your future deserves better.

So, what are you going to do about it?

Your Friend Who Refuses to Let You Stay Stuck,

Claudia

Need someone to challenge you beyond your blind spots? If you're ready to break the cycle and lead with wisdom, let’s talk. Reach out for a conversation that might just change everything.