What Happens When You Let Go of Being Right?
We all carry an idea of how the world should work. These “shoulds” are deeply personal—shaped by culture, gender, history (both personal and collective), and countless other influences.
Even if you consider yourself open-minded, if you pay attention, you’ll notice how much your judgments are rooted in your own beliefs about what should and shouldn’t be.
Here’s a question to reflect on: If my “should” is different from yours, and different from theirs—who’s right?
The answer: Everyone. And no one.
There’s immense freedom in letting go of the “should” framework. But for many leaders, this shift is challenging—especially when their success is built on deeply ingrained assumptions.
In our recent work with executive teams, we’ve uncovered some familiar “shoulds” that leaders operate from:
Everyone should see the big picture.
Everyone should solve the problems I see.
Everyone should recognize the same opportunities I do.
Everyone should understand the underlying condition I’ve identified.
Do you notice the common thread? These beliefs are often less about the “should” and more about whose picture, problem, opportunity, or condition is being prioritized.
Let’s look at a couple of real-world examples of what happens when leaders cling too tightly to their “shoulds”:
BlackBerry: Once a leader in mobile technology (remember our beloved “Crackberries?”), BlackBerry was convinced that physical keyboards were essential to smartphones. Leadership doubled down on the belief that phones “should” prioritize tactile typing, ignoring the rise of touch screens and the app-driven ecosystems that were reshaping the industry. By clinging to their assumption of what mobile phones “should” be, they missed the future entirely and exited the hardware business in 2016.
Blockbuster: The leadership at Blockbuster believed that in-store rentals were what customers wanted, dismissing the rise of digital streaming as a passing phase. If you recall, they even had the chance to buy Netflix for a mere $50 million—but they turned it down, believing the industry “should” remain as it had always been. That single “should” proved catastrophic. Blockbuster went bankrupt in 2010.
It's pretty clear: When we hold too tightly to our assumptions, we lose the ability to see beyond our perspective and adapt.
The Challenge of Leadership
As a leader, it’s natural to want others to see what you see. But here’s the real question: What if you allowed other pictures to form?
What if someone else’s framing of the problem revealed something you’ve overlooked? What if another perspective uncovered opportunities you couldn’t see on your own?
This isn’t about losing control—it’s about expanding your vision by loosening the grip of “shoulds.”
This is extremely difficult for highly compensated and successful leaders -- many of them have been right "so far" and are caught in the web of their own making.
The Path to Freedom
So, how do you accomplish this? The first step is awareness: recognizing that life doesn’t go the way it “should” or “shouldn’t.” Life just happens, no matter what you do.
The second step is action: practicing ways to let go.
You can:
Trust: Open yourself to trusting others’ insights and instincts.
Be Curious: Ask more questions, even when you think you already know the answer.
Show Compassion: Be kind to yourself and others as you navigate this shift.
When you loosen your “shoulds,” you create space for a more creative, open, and daring culture—one that isn’t tethered to a single way of seeing, solving, or succeeding.
Are you ready to learn how to lead in a freer, more expansive way? And in the course of it, free yourself?
It’s what we do. Let’s start the conversation.