How Challenging False Choices Moves Companies Forward

Why I Reject Either Or Thinking In Leadership

There was a moment in our last quarterly planning meeting when everything felt stuck. Two bold, risky options sat on the table—both capable of pushing the agency forward. But everyone kept saying the same thing:

“Which one do we choose?”
“How do we know what’s right?”
“If we pivot now, we lose all this work.”

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The tension in the room was real. Smart, capable leaders were paralyzed—not because we lacked ideas, but because we were trapped in an either/or mindset. But here’s the thing: I don’t do “or.”

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Your Question Is Flawed

This isn’t just a business philosophy; it’s how I live. Ask me if I want chocolate or vanilla? I’ll take the swirl. Champagne or grilled cheese? Depends on the hour—I’ll have both (highly recommend, by the way). Relax or go for a walk? Let’s take a sunset stroll.

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I see “or” as a challenge, not a limitation. When faced with two options, my brain immediately starts searching for the hidden third path—the one no one else is looking for because they’re too busy trying to choose.

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That’s exactly what happened in that meeting. We weren’t just choosing a direction; we were deciding our identity. And I wasn’t willing to let us backslide into comfort or take a blind leap that erased everything we’d built. So I started asking different questions:

• What if we take the best of both paths and integrate them?

• What if this isn’t a pivot, but an evolution?

• What if the answer is: yes, and?

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And just like that, we saw it—the way forward that had been hidden in plain sight. It wasn’t the easy choice, but it was the right one.

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Strategy Isn’t About Choosing The Better Option

Sometimes, the smartest move is refusing to accept the question as it’s given.

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This mindset has shaped my leadership again and again—but it’s not just for boardrooms. It’s how I approach my life.

• I want to work out and watch football? The game’s on my phone while I lift.

• I want to push hard at work and protect my energy? My calendar blocks downtime as seriously as client meetings.

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I’m always asking: Is there a way to get both? Can I create an outcome that doesn’t force me to sacrifice what matters?

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I don’t always get everything I want—but I never default to less just because the world tries to hand me an either/or decision.

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Leadership Is Full Of “Vs” Moments

Revenue vs. culture. Growth vs. simplicity. What you planned vs. what the business needs now.

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But the best moves I’ve ever made didn’t come from picking one. They came from asking:

• What would it take to do both well?

• Is the real answer hiding in a third option we haven’t even considered?

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That’s where true strategy lives.

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Your turn: When was the last time you turned an “or” into an “and”? What surprised you about the outcome? I’d love to hear your take.

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At StringCan, we help businesses break free from limiting choices and build strategies that truly move them forward. If you’re tired of false dilemmas and ready for real solutions, let’s talk.

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