In a mental spiral because you think you “should” have handled a situation better? Beating yourself up because that project or conversation didn’t go perfectly? You’re caught in what we call thinking traps or unhelpful thinking styles. They’re automatic, largely unconscious, and they mess with our leadership and our lives.
There are many thinking traps: catastrophizing, mind-reading, personalization, and more. Two show up with striking regularity in the leaders I work with: all-or-nothing thinking and the tyranny of the “shoulds.” Each one quietly undermines our effectiveness, our well-being, and our relationships.
All-or-Nothing Thinking
This trap shows up as black-and-white, either/or thinking—with no room for the messy, nuanced middle ground where most of life actually lives. A project isn’t stellar, so it’s a failure. A conversation doesn’t go perfectly, so you ruined the relationship. A team member stumbles once and they’re now a “problem employee.” It narrows our thinking, strains relationships, and makes it hard to recognize progress in ourselves or others.
Try this: Look for the spectrum. Where is this a 6 out of 10, not a zero? What’s working, even if everything isn’t? Reality is almost always more complex than our binary brains want it to be.
The Tyranny of the “Shoulds”
You know this one: I should be further along. I should have done xyz. Leaders shouldn’t be too directive, show emotions, etc., etc. These rigid internal rules create a steady hum of pressure and disappointment—and we can unknowingly impose them on others, too. I am frequently pointing out when my clients are “shoulding” all over themselves.
Try this: Swap the “should” for a preference. “I’d like to be further along” is more honest—and a whole lot kinder—than “I should be further along.” Small shift, real difference.
These traps don’t make us flawed; they make us human. The work is noticing them, naming them, and choosing differently.
Practices
- Where does all-or-nothing thinking show up most for you—in how you assess your own work, your team, your decisions?
- What “shoulds” are you carrying? Are they really yours—or were they handed to you somewhere along the way?
Practice:
- Catch yourself in all-or-nothing thinking and ask: “What’s the gray here? What’s partially working?”
- Spot a “should” this week and try reframing it: “I’d prefer…” or “I care about…” Notice what shifts.
Curious about other thinking traps? Check out this infographic.

