Why “Should” Is Your Biggest Career Trap — And How Coaching Frees You

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We all carry “shoulds” — those invisible, relentless expectations about who we ought to be, what jobs we should have, how success is supposed to look. From a young age, these “shoulds” shape our decisions: “You should pick a stable career,” “You should climb the ladder fast,” “You should be more confident.”

On paper, these expectations seem reasonable. They’re often the advice of well-meaning family, cultural norms, or internalized voices shaped by past experiences. But here’s the catch: what if the life we build around these “shoulds” no longer fits who we are becoming?

“Should” is a trap because it keeps us locked in a story that isn’t ours anymore. It can feel like carrying a heavy backpack filled with other people’s hopes, societal pressures, or outdated beliefs about success and identity. The more we try to live up to those “shoulds,” the more disconnected we feel from ourselves.

The Cost of “Should”

Living under the tyranny of “should” doesn’t just drain energy it suffocates creativity, passion, and authenticity. It creates a constant tension between our actions and our true desires, which psychologists call cognitive dissonance. This gap can lead to anxiety, burnout, and a persistent feeling of being stuck, even when everything seems fine on the surface.

For many women I’ve coached, the burden of “should” manifests in two ways:

  1. Analysis Paralysis: You know what you “should” do next, but it feels like a dead end. You overthink every option, afraid of making the wrong choice because it wouldn’t align with what “should” be.
  2. Quiet Resentment: You’re achieving goals others set or you once believed in, but inside you’re disconnected, exhausted, and wondering, “Is this really what I want?”

How Coaching Helps Break Free

Coaching offers a alternative to the pressure of “should.” It’s not about telling you what to do next. It’s about helping you uncover what you TRULY want beneath all those external expectations. Coaching invites you to question the story you’ve been living by and to experiment with a narrative that feels authentic.

Through thoughtful questions and compassionate listening, coaching creates a space where:

  • You identify the “shoulds” that no longer serve you.
  • You explore the origins of these expectations. Are they really yours or inherited?
  • You clarify what success means for you, not anyone else.
  • You gain permission to redefine your career and life on your own terms.

One client I worked with spent years climbing a corporate ladder because “that’s what success looks like.” Coaching helped her realize she was actually craving creativity and impact, not just status. She didn’t have to change her whole career at once, she just needed to try small things that felt right to her.

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