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Home Leadership

Why Career Regret Misses the Bigger Picture

August 29, 2025
in Leadership
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Why Career Regret Misses the Bigger Picture
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Have you ever found yourself wondering, “What if I’d stayed at that job?” or “Maybe I’d be in the C-suite by now…”? That nagging feeling—career regret—is more common than you think.

But it’s also often incomplete.

I recently spoke with a client who was reflecting on a previous role and questioning if leaving was the right move. We decided to play it out: what would staying have actually looked like—title, impact, personal life, happiness? The truth became clear quickly: staying would’ve crushed their sense of purpose and limited their personal growth.

It’s easy to fixate on a single element like salary or status. But those things don’t live in a vacuum.

When you’re tempted to second-guess your career path, remember to zoom out and consider the ripple effects—on your relationships, fulfillment, freedom, and growth.

The next time regret starts whispering in your ear, try this: imagine the whole alternative reality, not just the promotion you missed.

You may find that what you’ve built is far more valuable than what you walked away from.

Read More: It’s Not All About the Money



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