Why Career Regret Misses the Bigger Picture

YT career regret

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

Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.