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Career Decisions — When to Stay, When to Leave, and What Most People Miss (Stephen Short)
Description
My guest is Stephen Short, CEO of CareerFit and a career strategist focused on helping people make better decisions about their work.
This conversation is not about chasing a "dream job." It's about a deeper question:
How do you decide when to stay in a career—and when to leave?
In this episode, we explore:
• How to evaluate whether a role is truly a poor fit or just difficult
• How to distinguish between a passing interest and something worth pursuing
• What actually goes into making a successful career transition
• How to think about the future of work and the role of AI
• How to approach career decisions when the path forward isn't obvious
This is an exploration of how to think about career decisions—not a formula for finding the "perfect job." In decisions like this, the hardest part is often not choosing a path—it's understanding what problem you're actually trying to solve.