Featured on Find Your Dream Job Podcast:

Many professionals find themselves stuck in an exhausting cycle—jumping from job to job, only to realize, once again, it’s not the right fit. If this sounds familiar, you’re not alone. The reasons behind this pattern often run deeper than just a mismatch in skills or interests.

On a recent episode of Find Your Dream Job, I sat down with Mac Prichard to unpack why we repeatedly say yes to the wrong opportunities—and, more importantly, how to break free.   

Why Does This Happen?

Often, career missteps aren’t just about the work itself. They’re tied to:

• Misaligned Expectations: Choosing a job based on what "looks good on paper" rather than what truly aligns with your values and strengths.
• External Pressures: Family expectations, societal norms, or financial concerns can steer you toward paths that don’t actually fit who you are. You might chase a title, salary, or prestige without considering whether the work brings you fulfillment.
• Avoidance-Based Decisions: Instead of moving toward what excites you, you might be running away from something—like a toxic boss, industry burnout, or past job trauma. But choosing a role just because it’s not your last job doesn’t guarantee it’s the right one.
• Lack of Clarity: If you’ve never taken the time to truly define what you want in a career, it’s easy to fall into whatever opportunity presents itself. Without a clear direction, your job choices can feel like guesswork.

How to Break the Cycle

If you’re ready to stop taking the wrong job, here’s where to start:

1. Clarify Your Career Values – What matters most to you? Is it autonomy, creativity, impact, flexibility? Identifying these values helps filter out roles that drain you.

2. Recognize Your Patterns – Look at your past roles. Are you making decisions based on fear, comfort, or external validation? Awareness is the first step to change.

3. Set a Career Vision – Instead of simply job-hopping, define the long-term career you want. Where do you see yourself in 5-10 years? What steps will get you there?

4. Make Intentional Choices – Before saying “yes” to a job, ask yourself: Does this align with my values? Will this move me toward my long-term career goals? If the answer isn’t clear, pause and reevaluate.

Breaking free from the wrong-job cycle takes courage, but it’s absolutely possible. If you’re stuck, start by getting clarity—because when you know what you want, the right opportunities become much easier to spot.

Want to go deeper?

Catch my full conversation with Mac Prichard on Find Your Dream Job for more insights and actionable advice.

P.S. Follow me on LinkedIn for more highly-practical guidance.