Aug 22, 2025

Aug 22, 2025

When Every New Role Ends in the Same Familiar Restlessness

When Every New Role Ends in the Same Familiar Restlessness

Ron Pratt

You don’t actually have a career problem, you have a clarity problem.

You’ve probably been there too. Sitting at your laptop on a Monday evening, scrolling through job boards, convincing yourself the next role will finally be the one that makes you feel alive at work.

I know that feeling well because I lived it for years.

Each new opportunity felt like a fresh start. “This time, I’m going to love it.” And for a while, I did. But within 6–12 months, those familiar Sunday night scaries popped back up. Meetings left me drained, small tasks took everything out of me, and I’d find myself back online searching for a way out. I’d even find myself checking LinkedIn multiple times during the day or feeling envious of colleagues who lit up with excitement when talking about the projects they were working on.

The worst part? I started believing the problem was me. Maybe I was broken. Here I was, with roles other people would be grateful for and I felt… nothing. I told myself I was ungrateful, maybe even lazy. That shame grew heavier each time a new “fix” didn’t work.

And I tried everything. I chased bigger paychecks, more prestigious companies, and even considered entirely new paths. (I came this close to pursuing a Master’s in Human Development before ultimately choosing an MBA.) I kept thinking, “once I land the right role, everything will fall into place.” But no matter how many shifts I made, I eventually ended up back in the same place.

The turning point came while preparing for business school. I took a career assessment that said: your interests, not your abilities, determine your career satisfaction. That line hit me hard. It perfectly explained why I kept repeating the cycle. I didn’t have a career problem. I had a clarity problem.

I’d been optimizing for what looked good on paper instead of what actually felt good in my soul. Until I slowed down to clarify my values, motivators, and interests, no role was ever going to feel “right.”

I was constantly drained because I was going against my own grain. It’s like swimming against the current - every task feels heavier than it should. But once I got clear, the current shifted. I went from dragging myself through work to actually feeling energized by it. The moment I knew things were different was when, for the first time in years (maybe ever!), I ended a work week with more energy than I started. And I’ve had numerous weeks like that since. That was all the confirmation I needed.

If you’ve been stuck in this cycle, nothing is wrong with you. You’re not broken. You’re not ungrateful. You just don’t have clarity yet. But once you do, things start to change.

So before you update your resume again, pause and ask yourself:

  • When have I felt most alive and energized at work? What was I actually doing?

  • What do I need from my daily work to feel like the best version of myself?

Clarity comes first. And once you have it, your next career move doesn’t just look clear, it finally feels right.

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