How to stop repeating the same career mistake

When people say they’re stuck in their careers, they often think it’s because they don’t know what they want next.

But career clarity isn’t just about deciding what’s next. It’s about understanding where you’ve already been and how it shaped you.

In my work, I focus on three key layers that often get overlooked in career transitions:

1. The circumstance: Why you left.
2. The functional mismatch: What wasn’t working in the structure of the role.
3. The emotional imprint: How you felt when you left, and how that’s still influencing you.

Each of these shapes the choices you make next, often without you realising it.

All three have a significant impact, but for now, let's look at function mismatch. This is what most people overlook. When we leave a role, we’re quick to focus on the headline: “My contract ended,” or “I needed a change.”

But what’s underneath that? In many cases, the job was never a good fit for how you work best. The role itself, its structure, pace, values, and expectations didn’t align with who you are or how you operate.

A functional mismatch could look like:

• Being micromanaged when you thrive on autonomy.
• Repeating tasks when you crave variety.
• Getting stuck in logistics when you’re built for strategy.
• Working in isolation when you need collaboration.

When that mismatch goes unnamed, it leads to the wrong solution: “I’ll find a similar job at a better company”, but that’s not always the answer. If you don’t name what didn’t work in the structure, you risk recreating the same dynamic in a new place.

If you don’t understand what didn’t work structurally, you risk replicating the same setup in a new role. That’s why people end up switching companies and still feel the same problems.

You get the job. It looks better on paper. You tell yourself it’s a fresh start, but six months in, the same dynamics appear. Different teams, but with the same stress and disconnect. It might not be about bad luck, but the structure of the role, the tasks, the pace, the environment, and the expectations were never designed with someone like you in mind.

This is where coaching is different. In sessions, we get to build a really good picture around:

• What you were really good at and whether that was ever recognised.
• What gave you energy, and what drained it.
• What values were supported, and which ones were compromised.
• What needs you silenced, and what trade-offs you made.

This insight stops you from jumping into the next job out of panic or pressure.

It lets you design something that fits you, not just your CV. Once you see the mismatch clearly, you stop chasing better versions of the same dynamic. You stop asking, “What job would make sense next based on my CV?” and start asking, “What setup helps me work at my best?”

If you’re ready to stop repeating the same pattern and want to figure out what kind of work would actually fit, then coaching might be a great option for you.