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The Career Trap No One Talks About: “OK Land”

career development fulfilment human behaviour leadership personal development self refection Mar 20, 2026

Most people don’t need a new career. They just need to stop ignoring the signals from the one they’ve already got.

I sometimes think changing careers sits in a similar category to changing banks. You’re not overly happy with your bank, a few things frustrate you, you’ve thought about switching a couple of times… but it just feels like a bit too much effort, so you stay where you are.

The big difference, of course, is that you don’t spend 40 hours + a week at the local bank.

One of the things I’ve noticed over the years, particularly working with senior executives, is that we don’t spend a lot of time going deep on our careers. We spend a lot of time in them, but not a lot of time really stepping back and reflecting on them.

It's a missed opportunity but it’s understandable. Reflection takes time and energy occasionally it asks questions you’re not entirely sure you want the answer to. There’s a very human tendency to avoid information that might force a change. Because once you see something clearly, it’s difficult to unsee it. It creates a tension between where you are and where you think you should be.

And rather than sit with that tension, most of us instinctively step away from it. 

So instead, we tend to stay closer to the surface, we keep things progressing and assume that if we just keep going, it will all work itself out. Sometimes it does. But more often, without any real intention or adjustment, we just stay broadly where we are. Not unhappy enough to make a change, but not quite where we could be either. I’m going to call this “OK land”

In the online Career Reset course I run for senior executives, one of the simplest but most powerful things we build in is space to properly reflect. Not to overthink everything, just to pause long enough to ask a few honest questions.

The questions themselves aren’t particularly complex. Here are sample of three that I use regularly:

Am I actually learning and growing in this role, or have I just become very efficient at doing what I already know?

What parts of my work are giving me energy, and what parts are taking it away?

If nothing really changed from here, would I be happy doing this for the next year or two?

They’re simple questions, but they tend to cut through fairly quickly. And just asking them, without rushing to fix anything, often brings a level of clarity that’s been sitting there the whole time. Sometimes this may not even mean you need a new career, it may just be adjusting the one you have.

If you’ve got a few minutes today, it’s probably worth the check-in. There are never any guarantees, but if there is an opportunity to move on from “OK Land”  then we owe it to ourselves to explore it.

If this resonates with you and you sense you may be ready for a change, then check out my Career Reset Course for further details: https://www.jeneroenterprises.com/online-career-course-career-reset-for-senior-leaders