3 Signs You're Ready to Breakup With the Job You Once Loved

What's worse - leaving somewhere you love, or doing something you hate?

That's the question I've had to wrestle with at every pivotal career juncture. Deciding to leave a job that no longer serves you is a lot like deciding to leave a relationship that has run its course.

Think about it:

At first, there’s excitement—you can’t stop talking about your new job, proudly sharing the details with friends and family (just like gushing about a promising new relationship).

The job provides a sense of security and routine—you know what to expect (like the comfort of settling into familiar rhythms with someone you trust).

Your coworkers become more than just colleagues; they’re the ones who share your struggles, celebrate your wins, and make the grind bearable (like a partner who’s with you through the ups and downs of life).

And then... something shifts.

Maybe it's subtle at first, but it grows.

The job starts to let you down, repeatedly.

Things aren't the same anymore.

You're treated differently, as if you're no longer important.

The questions start creeping in: Is there someone else? Do I not matter anymore? WHERE DID WE GO WRONG?

I've been there, and I know how hard it is to navigate this crossroads. If you're struggling with this decision right now, let me help you think it through.

Here are three essential questions I've learned to ask myself at times like these.

1. Does This Culture Fit?

Harvard Business Review reported on an interesting study looking at culture fit and adaptability (source). For context, culture fit can be summarized as how well someone reflects the values, norms, and behaviors of their team or organization.

The research findings showed that employees who have a high level of culture fit tend to thrive. They receive more promotions, get better performance evaluations, earn higher bonuses, and are less likely to face layoffs.

Even more interesting was that those who could adapt to the culture were particularly successful, since they could maintain their fit even as organizational norms evolved.

But when there's a mismatch, people start feeling like outsiders at their own workplace.

Sure, you can just decide to adapt to a culture that's not quite right, and many do, but only you know whether or not that’s sustainable in your current environment.

So here's the first million-dollar question: do you fit into your current team or organization's culture and if not, do you believe that you can successfully adapt to it without making yourself miserable?

2. Are You Operating Within Your Strengths?

Here's a truth that might surprise you: in today's workplace, growth matters more than money (source).

We're all chasing something bigger than just a paycheck – we want to evolve, expand our skills, and feel like we're making real progress in our careers.

However, here's the reality:

• 34% of all American workers feel their companies aren't utilizing their full potential

• This number rises to underrepresented groups (46% for Black and 38% for Latinx professionals)

• Almost twice as many women (43%) feel underutilized compared to men (24%)

• 82% of women who feel this way are in individual contributor roles

• 80% of men who feel this way are in managerial or executive positions

• 47% of employees wish their companies had better visibility into their skill sets

• 43% want opportunities to work on more diverse projects beyond their current job description

Let's be real, we spend too many hours at work to settle for anything less than fulfillment. And true fulfillment comes from leveraging your best skills, making meaningful contributions, and knowing that your unique talents are valued. 

So the next question you need to answer is: when was the last time you felt truly energized by your work? Do you feel fulfilled and fully utilized in your current role, or are you just going through the motions?

3. Are You Still There Because You're Comfortable?

Have you ever heard of the Yerkes-Dodson Law (source)? It’s a psychological principle that explains the relationship between mental stress and performance. It suggests that there's a sweet spot of optimal engagement, where performance and stress are both sufficiently high enough to keep you engaged, focused, and attentive (source).

But there's danger on either end of the sweet-spot spectrum. Too much stress will leave you feeling overwhelmed and burnt out. And too little stress leads to boredom and lack of motivation.

All too often, we unintentionally settle for the low-stress end of the spectrum, convincing ourselves, “It’s not great, but it could be worse.”

Instead of seeking growth, we stick to what’s familiar, even when it no longer serves us.

So, ask yourself: Are you thriving, or have you let comfort keep you stuck?

Now What?

I know that these aren’t easy questions to answer. They push us to face uncomfortable truths about where we are and where we want to be. But just like in relationships, the hardest decisions often lead to the greatest growth.

Think carefully about where you are in your career, where you want to go, and whether your current job aligns with those goals. If you've found yourself answering "yes" to any of the questions posed here, it might be time to consider other options.

Some of you might be nodding along, realizing it’s time to move on. Others may feel deep down that you should leave but still want to give it one more shot—and I respect that.

If you’re in the latter group, my next article is for you. I’ll share the challenges that leave some high performers feeling stuck in their careers, and how to overcome them.

If you’re in the former group, checkout my last article and newsletter on performance management.

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