How To Know When It’s Time to Leave a Job You Love

Have you ever struggled with whether to leave a job or not? Check out our sure tell signs it's time to leave the job you love.

Some of us are lucky enough to have found a job we absolutely love. Maybe it’s the company, the people, or the actual work that makes this job rewarding for you. Whatever it is, you love going into work every day.

However, most amazing things end eventually (like that never-ending-pasta-bowl at Olive Garden). I hope this isn’t the case for you if you love your job, but for most of us, the reality is that we’ll leave our current roles and move onto different roles. For some, you might even leave a job you still love.

I recently left my “dream job” I had been at for nearly 5.5 years. It was my first job out of college and was the perfect job I had always dreamt of having one day; I was lucky enough that it was my very first full-time job. I loved the company, the people, and the work.

However, over the last year, something changed. My functional role became more and more specialized, and even though I enjoyed it, it wasn’t fresh and exciting anymore. I didn’t feel motivated to go to work anymore, and I needed a change. I needed a new challenge.

The decision to leave was the most difficult and emotional decision of my life thus far. However, through prayer and guidance, I realized moving on was the correct decision for me.

Only you can truly know when it’s time for you to leave your job, but here are some things you might experience when it’s time for you to leave a job you love (or once loved).

When Your Role Doesn’t Challenge You

One of the most rewarding aspects of a job is the challenge. Whether it’s figuring out a new plan for a patient you’ve never had to encounter before or it’s solving a problem that takes longer than you pictured, being challenged is a great feeling.

However, most challenging jobs become unchallenging at some point as you begin to master your role. If you don’t find challenge in your current role, and you’re unhappy about it, it might be time for something new.

How do you know when you aren’t being challenged? Here are some indicators:

  • You tend to lose interest in the things you normally enjoy in your job.
  • You start to make simple mistakes that you never used to make.
  • You’re often bored or feel stuck at your job.

If you realize your role doesn’t challenge you, that may be a sign you are ready to leave.

When You Dread Monday Morning

This is an obvious characteristic, and maybe the most glaring one. We’ve all had those Sunday nights where we don’t want to go to bed and wake up the next morning for work. We’ve all felt that the weekend was too short and we can’t wait for the next one. Even if we love our jobs.

However, you should never feel this way every single weekend. That’s a pretty big sign that you either aren’t excited for work or aren’t motivated to go. If you find you’re dreading Monday morning, think about why.

Do you dread encountering your coworkers? Do you dread sitting through another long workweek you can’t stand? Those are bigger situations and are probably signs you should consider switching jobs.

When You’re Too Comfortable

My former boss actually brought this reason to my attention. And this reason was the catalyst that made me consider other options.

Every good job makes you feel a little uncomfortable at times. The bigger issue is when this no longer happens.

When every single day is you in your comfort zone, you’re likely not improving (see next point) and you’re likely getting in too much of a groove. It won’t take long before you become bored – if you’re not already.

Even if you enjoy what you do, being too in sync and too good at your role is also a problem. Being the best in your role is great, but only for a short time. After a certain amount of time, you may stop taking things so seriously and may take your role for granted. Don’t do that.

Every job is a blessing, so make sure you’re treating your job as such. AND make sure you’re in a role you’re capable of appreciating.

When You’re Not Growing Anymore

Does it ever seem like it’s been a long time since you learned something new at work? You haven’t had to learn a new skill for your day-to-day tasks, and it’s starting to show.

I recommend taking an honest step back and think about all the ways you’ve improved over the last year or so. Obviously, you have to consider both hard and soft skills here.

Hard skills are those technical skills you learn that are directly related to your role (coding, project management, etc.)

Soft skills are the non-technical skills that indirectly make you better at your role (presentation skills, emotional intelligence, conflict resolution, etc.)

Don’t overlook the value gained from soft skills, too – even as a technical person. So, for example, if you’re a developer but you’ve had to make many presentations recently and you’ve become a better presenter, that’s still an improvement.

If you’re struggling to come up with any ways you’ve improved, this might be the perfect time to move on. If you’ve come up with things but you don’t believe these things are valuable to you and where you want to go in your career, you also might want to consider leaving.

When Prayer Guides You Away From Your Job

Don’t neglect the power of prayer in your career. Sometimes, prayer is the only solid answer you may receive in a challenging place in your life, and this is no different.

Talk to God. Make it a constant conversation about your career and your desire to glorify Him in the workplace. When you feel like you’re being called to work somewhere else in a different capacity, it’s probably time to leave.

If you feel like you’re in a role that doesn’t allow you to glorify God, you probably shouldn’t stick around. Not everything you do in your life will feel like it’s glorifying to God, but if you see that the role you’re in is definitely doing the opposite, it’s time to leave.

What I mean here is if you’re in a situation where you have to compromise your moral standards in any capacity, definitely reconsider the role. Even if you love your job, if you have to do things that don’t feel uplifting or morally sound, leave. You will regret sticking around. I can almost guarantee it.

When it Doesn’t Feel Right Anymore

You know what I’m talking about here. You’ve probably felt it before.

That’s when every day at work feels like you’re in a funk. You can’t seem to shake the feeling that you’re no longer in the right place anymore. Maybe one point in time you thought you could stay at this place forever, but you find it harder and harder to feel that again.

Trust your gut. Figure out if this “funk” is just a temporary situation or if it’s something you don’t see changing. If it’s because of a project you’re working on, wait to see if the completion of the project improves your mood about the job.

But, if after you complete that project (or you realize your job is now entirely that project for eternity) then it might be time to consider moving on.

When You Begin to Peruse Job Openings

A lot of people casually peruse job openings, even when they’re happy – just to see what else is out there. It’s when you start looking at other jobs and you start thinking “I could do that,” or “I’d love that job” that you might ready for a new role.

If you think you are happy in your role but suddenly you’re taking more interest in outside openings, first consider why this might be. Are you actually unhappy in your current role? Is something off? Perhaps, you feel overdue for a raise or promotion.

Or, are you getting in the “grass is always greener” mindset, assuming that even if you like your role, there has to be something better out there you don’t want to miss?

If you find that you’re constantly checking out job sites for the newest postings, or even more, you’re actually signing up and showing interest in postings, it might be the correct move for you.

When Your Attitude Changes

Have you come to the point where some of the inconvenient tasks you used to shrug off really start to bother you? Or, normal situations, while annoying, begin to really eat away at you? If either of these is true, there is a good chance that your attitude about your work has changed.

Maybe, this only requires you to step back and take a look at why you’re no longer in the correct mindset for the job. We’ve all had rough patches. Sometimes, it takes a bit of a mindset shift to get through it.

But maybe, it’s something more. Maybe you’re resenting your job, your employer, or your manager.

Try to pinpoint the time when your attitude changed and think about if you can come back from that. Obviously, if you once loved this job, there’s a chance you could love it again.

But there is also the chance that you won’t love it again. There is a chance that you might have to sever ties with your job before you resent the situation, permanently. There is absolutely no reason to ruin relationships you may want to utilize in the future simply because it’s time to move on.

When Others Must Convince You to Stay

Many of us have thought about leaving our jobs, even when we’re happy. Usually, we brush the idea away rather quickly, because we know it’s not the right time.

However, if you’re truly considering what it would be like to leave your current job, one indicator that it might be time to leave is if someone has to keep convincing you to stay. If outside sources have to keep convincing you to stay where you’re at, your mind might already be made up. If you’re unhappy but have to keep telling yourself “things will get better” over and over again over the course of months, consider moving on.

Maybe somewhere in your heart, you’ve already moved on. That’s okay.

When Fear of Missing Out Keeps You Here

This might seem counterintuitive but stick with me.

Okay, so before I left my job a few weeks ago, I had severe FOMO (fear of missing out). We had done so many cool things in the past that I didn’t want to miss out on in the future. I was scared to leave all the fun times we’d had as a team behind. I couldn’t make the decision to leave because I was terrified of leaving.

This quote kept playing over and over in my head during this decision-making process:

The reason people find it so hard to be happy is that they always see the past better than it was, the present worse than it is, and the future less resolved than it will be. -Marcel Pagnol

I spent so much time thinking about all the great things I’d miss that I forgot all the situations that made me consider leaving in the first place. It’s going to be okay to miss out on the fun team events or the cool new projects. The future won’t be as bad as you may be assuming, so sometimes you just need to take the risk.

When You Can’t Balance Everything

Some people can make 60+ hour workweeks work for them even over the course of several years. However, if you’re like me, that’s just not going to work for very long.

If your role is such that it calls you to put in wonky hours, too many hours, or otherwise causes another part of your life to be off-balance, keep a pulse of the situation. If it seems like it’s working okay for you now, make sure you keep it at the forefront of your mind so that something else doesn’t fall off the wayside.

For instance, if you realize an hour-long commute eats into dinnertime with your family or causes you to skip exercise, you might consider leaving. Or, if you’re taking calls at all hours and it causes you to lose significant sleep, you’ll become burnt out. There are many ways a job can put your life off-balance, and no job is worth putting what’s most important to you second.

So take some time to consider if your priorities are in check right now in your current role. Consider how, if anything, you would change the situation so that your life is more balanced.

In summary, take a hard look at your current role:

  • Are you missing a challenge?
  • Do you dread Monday mornings?
  • Are you too comfortable?
  • Have you stopped growing?
  • Does prayer tell you to leave?
  • Does something feel off?
  • Do you seriously peruse job openings?
  • Has your attitude turned sour?
  • Do others have to convince you to stay?
  • Do you have FOMO about leaving?
  • Is something off-balance in your life because of the role?

If several of these cases exist for you, it might be time to take on a new job.

Have you ever struggled with whether to leave a job or not? Check out our sure tell signs it's time to leave the job you love.

Eryn is a digital marketer by trade who gets to play around with websites both for a living and for fun. She has a passion for all things web, especially for optimizing websites, SEO, and marketing analytics. Eryn loves making things and curling up with a good book. She enjoys spending time with her husband, Kody, and her son, Drew (1).
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  • The Monday morning dread was the sign for me that I needed to move on with my job. It basically destroyed my Sundays, since I was so worried and stressed for the coming week.

    • That’s so tough when the stress and worry begins to eat into your weekend. I’m sorry to hear you dealt with that, but it sounds like you were able to move on.

  • The title of this post got my attention, because I truly love the people I work with and all that I have learned over the years in my position. Yet, something is stirring within me and I don’t want to miss where God is calling me. I am still waiting on clear direction, and your counsel has been helpful.

    • I’m glad to hear this post was helpful! I, too, was in a similar situation. It’s so difficult when you consider your coworkers close friends, because you don’t want to lose that closeness. I wish you the best in your decision!

  • Great article. Loaded with fine points. In my neck of the woods, most people are just looking for something to put food on the table. They simply can’t afford to leave their jobs. So I guess survival wins out against fulfilment in such cases. Cheers!

    • That’s an excellent point, Edith. Having any job at all is a blessing, and of course, survival is the first priority. There’s nothing wrong with a job that puts food on the table, and it’s incredibly respectable to work as a means of providing for your family. Not everyone has the opportunity to choose, and that’s okay, too.

  • Yes. We spend most of our lives working so I think you are exactly right. If you aren’t challenged or a dreading Monday mornings for a very long time its time to find something you enjoy. I think that’s why a lot of people are becoming entepreneurs and bloggers now days.

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