9 signs it’s time to leave your nine-to-five and pursue something else

The daily grind gets everyone down, at least sometimes. But if it’s really starting to get to you, you might start wondering if it isn’t time to do something else.

The marketplace has changed drastically in the past decade, especially since the Covid-19 pandemic, and the nature of work has really shifted.

But if you’re thinking about striking out in a new direction or even going it alone with your pet project, how do you know when the time is right?

To help you figure it out, I’ve put together a collection of 9 signs it’s time to leave your nine-to-five and pursue something else. And I hope it’s something you truly love!

1) You hate your job.

This might seem like a no-brainer. But you’d be surprised how many people think everyone hates their job.

This simply isn’t true!

Work is so often portrayed as dull and dreary or even soul-crushing, but it certainly doesn’t have to be.

Especially now:

Digital tools and communications technology are making more and more areas of work accessible, so maybe it’s time to get into something you’re way more passionate about.

If you’re hating the office vibe, the corporate culture, or the actual tasks you do day in and day out, there are certainly greener pastures to look for. 

Why sit and stew in a job that you don’t enjoy when you could be doing something that elevates you or at least doesn’t make you want to tear out your hair?

It simply isn’t kind to yourself to stay stuck in that kind of situation, so why not get out now?

2) You can’t get to work on time.

This is a sure sign that something just isn’t working. 

Some of us are definitely worse at time management than others, but if your job is always what’s losing out, this might be a subconscious clue that it’s not the right job for you.

I know that when I used to work in an office and had to commute half an hour to work in the morning, it felt like daily torture. 

I’d get up on time, usually, but there was always something that delayed me and stole my attention away from what I should have been focusing on – getting there on time.

And while I never really got chewed out for being late, it slowly became clear to me that I didn’t have the necessary commitment to the job that I should have.

My heart simply wasn’t in it.

Nothing’s all that hard if you want to do it, but it sure can be a struggle when you don’t!

3) Your “other job” is succeeding.

Sideline. Side hustle, night job to your day job. 

Whatever you want to call it, many people have them but only a very lucky few get to leave their nine-to-five jobs and start doing their own thing.

Or that’s what so many of us believe.

However, small brands are finding it easier to get noticed, and with a rising personalization of products and services in the marketplace, small businesses are able to fill small niches. 

Communication apps and online marketplaces have made it easier than ever to reach clients and get products to customers. And digital tools are making DIY easier by the day.

So maybe your side project actually does have a chance of succeeding!

If things are getting better and better, it might be time to take a serious look at the possibility that your side project might become more lucrative than your day job. 

You certainly already know it’s far more fulfilling!

4) You dream of being your own boss.

Some people are just fiercely independent or have such a clear drive that they don’t need structures and managers to stand in their way.

Instead, they do much better directing their own ideas and managing their own work. In other words, they’re made to be their own bosses.

Are you one of these people?

If you are, you’ll likely have a lot of ambition, very clear goals, independence, and heaps of self-motivation. You’ll also need a wide variety of skills in order to succeed in a more-independent set-up. 

But it can be incredibly rewarding:

Having control over your own work and having the final say on how to do things are conditions some people dream about, even while they give others the shivers.

If you have the working style and the constitution for it, becoming your own boss might be the most satisfying thing you ever do. 

But you’ll have to leave your 9-to-5 job to find out!

5) Offers are coming in.

9 signs its time to leave your nine to five and pursue something else 2 9 signs it’s time to leave your nine-to-five and pursue something else

What better sign do you need that it’s time to leave your nine-to-five and pursue something else than others asking you to do just that?!

There’s not much to say about this sign. It’s just great!

If you’re getting invitations from other employers or projects offering you positions and pay that are more attractive than your current job, you owe it to yourself to look into them.

And since they’re coming to you, the ball’s in your court, so to speak.

You can stay in your current nine-to-five job and let them court you until you find an offer that’s impossible to turn down.

6) This job and your core values don’t match up.

Sometimes the work that you have to do in your job really rubs you the wrong way.

And if you are doing something at work that really goes against your core values, the things you hold up as crucial and important, you can even feel physically sick doing them.

I just heard a story recently that’s a perfect example of this juxtaposition.

A friend told me how he used to work in a factory producing steel products and tools. Then management started doing something new. 

They started to coat the steel in chrome and market it falsely as stainless steel.

My friend was young and needed the job, so while he knew it was happening, he kept his mouth shut.

But one day, he found out that the factory had won a big contract to supply tools and equipment for a hospital. That was something he couldn’t stomach, and he walked off the job shortly after.

This is a pretty serious example, but you might have your own value conflicts you’re dealing with. 

Those feelings could definitely be a sign it’s time to move on.

7) Your 9-5 doesn’t give you the flexibility you need.

Juggling work, relationships, family, and hobbies can be hard work.

And sometimes you have to ask yourself, why is work always so rigid while the others have to bend around it?

Shouldn’t work be able to compromise at least sometimes?

Well, it might if you were in a different job or working on your own project.

Most large organizations struggle to be flexible since they have so much and so many people to manage. So perhaps a smaller employer, one that understands your unique needs, is what you should be looking for.

Or maybe you’d do better being your own boss.

If you feel your job is way too inflexible, that might be a sign you need to up and move on.

8) The money they’re paying you isn’t what you’re worth.

Just to be really clear, I mean this in the sense that they’re paying you less than what you’re worth, not more.

If you’re raking in way more than you’re worth, by all means, keep making that money. But don’t forget that this can put you in the precarious position of always looking over your shoulder, wondering when they’re going to find out!

No, I’m talking about being undervalued.

And there are two main reasons why you’re not getting what you’re worth at your current job.

One is that your value isn’t recognized. You might be given the opportunities to show what you can do, or you might simply be doing all the work and getting none of the credit.

The other is that they know your value but either can’t or won’t increase your pay. 

But just because you’re not getting paid what you should by your current employer doesn’t mean there isn’t another out there who will pay you appropriately.

And any employer who thinks a person would do the same job for less money than they can get elsewhere is going to find themself losing a lot of employees.

9) You’re reading this.

No, seriously. 

You may have been looking for signs from outside, but how about a sign from your own behavior?

If you’re reading posts about quitting your day job, spending your time daydreaming about doing something different, or constantly searching for new employment, you can’t be too satisfied with where you are, can you?

If it’s time to leave your nine-to-five job, there are signs to point the way. Look deep into your own feelings, and I’m sure you’ll find out the answer to that old question – should I stay or should I go? 




Picture of Marcel Deer

Marcel Deer

Marcel is a journalist, gamer, and entrepreneur. When not obsessing over his man cave or the latest tech, he’s failing helplessly at training his obnoxious rescue dog ‘Boogies’.

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