The honest answer is this: you start wondering if it’s time to leave your job long before you have a plan to replace it. The feeling doesn’t show up as certainty. It shows up as repetition.

“It’s the moment when you leave the office and think, what am I doing? Like, why am I doing this? This doesn’t feel like very good. This doesn’t feel like it’s supposed to be what I’m doing.”

That thought doesn’t come with instructions. It doesn’t tell you what’s next. It just sits there quietly, waiting to be acknowledged.

Most people don’t talk about that part. They talk about leaving once they already have something lined up, once the story makes sense. But the decision almost always starts earlier, in moments that feel small and easy to dismiss. I wrote about that exact realization in What Should I Do If I Have No Idea What I Want To Do With My Life, because that question usually arrives long before clarity does.

When the Question Keeps Coming Back

One bad day does not mean it’s time to quit. Everyone has days where work feels frustrating or exhausting. But there’s a difference between a hard day and a feeling that won’t go away.

“It’s also the moment when you feel burnt out and you feel like you have nothing left to give and you feel out of sorts and kind of out of whack.”

You stop feeling challenged. You stop feeling curious. You notice yourself opening job boards without any real intention.

“It’s the moment you start looking at Indeed for new jobs.”

That’s usually when people start negotiating with themselves. Maybe you’re just tired. Maybe it’s a rough week. Maybe things will feel better after the next project, the next raise, the next change in pace.

So you push the feeling down.

“It’s so much easier to be like, actually, I don’t really want to deal with you right now.”

But when the same thought keeps returning, it’s usually because something real is trying to get your attention. This is often the same moment described in How To Build a Great Career in Your 20s with CEO Of Barstool Sports, when stagnation starts to feel louder than stability.

Why Waiting for Clarity Doesn’t Work

One of the biggest misconceptions about leaving a job is that clarity is supposed to come first. That you’re supposed to know exactly what you want next before you’re allowed to admit that what you’re doing now isn’t right.

That’s rarely how it works.

“I know in my gut or I feel like I’m ready for something new.”

That gut feeling is uncomfortable because it doesn’t promise safety. It doesn’t promise that leaving will be easy or that the next thing will immediately feel better. It just tells you that staying exactly where you are feels heavier than it used to.

According to Harvard Business Review, most career pivots begin with dissatisfaction rather than a clear alternative. People leave because something no longer fits, not because they already know what does.

The reason so many people stay longer than they want to is not because they love their job. It’s because the unknown feels heavier than the discomfort they already understand.

“You’re actively jumping into unknown. You’re jumping into something that you don’t know the answer to.”

The Middle Part Everyone Avoids

Leaving a job rarely means stepping directly into something clear and exciting. There’s usually a middle part where nothing feels settled.

Applications. Conversations. Waiting. Wondering if you’re doing the right thing.

“That middle part can be super miserable.”

No one likes to talk about that phase because it’s messy and exhausting and full of second-guessing. But avoiding it doesn’t make it disappear. It just keeps you stuck somewhere you’ve already outgrown.

Research from Psychology Today shows that most people experience multiple periods of career uncertainty, even after making “successful” moves. The middle part isn’t a failure. It’s part of the process.

That’s why knowing it might be time to leave doesn’t always mean leaving immediately. Sometimes it just means stopping the internal argument and being honest with yourself.

“You don’t have to have all of the answers.”

Listening Without Forcing a Decision

There’s pressure to treat leaving a job like a single, dramatic moment. A resignation letter. A clean break. A bold leap.

But more often, it’s quieter than that.

“If I know that this thing isn’t right, but I start to figure out what I want to do next.”

You notice what drains you and what doesn’t. You notice what excites you and what you’ve been tolerating. You stop telling yourself that discomfort is something you need to ignore.

Some days feel manageable. Other days don’t.

“Some days it doesn’t feel right and some days it does.”

That fluctuation doesn’t mean you’re confused. It means you’re paying attention. This is the same awareness I explored in Why Do I Feel Lost In My Career, when staying starts to feel like inertia instead of progress.

And Here's The Thing

If you’re asking how to know when it’s time to leave your job, the question itself matters.

It means something in you is listening. It means you’re no longer willing to ignore how you feel just because things look fine on the outside.

“You don’t have to be so certain.”

Knowing it might be time to leave doesn’t require a perfect plan. It doesn’t require permission. And it doesn’t require immediate action.

Sometimes it starts with nothing more than admitting that staying no longer feels as easy as it once did.

And for now, that honesty is enough.

FAQ: Knowing When It’s Time to Leave Your Job

How do I know if it’s really time to leave?
When the same thought keeps returning. “It’s the moment when you leave the office and think, what am I doing?”

Do I need to know what I want next before leaving?
No. “You don’t have to have all of the answers.”

What if I’m just burnt out, not ready to quit?
Look for repetition. Burnout fades. Misalignment usually doesn’t.

Is it normal to feel unsure about leaving?
Yes. “Some days it won’t feel right, and some days it will.”

Should I ignore the feeling if I’m not ready to change yet?
No. Awareness is often the first real step forward.