In partnership with

Hi there, it’s Jill!

Deciding when to leave a job is one of the trickiest choices in anyone’s career.

Stay too long, you risk feeling stagnant.
Leave too early, you might wonder if you gave it enough time to grow.

The truth is: there’s no perfect formula. But there are clear signals and patterns you can pay attention to. Today, let’s break down four scenarios that often mean it’s time to take the leap.

01 You’ve Already Mastered the Role

After a certain point, your learning curve flattens. You’ve handled the toughest challenges, mastered the skills, and proven you can deliver.

Time in role does matter, but it’s not the only measure. For example, if you faced a period of high-intensity work, your growth could accelerate. A year of leading multiple high-stakes projects might teach you as much as three years in a steady routine.

Think about it: you’ve learned how to…

Navigate conflicts between teams
Motivate colleagues to cooperate
Balance competing priorities and keep stakeholders aligned

These are valuable, career-defining skills. But if every week starts to feel like déjà vu, you may be ready for a bigger challenge.

Staying to be the “expert” is fine—but if you’re seeking growth, don’t let comfort zone become a mental cage.

02 Your Growth Path is Blocked

Sometimes, you feel things have been stagnant for a while:

Maybe projects aren’t stretching you anymore. Maybe there’s no clear promotion path because there is no vacancy. Or maybe the opportunities are there, but you’re not seen as the “next in line.”

If advancing internally matters to you, speak up early. Many people miss out simply because their leaders don’t know they’re hungry for more. Share your ambitions, and ask directly: What skills do I need to demonstrate to be considered for the next step?

This does two things:

It puts you on your manager’s radar.
It gives you clarity on whether growth here is realistic—or if you need to look elsewhere.

If there is no clear sense on whether the opportunity to advance your career is there, keep having this conversation, until you come to your own conclusion. Patience is a virtue, strategic pivoting is, too.

03 The Culture is Draining You

It’s lucky to be in a team where the culture is healthy and inclusive.

However, if you consistently feel undervalued, or if the workload is unsustainable, or if the environment makes you feel like you don’t belong there, etc. If all these situations have been around for long enough, it’s not just a “bad week.” It’s a signal.

Even though I’m a big believer in resilience and growth through challenges…

There’s a difference between stretching yourself and burning yourself out. If your job is eroding your mental health, straining relationships, or making you dread every Monday, it’s time to reflect.

Sometimes the best move isn’t up, it’s out. Even a lateral shift can be a lifesaver if it gets you into a healthier environment where you can thrive.

04 It Doesn’t Align With Your Long-Term Goals

This one assumes you’ve thought about where you want your career to go (and if you haven’t, that’s perfectly normal—especially early on).

Your career path will rarely be a straight line. Passions evolve. Strengths shift. Entire industries change. With AI reshaping work at lightning speed, adaptability is more important than sticking to a rigid plan.

But here’s the key: if your current role is pulling you in a direction that no longer excites you, it may be time to course-correct.

Sometimes that means a bold pivot, even if it requires taking a step sideways or down. It’s not easy, especially mid-career when you’ve already built a reputation in one field.

But remember: short-term discomfort is often the price of long-term fulfillment.

Final Thoughts

Leaving a job isn’t just about walking away, it’s about moving toward something better.

The right time to leave usually comes down to one of these questions:

Am I still learning, or just repeating?
Do I see opportunity of advancement here?
Is this environment fueling me, or draining me?
Does this role align with the person I want to become?

If too many answers point to “no,” trust and stay true to yourself. Growth rarely happens without a leap.

If you are looking for the next role, this post is here to help👉 A Step-by-Step Guide to Land Your Next Job in 3-6 Months. All the best to your journey!

— Jill

Founder of Anchor Growth Newsletter

Your career will thank you.

Over 4 million professionals start their day with Morning Brew—because business news doesn’t have to be boring.

Each daily email breaks down the biggest stories in business, tech, and finance with clarity, wit, and relevance—so you're not just informed, you're actually interested.

Whether you’re leading meetings or just trying to keep up, Morning Brew helps you talk the talk without digging through social media or jargon-packed articles. And odds are, it’s already sitting in your coworker’s inbox—so you’ll have plenty to chat about.

It’s 100% free and takes less than 15 seconds to sign up, so try it today and see how Morning Brew is transforming business media for the better.

Check it out