Dear Job Seekers (and Hiring Managers),
You know the feeling.
Sunday evening rolls around and your stomach tightens a little.
You’re not miserable exactly. But you’re not excited either.
You’ve been in the role for a while. The work is fine. The money is okay. Your colleagues are decent enough.
But something is missing. And you can’t quite put your finger on what.
So you stay. Because leaving feels risky. Because the market is uncertain. Because better the devil you know.
And another year passes.
So how do you know when it’s time to leave your job, and when it’s actually worth staying?
Knowing when to stay and when to go is one of the most consequential decisions you’ll make in your career. Most people make it by default rather than by choice.
Today, let’s make it a choice.
Why Deciding Whether to Leave a Job Is So Hard
Leaving a job is rarely black and white.
If things were truly terrible, the decision would be easy. But most people don’t leave terrible jobs – they leave mediocre ones. And mediocre is much harder to walk away from.
There’s also the very human tendency to adapt. We get used to things – even things that aren’t good for us. A toxic team dynamic, a manager who undermines you, work that stopped challenging you two years ago. Over time, these things start to feel normal.
And then there’s fear. Fear of the unknown. Fear of making the wrong move. Fear of being worse off. Fear of what people will think.
All of this adds up to inertia. And inertia, in a career, has a cost.
6 Signs It’s Time to Leave Your Job
- You’ve stopped growing
In tech careers, career stagnation can become a real risk because tools, frameworks, platforms and hiring expectations change quickly. The industry moves fast. If you’re not learning, you’re falling behind – and you may not notice until you’re interviewing for your next role and realising your skills are two or three years out of date.
Ask yourself honestly: what have I learned in the last 12 months that I couldn’t have learned anywhere else? What new problems have I solved? What new skills have I built?
If the answer is very little, that’s a signal worth taking seriously.
- There’s no path forward
Ambition looks different for everyone. Not everyone wants to be a CTO. But most people want to feel that there’s somewhere to go from where they are.
If there is no clear career progression, no increase in responsibility, and no opportunity to deepen your technical or leadership skills, it may be time to explore other roles.
A conversation with your manager about your growth trajectory is always worth having first. But if you’ve had that conversation and nothing changes, that’s your answer.
- Your values and the company’s values no longer align
This one creeps up on you.
Maybe the company’s culture has shifted. New leadership, new priorities, a change in how people are treated. Maybe you’ve grown and your sense of what matters to you has changed.
Either way, when there’s a consistent friction between what you believe and how the organisation operates, no amount of salary or convenience makes it comfortable for long.
- Your mental and physical health is suffering
This is the clearest signal of all – and the one people most often rationalise away.
Chronic stress, persistent anxiety about work, dreading Monday mornings, difficulty switching off, physical symptoms that track with your working week. These are not minor inconveniences. They are your body and mind telling you something important.
No job is worth your health. If work is consistently making you unwell, that is reason enough to leave.
- You’ve mentally already left
You’re going through the motions. You do what’s required but nothing more. You’ve stopped caring about the outcomes. You watch the clock.
This isn’t laziness. It’s a very clear signal that some part of you has already made the decision. The rest is just catching up.
And it’s worth catching up sooner rather than later – for your own sake and for the team around you.
- You’re only staying for the wrong reasons
“I can’t leave because the salary is hard to replace.”
“I can’t leave because I’ve been here so long.”
“I can’t leave because the market is tough right now.”
These are real considerations. But if they’re the only reasons you’re staying, that’s worth examining carefully. Staying somewhere purely out of financial fear or sunk cost is a different thing entirely to staying because you genuinely value what you have.
5 Signs It’s Worth Staying in Your Current Role
- You’re still being challenged
If the work is still stretching you – if there are problems worth solving, skills worth building, and days that end with a real sense of progress – that’s genuinely valuable. Don’t underestimate it.
- The relationship with your manager is good
People don’t leave jobs. They leave managers. A great manager – one who advocates for you, gives you honest feedback, and actually cares about your development – is rarer than it sounds. If you have one, factor that in.
- You’re building something worth building
Context matters enormously in tech work. If you’re in the middle of something meaningful – a product launch, a significant build, a transformation project – there can be real value in seeing it through. Leaving mid-build has a cost to you too, not just the team.
- The discomfort is growth, not misery
There’s a difference between being uncomfortable because you’re being stretched, and being uncomfortable because something is wrong. The first is a reason to stay. The second is a reason to go. Be honest about which one you’re experiencing.
- You haven’t actually tried to fix it
Sometimes the answer isn’t to leave – it’s to have a conversation you’ve been avoiding. With your manager about your role. With HR about a team issue. With yourself about what you actually want.
Before you leave, make sure you’ve genuinely tried to improve things. Not because you owe it to the company, but because you owe it to yourself to know you tried.
How to Decide Whether to Stay or Move On
When you’re in the middle of it, clarity is hard to find. Here are a few ways to cut through the noise:
The one year test
Imagine yourself in this role, at this company, in exactly one year’s time. Nothing has changed. Is that picture acceptable to you? Exciting? Or quietly devastating?
Your gut reaction to that question tells you more than any pros and cons list.
The outside perspective
Talk to someone you trust who isn’t emotionally invested in your decision. A mentor, a former colleague, a trusted recruiter. Sometimes the view from outside your own situation is the one that cuts through most clearly.
The energy audit
For one week, notice when you feel energised by your work and when you feel drained. Not every task in every job will be energising – but if the balance is consistently and heavily weighted towards drained, that’s data.
The opportunity question
Sometimes the decision isn’t really about leaving – it’s about what you’re leaving for. If a genuinely exciting opportunity appeared tomorrow, would you take it? If the honest answer is yes, immediately – that tells you something about how you really feel about where you are.
For tech professionals, the decision to leave a job is rarely just about salary. It is usually about growth, leadership, alignment, challenge and whether the role still supports the career you are trying to build.
For Hiring Managers: How to Spot When Your Best People Are Thinking About Leaving
You often know before they tell you.
The energy shifts. The engagement drops. They stop putting their hand up for new projects. They go quiet in meetings they used to own.
By the time someone hands in their notice, the decision has usually been made weeks or months earlier. The resignation letter is rarely the beginning – it’s the end.
What you can do:
- Have honest one-on-ones about career progression before people start looking elsewhere
- Ask directly: “Are you getting what you need from this role?” Most people will tell you the truth if you create space for it
- Don’t wait for the exit interview to find out what went wrong – those conversations are almost always too late
- Understand that sometimes the right thing for someone is to leave. A good manager supports that too
The best retention strategy isn’t a counter-offer. It’s an environment where people don’t start looking in the first place.
TL;DR
Most people stay too long in jobs they have already outgrown, not because the role is terrible, but because mediocre feels safer than uncertain. Signs it may be time to leave your job include career stagnation, no clear path forward, values misalignment, declining mental or physical health, mentally checking out, or staying only out of fear. Signs it may be worth staying include being challenged, having a strong manager, building something meaningful, experiencing growth discomfort rather than misery, or not yet trying to fix the issue. Use the one-year test, an outside perspective, an energy audit and the opportunity question to decide whether to stay or move on.
FAQ: Should I Stay in My Job or Move On?
Q: How long is too long to stay in one role?
A: There’s no universal answer – it depends entirely on what you’re getting from the role and where you want to go. In tech, staying somewhere for 3 to 5 years while continuously growing is very different from staying 3 to 5 years and learning nothing new. Time alone isn’t the measure. Growth, challenge, and alignment are.
Q: I want to leave but the market feels uncertain. Should I wait?
A: It depends on your situation. If you’re in genuine distress, waiting for perfect market conditions isn’t worth your wellbeing. If you’re simply restless, a few months of preparation – updating your CV, strengthening your LinkedIn, quietly reconnecting with your network – puts you in a much stronger position when you do move. Don’t use market uncertainty as a permanent reason to stay somewhere that isn’t working. It rarely gets more certain.
Q: Is it okay to start looking while I’m still employed?
A: Not only is it okay – it’s the smarter way to do it. You negotiate from a position of strength when you already have a salary coming in. You’re less likely to accept the wrong role out of desperation. And you’re more attractive to hiring managers, who generally view employed candidates more favourably. Just be discreet. Don’t job hunt on company time or devices, and keep your search confidential until you have something to announce.
Q: How do I know if I’m leaving for the right reasons or just running away from something?
A: Ask yourself what you’re moving towards, not just what you’re moving away from. Leaving because a role is genuinely wrong for you is healthy. Leaving because you’re avoiding a difficult conversation, a challenging project, or your own discomfort – and expecting the next job to feel different – is a pattern worth examining. The grass isn’t always greener. But sometimes it genuinely is. Know the difference.
Q: What if I leave and regret it?
A: You might. Career decisions rarely come with guarantees. But staying somewhere that’s wrong for you has a cost too – it’s just a slower, quieter one. Most people who make a thoughtful, well-prepared move don’t regret it, even when the new role isn’t perfect. What people tend to regret most is waiting too long.
Have you ever stayed in a role longer than you should have, or made the leap and realised it was the right decision? What finally made it clear for you? Share your experience in the comments.
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Helping people make the move at the right time – for the right reasons.
Therese Otten is the founder of DataTech Recruitment since 2019, and a Senior IT Recruitment Consultant based in South Africa with 20+ years of Recruitment experience. She specialises in connecting top tech talent with SMEs and start-ups and companies building their tech teams, with a focus on developers, architects, testers, IT leaders and many more. Known for her honest, consultative approach, she is passionate about candidate care, client partnerships, and raising the standard of recruitment in the South African market.
Looking to hire? Get in touch: therese@datatechrecruit.co.za
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