It’s a question that surfaces in almost every coaching or mentoring relationship at some point: should I leave my job?

The question rarely comes from nowhere. It usually emerges after months, perhaps years, of quiet frustration, shifting priorities, lack of relevant leadership, or a sense that something’s missing. You may have ticked off your goals, mastered your stack, delivered another successful project, but still feel something stirring beneath the surface.

Your head may tell you it’s time to move on. The logic is clear: the organisation has/hasn’t changed, leadership has shifted, the culture feels stale, or the opportunities to grow seem fewer by the day.

But the heart often tells a more complicated story. You might still care deeply about the people you work with. You might still feel a sense of unfinished business, or loyalty to the mission. And sometimes, even when your head screams “Go!”, your heart whispers, “Not yet.”

Understanding that tension, and learning how to listen properly to both, is at the core of making a wise, intentional career move.

Most of us are conditioned to lead with logic. In technology especially, we’re trained to analyse problems, assess risks, optimise systems. When applied to our own careers, that same mindset can lead to very rational-sounding justifications for leaving:

• “I’m better than my boss”
• “The leadership doesn’t get it”
• “The architecture is a mess and nobody cares”
• “I’ve hit a ceiling, there’s nowhere to go”

And sometimes, these statements are entirely true.

But here’s the question I often ask people who find themselves listing reasons like these: “If all of those issues magically resolved tomorrow, would you still want to leave?”

If the answer is yes, that’s not your head talking anymore, that’s your heart signalling that something deeper is missing.

There’s a particular feeling that comes when your heart has quietly checked out of a role.

You may still show up. You may still deliver. But the spark has gone.

• You stop volunteering for new challenges
• You attend meetings but don’t engage
• You find yourself looking at the clock more often
• You scroll LinkedIn out of habit, not intent

In coaching conversations, this stage is often described as psychological disengagement. It’s subtle at first, then accelerating. Once your heart leaves a role, it’s almost impossible to fully come back; because engagement isn’t just about what you do, it’s about what you feel.

And yet, many people stay. Sometimes out of loyalty. Sometimes out of fear. Sometimes out of lethargy. Sometimes simply because change feels too big.

But staying after your heart has gone is rarely sustainable. You can “tough it out” for a while, but emotional withdrawal often precedes performance decline, and eventually, resentment creeps in.

On the other side of the spectrum lies another risk, leaving too quickly.

When frustration builds, it’s tempting to see escape as the solution. But in many cases, leaving without reflection simply transfers the problem from one environment to another – this is what led me to become an executive coach!

In coaching, we talk about push and pull factors.

• Push factors are the things driving you away: toxic culture, burnout, boredom, lack of recognition
• Pull factors are what attract you elsewhere: growth, learning, purpose, autonomy, balance

If your decision to leave is 90% push and 10% pull, it’s worth pausing. The best moves are made when you’re drawn toward something, not just escaping something else.

Jumping from frustration can lead to poor alignment with the next role. You might accept a job that looks better on paper but offers the same underlying challenges: mismatched values, unclear purpose, or a culture that doesn’t fit.

That’s why timing, and readiness, matter.

Readiness isn’t about desire; it’s about preparation, both practical and emotional.

Before you even start applying for roles, ask yourself:

• Is my LinkedIn profile current, authentic, and aligned with the type of work I want next?
• Does my CV tell the right story, not just listing responsibilities, but articulating outcomes and impact?
• Have I maintained my professional network? Are there people who would advocate for me, or introduce me to opportunities?
• Do I understand the market, what’s changing, where the demand is, and where my skills fit best?

Many professionals neglect these basics because they’ve been “heads down” for years. But without these in place, you may find yourself under pressure to make fast decisions or accept the first offer that comes along – out of the frying pan into the fire 🔥

This is the harder part.

Leaving a role is rarely just a transaction, it’s a transition. You’re not just moving to a new job; you’re stepping out of an identity you’ve inhabited for potentially years.

In coaching, we often use William Bridges’ Transition Model, which distinguishes between change (external) and transition (internal). You can change jobs overnight, but the transition, the psychological adjustment, takes time.

Ask yourself:

• Have I made peace with leaving, or am I still hoping something will change?
• Am I clear about what I want next, or just clear about what I don’t want?
• Do I understand the emotional “cost” of change, the uncertainty, the learning curve, the loss of familiarity?

Readiness is about ensuring you can walk into your next role with confidence, energy, and clarity, not exhaustion or bitterness.

Once you’ve recognised that it’s time, and you’ve ensured you’re ready, the next step is to leave well.

Leaving well means maintaining integrity, relationships, and self-respect. It means not burning bridges or letting resentment define your departure.

Here are a few coaching tips to make that transition intentionally:

• Clarify your story – be able to articulate why you’re leaving in a positive, forward-looking way. “I’m looking for a role where I can have more influence on architectural strategy” sounds very different to “I’ve had enough of the politics”
• Set boundaries for reflection – don’t let your current frustrations dominate your energy. Focus on what you’ve learned, what you’ll take forward, and what you’ll leave behind
• Stay engaged until the end – how you leave is often remembered more than what you achieved while you were there. Finish strong
• Give yourself space before jumping in – if possible, take a short break between roles. It helps you reset emotionally and start the new chapter refreshed

If you are considering looking for a new role, check-out my post: 

Even with clarity, leaving a job is rarely easy.

For many people, fear is the biggest barrier, fear of the unknown, of financial instability, of making a mistake. Technical professionals often prefer certainty, predictability, and control. Stepping into ambiguity can feel deeply uncomfortable.

But in reality, almost every meaningful career move involves a degree of uncertainty. Growth and comfort rarely coexist.

That doesn’t mean being reckless. It means trusting that you’ve done the reflection, built the readiness, and made the decision consciously.

When I hear people say, “It’s time for me to leave,” I often think: “Maybe. But let’s find out what’s really driving that thought first.”

Because the answer isn’t always to leave. Sometimes, it’s to reconnect, to rediscover what once made the work meaningful. Sometimes, it’s to renegotiate, to reshape your role, relationships, or boundaries. And sometimes, yes, it’s to release, to close the chapter and move on.

Whatever the outcome, the process of examining both head and heart is valuable in itself. It builds self-awareness, intentionality, and resilience, qualities that will serve you well in every future decision.

So if you’re standing at that crossroads now, pause before you leap.
Ask:

• What is my head telling me?
• What is my heart telling me?
• What is my gut quietly whispering that I haven’t yet listened to?

Then act not from frustration, but from clarity.
Not from fear, but from readiness.
Not just to escape, but to grow.

Because when your head, heart, and timing align, that’s when you’ll find not just your next job, but your next chapter.