Should I Stay or Should I Go?

The Summer Tension Is Real

You’re staring out the window between back-to-back meetings, wondering how it’s already June and why you feel so damn stuck.

You’re not miserable. You’re not failing. But you’re definitely not excited, either.

And there it is: the thought you’ve been avoiding.

“Should I stay in this job… or is it time to move on?”

That question hits harder in the summer. Maybe it’s the extra daylight giving you space to reflect. Maybe it’s the sense that everyone else is moving forward while you’re treading water. Either way, if you’re feeling it, you’re not alone.

Here’s the truth: not every uncomfortable season means you need to leave.
But pretending everything is fine won’t lead to clarity, either.

Let’s talk about how to figure out what’s really going on so you can stop second-guessing and start making moves that feel aligned.

First: What Kind of Misalignment Are You Experiencing?

Before you jump to conclusions (or overhaul your résumé at 2 a.m.), take a beat.

Not all “something feels off” moments mean the same thing.

Here are three common types of career misalignment and what each might be trying to tell you.

1. Role Misalignment

You believe in the company. You support the mission.
But your actual job? It’s draining you.

You might be doing work that doesn’t leverage your strengths anymore. Or maybe you’ve outgrown your role, but you’re still operating under an old version of who you were when you started.

Clues:

• You’re bored, not challenged

• You’re doing tasks that feel like busywork

• You feel like your potential is being wasted

Ask yourself:
”Would I enjoy this more if the responsibilities or scope changed?”

2. Cultural Misalignment

You’re good at the work. You may even enjoy it.
But the environment? It’s grinding you down.

Whether it’s toxic leadership, lack of trust, performative values, or just a subtle “you don’t belong here” feeling, it matters.

Clues:

• You’re shrinking to fit

• You feel like you can’t be yourself at work

• You’re constantly on guard

Ask yourself:
”Do I feel seen, supported, and safe here? Or am I just surviving?”

3. Purpose Misalignment

You’re doing what you set out to do.
You’ve hit the milestones. But now… you’re not sure why you’re still doing it.

This is the kind of misalignment that sneaks up on high achievers. You’ve built your career around goals that once mattered but your life, priorities, or identity have evolved.

Clues:

• You feel emotionally flat

• You’re successful but unsatisfied

• You keep asking, “Is this really it?”

Ask yourself:
”If I weren’t already here, would I choose this again?”

Pause here if you want to journal it out: Which type of misalignment resonates most right now, and why?

If You’re Leaning Toward “Stay”

Not every misalignment means it’s time to leave. Sometimes, the answer is to reframe, renegotiate, or reset where you are.

Here are a few starting points:

1. Reclaim What You Can Control

   Not everything will change, but something probably can.

   • Is there a project you can take on that taps into your strengths?

   • Can you ask for clarity or restructure your role to focus on more meaningful work?

2. Set (or Reset) Boundaries

   Burnout isn’t always about the job, it’s often about how we’re doing it.
   Start with a few non-negotiables. Protect your time and energy like they matter… because they do.

3. Reconnect With Your Why

   Remind yourself what originally brought you here. Has your “why” evolved? Can you find new purpose in the work?

   If the answer is yes, you might not need to leave. You might just need to realign.

If You’re Leaning Toward “Go”

If you’re honest and realize the role, the culture, or the purpose no longer fits then leaving might be the aligned choice.

That doesn’t mean quitting tomorrow. It means owning the shift.

Here’s how to do that intentionally:

1. Give Yourself Permission to Grieve

   Even when a change is right, it’s hard. You’re letting go of what once felt safe, respected, and maybe even identity-defining.

   Grieving is part of growing.

2. Wait for Conviction, Not Certainty

   You don’t need every answer before you take action.
   You just need to stop pretending you’re okay when you’re not.

   Start with one step: update your résumé, schedule a call, book a coaching session. Momentum builds clarity.

3. Trust That the Real You Is a Good Bet

   If you’ve lost faith in your work, it may be because you’ve lost trust in your voice. Rebuilding that starts with taking action that aligns with who you’ve become, not who you had to be to get here.

A Real Story: From “This Is Fine” to “This Is Aligned”

One of my clients had been with the same organization for over a decade. He was known as the dependable one. The steady one. The “rock.”

But quietly, he felt stuck. Not miserable. Just… numb.

His job hadn’t changed much. But he had.

After a few sessions, it became clear that what once fit no longer did. His values had shifted, but he was still operating under old expectations. Not because anyone forced him to, but because he hadn’t stopped to reevaluate.

Once he gave himself permission to explore, he found a role in the same industry that honored his new season of life. Same field. Same skills. Entirely different energy.

Final Reflection

You don’t have to overhaul your entire life to move toward alignment.
But you do have to stop pretending everything is fine if it’s not.

Here’s the question that matters most:

“What needs to change for me to feel like I’m moving toward who I want to become?”

That answer might lead you deeper into your current work, or toward something entirely new.

Either way, it’s yours to claim.

Want to journal it out? Try this:
“If I gave myself permission to be honest, I’d admit that ___________ no longer fits.”

Takeaway

This isn’t about quitting or clinging.

It’s about choosing with intention.
You deserve a career that fits your life and not just your résumé.

And you don’t have to wait for the perfect moment.
Start with truth. Start with one step. Start now.