How to Know When It's Time for a Change
Some of the hardest career decisions aren’t made when something is obviously wrong. They’re made when much of your career still looks right. You have a good position. You’re respected. You earn a good salary. You’ve built relationships and credibility. Maybe you’ve spent years—or even decades—with the organization.
And yet something has changed. You find yourself thinking: “Is it time for me to leave?”
I’ve explored this question with many coaching clients over the years. And rarely is there an immediate yes-or-no answer. Sometimes leaving is exactly the right decision. Sometimes staying is. The challenge is figuring out which one is right for you.
Start With What's Changed
Before deciding to leave, try to understand what is driving the question.
- Has the organization changed?
- Has your leadership changed?
- Has the culture changed?
- Have your responsibilities changed?
- Or have you changed?
Sometimes a job that was right for us five years ago isn’t right anymore. Perhaps you’re no longer learning. You’ve stopped feeling challenged. Your values no longer align with the organization’s direction. You’re repeatedly overlooked for opportunities. The work that once energized you now drains you. Or perhaps nothing is particularly wrong. You feel more and more ready for something different. That’s worth paying attention to. Not every desire for change signals you should leave. But it may signal it’s time to start asking questions.
Don't Confuse a Bad Season With the Wrong Career
Every job has difficult periods:
- A demanding project
- A disappointing performance review
- A new boss
- A reorganization
- A missed promotion
- A conflict with a colleague
One frustrating experience can make another opportunity look very attractive. That’s why I encourage clients not to make major career decisions solely in reaction to a difficult moment.
Ask yourself:
- Is this situation temporary, or has it become a pattern?
- Is the problem my role, my manager, or the organization?
- Is there something I could change without leaving?
- Have I clearly communicated what I need?
- Are there opportunities elsewhere in the organization I haven’t explored?
- If this particular problem disappeared tomorrow, would I still want to leave?
That last question can tell you a lot.
Are You Running Away—or Moving Toward Something?
There’s an important distinction between wanting to escape something and being genuinely drawn toward something new.
If your only thought is: “I need to get out of here,” you may know what you don’t want—but not yet know what you do want. Before making a major decision, flip the question.
What are you moving toward?
- More responsibility
- Less responsibility
- A healthier culture
- Greater flexibility
- More meaningful work
- Better compensation
- A chance to lead
- An opportunity to learn
- More time for the rest of your life
Sometimes we focus so much on what’s wrong with our current situation that we forget to define what we want to be different in the next one. Leaving something behind is only half the decision. The other half is knowing what you want to move toward.
Take a Hard Look at Your Values
Culture matters.
So do values.
You can be highly successful in an organization and still reach a point when you no longer feel you belong there. Perhaps decisions are being made in ways that conflict with your values. Maybe the leadership style has changed, or you’re now working for a leader whose values or approach no longer align with your own. Maybe collaboration has given way to competition. Maybe you no longer believe in the organization’s direction. Or perhaps you’ve changed, and the organization hasn’t.
Misaligned values are difficult to ignore indefinitely. Ask yourself:
“Can I continue to be the leader I want to be in this environment?”
That’s a very different question from:
“Can I continue doing this job?”
You probably can. The more important question may be whether you still want to.
Don't Let What You've Invested Make the Decision for You
This can be especially difficult for long-tenured leaders. You’ve invested years building your reputation. You know how things work. People know you. You have influence. You may have compensation, benefits, or incentives that are difficult to walk away from.
Starting somewhere else means becoming the new person again. That’s scary. And sometimes staying is absolutely the right decision. But don’t stay simply because you’ve already invested twenty years. Those twenty years aren’t lost if you leave.
You take them with you—the experience, relationships, judgment, lessons learned from mistakes, and leadership skills you’ve developed. Leaving an organization doesn’t erase what you built there.
Sometimes the hardest career decision isn’t whether you can stay. It’s whether staying is still the right choice for who you’ve become.
Test the Waters Before You Decide
One of the most useful things you can do when you’re uncertain is gather information. You don’t have to resign to explore what’s possible. Look at jobs that interest you. What responsibilities do they have? What do they pay? What skills are employers looking for? Talk with people in other organizations. Reconnect with former colleagues. Speak with recruiters. Research companies whose values appeal to you.
Consider whether you want another demanding leadership position—or whether this stage of life calls for something different. Perhaps you want fewer hours or a smaller organization. Maybe you’re ready for a different kind of role – consulting, teaching, board work, or even a completely different industry. Or perhaps you’ve always dreamed about starting your own business or going back to school.
And yes, I often encourage clients to go on a few interviews. Interviewing isn’t committing to leave. It’s gathering information. You learn how the market sees your experience. You discover what excites you—and sometimes what doesn’t. You hear about possibilities you hadn’t considered. You may even discover that what you already have looks pretty good. That’s valuable information, too. You don’t always have to leave to discover whether it’s time to go.
Be Honest About Fear
Sometimes we know it’s time to make a change long before we’re willing to admit it. Fear gets in the way:
- “What if I make the wrong decision?”
- “What if I don’t find something as good?”
- “What if I leave and regret it?”
- “What if I’m too old to start somewhere new?”
- “What if I fail?”
Those are legitimate concerns. But there’s another question worth asking:
“What happens if I stay?”
Imagine yourself one year from now.
Three years from now.
Five years from now.
If nothing changes, how do you feel? Relieved that you stayed? Or disappointed that you never permitted yourself to explore something else?
Sometimes the risk isn’t leaving.
Sometimes the risk is staying too long.
You Don't Have to Decide Today
You don’t have to decide today. Give yourself permission to be curious before you force yourself to be certain. Talk with people you trust. Work with a coach. Gather information. Explore possibilities. And pay attention to what you’re learning about yourself along the way. Clarity often develops through exploration.
You may ultimately decide to leave. You may decide to stay and make changes where you are. Either can be the right answer. The goal isn’t to decide quickly. It’s to make an intentional one.
Final Thoughts
In almost every successful career, there are moments when we wonder whether it’s time for something different. Don’t ignore the question. But don’t let a difficult week answer it for you either. Take the time to understand what’s changed, reconnect with what matters to you, explore what’s possible, and determine what you want your next chapter to offer that your current one does not. Then ask yourself:
“Am I staying because this is still where I want to be—or because I’m afraid to find out what else might be possible?”
The answer may tell you more than any pros-and-cons list ever could.
“A successful career isn’t measured by how long you stay. It’s shaped by knowing when staying still serves you—and when it’s time to consider what’s next.” — Katie Weiser
Continue Your Journey
Career decisions become especially difficult when there isn’t an obvious right or wrong answer. If you’re questioning whether it’s time to stay, leave, or explore something entirely different, coaching can give you the space to step away from the noise, clarify what matters most, and make a thoughtful decision about what comes next.