How to Tell If It’s Time to Leave Your Job — and What to Do Next

If you’ve been feeling stuck, restless, or quietly discontent at work, you’re not alone. I work with many mid-career professionals who reach a point where the job that once fit no longer does. But how do you know if it’s just a rough patch… or a sign it’s time to make a change?

Below is a practical checklist to help you get clear on what’s going on—and what steps to take if it’s time to pivot.

Signs It Might Be Time to Leave Your Job

• You dread Monday by Sunday morning.
  If the weekend never feels long enough and your stomach knots up by Sunday afternoon, that’s worth paying attention to.

• You’ve outgrown the role.
  You’re not learning, growing, or being challenged—and promotions or new responsibilities aren’t in sight.

• You feel disconnected from the mission or values.
  Maybe your company changed… or maybe you did. Either way, you no longer feel aligned with why the work matters.

• You’re constantly burnt out.
  If even time off doesn’t recharge you, and stress has become your baseline, it might not be the workload—it might be the environment, culture, and the misalignment causing the drain on your energy.

• You’re staying out of fear.
  You tell yourself, “It’s too late to start over,” “I wouldn’t know where to go,” or “This is the safe choice.” Staying out of fear is rarely the best long-term strategy.

• You fantasize about doing something else—but never take the first step.
  Whether it’s a different field, role, or even lifestyle, you’ve had the same dream on repeat. You just haven’t acted on it. Yet.

Reflection Prompts to Explore What’s Next

• What part of my current job still energizes me? What part drains me most?
  (Clarity comes when you separate the good from the bad.)

• If I didn’t have to worry about money or status, what would I want to do next?
  (Sometimes our most honest answers are buried under fear.)

• Am I staying because it’s “comfortable”—or because it’s right?
  (There’s a big difference.)

• What am I curious about right now, even if I don’t know where it will lead?
  (Curiosity is often a breadcrumb trail to purpose.)

What to Do Next (If You’re Thinking About a Pivot)

1. Start a Career Journal.
   Track what excites you, frustrates you, and interests you over the next 2–4 weeks. Patterns will emerge—and they’ll guide your next move.
   (We’ve got a great journal available in the shop if you need help, guidance, or inspiration about journaling: kendracourt.com/shop)

2. Talk to someone in the role or field you’re curious about.
   Informational interviews are low-pressure and high-value. A 30-minute chat can save you months of guesswork. Invite someone for a coffee or quick Zoom chat.

3. Update your LinkedIn and resume—before you need to.
   This builds confidence and gets you into motion. Even if you don’t apply for anything yet, it signals to yourself: I’m preparing for a shift.

4. Test-drive before you leap.
   Take a course. Volunteer. Freelance on the side. Explore before you exit—especially if you’re still uncertain.

5. Work with a coach, mentor, or accountability partner.
   You don’t have to navigate this alone. A second set of eyes can help you see options you didn’t know you had.

Remember: You’re Not “Too Late”—You’re Just Ready

Mid-career isn’t a dead end. It’s a powerful place to pivot from, because you bring experience, perspective, and self-awareness to the table. If you’re on the fence, use this moment as an invitation—not a crisis.

Sometimes, the boldest move isn’t quitting tomorrow—it’s finally starting to ask better questions about what you really want.

And once you start asking, the path ahead gets clearer—one step at a time.

Want more support navigating your next chapter?

Work with me 1:1 here or grab my free guide: “3 Steps to Kickstart your Career.”

Let’s make your next move intentional.