When I Finally Admitted It Might Be Time to Retire

Are you quietly wondering if it’s time to turn the page on your working life?

I’ve been there, too.

For over 20 years, I poured my heart into my work as a child development specialist and preschool teacher. It wasn’t just a job…it was part of who I was. I loved helping little ones grow, watching their faces light up with curiosity, and partnering with families during such meaningful years.

That made my decision even harder. For a long time, I wrestled with that quiet but persistent question: “Should I retire… or keep pushing through?”

I felt torn. Part of me wanted to slow down, and another part kept whispering, “You’re not done yet.” So, like many of us do when we’re unsure, I decided to test it out.

I accepted not one but two different positions over a span of a few years, convincing myself that maybe the right role would reignite that spark. I needed to know if I could still be happy in that world.

But here’s the truth: I wasn’t.
Neither job filled the space in me that used to feel alive with purpose. I was going through the motions. My heart was somewhere else.

That’s when I began to notice the gentle signs…the whispers that maybe, just maybe, it was time to let go of that chapter and make room for something new.

Below are the signs that helped me decide. Maybe they’ll help you too.

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1. You’re just over it.

The job that used to excite you now just feels like a mental block. The projects that once lit a spark feel like heavy checklists. You’re showing up, but your heart isn’t. And deep down, you know that kind of “checked out” isn’t fair to you, or anyone else.

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2. You’re worn out.

You’re tired more often, stressed more easily, or your health is slipping. It’s not just a bad week or a rough season. It’s a pattern. Your energy is going toward keeping up, not living fully. That’s not something to ignore.

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3. You feel financially secure.

You’re not worried about paying the bills if you step away. You’ve created a plan and that stability can give you freedom. It’s a sign that the “someday” you’ve talked about might actually be now.

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4. You daydream about not working.

Trips, grandkids, hobbies, sleeping in…it all sounds better than another day of work. Those daydreams aren’t meaningless distractions—they’re clues pointing to where your heart longs to go next.

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5. The work no longer fulfills you.

What once gave you meaning or purpose now feels empty or routine, even on good days. When fulfillment fades, it’s usually not a sign of failure…it’s a sign of growth. You’ve outgrown a season.

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6. You’re craving freedom.

You want to wake up and choose how you spend your time, not have your calendar decide for you. You’ve spent years showing up for others; now you’re yearning to show up for yourself.

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7. Your priorities have changed.

Peace, health, and free time matter more than being employed. The things that used to drive you…status, routine, responsibility, don’t hold the same weight anymore. Your values have shifted, and that’s okay.

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8. Work feels like a different world now.

The new tech, new rules, new culture…it’s all somewhat too much. It’s not about resisting change—it’s about recognizing when the world you worked in for so long no longer feels like yours.

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9. It feels like work is in the way.

Instead of giving you purpose, it’s keeping you from the life you want. Maybe it’s time with your spouse, grandchildren, or simply slow mornings and quiet coffee. When work becomes the obstacle instead of the outlet, it may be time to reevaluate.

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10. You just feel done.

You’ve given it your best. Now you’re ready for a new chapter. That feeling isn’t laziness or selfishness…it’s a nudge toward what’s next.

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A Gentle Reminder:

Do any of these hit home?

Here’s the truth: There may never be a perfect moment to retire. But there is a moment when your heart starts to say, “I’m ready.” And when that whisper turns into a steady voice, it might be time to listen.

This next season doesn’t have to be scary. It can be full of rest, purpose, new adventures, and rediscovering what makes you come alive again.

Save this list or share it with a friend who’s thinking about retirement too. And tell me in the comments…what would you add to this list?

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#retirement #signstoretire #itmightbetimetoretire