Should I Retire If I Don’t Feel Ready? (The Deeper Reason You Can’t Let Go of Work)
- Kasey Barret
- Jul 24
- 3 min read
(Questions for Kasey: Calm for the Busy Brain)
Not ready to retire, even though you can? Here’s why stepping away from work feels unsettling, and how to find clarity about what you really want.
Dear Kasey,
I’m at an age where most people retire. I have more than enough to live comfortably, and my family keeps telling me it’s time to slow down. But I can’t seem to stop working. I tell myself I still enjoy it, but deep down, I’m not sure who I’d be without it. Should I retire if I don’t feel ready?
-Anonymous
Dear Not-Quite-Retired,
First, please know that there’s nothing wrong with you for not feeling ready. Work isn’t just about money. It gives you a sense of purpose, structure, and belonging. For many people, (especially those who have always been driven and high-achieving) it becomes part of who they are. So of course the idea of stepping away brings a sense of unease. It’s completely normal.
But here’s something to sit with: sometimes the hesitation to retire isn’t just about enjoying your work. It’s about what work protects you from feeling. When your worth has been tied to productivity for decades, or when staying busy has been your way of avoiding the deeper emotions beneath the surface, stopping can feel unsafe to your nervous system.
Retirement isn’t just an ending, it’s a shift in your identity. And that’s huge. There’s grief and loss tied to that. It’s completely normal to wonder: Who am I if I’m not working? Will I still feel valuable? Will I still feel needed? What will I do with myself?
So here’s my answer: instead of pressuring yourself with “Should I or shouldn’t I?”, drop the urgency and try considering different questions:
What am I afraid I’ll lose if I stop working?
Does work give me something emotionally that I’m not sure I can find anywhere else?
If I didn’t have to prove or earn anything, what would I want my life to feel like now?
Retirement doesn’t have to be all-or-nothing. You could scale back, consult, or try a “trial retirement” for a few months to see how it feels. And if you decide you truly love working? That’s okay, too. The key is making sure you’re choosing it from a place of alignment, not from a place of fear.
Your next chapter can be deeply meaningful, AND it might look different than the version of success you’ve known up until now.
With so much care,
Kasey
If you are feeling uneasy about retirement, remember that you’re not just leaving a job, you’re stepping out of an identity you’ve held for years. Take your time. Get curious. Fear of the unknown isn’t the same as not being ready.
Got a Busy Brain Question?
Questions for Kasey: Calm for the Busy Brain is an advice column for high-achievers, perfectionists, and overthinkers who want to feel more grounded and at ease. I’m a trauma-informed therapist and coach offering in-person sessions in Old Saybrook, Connecticut, and virtual therapy throughout Connecticut, Massachusetts, and Rhode Island. Coaching is available nationwide for those ready to move beyond anxiety, overthinking, and burnout to find more alignment and ease in their lives.
Comments