Moving Into Your Next Season – A Reflection Guide

Moving Into Your Next Season – A Reflection Guide

Some people call this chapter “the autumn of life.” But I don’t use that phrase—and here’s why:
Autumn implies that all that’s left is decline, harvest, and fading light. But many people entering their next season after leaving full-time work (whether by choice or circumstance) experience an inner spring—a time of renewal, rethinking, and rediscovery. And later, a summer—a season of energy, generosity, even joy.
This is not the beginning of the end. It’s the beginning of something new.

Common Roadblocks on the Journey (and What to Do About Them)

"I’ve lost my identity."

This is something many people feel after leaving behind a role they’ve held for years or decades. When so much of your identity has been tied to what you do—your title, your responsibilities, your usefulness—it can be disorienting to suddenly be without those markers. It’s not that you don’t exist anymore; it’s that you’re meeting yourself again, without the external frame. And that takes time.

Try this:

List three things about yourself that have nothing to do with your job title. Now ask: What would it look like to build a life where these things matter more?

"I don’t know what I want."

After years of following routines, meeting expectations, and often prioritizing others, it’s completely normal to lose touch with your own desires. You may be so accustomed to focusing on goals or productivity that simply asking yourself what YOU want feels unfamiliar. But that voice is still there—it’s just been quieted for a long time.
Try this: Write freely for 5 minutes in response to: “If I didn’t have to prove anything to anyone, what would I try or explore this year?”

"I should be grateful. Why am I restless?”

You may have everything you were told to want—freedom, time, security—and yet feel a surprising sense of dissatisfaction. This tension often arises when what you truly need is meaning or connection, not just rest. Gratitude doesn’t mean settling. You can appreciate what you have and still long for more expression, engagement, or purpose.

7. Use It—Don’t Just Nod and Forget

You’ve heard you interrupt too often, or that your tone in emails can feel cold. Now what? Make a plan. Pick one thing to shift. Small adjustments compound. Growth doesn’t come from knowing—it comes from doing.

Try this:

Draw two columns. In one, write what you’re grateful for. In the other, write what still feels unfinished or unexpressed. Now circle one thing from column two. What’s one small step you could take this week to honor it?

Guided Exercise: Mapping Your New Season

Set aside 20 quiet minutes. Use a notebook or print this guide. Ask yourself:
  1. What am I leaving behind that I want to honour?
  2. What am I ready to release?
  3. What am I curious about that I’ve never explored?
  4. What do I want my life to feel like six months from now?
  5. Who can walk beside me in this process? (Community matters.)
  6. What’s one commitment I can make this week to begin showing up for this version of me?
You don’t need to have all the answers today. You just need to start asking the right questions.