The Season Between Who You Were and Who You’re Becoming

The Season Between Who You Were and Who You’re Becoming

Founder's Notes

natalie eng

November 25, 2025

Every year around this time, life slows just enough for our inner world to catch up with us.

We’re still going through the motions of work, family, relationships…
but something inside us starts shifting because of what we make the time of the year mean.

A softness. A discomfort. A nudge.

A sense that we’re standing between who we’ve been… and someone we’re not yet able to name.

I know this season intimately from my own journey moving from the predictability of corporate life into the unfamiliar grounds of entrepreneurship.

There was a period where I could no longer go back to my old identity… but I also wasn’t fully living the new one.

It was the limbo stage of feeling uncomfortable, disorienting but also humbling and strangely beautiful all at once.

And now, after coaching more than 40 clients through their own transitions this year, I’ve come to see that this “in-between” season is far more common and far more transformative than most people talk about.

Across different clients (from new parents to entrepreneurs, from consultants to creatives, from people entering new relationships to people ending them), this season shows up in similar ways.

1. Here are the three patterns I see most often:

1. Your old ways of coping don’t work the same anymore.

Maybe it’s:

  • pushing yourself as hard as before but feeling empty
  • trying to hustle your way out of discomfort
  • striving for “old goals” that no longer feel true
  • relying on emotional shutdown or autopilot, only to find it doesn’t soothe you like it used to

In my own transition out of corporate, I remember feeling frustrated that the strategies that once made me successful suddenly created friction.

For example, I used to calibrate my sense of progress from external feedback such as a rating, a comment, a promotion cycle.

But in entrepreneurship, there’s no performance review waiting at the end of the quarter. I had to learn to trust my inner metrics instead of waiting for permission. I came to terms with the realization that I did not lose my capability, I was simply outgrowing the identity those strategies belonged to.

It is human nature to crave familiarity/predictability over ambiguity/uncertainty as it is more comforting. But accepting this new reality helps us through it in significantly better ways.

2. Your emotions get louder.

Clients in this season often tell me things like:

  • “Why am I more anxious than usual?”
  • “Why do small things feel bigger now?”
  • “Why do I suddenly feel everything so intensely?”
  • “I’m doing ‘fine’ on the outside, but inside feels messy.”

And honestly… I’ve been there too.

During my own transition, the emotions I’d tucked neatly behind performance and busy-ness finally had space to surface. Not to overwhelm me but to show me what needed care, clarity, or closure.

These emotions actually hold much data for us to mine for insights.

When life shifts, our inner world shifts too as we need a recalibration.

3. You begin questioning long-standing beliefs about yourself.

Every identity transition (e.g personal, relational, or professional) brings up questions like:

  • “What truly matters to me now?”
  • “Who am I responsible for… and who am I no longer responsible to?”
  • “What version of success actually feels good in my body?”
  • “What do I want to carry into my next season and what have I quietly outgrown?”

I asked myself these same questions when I left corporate. And I still ask them now at every turn of a new quarter as it is important for us to evolve our beliefs as our goals and paths ahead evolve.

2. Why this season feels heavier near the end of the year

Endings naturally bring things to the surface:

  • the gap between where you are and where you hoped to be
  • the goals you’ve outgrown
  • the relationships or habits you subconsciously want to shift

It’s like your inner world finally gets a chance to speak.

And sometimes, it speaks through:

  • restlessness
  • comparison
  • irritability
  • numbness
  • longing
  • tenderness
  • a quiet ache for something more aligned

Nothing is wrong with you. These are things that are within us that finally have the space to come up to the surface.

3. How we can approach this season instead

A. Honesty over performance

Noticing what no longer fits – work, roles, expectations, old dreams or relationships.

B. Gentleness with your emotions

Allowing the discomfort instead of outrunning it. Letting your feelings guide, not dominate.

C. Rebalancing your inner system

Tending to the part of you that’s tired, not just the part that wants to push. Giving attention to neglected areas (health, relationships, creativity, rest) as the year winds down.

D. Redefining success on your terms

Not the version of success you were praised for but the one that actually fits the person you’re becoming.

4. Here are some reflection questions as we start to close the year:

Instead of asking:

  • “Did I achieve enough?”
  • “What should I fix?”
  • “Why am I behind?”

Try these instead:

  • What part of me is ready to rest?
  • What part of me is ready to rise?
  • What did I outgrow this year even if I haven’t admitted it yet?
  • Where did I surprise myself?
  • What version of myself is quietly forming beneath the surface?

And most importantly:

What would it look like to support the person I’m becoming… not the person I used to be?

In this transition, this season is where the next version of you gathers strength and we can help hold it with more patience, courage and compassion.

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