Greetings from the 'messy middle'


Hello Reader,

A small note before we begin

I’ll start this month’s letter with a small confession.

I’m not entirely sure who this one is for.

Maybe it’s for the person building something meaningful who is quietly wondering if it will ever fully take shape. Maybe it’s for someone standing in a season of transition where the old story no longer fits but the new one hasn’t quite arrived yet. Or maybe it’s simply for anyone who has ever found themselves in what I often call the messy middle of a life that is still unfolding.

Wherever you happen to be reading this from, welcome.


From My Chair to Yours

Over the past couple of weeks I’ve been sitting with a familiar but uncomfortable part of the creative and entrepreneurial journey, the stretch of road where you’ve already taken the leap but the evidence of where that leap will land has not yet fully appeared.

There have been small moments that stirred this reflection for me. A gathering that only one person registered for. A message sent out into the world that met a quieter response than I expected. The kind of moments that can easily send the mind spinning with questions about direction, impact, and whether the work we feel called to do is truly finding the people who need it.

When that happens, I often turn to music, and anyone who knows me well knows that U2 has been the soundtrack of my life for decades.

This week the song on repeat has been Acrobat, a track that somehow captures the strange mix of defiance, exhaustion, and hope that tends to appear when you are trying to build something meaningful in the world.

If you’re curious, you can read the lyrics here: Acrobat U2 Lyrics

There is a line in the song that has been echoing through my thoughts all week:

“You can dream… so dream out loud.”

Dreaming out loud is exactly what many of us are doing when we share ideas, write newsletters, build businesses, change careers, or begin speaking truths that once lived quietly inside us.

And dreaming out loud also means that sometimes the response from the world arrives slowly, unevenly, or not at all in the beginning.

That is the territory of the messy middle.


The Lens

Here is one insight that has surfaced for me during this season of reflection.

The messy middle often appears precisely when something meaningful is trying to take shape.

It is the stretch of time where the old identity has loosened its grip, yet the new form of the work has not fully clarified itself, and in that in-between space it can be tempting to interpret the discomfort as failure rather than as transformation.

I have come to believe that this stage requires a particular kind of courage, the quieter courage of staying present long enough for clarity to emerge rather than rushing to fix the discomfort by abandoning the path altogether.

In other words, sometimes the work is simply to remain curious while the tide slowly turns.


A reflection for you

Most thoughtful leaders I know are navigating some version of a messy middle in their lives right now.

It might be a career transition, a leadership challenge, a personal shift in priorities, or the quiet realization that the life you built five years ago is asking to evolve into something new.

So here is the question I’ve been sitting with this week, and I offer it to you as well:

What messy middle are you standing in right now, and what might it be trying to teach you before the next chapter becomes clear?


For now, I’m allowing this season to unfold without forcing answers that are not yet ready to appear, trusting that insight has a way of revealing itself when we are willing to stay present with the questions.

And as Bono reminds us in that same song…

Dream out loud. Keep building. Keep loving.

And whatever you do, don’t let the b@stards grind you down.

Until next time,

Joanna

Joanna Douglas

I’m Joanna Douglas, leadership coach, speaker, and founder of Enneagram Ensight. I help conscious leaders reconnect with their personal power, emotional intelligence, and authentic leadership voice. After two decades in corporate leadership, I learned the hard way that success without fulfillment leads to depletion. Today, I coach leaders to lead with clarity, courage, and presence — without losing themselves along the way.

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