The Messy Middle: Embracing the Space Between Who You Were and Who You’re Becoming

Author: Jess Dahl
September 29, 2025

We all encounter it, the in-between season, the space where the person we were meets the person we’re becoming. I call it the messy middle. It’s uncomfortable, uncertain, and sometimes downright frustrating. And yet, it is often where the most profound transformation happens.
In this solo episode of the Say Yes Anyway Podcast, I dive into my own experiences navigating the messy middle and offer guidance for anyone feeling stuck in this transitional space.

Letting Go to Make Space
One of the most pivotal moments in my own journey happened when I had to let go of my first nonprofit. It was a project I poured my heart into, one that had shaped my identity and purpose. Letting go felt impossible. I wrestled with grief, fear, and self-doubt. And yet, surrendering to the unknown became the first step toward something greater.

The messy middle challenges us because we crave certainty. We want a roadmap, a guarantee that every step will work out. But transformation doesn’t come with a step-by-step manual. It asks us to trust the process, embrace discomfort, and step forward even when the path isn’t clear.

Growth Happens in the Unknown
Instead of resisting the uncertainty of the messy middle, I encourage you to reframe it as a training ground for growth. Growth is rarely comfortable, but it is always necessary. The middle isn’t a waiting room, it’s a place where resilience, courage, and clarity are cultivated.

Here are a few strategies I’ve found helpful in navigating this season:

• Move your body to shift your state. Physical movement helps release stress and gain mental clarity.
• Take one bold step. You don’t need to know the whole path, just take the next right action.
• Surround yourself with the right people. Find those who remind you of who you’re becoming.
• Resist the pull of familiarity. Just because something is comfortable doesn’t mean it serves your growth.

Every fulfilled person has walked through their own messy middle. Think about someone who almost quit but kept going. That season shaped their character, strengthened their faith, and prepared them for the next chapter. Your messy middle is no different. It isn’t the end of your story, it’s the making of it.

Courage, Community, and Clarity
The messy middle is easier to navigate when you have support. That’s why I created the Camino Retreat, a transformational journey along the historic Camino de Santiago. It’s designed to help participants embrace uncertainty, build community, and move forward with purpose and courage. By stepping into this pilgrimage, you create space to reflect, reset, and rediscover your clarity.

If you’re in the midst of your own messy middle, remember: you are not lost. You are becoming. Every small step forward is a declaration of faith in yourself and in the journey ahead.

? ? To learn more about the Camino de Santiago and how you can join us on this incredible journey, book a call here or get on our waitlist for May 2026 here!

To explore your own journey through coaching and community, visit my Instagram @jessdahl_ or book a call at jessdahl.com.

And to stay inspired and receive updates on new podcast episodes and resources to help you say yes to your life, join my newsletter here:
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Listen to the full episode here, leave a review and tag me if you share =)

Thank you for tuning in. Keep saying yes to the moments that shape you, even in the messy middle.
Jess Dahl

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