How CEOs Find Strength in the Messy Middle

I've been called resilient, and it makes me cringe.

Divorce with three kids 5 and under. 60+ days in the hospital with frightening side effects from 5 rounds of chemo. Losing jobs...

While I've weathered storms, so have you and countless others.

Why is resilience a thing...why does it matter?

On the other side of struggle, what I've felt wasn't some grandness of resilience.

I'd never, ever have that thought. Instead, my mind asks why? And other questions...

-What's wrong with you?

-What did you do wrong?

-Why is it always so hard for me?

-Is my life spiraling into chaos?

I saw this post on Instagram that helped me reframe the cringe. Dr. Becky took me right back to school, in a good way!

Most of the time, we don't even realize we're being resilient until we've emerged from what she calls "the messy middle."

It's that raw, vulnerable space between UNKNOWING and KNOWING.

It doesn't feel resilient at all. It feels like I'm drowning.

If you're feeling overwhelmed, frustrated, depleted, challenged, those feelings aren't obstacles to growth; they're evidence of profound learning.

If you don't believe me, borrow my belief and keep reading.

One of my coaches says it perfectly: "If you are not winning, you are learning."

It hurts. It does hurt. But to not feel that pain robs you of the transformation waiting on the other side.

It sucks yes, but I believe it sucks more not to have experienced it.

The messy middle - that space between the unknown and the new knowing - strips away pretense and reveals your true essence.

Growth happens in that uncomfortable space where we're gasping for air outside our comfort zones.

The alternative to growth isn't staying the same—it's withering away [dare I say dying].

For me, resilience has been both life-saving and life-generating. Each time I emerge, I carry new knowing. I understand more about myself, my purpose, who I am, and who I still hunger to become.

I wish I'd sat in Dr. Becky's class earlier to learn that to expect something other than the messy middle only leads to disappointment and the disease of entitlement.

Here are 5 more real-life skills classes I wish I had:

  • Mindset Management and Identity Work: Understanding how to manage the monkey mind and who we are beyond the badges and titles we wear.

  • Financial Literacy: From money management to understanding P&Ls and conquering the money mindset that keeps us playing small.

  • Professional Development: Personal branding, networking, and the art of being a magnetic mentee. This is an area where I wish I'd recognized its importance sooner and invested more deeply in it. How are you nurturing yours this week?

  • Communication Mastery From navigating difficult conversations to mastering daily written and verbal communication that moves hearts and minds.

  • Self-Advocacy Learning to champion ourselves and negotiate effectively. Not chest-pounding bravado, but laser focus on our authentic strengths, capabilities, and capacities as the currency—not just for negotiation but for making an indelible mark on our work and legacy.

I would have understood and enjoyed life sooner with these skills, but it's never too late to build your own curriculum filled with books, podcasts, courses, and real-world experience to change how you show up in the world.

Resilience is showing up in that frustrating learning space, again and again, even when every fiber of your being screams to retreat.

On the other side, a new becoming.

As Ernest Hemingway so powerfully captured:

"The world breaks everyone, and afterward, many are strong at the broken places."

You are getting stronger every day.

Remember that learning is never just about the how—it's fundamentally about the who.

Sometimes the most profound learning comes from connecting with the right people who support the path when you can't see beyond the next step.

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Why High Achievers Struggle with Confidence