How our darkest seasons incubate our greatest gifts

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.

I watched the leader's eyes in front of me fill with tears as he shared that he’d just gone into his daughter's preschool and asked to be put on a payment plan. He couldn’t afford tuition this month.

There was so much beneath the surface: frustration, shame, disappointment. He shared how heartbroken he felt. How it made him question whether he had what it took to stay in the work he loved.

As I listened, my heart filled with compassion. I remembered my own seasons when the success and the money weren’t coming. When I felt full of doubt, convinced I couldn’t have the life I desired. That I couldn’t make the work I loved into something sustainable. That maybe I was a fraud. Everyone else seemed to be succeeding. And I was stuck.

We kept talking. And as I asked questions, he began to share about a few recent moments that had surprised him.

Moments when others had seen something in him—something powerful. Moments when, in the slowness and difficulty of this season, he’d found himself showing up in a deeper way for the people around him. Moments when, even without answers, he was staying close to the questions.

As we continued talking, we began to see together...

In the very same week when he felt the most inadequate, the most uncertain, the most afraid… life was putting a spotlight on his deepest gifts.

That maybe—just maybe—this week wasn’t a sign that he was failing. But rather, it was a sign that he was being shaped.

I could see this in part because I’ve my own version.

The gifts I bring to my coaching, my marriage, my parenting, my friendships—most of them didn’t come from my best seasons.

They were forged in the hardest ones.

When I thought I was falling apart, I was actually being formed.

Like seeds that need to be roughed up by nature in order to crack open and take root.

My gifts began to bloom in my darkest hours: as a human, as a founder, as a single parent.

Steve Jobs once said you can only connect the dots looking backward. I don’t agree with everything he’s said, but that one—I feel in my bones.

I know this man will look back and see that this season was a turning point. That it gave him gifts not just for himself—but for others. And I am honored to bear witness.

I don’t know where you are today. But I know that most of the founders, investors, and leaders I work with carry some fear, doubt, or shame at points in their journey. If that’s you—you’re not alone.

And if you are finding yourself in a particularly dark time, this might be a season of formation. Of investment. Of deep growth.

You might be developing gifts you don’t even see yet.

Gifts that will become central to your life, your leadership, your love.

Gifts for you—and for the people you’re here to help.

I appreciate that you are here. If you’d like to get these posts in your inbox, you can subscribe here.

Wherever this season finds you—sending a big hug from my desk in Los Angeles.

And if I can support you in your journey, I’d be honored.

-Matt

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.