Nineteen Stops

On the difference between what we want and what we long for — and the courage that was already there.

Prefer to listen? A short audio companion to this essay — my own CourageLine, in my own voice — is right here.

THE COURAGELINE

I did something today I've been telling others to do for months.

Not a metaphor. An actual line, drawn across a page. Birth on the left. Today on the right. And in between — every moment I could remember where courage was required. Not the moments that looked impressive from the outside. The moments that cost something on the inside.

I sat with a pen for longer than I expected. And they came. Slowly at first, and then all at once, the way memory does when you finally give it permission. By the time I put the pen down, I had nineteen stops. Age seven to fifty-nine. A whole life, measured not in graduations or job titles or the things you'd put on a resume, but in the moments I almost didn't do the thing — and did it anyway.

I have spent so much of my life measuring against the outside of things — job titles, milestones, what looks impressive from a distance. This line asked a different question. Not what did you achieve. What did it cost you to become who you are.

Here is what I had to sit with before I could even draw that line — a harder question than the one I expected.

What do I actually want?

Not the surface answer. Not the version that fits neatly into a sentence — a new client, a finished project, a good night's sleep. Those are desires. Desires are specific. Desires are achievable. Desires live close to the surface, and there is nothing wrong with them, but they are not what moves us.

Longings live deeper. A longing isn't about what you want to have. It's about what you want to feel, what you want to be. On a forest walk in January, when I asked to know courage and asked to be fully open, what came back wasn't a to-do list. It was longing, plain and unfiltered: rest. Peace. The freedom to blow where the wind takes me. Partnership and community. To laugh deliriously. To be used for something that matters. Freedom from carrying responsibility for people who were never mine to carry.

Those longings had been there the whole time. I just hadn't been quiet enough to hear them.

So I drew the line. And here is what nineteen stops taught me, in no particular order and without much editing, because the CourageLine doesn't ask you to make sense of your life. It only asks you to remember it.

Age seven, walking into a child therapist's office for the third session, when the first two had felt like nothing but a room full of silence.

Age eleven, climbing out a window because staying inside was no longer survivable.

Age eighteen, moving in with my mother during chemo, when everyone my age was moving toward independence and I was moving toward her.

Age twenty-two, picking up the phone to call a company that had just won a contract, while they were still celebrating — because the alternative was staying quiet and letting it go.

Age twenty-nine, driving to my mother at three in the morning. Cradling her as she took her last breath.

Age thirty-four, taking my golden retriever to be put to sleep, and — the very same year — quitting a president's job the day I could no longer square it with my values.

Age forty, choosing to get pregnant. Trusting my husband John completely, and being terrified the entire time.

Age forty-five, John's death.

Age forty-six, quitting everything and starting my own business. A December in Mexico. A porch. The moment I first believed I might actually be able to do this.

Age fifty, moving to Bainbridge Island. Buying a house alone, against my family's wishes.

Age fifty-six, hitting the bottom of a codependency I'd built my whole identity around.

Age fifty-seven, diving into grief after my son Matthew's departure — and, that same year, deciding to parent differently. Surrendering the illusion of control I'd been gripping so tightly. Driving my daughter Kaya to rehab in California.

Age fifty-nine, coming out from behind a brand I'd built to be safe — a learning and development company, professional and impersonal — and returning, fully unfiltered and finally aligned, to simply Kathy Clifford and Truth in Leadership. The name I'd actually started with, thirteen years earlier. It wasn't a rebrand. It was me, all along, deciding to stop hiding behind the version of myself that felt easier to sell.

That same year, a quieter version of the same courage. Creating an online dating profile. Putting an honest photo and a few unguarded sentences about who I actually am out into the world, with no editing and no armor, and letting myself be seen by total strangers without knowing if anyone would want what they saw. Different room, same threshold. Stepping out of hiding, out of self-protection, into being visible on purpose.

Nineteen stops. And when I finally sat back and looked at the whole line, one thing was unmistakable.