I’ve learned something about myself over the years. For all my spontaneity, sass, and willingness to leap before looking, the hardest decisions I’ve ever made all come down to one thing:

Leaving.

Not staying.
Not choosing.
But leaving.

Every major inflection point in my life has felt like a forked road with a big neon sign that reads: “Well? You going or what?” And time and again, I’ve walked toward the unknown with equal parts courage and heartburn.

When I left for boarding school at such a young age, I didn’t fully understand the weight of that choice. I only knew I was choosing possibility even though it hurt. And once you make one hard decision that early, you build a kind of muscle and a resilience fiber you don’t appreciate until years later.

That muscle made it possible for me to leap again. To spend a year living in Spain. To pack my bags and leave New York for Washington, D.C. after college.
To leave the East Coast entirely and take my life to California.
To leave my first long-standing job where I had risen, thrived, and found comfort because I knew it was time to carve my own path and begin the CEO trajectory I eventually stepped into.

Every single time, the leaving was the hardest part. Because leaving means giving up the known.
Leaving means letting go of the cozy corners where you know where the light switches are.
Leaving means trusting yourself enough to head into the unmarked territory.

But I’ve always needed the unknown to grow. Comfort is nice, but it can seduce you into stillness. And I’ve never been one to stagnate. Now. Now my son is preparing his college applications, and suddenly he’s the one who will leave.

And I’m not super ready.

I’m immensely proud. I get it; I understand it; I support it. I raised him to be someone who can walk toward his own future. But the mother part of me is standing at the doorway of a familiar room, clutching onto the doorframe like it’s going to keep time from moving.

This next generation is different, too. Many of them are more comfortable in the known. They are more tethered, more cautious, more deliberate. And maybe some of that is our doing. We have worked hard to give them stability, safety nets, and predictable ground.

But here’s the balance we’re learning in real time. We want them safe, but not stifled. We want them supported, but not stuck.
We want them close, but also to grow their wings.

Leaving is hard.
It always has been.
But growth rarely happens in the plush seat of the familiar.

And maybe that’s the lesson I’ve circled back to now. The hardest goodbyes are also the biggest gifts. That leaving isn’t just an ending. It’s the opening to a new story.

My son will leave soon, just like I did many times. And I’ll stand there with pride and maybe some Kleenex, reminding myself that the unknown made me who I am. And it’ll shape him too.

Because life’s greatest leaps nearly always begin with a door closing behind you and a deep breath before you walk away.