Castles in the Clouds (Now with Structural Integrity)

Over the past seven years, I’ve had the honor—and let’s be honest, occasional heartburn—of watching each of my kids graduate from high school and make their way to college. And just this spring, I watched my youngest cross that stage, diploma in hand, looking ahead to college and new opportunities to perform on stage. Not long ago, I stood in similar crowds as both my oldest daughter and my son graduated from college in 2015 and 2017, respectively—she now heading to medical school, and he just beginning his professional journey. Five graduations in seven years. One by one, they’ve crossed stages and thresholds, each carrying their own hopes, anxieties, and a slightly wrinkled gown we definitely didn’t press well enough.

And with each of them, I found myself standing at the edge of something too—part pride, part panic, and part wondering: What now?

Not just for them, but for me.

Because no one tells you that watching your kids leave the nest doesn’t just mean you’ve finished building their launchpad—it means you’re suddenly staring at a big stretch of sky and wondering if it might be your turn again.

That’s where Thoreau comes in:

If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them.

I love that quote. It sounds dreamy at first, but dig deeper and it's rock solid. Dream big. But then—get to work. And not just once when you're young and fearless, but again and again as your dreams evolve. My mom actually gave me a card with that quote when I graduated from high school. At the time, I probably didn’t grasp the full weight of it—too distracted by tassels and the vague smell of barbecue from the grad party—but it stuck with me. Decades later, I see how right she was to press that wisdom into my hands. It’s not just advice. It’s a blueprint. One I’ve watched my kids begin to follow in their own way—and one I’m finally coming back to myself.

It reminds me, too, of a softer take from Little Women:

Wouldn’t it be fun if all the castles in the air which we make could come true, and we could live in them?

There’s something tender and hopeful in that. Because of course, dreams can come true—but not by accident. They’re built slowly, intentionally, with more elbow grease than fairy dust. That’s what I’ve tried to teach my kids. And what I’m still learning myself.

Watching my kids head off into the world reminded me that dreaming isn’t a phase—it’s a practice. And while they’ve been sketching out the first spires of their castles, I’ve been quietly digging up some blueprints of my own—the ones I tucked away years ago under a pile of permission slips, grocery lists, and sports schedules. Dreams don't expire, it turns out. They just wait for quieter mornings.

Still, this post isn’t just about me dusting off old ambitions. It’s also a note to my kids—and anyone else standing on the edge of graduation, or reinvention, or just the next big thing.

If I could give you one more speech (the kind you don’t have to sit through in a folding chair), I’d borrow heavily from Paul Graham’s brilliant essay, What You’ll Wish You’d Known. It’s the kind of advice that skips the clichés and gets to the good stuff. So here goes:

1. You don’t have to know what you want to be.

Seriously. You’re not behind if you don’t have a 10-year plan. Let curiosity lead for a while. Try things. Follow what fascinates you. Most people don’t find their path—they stumble into it while doing something else.

2. Work hard at things that feel fun to work hard at.

This is the secret sauce. Don’t chase status. Chase flow. If you find yourself losing track of time while building something, learning something, fixing something—that’s a clue.

3. Don’t be afraid to be bad at something.

The early stages of any good project—whether it's a podcast, a physics degree, or a life—are messy. Ugly, even. You have to wade through awkward to get to awesome.

4. Pay attention to the things that bother you.

What frustrates you about the world? What would you change? That’s often where your purpose lives. Don’t be afraid to ask, “Why is it like this?” and then go fix it.

5. You’re not locked in.

Change your major. Change your mind. Change your definition of success. Anyone who tells you that you have to pick a lane at 18 probably sells traffic cones for a living.

And to my kids specifically—thank you. For letting me walk alongside you as you started your own builds. For teaching me that dreams are not a one-time event, but a renewable resource.

Because watching you chase your castles has reminded me: I’ve got some unfinished architecture of my own. And now, with a little more time, and a lot more perspective, I’m putting those foundations in.

So wherever you are—clouds, sky, or air—keep building. Keep learning. Keep asking better questions. And don’t worry if the blueprint changes along the way.

Oh—and come home sometimes. I’ve got snacks.