A person swinging under a tree by the water, a reminder to dream before you plan

Walking on Air: How to Dream Before You Plan

What if the key to better plans isn’t more rigid tactics, but learning how to dream before you plan?

When I was a kid, I was obsessed with the theme song from The Greatest American Hero. My best friend and I would swing as high as we could at the park, hair flying, feet reaching the sky, and we’d sing at the top of our lungs:Believe it or not, I’m walking on air…”

We didn’t care that we (I) couldn’t sing. (She sounded like a bird. I did not.)

We didn’t know the world (or future selves) would one day curb our dreams. We just knew what free thought felt like. And for those few minutes, anything was possible.

I think about that feeling often. That pure moment of possibility. And I come back to it intentionally.

As a coach, creative, and human living in this busy world, I’ve realized something big:

“Before you can plan with clarity, you need to dream before you plan, with spaciousness and intention.”

When was the last time you gave yourself full permission to dream?

Start Here, Not There

It’s tempting to dive straight into structure: goals, plans, to-do lists. But if we start from depletion or pressure, even the smartest plans feel like obligations instead of intentionally aligned moves.

And that’s why I invite you to pause and get dreamy. Not flaky dreamy. Intentional dreamy!

The kind of dreaminess that helps you remember who you are and what you care about. The kind that tunes your body and mind to possibility, before decisions are made.

Your Dreamy Ritual

Here’s a simple practice I use before mapping anything important in my life or business:

Step 1: Choose a song, scent, or memory
First, find something that brings you back to a moment when life felt big, open, full of potential. It might be a childhood song (hello, 80s theme music), a smell like fresh-cut grass, or a photo of you glowing in your element.
Play the song. Light the candle. Take a walk. Whatever shifts your state.

Visualization is a proven creative tool. This quick Forbes read shows how imagining outcomes can actually help bring them to life:
Creative Visualization: How To Picture (And Achieve) Real Change – Forbes

What memory or sense brings you back to a more expansive you? Jot it down, or share it with me.

Step 2: Stay there for a while
Now, let yourself remember what it feels like to be wildly possible. Not “productive.” Not “on brand.” Just alive.

Step 3: Ask yourself
“From this dreamy place, what do I know I care about?”
Let the answers rise. Voice note. Journal. Dance it out. No pressure.

Step 4: Don’t rush the plan
Linger in the want. The plan will come and when it does, it will come from alignment, not panic. Stay walking on air a little longer.

Try this before your next big project. Even five minutes makes a difference.

Rooted in Possibilities: Why You Should Dream Before You Plan

You are allowed to live and lead from possibilities. It’s also OK to set goals from your soul, not just your calendar. And yes, you are allowed to swing high, feel free, and build your vision from there.

That’s what I call walking on air and yes, it’s where your next plan belongs.

Want to bring this kind of dreaming into your next planning retreat?
Let’s talk. I’d love to hear what you’re dreaming up.


~ Cathy
Clarity & Strategy Coach for Leaders
Helping high-achievers pivot fast and lead with integrity


Feature photo by Christine Johnson from Pexels

P.S. Need more focused time to even get to that dreamy place? Here’s one of my favorite ways to create intentional space for strategic thinking:

Pomodoro Sprints: A Simple Tool to Help You Focus on Strategy