The Big (Beautiful) Return

Turning 50, trusting what calls, and recalibrating toward what matters most.

I turn 50 in a few weeks.

I can hardly believe I’m this deep into midlife — not early midlife, where you’re still in the throes of building a life, not later midlife, where you're starting to think about slowdowns and soft landings — but right here, in the deep, rich middle of the middle.

Lately, my heart has been asking:
What do I want this next decade to feel like?
What do I want to create, to say, to live into?

Twenty years ago, when I was 30, I picked up a paintbrush for the very first time.
I started writing, too.

Before that, I was a medical social worker who had no idea a creative life (and business!) was waiting for her — one that beautifully unfolded when she simply listened to an awkward, strange whisper to start painting and writing.

Photo by In Her Image

It’s been twenty years of seasons I could have never predicted.
Messy. Magical. Full of creativity, community, healing, and eons of small brave steps.

I’ve joyfully built and deconstructed, too. There has been ease — and there has been the holy mess of burnout, too.

I’ve created and led countless online courses and international retreats, coached beautiful humans, licensed my art, written a book, created products, and formed incredible partnerships and teams of brilliance and heart.

Along the way, I had a son — we named him True. He’s 14 years old now, and my heart bursts daily.

There have been years of unbelievable abundance and years of scraping by. I mothered and partnered and embarked on countless healing paths of learning and unlearning.

I've made remarkable mistakes — so big they brought me to my knees — before eventually turning into their own kind of grace. And I've celebrated so many big and tiny wins, too.

Through it all, listening to my whispers has been my compass, every time.

The ones that tug at my sleeve.
The ones that keep circling back.
The ones that keep me brave, true, and aligned.

It all started, though, by listening to the ones calling me toward painting and writing. A whole life bloomed and unfolded from there.

Photo by Kimmie Kelly

And now, twenty years later, as I stand at the edge of 50, I can hear the whispers again, growing louder: Kelly Rae, make your paintings. And please, get back to your writing.

And so, I'm making some big recalibration moves over here.
I'm envisioning bigger, looser, braver paintings — the ones that have lived in my heart for years and years. And I'm picking up my pen again, telling the stories I haven’t yet told and rewriting the ones my soul needs to tell again.

Not because I have a plan.
But because the longing is reason enough.

To help me show up for this new season, I’m starting this Substack:
The Possibilitarian Life.

I’m excited to have a place to journal my way through this season of returning —
to what feels most true.

I’m curious what will come through now, with the wisdom that only experiencing, living, healing, wondering, creating, building, unlearning, and returning can bring.

That’s what I’m here for.
That’s what I’m trusting.

Thanks for coming along.
I’m so glad you’re here!
Truly. Dearly.

Big love,
Kelly Rae

P.S. If you feel called, I’d love to know: what longings, whispers, or creative nudges are you listening to these days? Tell me in the comments — I’d be honored to witness.

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