I went to Portland couple of weeks ago and had an experience that felt like a mixture of grief, awakening, and creative bursts all at once. Intense, illuminating, and ultimately really really GOOD.

First, the grief. It’s been so long since I’ve been back and I wasn’t expecting the heavy sadness that arrived almost immediately upon entering the city. Oh, these trees! These neighborhoods! My old garden! And studio! And house! Oh, and that favorite store and restaurant! It felt like being reunited with a piece of yourself that lives in an important part of your heart, but you hadn’t checked in on her in awhile. I didn’t realize how much I missed Portland, but also how much I missed that old life, that previous version of myself, that previous version of our family.

I got engaged there. Found my creative callings there. Built a thriving art business there. Created community, started a family, and on and on. 20 years of living and loving and learning and growing and stumbling and creating a life I loved. I’m known for my delayed reactions to big life events, and my goodness was this a delayed grief response – three years after packing up our belongings and moving on. I sobbed my way through my first 48 hours of our visit. And it was good, needed, and a long time coming.

In the end, I’m very happy we made the decision to move to sunnier, small town Sisters, OR and I love what we’re building here, but I also now know that Portland will always be home and that I need to make more time to visit. So glad there are airbnb’s to visit!



Second, the awakening. I was SO inspired in my old city. The trees, the landscape, the people, the creative energy – it all had me stirring in possibility, like the kind I always seemed to have when we lived there. In some ways, my visit felt like I was getting reacquainted with myself.  Oh this is who I am! I think travel, especially back to our home spaces – the places where we were formed – does this to us. Reminds us of our essence, of our undeniable selves waiting to be revealed again and again. That’s what it felt like. A little like a reawakening, like a spark lit, like a treasure being found.


(New art! Available here in a variety of sizes)


Then, creative burst. With grief and awakening stirring in the soup of emotions, I was having many conversations with my Portland friends and with myself around what’s next for me (another book? a different signature course? etc?). You know how we feel the call toward something, and sometimes we’re not sure why the call, but we Trust it, make moves toward it, and then we sort of wait for life to adjust accordingly? All the while, we’re just sort of in The Mystery, fully trusting that we made the right call? The last three years or so since moving from Portland, I’ve definitely been in The Mystery.

Being in The Mystery has looked like this: Listening  to the call and moving out of the city and into a tiny town. Retiring all of my e-courses. Scaling back my licensing, getting off social media, and super simplifying my life. Meanwhile, I’ve been humming along over here in The Mystery soup, sort of wondering what this next season of living will hold.

And then I went to Portland and I’m pretty certain I received the answers to those questions. Oh, this is what I’m supposed to do now? Oh. Oh! Of course! Now I understand why that happened, and I made that decision and how being in The Mystery has lead to now! And you know how once you get the message/the aha/the gift of clarity, all sorts of synchronicities and messages from Spirit began to arrive? That’s the part I love, and they started popping up EVERYWHERE!

It makes life living so fun and meaningful when we are in deep consideration of a path to take and then the signs from Spirit arrive, affirming our inclinations, “Yes, this way!  Yes, yes, yes!”  



So that’s where I’ve landed, friends. I’m learning so much about myself right now, about life really. And I’m so so glad I’ve got some clear direction for what’s next while also integrating all that I’ve learned from my previous seasons into the one I’m headed into. Art and writing are what’s next, so not a huge shift, but also a big shift from what I’ve done before. I’ll share more as the weeks unfold, but for now I’m so grateful to have you witness this journey. I adore this community more than I can say.



If you’re feeling a little bit in The Mystery, consider getting reacquainted with yourself. So somewhere – anywhere – where you feel deeply alive. Maybe it’s visiting a city where formative years were spent. Maybe it’s visiting with an old friend that knew you when. Maybe it’s visiting older journals. Either way, allow this version of yourself speak to you from where you are now. Allow her to guide your next move while also celebrating all that you created in that previous season of your life. If you need, grieve that previous season/version. And then let the gifts from that season help you pave the next path. Life is magical.

XO, Kelly Rae

Hi, I'm Kelly Rae Roberts!

Before I picked up my first paintbrush at the age of 30, I was a medical social worker. I followed my whispers and started playing with paint and everything changed.

Now I’m a full-time artist, author and Possibilitarian, who helps women explore and nourish their creative souls.

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