Some thoughts on my professional journey this year.

Aug 18, 2022 | Entrepreneurship, Life in Progress


I’ve been thinking a lot about the early years of my creative business. I was so new, no naive, so full of wonder, and filled to the brim with I-have-no-idea-how-to-do-this thoughts. I didn’t really have any steady mentors, but I had a handful of friends who were doing what I was doing: figuring it out along the way.

Those years were exciting, filled with hard work, trial and error, and tons of adventures.

This year, I’ve had the pleasure of focusing much of my work on guiding + mentoring a few budding creative entrepreneurs – some 1:1, some via weekly online group sessions, some via a week-long retreat in the UK (psst: I’m doing that again next year, too!). In all these instances, I’ve noticed a little piece of myself coming alive, like a little burst of sunshine emerging from my heart saying, “Ohhhhh! We like this! This feels like an important step in your path. Pay attention.” I’m still sorting it all out, but all this mentoring has me wanting to step deeper into big sistering other women toward their creative callings. I know from my own early years how powerful it can be to have just a few other people in our worlds who are also following their callings and figuring it out along the way.



This week, as my mentoring circles come to a close, I’m reflecting on how grateful I am to travel with women in these kinds of heart-led ways. The witnessing. The shifts. The powerful awakenings. The vulnerabilities that connect us all. The sense of belonging.  It is soul deep nourishing. 

As a teacher, I felt challenged to fully show up to my edges, to challenge old harmful beliefs / wounds / narratives around taking up space. As a human, I learned to be a student of the brilliance that already exists within each of us.

All of this is to say that after a few wobbly years in my own business (ie, tons of transitions, moving, pandemic, etc), hanging out with brave, authentic women in these intimate ways this year has reminded me of who I am, why I do what I do, and what a privilege of a lifetime it is that I get to be a creative woman in the world and work with amazing creative hearts. Even in tough years. Even when we’re deep in the mystery of not knowing how anything will ever make sense. Even when we think it couldn’t get any better.

It really is beautiful life.

Big love,
Kelly Rae

PS: In keeping with my mentoring theme this year (as well as hanging out with amazing women!), don’t miss my collaboration with my dear friend Andrea Scher. It’s going to be such a beautiful, ease-filled time.

Sending much love,

Show/Hide Comments (2 comments)
  1. Peggy

    Kelly, I couldn’t help but notice you mentioned the word sistering other woman in your post. It seems serendipitous , since you live in Sisters , Oregon. Have a wonderful day

    • Kelly Rae Roberts

      Ohhhhh! Goosebumps! I also love that ‘sistering’ is a construction term as well – when boards are used to brace/hold up other boards 🙂


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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 creative whispers, and today I’m an artist & Possibilitarian. I’m passionate about creating meaningful art and experiences that awaken and inspire our spirits.

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