Coffee With Ashlee Sikorski

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I walk up to the building just off of N. Interstate Ave, a beguiling, but humble display of industrial architecture. Encased in brick, the building stands as a relic of things past, its beauty revealing itself gradually and quietly in the consideration of form and utilitarian aesthetic. Large windows scale the sides, hinting at the light-filled rooms contained within.

Train tracks run several feet behind the building, obstructing the route of arrival. It’s an indirect course you take to the Weller Society, resulting in a place you come to with purpose, making the trip with intent. And that’s exactly what I’m doing here, when I walk into the Weller Society for coffee and conversation with Ashlee Sikorski.

In addition to her work as a Certified Emotional Intelligence Coach, Ashlee is the Community Director at The Weller Society. It’s an apt description of her nature—Ashlee exudes a certain kindness that’s revealed even before she speaks. Her disposition is one around which people unknowingly gather, attracted to the promise of connection, presence, and attention, all of it from a person so evidently standing as a catalyst for community.

Reflecting on this, I think about how her character illuminates the consistency in these two positions. Ashlee supports professional teams and individuals in reflecting upon and examining their lives, identifying where they are most unsatisfied and exploring where they have the most potential for growth.

“The world would operate so much better if we were all doing something that fulfills us.”

I ask Ashlee more about her work, and what inspired her to pursue the path of coaching. She pauses before answering, and her eyes give off the glint of excitement as she responds, “It’s the people I work with. They’re making strides for good in their communities and having a large societal impact. I love helping people, and seeing them find their role in society and feeling fulfilled. The world would operate so much better if we were all doing something that fulfills us, and it’s both that small-scale and large-picture view of what I’m doing that inspires me.”

I love this. I love speaking with people who find a depth and meaning in their work that serves not only themselves, but those around them as well, I’m reminded of all the possibilities for good, all the potential for altruism and compassion. I want to know more, and I dive further into the root of Ashlee’s interest.

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“Before becoming a coach, I thought I wanted to work with young adults. I was working in higher education and lived for professional development days. I always led the team retreats, introducing different personality assessments and researching them. I was always so curious why people were wired a certain way.”

It’s clear that this discovery of her interest was the motivation for her move into coaching. It’s a certain type of person that loves delving into the intricacies of human thought and concern. Sometimes, they’re a coach. Sometimes they’re a writer. Sometimes they’re bagging your groceries or making your Sunday morning latte. Empathy exists across a spectrum of careers and professional choice, and it manifests itself differently within all of these ways of existing.


“I feel honored to hold people’s stories.”


Ashlee continues, “I really believe I was wired to be a coach. Many people have the misconception that coaching is telling someone what to do, but it actually assumes that the person you’re working with is the expert of their own life, and that they’re emotionally stable, creative, and whole. They just need some digging to help them find their next steps, and I’m the facilitator of unearthing whatever those are.”

I reflect on her words, surprising myself by realizing that I shared in that false impression of a coach’s task. But it’s not giving all the possibility for epiphany and realization over to another person. It’s not believing you’re insufficient or presenting some lack. Coaching is a co-discovery, it’s a dual navigation of the space we each take up in the world.

I voice this, and Ashlee nods, agreeing with my understanding of what she’s explained. “As a coach, I’m leaving this person with tools and perennial feelings of freedom and joy. After they’re done working with me, and they run into a snag, they’re equipped with the insight to recognize those patterns and how they play out, approaching them with greater awareness and understanding.”



“It’s incredible, the amount of truth that lies within people’s hearts.”



I’m listening, and my mind laces together a multiplicity of impressions. Ashlee is both witness to, and a participant in, her clients’ discoveries, their revelations of the abundance of possibilities that lay open before them. I share this observation with Ashlee before I can articulate it completely, and she responds thoughtfully, a succinct phrase that stays with me hours after the words are spoken: “It’s a privilege to hold people’s stories and to see their breakthroughs. It’s incredible really, the amount of truth that lies within people’s hearts.”

This exchange seems limitless, the depth of this conversation inexhaustible, but I grow mindful of time constraints, and transition to Ashlee’s work with the Enneagram. In terms of my knowledge, it’s a topic similar to coaching, with thoughts, words, facts, and opinions flitting about me, but nothing landing to create concrete understanding. I ask Ashlee about it, eager to fill in the spaces of what I don’t yet know.

“A mentor introduced the Enneagram to me eight years ago, and it’s been a powerful presence in my work and my life. I teach workshops on the Enneagram and it’s a great way for people to learn about it. Enneagram is an oral tradition and its origins trace back more than two thousand years ago. It only began to be written down in the 1950s, when it gained popularity in the west.”

At first, I’m surprised. Working in the health and wellness space, I’ve seen the growing interest in personality tests as a means of self discovery. I was hesitant at first to adopt the shift myself, quick to pass the Enneagram off as a buzzword or trending topic, but Ashlee’s words position it in a way where it presents not only longevity, but meaning, importance in what it allows us to uncover about ourselves, and significance in how it brings us deeper into ourselves and promotes our personal growth.

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But this connection isn’t only internal, and it’s this realization that directs me to the common theme beginning to reveal itself through our conversation. It’s a return to the community that Ashlee builds in everything she does—everything she’s involved with and everything she creates herself. The epiphany returns me to the interview, and I ask about her most recent project, Nine Shapes.

“I wanted it to mirror what I believe about the Enneagram, that it’s about transcending your type and embracing the possibilities of all the others.”

Using the Enneagram as a foundation, Nine Shapes is a card game intended to foster meaningful conversations, revealing and raising truths we wouldn’t have otherwise uncovered. Whether your intent is to grow deeper into your current relationships, or to support the development of new ones, Nine Shapes applies to and works across a spectrum of contexts.

“Nine Shapes was really born of curiosity. In conversation, people would casually ask me about my Enneagram type and share their own. I realized that people were talking about it, but I wanted their interest to come out of a deeper, more intense desire to understand themselves and others.

“So I began keeping a notebook where I’d write a new question almost every day until I’d written 100 questions. At the same time, I was working with an artist friend to create visuals for my Enneagram presentations. Looking at what we’d been making together, I realized that it was too much of a simplification of what the Ennea-types indicated about a person. I wanted the art to be more representative, more fluid in what someone could garner from it. I wanted it to mirror what I believe about the Enneagram, that it’s about transcending your type and embracing the possibilities of all the others. It’s a lifetime journey of discovery, and I wanted Nine Shapes to reflect that.

“It’s not my intention that people develop a single, concrete understanding of the various types or what that says about who they are. Sometimes, language doesn’t cut it, and words can’t get down to the truth of what you want to say, express, or communicate. And so all the colors I use in the game’s design, all of the angles, and the movement shown in the Nine Shapes are there to call upon interpretation, and to point to our mystery and the wonder of human personality.”




“Some things are so mysterious that you need art to help you experience it.”


Ashlee talks about developing the game, sharing with me her creative process and how she sees herself in relation to what she’s made. “Whether or not I was the one to create it, Nine Shapes needed to exist. I just felt this responsibility of being its conduit, the channel through which it took shape.”

It’s refreshing, both the way Ashlee articulates this creative partnership and understands her relationship to what she’s bringing into the world. In the past, I’ve always thought of creativity as something inextricable from my essence—a direct reflection on who I am. It’s isolating, believing that you’re separate from what you work with, from the representation and expression you seek to manifest. But it’s almost jarring, the sudden and shocking shift that Ashlee’s words instill within me, and the inspiration arising from what she shares.

“Two months ago, I got the feeling that someone else was working on the same project, and the day after I launched my Kickstarter, another Enneagram game launched on the platform as well. Very different concepts, totally different games, but I think I’ll always wonder if that feeling, that sort of premonition, was the impetus I needed to get going on Nine Shapes.”

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I love that overlap and the sign the universe was communicating to her. It’s not something to be explained, not something to be judged or critiqued, but something simply to experience instead.

Our discussion turns to Ashlee’s life outside of her work, and I ask what she does that both inspires and provides her with a source of respite and breathing space amongst the busyness of the everyday.

“I’m very intentional with my rest. If I’m tired, or not emotionally centered, then my calls are off. It’s a responsibility that I take seriously, because when I don’t show up well, I’m wasting someone else’s time.

“I love gardening and being outside. I have an herb garden that I tend to, and fruit trees and vines around the house. I take long walks and spend time with my goats. It feels like therapy to go out there and sit with them, just petting them and talking to them. I’m sure the neighbors think I’m crazy, but I love them. And they teach me a lot, too. They’re really curious, and wildly intelligent.”


“I’m very intentional with my rest.”


Ashlee says this, and I’m reminded of a house a few streets over from where I used to live with three goats that I would pass by on my walks through the neighborhood. It became a habit, my routine of checking on them. I loved how explicit the goats were in their responses. There was no nuance, nothing hidden in a hesitancy to reveal their emotions. They stood as a reminder of all there is to revel in, all the simplicity we have access to, all the joy that can be garnered simply from paying attention, from giving ourselves over to presence and the modesty of each moment and every day.

I say this, with an easily-discerned excitement in my voice. Ashlee smiles, an infectious warmth in her voice as she says the words that wrap up the conversation:

“There’s so much to be learned from just holding things as they are.”





You can learn more about Ashlee’s work, the Nine Shapes, and her Kickstarter here.