Ashlee’s Story

“Mistakes are like an algorithm of learning yourself.”


When you were in college, what did you think your life would look like after graduation? Married, single, roommates, no roommates, dream job?

I imagined living on a farm and having close, deep community. Think Gregory Alan Isakov!

I pictured myself not married. I didn’t specifically have anything against marriage. I just hadn’t ever experienced a relationship I thought was healthy or worked. There were always things in life that seemed more interesting to me than marriage.

I wanted to produce something in the world that was important, like art. I’m not sure what the medium is, but maybe doing something with my hands, anthropological work, scientific discovery, and again, building good community.

In short, my dream job was artist/world changer. The next Ghandi. Kind of ambitious.

Is that what happened after college, and if not, what did happen?

I met Trevor (my now husband) in college. I fell in love with him and he was a catalyst for me becoming a better person. He’s a great support to me. When I first met him, what stuck out to me about him was his strong character and lifelong learning. He is always learning, staying sharp, and challenging me!

I have stayed more “rooted” than I expected. We graduated in a city that wasn’t super affordable, moved away from California to a more affordable place, and bought a house. I have found more satisfaction and adventure in what people might consider a boring or mundane life. There’s beauty in the backyard, not only in big discoveries and field research or being part of a world-changing nonprofit.

What are you learning right now?

Margin. Do less. Saying yes to one thing means you are saying a hard no to 99 other things and that is okay. I’m starting to hone in on my life’s mission and what’s important. 

During the first half of my 20s, I was expanding –– friendships, career options, etc. Anything I was invited to, I said yes to because I was exploring. I thought, I could start a blog! I could start a podcast! I could make a card game! I could … fill in the blank.

By saying yes to everything, you’re just giving a little bit to everything and it’s less quality. By actually saying yes to a few things, you focus on those and make them as good as they can be.

I’ve been trying to trim back everything –– what workshops I say yes to teaching, what friends I hang out with. Previously I felt like I needed to hang out with everyone or give myself to everyone, but it takes a lot of energy to just give yourself to yourself. And I’m married and that takes a lot of energy. It’s OK to have just a couple deep friends. 

When you focus on a few things, you can improve the quality of those few things. I only have 30-50 good years left in me. If I’m actually going to impact the world, I need to get focused and do less.

What do you love about your life right now?

I recently have started reclaiming my life and personal agency. I stepped into new dreams and shedding and mourn old dreams. 

With my young 20s being about lots of discovery, now I am eating the fruits of that exploration. 

I like my rhythms! Cooking, friends, meditation, swimming in Oregon rivers, working from home + coffee shops, canning, and I have pet goats. 

I did counseling for five years and I’m enjoying being somewhat healed and a healthy person. I find true pleasure in my interior world, and I didn’t really enjoy walks or quiet times in the past because it was a confusing place. Now, I love quiet and nature, and I’m enjoying being comfortable in my own skin. 

No matter where you are, where you work, where you live, how much money or friends you have, if you haven’t done the internal work of healing yourself, it doesn’t matter. Because you’re still carrying a super heavy backpack. Unload it first. Then hike.

Walk me through the step-by-step process that you went through to get to where you are today. What was the first thing you did? Next?

-Followed my passions (80%)

-Honed in my passions and skills (20%) 

That might even be 90/10, and another way to say “following your passions” is failing and making a lot of mistakes. Mistakes are like an algorithm of learning yourself. It took awhile for me to believe in myself. 

I moved to Portland. I worked as a florist at a grocery store. I thought I wanted to work in higher education because my undergraduate experience was so impactful. So I got a job in higher ed and disliked it! So bureaucratic. The change I tried to create wouldn’t happen. I realized I didn’t necessarily love higher ed; I loved seeing people work out of their passions and strengths.

While working at a university, I discovered coaching and fell in love with the discipline.

I’ve been building my coaching business for the last two years. AND THAT HAS BEEN CRAZY. To make ends meet, I’ve nannied, done random part time jobs (making and selling flower arrangements and necklaces, coworking in a shared office space, trades … I just said yes to everything!).

How long were you running your business before you started paying yourself? How did you live through those first few months/years?

One year. In tension, wondering if it was the right choice. 

What brings you joy/fills your soul? 

Sitting with someone without their mask. Or, getting glimpses into other’s internal worlds. 

My journey since college has been an adventure in finding that that is what brings joy to my soul. As a recap …

  1. I graduated.
  2. Then I moved Portland.
  3. A year after college graduation, bought a house then got married –– three huge transitions within 12-14 months.
  4. Became a florist in a grocery store –– which felt very existential.
  5. Got a big girl job at a college –– existentialism followed because people believe in you in college, but not in the real world. That’s when I realized I need to believe in myself. No one’s going to check on me and ask if I’m going to counseling or taking care of my soul. So I started healing what I think about myself through counseling, and found that all the exterior pieces don’t matter. What you think about yourself is what stays with you. At my university job, I thought I wanted to work in student life because that department impacted me profoundly as a student. I learned that I really was inspired by people living their passions. University structure is too bureaucratic for my personality style. 
  6. I am passionate about people knowing themselves and living their passions. I noticed I lived for retreat days –– which only happen twice per year! I taught for the university what I’m now doing full-time.
  7. I got a certification in coaching. 
  8. I was dreading going to work every day, so I quit. I have low risk aversion, which my Enneagram type explains, which is helpful for me! So I jump in and then realize I didn’t think it through. I started my coaching business and was like, “Great! I’m open for business.” “Oh, no clients are calling me. This is bad.” I learn things as I do them.
  9. To make ends meet, I applied for a bunch of nonprofit jobs when I left the university. NO ONE called me back. I couldn’t even get a job at the local ice cream parlor, which was surprising. These setbacks definitely made me trust there is a God. I actually felt forced into starting my coaching job. I kept trying to get normal jobs, but no one would hire me. Meanwhile, people started hiring me to coach them for the first time. I’ve been building my coaching business for 1.5 years, and this is the first year I’ve been making money solely from coaching.

If a kid walked up to you asking for your advice and you only had a few minutes to give them your best tip, what would it be?

Spend time with yourself. Learn to love who you are and nourish your interior life. IT IS YOUR BIGGEST ASSET –– the only thing you will have with you always.

You always have yourself. You’ll always have your body. You’ll always have your mind. Take care of those things! Value investing in who you are.

What do you wish everyone knew about being a coach, starting your own business, the Enneagram, and/or marriage? 

Coaching is 25% taking care of yourself. I need to work hard to stay in tune myself and be grounded or else I won’t show up well for my clients. I think this also translates to other professions. I’ve been surprised by how much of my coaching work is not production, but being a steward of my own emotional health. 

It takes a lot of work for me to be grounded and to show up to a coaching call in a good headspace. What I want to show is that we all have our work to do. And I think a lot of times people think coaches have everything together –– which I think they also think of leaders.

In marriage, it’s important for both partners to build themselves apart from their spouse. You have to know who you are outside of your marriage. A seasoned psychologist Esther Perel talks about how most people will be in four committed partnerships throughout their lifetime.

If you’re married or have a long-term partner, those four will take place within that one person. That’s exciting to me because I’ve been with Trevor for eight years. It keeps it very interesting that he’s a different person –– now a poet/artist I never thought he would be. There’s a death that’s happening to the prior relationship and our prior selves.

I think people get scared and try to hold onto their old selves and their partners’ old selves. But you have to invite change, relearn each other, and trust the process. Take time to learn yourself and allow yourself to “fail” –– it’s a great learning opportunity. 

The Enneagram is a powerful tool. And if you’re going to use it, it takes a lot of study and honest self-observation. It’s not so much just sharing your type with everyone you know and putting it on your Instagram bio. It takes a while to sit with the tool and yourself. It’s not an easy assessment, but it’s worth the excavation. From fixation to freedom, as they say.

How can readers connect with you?

Subscribe to my email list where I send out quarterly thoughts at!

Follow along on Instagram: @a.s.coaching // @nineshapes

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