The Embossed Way: Cassady Coulter

On trusting the process and listening to your intuition

Welcome to The Embossed Way, a monthly series here on CEOverthinker featuring conversations with women who are making their mark, paving their own way, and embodying what it means to be the boss of your own life.

If you missed the first three editions, you can check them out here, here, and here.

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Author’s Note: It’s been a rough week since the election. There’s a lot I could say, but truthfully, I don’t think I could say it better than the posts I’ve read like this one. I will, however, say that it now feels all the more important to lift up women and their voices. So in lieu of a post with my thoughts (and feelings) about the election, here is a conversation with a very special and inspiring soul.

You know those people who make you think, “Wait, are we the same person??” That’s exactly how I felt when I met today’s guest, Cassady Coulter. Cassady is a long-time family friend of my in-laws, the first-ever friend of my husband (they technically met in utero when their parents were in the same birthing class!), and now my forever friend. I’d always heard her name and seen her photo on the fridge, but somehow had never gotten to meet her. Finally, the day came (two full years after I’d started dating Will; we still joke that he kept us apart for too long), and we immediately hit it off, bonding over our shared misery working in PR agencies. Like me, Cassady didn’t appreciate the cut-throat hustle culture. I could immediately see she was – and is – a kind soul who values personal connection and creativity over climbing any sort of corporate ladder.

Cassady is actually one of the people who inspired me to pursue freelance. Until I saw her choose to work for herself after leaving a job that didn’t align with her, I hadn’t even realized something like that was an option. I had never considered the fact that I could quit corporate if it wasn’t serving me and do something different. She’s a true trailblazer – one who always follows her heart. Her story is one about knowing yourself and your values, listening to your intuition, and trusting the process. I can’t wait for you to meet her.

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Lauren Scott: What did you want to be when you grew up and why?

Cassady Coulter: Growing up, I always wanted to be a Zoologist (particularly, I wanted to be Jane Goodall). When I learned about her legacy, I was absolutely captivated and inspired. I always thought if I could be like her and help animals for a living, it would be the coolest job I could dream of.

LS: How does that compare to where you are now?

CC: Unfortunately for me, becoming a zoologist would have required a lot of math and science classes, and, as I would come to find out, those were my least favorite subjects. So, though I didn’t end up studying chimpanzees like Jane Goodall, where I found myself was a career where I could be inspired and use my creativity. This eventually landed me in the world of writing, which is truly one of my first and purest joys.

LS: Tell us more about where you’re at how you got there. What was the journey like? What bumps did you hit along the way?

CC: My career path has been more meandering than I ever could have expected. I don’t have any regrets, and I think that all the steps I took helped shape me into the person I am today, even if some of those chapters were tougher than others. I was very fortunate to be able to intern for magazines and newspapers after college. From there, I truly feel like I stumbled into my next job, which was a data entry position at Expedia onboarding new hotel properties. I spent nearly 7 years there, and was lucky enough to call myself an SEO Content Strategist by the end of my tenure. Though I’ve had some amazing career opportunities, the bumps have been frequent and unexpected. I took jobs that seemed great at the onset and didn’t turn out to be a good fit for one reason or another. I felt really lost and purposeless for a while, and my self esteem suffered when jobs didn’t work out as I had hoped, often leaving me questioning if I was even good at what I did. All the while, I was seeking a feeling of belonging and purpose, and I just had to trust that if something didn’t feel right and my mental health was suffering for it, it was something worth listening to.

LS: Tell us something you still dream about (something you still want to do/experience/accomplish).

CC: When I left Expedia, I jumped around a bit but ended up finding myself as a freelancer off and on for the last few years. I found I really liked the intimacy of helping small businesses in a more one-on-one capacity, and the way each day felt different. I still dream of having a burgeoning freelancing agency where I can help people solve content problems and help small businesses I care about make an impact.

LS: Knowing what you know now, what is something you would tell your younger self?

CC: I think I would tell my younger self to trust the process. I spent so many years in college and the years after really stressing about finding the exact right thing. I chased a lot of things that ended up being wrong for me (and learned the hard way that no matter what someone offers to pay you, that does not equate to happiness). I find myself now, at 32, probably the happiest I’ve been in a long time, largely due in part to where I’m working now, at a craft brewery in Redmond. I spend every day surrounded by people I really enjoy, in a unique, beautiful community, connecting with others on a daily basis and understanding how they got to where they are. There’s really nothing more inspiring as a writer than getting to be part of the tapestry of a niche community as it swirls around you. This job has actually been fundamental in helping me trust that people are generally good and kind. It has taught me to appreciate little acts of kindness and to see the beauty in simple gestures and small moments. 

LS: What does “being the boss of your own life” mean to you?

CC: Being the boss of my own life to me is about being at peace with where you’re at, leading a life that feels authentic to you, and making small steps every day toward becoming your best self. As someone who has been – and always will always be – a creative soul at heart, I think being the boss of my own life has come to mean living as true to my values as I can and embodying that every day.

LS: The cover image for this article features a photo of something that inspires you. Tell us more about it. What does it mean to you?

CC: This is a photo of my dog, Ember, that my husband Jake took. She’s one of the best things in my life and a constant source of happiness and inspiration. This photo makes me giggle because I feel like it showcases Ember in her truest form— joyful, free, and goofy as ever. She reminds me to be present every day and appreciate the small moments in each day.

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Thank you for reading this edition of The Embossed Way! You will find new editions in your inbox once a month. My hope and goal for the series is to lift up female voices, showcase how they’re doing things differently (i.e. not taking the traditional path society tells them they have to, whether in work or in life in general), and inspire others to do the same.

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