The Embossed Way: Cären Gillespie

A conversation on counseling, confidence, and connection

Sep 11, 2024

Welcome to the second edition of The Embossed Way, a new 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 edition, you can check it out here.

I’m so excited to introduce you to Cären Gillespie, one of the wisest souls I’ve been lucky enough to know. Cären is a Certified Master Life Coach who specializes in helping women silence their inner critics, recover from burnout, and realize their potential. I came to Cären in the year after my layoff, the one that upended my life and left me feeling like a failure, completely raw and blinded by grief. She helped me recognize how much of my self-worth was tied up in my job and my bank account and helped me find the confidence to pursue freelance, something I’ve now been doing (successfully, I might add) for two years.

A conversation with Cären is a masterclass in self-trust and seeking help when you need it. Her approach to life is one I not only admire, but one aspire to adopt for myself. I hope you find it valuable, as well.

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

Cären Gillespie: For years, I wanted to be a teacher. I had so many great teachers who inspired me to be one. I received a large chalkboard for Christmas and had all of my younger friends come down for “lessons.”

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

CG: I guess I am sort of a teacher now in the sense that I help women navigate their paths in life as a mentor, consultant, and counselor. I often find myself relaying knowledge I have gained through the years to younger women.

LS: Tell us how you got there. What was the journey like? What bumps did you hit along the way?

CG: I have always been a sort of counselor to others since I was very young. It comes naturally to me and others have told me I am disarming and they feel safe to be vulnerable around me. I was that friend to others, even their mothers asked me advice on their lives. I never really thought of it as a profession so I went about my life, graduated college, and went into recruiting where my skills as a counselor and mentor were utilized often with the candidates and managers I worked with.

The bump? Children! I gave birth to my first child and suffered undiagnosed postpartum depression for two years. I thought I made the wrong choice about children because there I was, stuck in my basement crying every day waiting for things to get better. Motherhood did not come naturally to me and my son had a few health issues and cried a lot! I had trouble bonding with him. I had my daughter 3.5 years later but put the right support in place for having her. I quit my recruiting career to stay home with my children and still wasn’t really sure I was cut out for motherhood.

My kids are grown now, one in high school and one in college, and are my favorite people on this earth. We have a very close relationship and I found my strengths in mothering them was to see them, normalize their emotions, and give them the right dialogue for their feelings. They are very emotionally intelligent humans and I like to think that giving them a safe space to be themselves helped in that. I now help other women who are maybe just in the muck of their parenting or are starting new careers. I help them navigate and normalize their emotions and aspirations and help them get out of their way when they start to second-guess themselves.

I have always been a sort of counselor to others since I was very young…I was that friend to others, even their mothers asked me advice on their lives.

LS: You’ve definitely helped me push past second-guessing, which has helped me dream bigger and take steps toward those dreams. Tell us something you still dream about (something you still want to do/experience/accomplish).

CG: Living in France at least part time. It has become my other home, but now I just visit for 2 weeks per year. I would love to live that life regularly sometime. I also dream of owning an ‘80s dive bar. All ‘80s everything.

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

CG: Spend your money on travel and language lessons. Getting to know others in this world, especially in different cultures, is so enriching and fulfilling. Don’t give up your career completely when you have kids. It’s harder to come back after 18 years.

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

CG: Not letting others dictate what is right and wrong. There are no real rules to what one can do. We are born with free will. Take responsibility for yourself and live how YOU want to live, regardless of what others say. Drop resentment, it does not serve you.

Getting to know others in this world, especially in different cultures, is so enriching and fulfilling.

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

CG: This is a photo from Salt Creek on Washington State’s Olympic Peninsula. The ocean and the sky are my greatest sources of inspiration. If I could spend hours by the ocean, beneath a changing sky, I would feel truly fulfilled. Their blend of predictability and unpredictability both calms and excites me. The ocean puts things into perspective—its vastness reminds me of my own smallness. From the soothing sounds of the waves to their fierce crashes, and the water's softness, whose strength can reshape the earth. In our own small ways, humans have a similar potential. We can create change, act gently, and have a powerful impact if we allow ourselves. “Nothing is softer or more flexible than water, yet nothing can resist it"-Lao Tsu

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.

If this post inspired you – or if the series and/or entire CEOverthinker publication inspires you – consider sharing it with someone so they can be inspired too. 🤍