Today we’d like to introduce you to Holly Coneway.
Hi Holly, we’d love for you to start by introducing yourself.
I grew up in a small town in Texas, the daughter of a farmer and small-business owner and a teacher turned professor. That world gave me a deep respect for community, work ethic, and the kind of steadiness that holds people together. It also gave me a curiosity and a zest for more that I have never been able to quiet. Both have shaped everything I have built since.
I went to Texas A&M for undergrad, where I fell in love with writing and the healing power of being able to put words to what is going on inside your mind, heart, and life. Something cracked open there. Once you learn that language can do that kind of work, you cannot unlearn it.
After A&M, moving to a bigger city like Houston made sense. The pace and complexity and vast array of stories matched the yearning for more and curiosity that had started years before. I love cities for the same reason I love people. So many lives intersecting, so many versions of what life can look like, all of it happening in the same square mile.
I trained as a therapist because I wanted to understand people at the level most never get to see. The interior. The patterns underneath the patterns. The places where the real work lives. I moved into coaching because coaching has a global reach and a philosophy I believe in. Human flourishing has universalities. Good leadership has universalities. Both start with self-leadership, and self-leadership is something anyone, anywhere, can be invited into.
Along the way I fell deeper in love with poetry and yoga, and I am a forever student and teacher of both. Poetry taught me that the most precise language is often the least literal. Yoga taught me that the body often knows things the mind has not caught up to yet. Both of them live inside everything I do now, whether the room knows it or not.
From there I kept building. Executive coaching. Workshop facilitation. Corporate consulting. Writing. Beginning to train and mentor early career coaches and therapists. None of it was a pivot. It was the same questions taking different shapes, depending on who was in front of me and what they actually needed.
The people I work best with are wired the same way. High-functioning, multi-dimensional, allergic to being flattened into one thing. Founders, executives, emerging leaders who are good at almost everything they touch and quietly tired of pretending that is the whole story. They are both ambitious and tender, rigorous and intuitive, deep-thinking and ready to be known. The both/and is the whole point.
Today I work with those people, in one-on-one and inside their companies, on the deeper parts of leadership and identity that the usual frameworks often miss.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
The road has not been smooth, and I would be skeptical of anyone in this work who said theirs was.
My particular struggle has been this: My curiosity has led me to become a very expansive thinker. I see the interconnectedness between ideas quickly, and I move in webs rather than lines. I now know that this is a real strength in the room with a client. It is what lets me hear what someone is actually saying underneath what they are saying. It is what lets me hold a person’s psychology, leadership, relationships, story, and meaning-making at the same time, because in real life those things are not separate.
The struggle has been the world’s preference for the simpler version. The single niche. The tidy framework. The algorithm. The label. The one-line bio. I feel the world asking us, again and again, to flatten ourselves into something a stranger can categorize in three seconds. There is a real cost to that flattening. For a long time I didn’t have language for the cost, I just knew something in me went quiet every time I tried to fit.
What I have learned is that the flattening was never the path. The integration was. The people I am here to serve are not looking for the simpler version. They are looking for someone who can hold the full complexity of who they are without needing to reduce it.
I know the struggle is not over. It just stopped being a problem.
Appreciate you sharing that. What should we know about My Insight Service?
My business is called My Insight Service. I am a Licensed Professional Counselor and an ICF Professional Certified Coach, which is why I do my work in the way that I do.
I work with founders, executives, and high-achieving people in three different, but inter-related, ways: coaching, therapy, and work inside organizations. I move between them fluidly because I have spent more than a decade sitting at the place where high-achievement and self-knowledge either come together or start to quietly pull someone apart.
The coaching I do falls into 2 categories: Executive Coaching and Leadership Coaching. Executive Coaching is for founders, executives, and senior leaders already in the roles and the Leadership Coaching is for people who are newer to leadership or carrying a role no one really ever prepared them for. The work I do with both goes beyond strategy. A lot of it lives in the realms of workplace relationships, presence, communication, and all the human parts of leading. To me, those are the most interesting and foundational parts of leadership, not just the cherry on top at the end.
The therapy side also has 2 categories: Executive Therapy and Individual Therapy. The Executive Therapy is for leaders in high-impact roles, where their work and life have to be allowed in the same room because, in those seats, they aren’t really able to be separated. The Individual Therapy is for any high-achieving person who wants a place to think clearly about a life that is mostly working, but still holds some questions (as life always does!). I pull from several different schools of training, which lets me meet a person where they actually are, instead of running everyone through the same approach.
Inside organizations, I do leadership development, workshops, consulting, and ongoing advising. Built around where your team actually is and where you want them to be.
What I am most proud of brand-wise is how the whole approach fits together. The therapist, the coach, the facilitator, the consultant are not different offerings stapled together randomly. It is a partnering together to see all the different ways we can truly build a life you feel proud of. People who think this same way, who see and fell how all the roles they play are inextricable intertwined, tend to resonate quickly when I tell them how I work.
Can you talk to us a bit about the role of luck?
I truly believe the old line that “luck is where preparation meets opportunity.” So, when I look at what people might call my “good luck”, a lot of it is actually preparation that started long before I was old enough to know I was being prepared. I was born to parents who modeled work ethic, steadiness, kindness, and looking out for others. An education and preparation I didn’t ask for but was lucky to receive. That kind of foundation doesn’t feel like luck when you are inside it, i just feels like how life works. Looking back, I know it was both.
The other piece of my “good luck” has been a belief in the power of just saying yes and showing up. I have built a lot of my life on the belief that if I keep saying yes to what feels right and keep showing up fully, it will all shake out how and when it is supposed to. I do not always know what something is going to become when I step into it, but I trust that the doing is part of the figuring out and that the picture clarifies in the doing.
The harder side of luck, for me, has mostly looked like the lack of exposure and the waiting that comes from those same places that also brought me the “good luck”. Being born a female in the 1980s in small, town Texas has often left me feeling like I am starting from behind and having to play catch up. Thus the belief in always saying “yes”. However, sometimes I say yes and show up and then have to sit in a long stretch of not knowing how or if it might all come together. I often find myself saying things I know are true, things I have done the work to understand, but maybe in a room, a season, or a moment where the people or the world aren’t quite ready to look at that yet. That can feel like “bad luck” in real time. The patience required to endure it is not small. You start to wonder if you are wrong, or early, or just talking to the wrong people. The work is to stay with what you know, keep refining it, and trust that the moment and the message come together when they are supposed to.
So my honest answer is that luck has played a huge role, and almost none of it has been random. The good has been the meeting of preparation, willingness, and opportunity. The hard has been the gap between knowing something is true and the world being ready for it, and the patience to wait for the pieces to fall into place. Both have and still shape me.
Contact Info:
- Website: https://www.myinsightservice.com/
- Instagram: https://www.instagram.com/myinsightservice/?hl=en
- LinkedIn: https://www.linkedin.com/in/hollyconeway-pcc-lpc/
