
About Dave O’Connor
Scroll down to learn about me and what I do!
My Good Soldier Story
I remember the office with outdated furnishings and incandescent overhead light, the corporate black landline phone I was on, and the dreary parking lot I was looking at through a window of old slit blinds when I was told by an appointed advisor to the startup I was leading, "you'll do what they [the private equity group] tells you, because you're a good soldier, aren't you?" That was my turning point. I didn't quit that day.
It took another year plus of me witnessing myself being a "good solder" before I finally snapped. And snapping wasn't dramatic either. It was just a quiet conversation with a superior about an operational decision we couldn't see eye to eye on. But we both knew it was the end. Thank God that advisor - with whom I never spoke again after that phone call - spoke freely, if not carelessly, because it was the seed I needed planted in my mind and body to get me to one day move on. Moving on scared me. It scared my wife. I remember calling my parents and explaining how I would start a coaching business and they were, essentially, speechless. Only worried, and barely hopeful.
But I knew. I saw how my life would work out if I finally listened fully to myself, even if it meant being abandoned, doubted, or distrusted. Because I trusted myself so very deeply, almost delusionally. And I've been able to now model that self-trust for countless clients and followers of my work who had strived or are striving to break out of their own "good solder" roles - whether in the office, in their industry, or at home.
I started out with Funbringer, LLC, and then boldly stepped out at Hey Coach Dave. Locally, I'm known as Dave O'Connor, Executive Coach - since that's what my office shingle says. Now, I am firmly planted in my origin story of personal and professional freedom and fully own what's going on here: I am no good solder and I am here to support those who don't want to be either.
Whether you are upsetting the status quo inside an organization you wish to remain at, you want to upend the way business is done in your industry, or you want to break out of your routine and explore new ways of leading or living, I'm your guy.
In other words, I'm on a mission to liberate the good soldiers.
My Expertise
Dave O’Connor is a renowned executive coach and thought leader whose work centers on helping high-achieving men and women rediscover meaning, confidence, and clarity. With a unique blend of empathy and pragmatism, Dave has empowered countless executives, business owners, and industry leaders to navigate the complexities of life’s prime years, aligning their professional success with personal fulfillment.
Dave is an International Coaching Federation (ICF) Associate Certified Coach (ACC) with over 400 hours of coaching experience. His coaching education includes training from the Co-Active Training Institute, the Harvard Institute of Coaching, and Dr. David Drake, the creator of the Five Maturities and founder of The Moment Institute, as well as independent study. He also engages in ongoing coach supervision with Katie Drescher, JD, MCC, ESIA, SP.
Dave’s clients include senior executives, business owners, and high-achieving professionals who seek clarity, confidence, and renewed energy as they face pivotal career and personal decisions. Known for his approachable and grounded style, Dave’s sessions offer these individuals a sanctuary for authentic reflection, growth, and strategic insight.
Away From My Desk
Dave and his wife, Meg, live in Lake Forest, Illinois, where they enjoy the charm of the local community and take frequent walks with their two spirited terriers. A lover of golf and standup comedy, Dave also finds creative expression through fine art drawing and painting, which brings a meditative balance to his work.
HOW I CAN HELP YOU
Develop risk-taking and decision-making skills
Develop personal values, purpose and manifesto
Strengthen work-life balance
Grow self-awareness and mindfulness
Expand emotional awareness
Improve emotional management
New time management skills
Leadership development
Improve Interpersonal dynamics

BOOK DISCOVERY CALL
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BOOK DISCOVERY CALL 〰️
DISCOVERY CALL
On our free 30-minute discovery call, you can ask any questions you have related to my expertise, coaching methods, and session structure. We will be able to discuss your needs, objectives, and expectations from coaching.