Why I Chose to Be an Executive Coach

When I was in the throes of entrepreneurship, running my struggling commercial printing company and my struggling tech company simultaneously, I had a vividly clear thought in my head.

I thought, “If I could pay someone a thousand dollars to just listen to me talk about my business problems, I would.”

And that, fundamentally, is why I am an executive coach today.

Starting off my career as an investment banker, then a corporate attorney, I felt very limited. As a banker, my life was all about standing by the fax machine (yep — I just dated myself), traveling, and managing spreadsheets. As an attorney, my life was all about reading, writing and billing.

I always felt like I had more to offer the world than just my liberal arts skills. I felt like I could recruit, sell, create a vision, craft strategy, build product, manage, code and more. I felt like I needed entrepreneurship to truly maximize all of my skills and really challenge myself.

And boy did I ever get that challenge. Entrepreneurship was by far the hardest challenge and most rewarding experience I’ve ever had in my career. I have been an entrepreneur now for more than 15 years.

Entrepreneurship can be thrilling, but also brutal. (So are other professions, of course, and I don’t mean to discount the challenge of other professions, but I am writing simply from my personal experience).

I was sole owner and CEO of my commercial printing company, where 1,000 things went wrong per day, and I was sole founder and CEO of my tech startup, where 1,000 other things went wrong per day.

Though I consider myself to generally be pretty level-headed and even-keeled, I was frequently on edge as an entrepreneur, and I often carried with me an enormous and unwanted baseline of stress.

Being an entrepreneur (especially without partners) is a hellaciously lonely existence. Nobody cares as much as you do, there is a line between you and your employees, and the stakes are very high. It is hard to find empathy, and it therefore makes for an extremely emotionally vulnerable position to be in. Even having co-founders and partners is no panacea. In many cases, having co-founders can even compound stress if founders are at odds with each other.

Entrepreneurs need a listening partner. I firmly believe they need a coach.

They need someone who is paid to simply sit there and hear them brag about their successes and cry about their failures. Entrepreneurs need to talk about all of their fears, their fear of failure, their fear of embarrassment, their concerns about their business, their investors, their employees, and frankly, the whole kitchen sink. They need to be able to speak with grandiosity, pride and even pain without fear of judgment.

They also need a sounding board. The echo chamber of one’s own head makes it impossible to have any perspective on what is really going well and what isn’t, what are the right moves to make and what aren’t. It is too hard to self-assess when you are the sole creator of your own business universe.

It is vital for mental health and peak performance to speak to someone you trust who is focused on hearing you. I believe this with all my heart.

And so, when I stepped off the entrepreneurship train after selling my company last year, I wanted to dedicate my time to helping other entrepreneurs who are on this warpath.

I feel particularly equipped to help others because I have been an entrepreneur twice for over a decade, and I have the financial and legal acumen to buttress my general advice with specific time-worn knowledge.

Furthermore, my personal qualities made me feel like being a coach would be a natural path. I love talking to people one-on-one, and I am most proud of my ability to understand and connect with people.

I didn’t actually seek out my first coaching engagement. A former student of my business class at General Assembly reached out to see if I would be interested in coaching him. During my class, he developed a startup idea, and shortly after, raised seed funding. I am forever indebted to him for being the first to trust me as a coach, and for lighting the pathway to my current career.

Taking my first few steps in the coaching world, I was afflicted with an initial and mild dose of impostor syndrome. Are coaches charlatans? Does anyone need them? Are they just a crutch and a dependency? Do I even know how to coach someone? Do I need credentials or training?

I have been coaching for nearly a year now, and I am happy to say that these questions don’t bother me anymore. I absolutely love coaching, and I have been relayed heaps of positive feedback by my amazing coachees.

One of my favorite pieces of feedback came from a wonderful founder who expressed in the most “millennial” way possible his appreciation. At the conclusion of our second session, he exclaimed, “Holy frick! This is soooo incredibly helpful!”

Holy frick, indeed. I love coaching, and this is how I got here.