My Journey to Coaching, Part II

In the summer of 2023 I started working with a coach for the first time with the goal of helping me hone in on what the next chapter of my career might look like after being in a family business for thirteen years.

I had no idea what to expect from the process. In our first session she asked me question after question, pulling out from me a list of values, a list of what mattered deeply to me. In my normal default mode of pushing the attention back off myself, I tried to asked her questions:

  • What do you think about this decision?

  • What do you see your other clients doing in a situation like this?

And like any good coach she would turn these questions back around to me.:

  • What do you think about this decision?

  • What is important to you about the potential outcome of this situation?

(Looking back it is strange that I would be looking for validation, or even outright direction, from basically a stranger. At the time we had maybe spent 200 minutes together.)

Early on this proved to be deeply uncomfortable for me. I don’t like to be seen. I don’t like to be the one answering questions. I’m usually the one deflecting questions back at someone else. And hell, isn’t a coach supposed to tell you what to do? Any athletic coach I've had did exactly that. They tell you what to do, how to shoot, when to cut, how hard to sprint.

But now I had this person focused 100% on me, asking me to search for my own answers. It felt like for the first time in my life I was staring at a completely wild jungle in front of me and I had to figure out where and how to cut my own path. This was the first time in my life since graduating college that I did not have a full-time job where I'd sit behind a computer with email to respond, tasks to complete, with a job to do.

The first homework she gave me was to create a list of all the things I want more of in life and all the things I want less of in life. In hindsight, this is such an obvious exercise for anyone to undertake on a regular basis but it was not something I had ever done.

As I reviewed the list, it became so obviously apparent why I always felt something was off in many aspects of my previous jobs. Those jobs, while fulfilling in certain respects, were filled with a whole bunch of things that I wanted less of. Things that drained me of energy rather than giving me energy. Now I am not so idealistic to think that a job will be perfect, but it does make sense, as much as possible, to lean into your innate strengths. To do more of the things that give you energy rather than the other way around. This is the foundation of Gallup and CliftonStrengths.

What became apparent was that in order to focus more on the things that gave me energy, I had to first make space for them. It led to a summer of reduction. What that looked like for me was accelerating my transition out of my day job, selling a plane that I had owned for two years, taking a break from flying, and drastically reducing, then ultimately severing, my alcohol use. And in the space created I was able to devote time and energy to some pursuits that I hadn’t given myself the permission to explore. I started writing more for fun, enrolling in two different writing classes. Tapping into a buried creative side, while creating questionable quality output, still felt incredible.

It is funny how this coaching-thing can work, and ultimately why I’ve come to believe in the power of whole-life coaching. I came to my coach with the straightforward goal of finding my next career path. But in order to get there I had to first turn my attention to other aspects of my life.

Ultimately I leaned more fully into a passion and desire to have a direct impact on individuals. My coach, and past athletic coaches, have had such a profound impact on me, that I felt it would be a gift to be able to provide this service to others. It is clear to me that most of us could benefit from having a coach-type relationship with someone, whether it is a commercial relationship or not.

So in the fall of 2023 I dove into training with the Co-Active Training Institute. By May of 2024 I finished the 100 hours of their interactive core-curriculum and started working in earnest with clients.

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What is Coaching Anyway?

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My Journey to Coaching, Part I