Why coaching?

My first experience with coaching was as a client, and the impact that coaching has had on me is an enormous part of why I’m now a coach myself.

Initially, I had no clue that coaching existed - at least outside of sports. And yet I started benefiting from coaching almost immediately. As I do now, my coach started with a free intro conversation lasting about 20 minutes, and in that time we explored what I was looking for and how she could help. Right away, I felt my burden start to ease, and with every word I spoke, the load seemed to lighten. I realized I no longer had to struggle through my stuck place all by myself, with the same, circular thoughts running through my mind. In fact, here was someone who not only didn’t say I was crazy, but seemed to understand what I was going through. And had somehow worked with other people who had been through something similar! 

Here’s how I arrived at that moment.

In college, my friends and I had started a sketch comedy group - ala SNL or Key & Peele - and after graduating, we were determined to go pro. This was no easy feat! And yet, incredibly, we made it happen.

That’s right: I’m a former sketch comic.

After about a year of working grueling day jobs, rehearsing in the unfinished basement of the cheap apartment we rented, and performing at comedy clubs around Boston, we hit the road for our first tour, and we didn’t stop for over five action packed years. That was my life for the better part of my 20s: no boss, no office - just a used van, a ton of creative problem solving, and a shared distaste for the kind of conventional thinking that prevented people from doing things like starting nationally touring sketch comedy groups out of thin air.

We performed at hundreds of venues in dozens of states for thousands and thousands of people - as many as 3,000 at a time - and even created viral videos in the early days of YouTube that attracted over 12 million views. We may not have become rich and famous, but we most certainly did what we set out to do: an incredible feat that few dare to try.

So why, when we decided to quit touring, did I feel like I had somehow failed? We had done the impossible, and yet I was left with a nagging sense of having fallen short. It was sapping my creative energy and self-esteem and blocking my vision as I pursued my next chapter.

That’s when I found coaching.

A friend of my wife’s who was tuned into my struggle knew of this great career coach, and the next thing I knew, we were on the phone and that burden I’d been carrying around solo was starting to ease.

My coach helped me realized that I hadn’t failed at anything. In fact, as hard as it was, I’d achieved my goal! Getting that internal, biased narrative straightened out was a huge first step. The next part involved figuring out what I wanted now, and how to get there. Thanks to the support of my coach, I got there. I reinvented myself as a food writer, and after a few years of writing freelance for publications like the Boston Globe and Smithsonian, I landed a job as an editor for Eater. And at several junctures throughout, I called up my coach. She was always there to help me navigate the places I felt stuck, whether it was figuring out how to improve my work-life balance, negotiate a raise, or giving me the space to pick my head up from the daily grind in order to look toward the horizon and dream big about what I wanted next.

I can honestly say that I wouldn’t be where I am today without the support I received through coaching. It can be a truly powerful, transformative experience, and it’s my honor to now participate in the process as the coach.

If there’s something off about your experience of work or life, and you’re telling yourself that there’s nothing you can do about it - no offense, but you’re probably wrong. And I hope you can experience the relief, support, and satisfaction that I and so many of my clients have through coaching.

If you’ve read this far, I would say you’re actually pretty well along your coaching journey! The next step? Let’s start the conversation. 

[Photo: Neil Thomas via Unsplash]

Next
Next

Do it Your Way, You Beautiful Albatross: Seeing what sets you apart as a strength