top of page
  • amychesterton

That time I hired a business coach

 The shift into a new year always makes me hold my breath... just a little. 

It’s a time where many of us, with the very best of intentions, set out on a new something or other that we think we should set out on. 


These something or others run the gamut, from getting fitter, working harder, to being happier, and they are wildly dependent on so many things. Things like where we live, what our peers are up to, how our health is going, how thick our pocketbook is feeling, and so on and so forth.


Honestly, I’ve never had much success with a resolution, but one year, in my previous work life, I did set out on a lofty goal. I was running my own small business that I enjoyed, but it was more intense to manage than I had ever imagined possible.  The business was “successful” by common terms of the word, but it took everything I had in my bag of tricks to make it so, and then keep it so.


I was energized yet burned out.  I was inspired yet overwhelmed. I was thankful yet terrified.  I had “flexibility” yet worked to the bone.  If my body was not actually at the business, my mind surely was. The business itself was loaded with personalities, intricacies, pitfalls, triumphs, and many boring layers of to-do’s just as most small businesses usually are.  Overall, I loved it and my work life. 


Except early out of the gate there was a tiny whisper of a gnawing little feeling that I could not name.  As the years ticked by, that gnawing feeling slowly and steadily started to get more entrenched in my gut, but I still didn’t really put my finger on what “it” was.  I was busy, after all, and didn’t have time to get stuck in any explorations of the gut or feelings.


I was so busy, in fact, that I regularly missed dinners, celebrations, school functions, date nights, family gatherings, and had to be coerced into taking vacations.  As much as I tried to ignore it, I was choosing what I thought should be prioritized and sidelining people that I care about in the process.  It hurt to know this, but it was what it was.  I was in it, I had to make things work, and no one was complaining, out loud anyway. As the gnawing filled my gut more and more it seemed to me, at the time, that the only way to justify all the devotion to the business was to earn more money. 


So, I hired a business coach.   As you know, there is not a magic wand that is waved to make more money.  There are strategies and there are approaches, and as was the case here, they all usually require more.  More effort, more thought, more coordination, more to-dos, more hours, (ironically) more money, and more doubling down on the very thing that drove me here— letting everyone around me down.


The business coach had a complicated system, schedule, and written agreement, and an equally intense payment structure; I was in!  I did the work, I spent the time, and I wrote the checks. The structure did eventually help me get to the (inconsequential) goal of earning more bucks, but of course the coaching itself was a failure, I just didn’t know it yet.


Fast forward a couple of years. I am standing behind the reception desk at my business when someone mentions: “I was at the school breakfast this morning and they called your son’s name- 3 times!  I didn’t ever see him. Was he there?”


I had missed the award breakfast, again.   Probably no less than the 4th time I had missed it, yet this time hit hard. This time, I hadn’t even known it was happening.  My heart crumbled, and I broke into tears.


I am deeply embarrassed about this moment for multiple reasons, but there is no use in not being transparent as it shifted the wind enough to finally flutter the curtains open on that unnamed gnawing feeling. All my failures as a mother, a wife, a daughter, a friend, came crashing down.  Worse yet, I was dangerously close to being untethered from what really mattered to me.

That one moment might seem like a very different issue than hiring a business coach, but then again, was it?


I had purposely taken on the business for many clear reasons, aka; “my whys.”

At the top of that list: work/life balance.  Next up: it was a functional business with resources and safety nets in place. And last but certainly not least—it made me happy.  But, by the time I thought a business coach was the answer to my growing pains, I was mostly out of touch with the very things that had started me on the path to begin with.  It was not the business coach’s fault that I was putting pressure on myself to move the money meter.  It was not her fault that I sometimes felt competitive, overwhelmed, insecure, directionless, burdened, and exhausted and that I thought more money coming in would help to fill the holes.


Yet, the foundation of coaching, when done with care, is built on exploring why someone chooses something, or doesn’t choose something. It is a shifting work in progress, partnering with, and supporting people as they flush out their strengths, fears, hopes, weaknesses, values, desires, and their most personal of goals. “Wanting to make more money” is a blanket statement. Wanting to know why someone says that and then getting to the core of what they actually want is where the magic is.    


I didn’t need a coach to point out that I was busying myself with insignificant financial goals to cover up how unsettled I had become. I had more balls in the air than I had anticipated, or wanted, and the impact was greater than I knew how to handle. I had become hyper focused on one aspect of my life while letting others speed along on cruise control with no one behind the wheel.


It took the missed breakfast to finally knock some sense into me. What in the world was I doing?  How had running this little business become my entire focus? Why was I missing personal emails, events, ball games, and awards?  Worse yet, what else was I missing that I didn’t even know about? Was any of this worth it?


I vowed to do better and shifted from tracking balance sheets to hiring a more robust staff, from countless hours at my desk to more time with my family. My intentions were set on reclaiming the work/life balance that I had always assumed I would have. Enough was finally enough.  


I assumed that I’d have another chance to get to one of those darn school breakfasts, but it didn’t work out that way. I was well on my way to finely tuning my own yin and yang of business and family when the universe gave us all the ultimate upheaval in both. Life after all, is never as straight forward as we think it will be.


The takeaway from my “goal” seeking is that, yes, your gut does know when things are off. Also, that adding resources such as coaches, therapists, or other when things are out of whack can be immensely valuable—if they are willing to roll their sleeves up and help inspire you to explore your aspirations and your underlying whys.  Digging in is an exercise in honesty and in getting to know yourself.   It is not always easy but is always worth it.  I encourage you to learn about yourself, frequently, so that you may get what you need and desire from this life that you have been given. 


“Shoulds,” busy-ness, and balance sheets are usually not the answers when it comes to health, happiness and a life well lived.


That said, I wish you a very happy new year full of peace, balance, and joy.









Recent Posts

See All


bottom of page