What Do You Dislike Most About Your Business?

It’s astounding how much I paid to have someone ask me that question. And they didn’t ask me just once, not twice, but six times. Yet it was worth every penny.

Something was brewing inside of me that simply had to be dealt with. It’s probably brewing inside of you too. It was nagging at me, an unanswered question, and a pain that just wouldn’t go away. It was the thing that caused me to invest a lot in a consulting relationship that began the process of changing just about everything for me.

The question is so simple, yet has profound insight attached to it. When he asked me, over and over, what I disliked most about my business, I was forced to reckon with the pain of what I had tried to hide. I loved – and still love – what I do, yet that one thing that kept me from moving forward was the thing that I had reasoned had to be something I did for the rest of my career.

My response to that question will be different than yours, so there’s no benefit in me telling you what I said after he asked me the sixth time. This is about you, not me. This is about you confronting the very thing that’s holding you back from being the very best at what you do.

You see, each of us has unique ability. The great Dan Sullivan, of Strategic Coach, has done an amazing job of helping us see that. We’re each wired to do amazing things, but just not as many amazing things as we might have thought. No, we’re supposed to do fewer things, allowing us to become even more amazing at an alarmingly few number of things. By confronting the part of my work that I disliked most, I was seeing for the first time the path forward to doing more of less.

Let me ask you: “What do you dislike most about your business?” Now tell me why that is.

Great, now what would you do differently to never have to do that thing again? Describe it in great detail.

If you were to take that path, and never have to do that thing again, perhaps allowing someone else to do it profoundly better than you’ve been doing it, what would that mean for you?

If you could make this dream a reality, what would be true about you, your business, your clients, the team of people surrounding you? 

None of us was intended to be great at all the roles and responsibilities in our business. Not me, not you. By asking yourself what you dislike most about your business and having the courage to talk it out with a friend or a business partner, you’re opening yourself up to the opportunity to change it. You’re seeing for the first time, a way out of the dreaded (fill-in-the-blank).  For me, it didn’t happen instantly. In fact, it took a couple of years for the solution to appear, but appear it did. For the first time, I can see this dreaded thing as the very thing another person loves to do, and does so very well. 

My suggestion: have a friend ask you this question over and over, out loud (or call us and we’ll ask you). It’s only then will you be able to fully articulate your response and your reasons for feeling the way you do. You’re smart, and that nagging feeling in you is there for a reason; you just need a way to pull it out and into the light of day. The tool is simply a question. Will you have the courage to answer it and do what’s necessary to address it? Everything may change for you.


Newsletter July 2022: Business Builder

The biggest breakthroughs in our business generally happen because of one of two reasons: 1. We approach a problem from an entirely new perspective, or 2. From an extremely painful experience, which generally causes the new perspective in option #1. In other words, it’s the obstacles that we confront that lead to the biggest breakthroughs.


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Haley Wilkins

Haley Wilkins

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