Virtually every business owner reaches a point where improvement is difficult and the passion is gone. Try as they might, they cannot by force of will move the company further. I call this the Entrepreneur’s Glass Ceiling. It’s glass because many business owners can’t see it and don’t acknowledge it exists. But it is a glass barrier made entirely of our own choosing. As such, it can also be shattered by us!

Points A to B are not the same as B to C

Obviously if you’re fortunate enough to have a very successful business, you will encounter things you’ve never experienced before, don’t have the expertise to handle, and must look to outsourced experts to help. Many times though, the entrepreneur floats up to the Glass Ceiling and doesn’t realize it. What got the founder to where they are currently is exactly what keeps them from proceeding further. I’m certainly not the first to observe this. Wasserman noted in The Founder’s DilemmasIn How the Best Get Better, Sullivan discusses the change of paradigm from the bootstrap/hard work mentality of startups with one that focuses on collaborative teamwork based upon expertise.

My personal experience was that I was working harder with declining results. I was frustrated both with myself and with my team. We’ve done this for 15 years. Why is it not still working? Simple answer – Me. I was limiting the company’s progress because the way I did things before could no longer be scaled to take us to the next level. The company had grown to MY capacity to manage it, and could not grow further unless I involved others.

So why do business owners struggle with letting go and letting others help them? Here are my own experiences and those based upon working with hundreds of business owners.

They think they are the only ones

Pure and simple, this is ego. Intellectually, the owner will tell you that sure, there are people who can do what they do. Rarely do they allow that to happen, however. Because you’re dealing with the ego, and the unconscious mind, often the owner doesn’t see their self-destructive behavior. They will hire someone who clearly isn’t capable, and set themselves up as the White Knight to rescue them when that person fails. Or they will hire someone competent but never really turn over the control. This often manifests itself in always having to give final approval on things. This undermines the person and sets them up for absolute failure.

They don’t know what else they would do

“What else would I do? I don’t want to play golf and I sure don’t want to piddle around the house.” The business becomes their identity. It becomes who they are. Consequently they can’t envision what life would be without it. One of my good friends was struggling with a lack of satisfaction with his business. We discussed what he did on a daily basis, and after careful thought, we came to the conclusion that he could easily hire someone to do what he was doing, and still have a nicely profitable business. “Yeah, but would I do?” he asked. “I don’t know. Whatever you want!” I answered. He literally was sitting on the golden ring entrepreneurs search for, but he couldn’t see it. And when he did see it, he wasn’t sure he wanted it! This dove tails beautifully into the last reason.

They feel guilty

Hard work (translated: considerable amounts of time) is the American way of life. And quite frankly, most businesses wouldn’t get off the ground without this time and effort. But what about when the activity becomes the raison d’etre? If I don’t work a lot of hours, then I’m not worth anything. Some people literally cannot watch an employee do something that they could be doing themselves. They will do it themselves and call themselves thrifty.

I found myself following routines of work. Doing the things I had done out of habit. Literally staying until 5:00 if I didn’t have anything to do, just because I thought I was supposed to. Giving myself permission to accomplish “enough” for the day was liberating. If I have three things on my list and I’m done, I’m done. If that’s at lunch, then that’s OK. The other habit I learned from How the Best Get Better was to stay away from the office unless I had a meeting. I found that when I went to my office and desk, I tended to slip back into my routine. Again, giving myself permission to not be at the office was HUGE. I became more productive and more satisfied.

We live in an incredible time, with amazing opportunities. Much as the industrial revolution caused massive disruption in economics, social structure, family, education and virtually every other facet of life, this nascent Information Age is going to change all of us in ways we have yet to imagine. A simple question to ask yourself – How is that working out for you? If it’s not, then feel free to let it go!

We Are Here To Help

If any of this sounds ideal to you, we can help you get there. Core offers a no-cost and no obligation (really) two-hour Business Alignment Strategy Session. Email me at to schedule a time that works for you. I would love to share my success and freedom with you! Contact our offices in Oklahoma City: 405-720-1244 or Tulsa: 918-477-7650 to get the help you need.