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Work On Your Business, Not In Your Business

Updated: Dec 1, 2023

Work On Your Business

If you’re like most business owners who often search for opportunities and business advice at odd hours of the night, you’ve probably come across the advice that you should spend more time “working on your business, not in your business.”

Hearing this advice, accepting it and actually living it are three distinct stages


I hope my story of working through these stages can assist others in their quests to create scalable businesses they will one day be able to sell and, in turn, create a legacy for their families.

Within a few months of starting my first business (a flight training business), I was regularly working six to seven days per week and often ten to twelve hours per day.

Success was within reach, and like most young entrepreneurs, I thought if I could just squeeze another few hours into a week, I would obtain it. I fell into the E-Myth trap, as described in Michael Gerber’s book by the same name.

Fortunately, I had a client who had successfully navigated the same entrepreneurial journey I was embarking on. He was one of my flight students who had started his business from scratch and had grown it to over 50 locations in several states.

I’ll never forget our conversation spurred by my usual small business owner complaints. He asked, “David, do you want to be a flight instructor or do you want to grow a business?”

Puzzled as to why these would be mutually exclusive I answered, “I want to grow a business.”

“Stop flying airplanes and work every day to ensure you’re offering compelling value to the community in a way your competitors will have trouble duplicating. Take a week off and make sure your model is profitable and scalable before wasting any more time.”

“You’re crazy. I can’t take a week off. I’ll lose customers. You don’t understand.” I was telling the successful millionaire entrepreneur he was the one who didn’t understand!

He didn’t give up and beat this message into me for months.

Finally, after several months, I realized he was right. There weren’t any more hours in the day for me to work. While I had been flying airplanes every day in a business that had grown only slightly, my competitors (some of whom weren’t even pilots) had been busy growing businesses that were surpassing mine.

Even this epiphany didn’t drive me to immediate action. Entrusting all frontline client interactions to employees was terrifying to me.

But I finally did it. One momentous day I felt I was playing Russian roulette and removed myself from our list of active flight instructors.

It was the single most transformative day of my career. While our revenue and my personal income did take a hit for a few months, I quickly adjusted to my new, more valuable role and our business began an upward trajectory.

Several years later I reflect back on that experience. Creating a growing business is different than being a professional in a particular field. Both are equally noble career paths, but the daily work of each is drastically different.

Frustration arises if we attempt to continue the normal tasks of working in our field while we fool ourselves into thinking we are growing a business that will create value that lives beyond us. While industry knowledge and expertise are certainly valuable in excelling in a particular industry, unless we spend our days finding unique ways to organize our resources into a scalable platform for delivering compelling value for our customers, we’ve created a job-with-no-boss-and-a-few-employees for ourselves in our chosen field, not an independently valuable business.

Even those who have created organizations generating several tens of millions of dollars can have trouble selling for a desired price if they haven’t realized which path they are actually on. There is nothing wrong with this. Successful doctors, lawyers, plumbers and electricians do it all the time. They have rewarding careers and build nice retirements. But we must recognize that this is a different path from one on which we work “on our business” and create scalable value beyond ourselves that we will be able to realize upon an eventual exit from our business.

This article was originally published on the EO Global Octane Blog.


About the Entrepreneurs’ Organization (EO) Cincinnati

The Entrepreneurs’ Organization (EO) is a global, peer-to-peer network of 13,000+ influential business owners with 188 chapters in 58 countries. Founded in 1987, EO is the catalyst that enables leading entrepreneurs to learn and grow, leading to greater success in business and beyond.

For more information about the Entrepreneurs’ Organization, visit

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