Overcome the Entrepreneurial Paradox

Learn how to embrace change and the unexpected responsibilities of business growth.

Entrepreneurial Paradox

If you’ve ever found yourself telling anyone who would listen that you’d sell your company for an offer of 20 bucks, then you’re probably experiencing a condition I refer to as the entrepreneurial paradox. This is a state brought on when entrepreneurs grow their company to a point where they are required to do work they don’t want to do and never anticipated having to perform when they started the business. In other words, they grew themselves out of a fun job.

This phenomenon can happen at any level of a company’s growth. Sometimes, it occurs early on when the owners hire people to do the work they were originally doing when they started the company: delivering outstanding service, talking with customers, filling orders, and enjoying reasonably flexible hours. One minute it seems we’re doing the fun work we wanted to do, then the next minute we find ourselves managing the people now doing that really fun work (and enjoying themselves doing it). “How did this happen?” we ask ourselves. 

Company growth brings challenges

The entrepreneurial paradox can happen when company growth requires the owner to hire then manage supervisors to oversee the workers. This can get frustrating fast when you consider that many entrepreneurs aren’t great managers. We’re used to getting things done, having things our way, hip-shooting decisions. Who has the time to plan, organize, think things through, or get other people’s opinions?

Sometimes, the paradox doesn’t happen until later when the company is much larger, and owners find themselves trying to handle issues and understand concepts they may not have even known existed when the company was smaller. Terms like recapitalization, glass ceiling disparate impacts, cost performance indexes (CPI), variable resource allocations, and subordinated debt may have them scratching their heads. These terms are hard enough to spell, much less understand. Many entrepreneurs are poorly trained and ill-equipped to deal with issues like these.

The entrepreneurial paradox gets even more complicated in family-owned businesses, which account for 90% of all companies in North America, according to the U.S. Census Bureau. If you’re the founder of the company and have children working in the business, your frustration might be related to your son or daughter not being capable of or willing to run the business the way you did. If you’re running the business with a sibling, your frustration might be driven by the fact it’s no longer appropriate to settle disagreements the way you did when you were growing up—by wrestling with each other on the floor, calling each other names, or shouting, “You’re not the boss of me!” Using tactics like these tend to alarm the staff.

Small business owners are frequently blindsided by the entrepreneurial paradox. They don’t realize what’s happening until they’re in knee-deep and it seems too painful to back their way out. But the entrepreneurial paradox doesn’t have to be debilitating and it doesn’t have to be permanent. 

So, how do we resolve this paradox? How do we address the conflict that arises when we grow ourselves out of jobs we enjoy doing? Here are a few suggestions:

  • Grow the business to your perfect size—It’s easy to fall into the trap of the Wall Street myth of “grow or die.” If your business is huge and it’s caught up in the world of “eat or be eaten,” large growth is probably necessary. But for the overwhelming majority of businesses (more than 96%) that generate less than US$10 million in annual revenue, excessive growth is crazy. There’s a lot of financial value and personal fulfillment that can be gained from our business without having maniacal obsessions with revenue growth.
  • Don’t let your ego overrule your joy—Too many times, we weigh our own success against that of our friends or competitors. If our competitors grow big companies, why can’t we? If our friends who own businesses grow large, successful companies, so should we. Trying to keep up with the corporate Joneses can be exhausting … and lethal if we’re not careful. 
  • Learn to embrace change—We all know the old saying, “Change is inevitable, but growth is optional.” When we become life-long learners, change and growth are sure to become a lot more fun. Oftentimes, we realize talents we don’t know we have until we try new things. There are many stories of successful companies that began as a result of their founders being forced into completely foreign and uncomfortable circumstances. That just might be you.

When we commit to owning a business, we need to accept that there will be times when we’ll be called on to do jobs and perform tasks we don’t enjoy, that we may not be particularly good at, or that we don’t even want to do—but that need to be done anyway. This responsibility comes along with the privilege of business ownership. 

Posted On June 3, 2021

Chuck Violand

Founder and principal of Violand Management Associates

Chuck Violand is the founder and principal of Violand Management Associates (VMA), a highly respected consulting company in the restoration and cleaning industries. Through VMA, he works with business owners and companies to develop their people and their profits. To reach him, visit or call 800-360-3513.

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