Recently, I was listening to the classic Tom Petty song, “Learning to Fly.” As I paid close attention to the lyrics about growing up and learning life’s lessons “on the fly,” I realized how closely they mimicked the lessons we learn running small businesses. 

Every day that a business owner walks through the door of his company, he’s entering a place he’s never been — willing to face new challenges that he may be ill prepared to address.

Yet, he enters anyway. He tries to do his best to find his way through the unfamiliar territory, frequently doing so without the aid of a flight plan.

In spite of what it may look like from the outside, or how hard he tries to make it appear, the only wings he has are his guts, perseverance, a never give up attitude and a little luck that nature might throw his way.

He works day and night and hopes and prays he’ll have enough lift under his wings to keep the company aloft. He does everything he can to anticipate bad weather so it doesn’t knock him out of the sky, and to outsmart his competitors so they can’t do the same.

The ups and downs

Some business owners learn the laws of gravity the hard and sometimes painful way: That what goes up must come down.

The wise ones realize that doesn’t mean things necessarily have to crash on the landing. They prepare for the descent when they’re on their way up… and know things that go down usually can go back up.

We learn that the skills helped to launch our companies usually aren’t enough to keep them aloft and certainly not enough to help them soar among the clouds. Having to continually re-learn the same lessons will ensure they don’t escape the launch phase. If we want to soar among the clouds we’ll have to be willing to learn new lessons.

We learn the attention deficit disorder (ADD) behavior that may have served us well in the early years tends to get in the way as our companies grow. The more competent people we hire to help us operate our larger companies aren’t as likely to write our behavior off as quirky and entrepreneurial. Instead, they see it as counterproductive and take note of how it gets in the way of company growth.

Some of us start out flying just for the thrill of it. Over time, many of us learn it’s much more fun to fly when we have a destination in mind and a flight plan to follow. 

We learn that we’re better off and not as likely to exhaust ourselves if we learn to fly with the air currents rather than fighting against them, even when we’re not sure where they’re taking us. Sometimes, it’s a better strategy to adjust our wings, or adjust our attitudes, to take advantage of what others might think of as unfavorable winds.

Perhaps the biggest and most unnerving challenge with flying is that there are times when we’re both the student and the teacher. While there are schools, seminars, books, and workshops to attend in an effort to acquire as much business knowledge as possible, nothing can cover every situation that will arise, or every problem we’ll encounter in the day-to-day firefight of running a business.

Sometimes, we just have to learn to fly “on the fly.”

Chuck Violand understands the unique challenges of small businesses, having owned a commercial cleaning and water damage mitigation company for 26 years. He founded Violand Management Associates (VMA) in 1988 as a consulting, teaching and training resource for owners of small businesses. To learn more about VMA's services and programs, visit or call (330) 966-0700.