Before I became a business owner I was a good employee. Keeping my head down and working hard and with purpose, I felt I brought a high level of commitment to any job I had.

However, something drove me to start a business when I was 19 years old. Married with a son and dealing with a full load of classes at college, I did “Happy Hands at Home” work for anyone willing to pay me. Working 40 hours a week as that “company” plus all the above for three years took some grit.

The longest stint I had at any job working for someone else was under two years. Almost from my very first job I was doing side jobs. That is what pulled me into starting Winans Construction when I was 26.

What made me not a long-term fit as an employee? Why did I become a business creator and owner instead of working for someone else? I think these are the reasons:

Comfort with Risk
Two of the jobs I had were 11-month temporary positions, one with the Army in the carpentry shop at The Presidio in San Francisco and one with the National Park Service at the Golden Gate National Recreation Area headquarters at Fort Mason in San Francisco.

I was offered permanent jobs in both cases. But the prospect of spending years in either position was scary. The performance expectations were not high. There was a lot of time to kill. At the same time, those who had these jobs for decades got good pay, great benefits, and an attractive pension.

What was missing for me was risk. I needed some sense of risk to make going to work daily more meaningful. How could I get the next contract signed so we would have more work? Who would be the best person to hire? What types of projects could we do successfully? What should we avoid doing?

These and similar questions fascinated me. Working for someone else meant I did not have the opportunity to answer them.

Too Many Ideas
At every job I had I would be thinking, “How could this be done more efficiently with less cost and less time?” I do that even now with most anything I do.

Any time something needed to be done, I would try to do it the most efficient way possible. This would create some pushback from people who had been there a long time because it meant, if I kept it up, that they would be expected to do the same. Some folks wanted things to stay just as they were. And, remarkably enough, often their boss wanted that, too. I needed to be somewhere I could take the initiative without interference.

Too Much Energy
One job I had was operating the shrink-wrap machine at a record factory (you either remember LP vinyl records or you now prowl record shops for them). The machine broke down all the time. That was the way it was, I was told. I got that machine to run with next to no downtime.

So I went to the boss and asked for a raise from my minimum wage. I was told I would not get one, because if I quit they could find someone else who would do the job in an okay manner. I quit.

My desire to give it my all was not a fit for that job, but it is essential if one is going to run one’s own company.

Ingrained Culture and Habits
I worked with some good people at a good company for several summers while in high school. The owner was the father of people I went to school with. He had his own way things were supposed to be done. That worked for him.

I learned so much working for this man about craft. But what took the company down was the owner’s inability or lack of inclination to become a better business person. He needed to work more closely with the few employees he had so they became more of a team.

I knew things would never change at this company. What I needed was at my company where I could work with others to continually find the best way of doing things, not be stuck doing it “my way.”

Too Little Time
While I ran the Happy Hands at Home company, the housewives who were home while I was working on their homes would sometimes give me lunch. One day, a housewife I was working for gave me lunch and sat with me while I ate. She had helped her husband start up a pharmacy. The pharmacy became successful enough that she did not have to work there and so she stayed home to raise their children.

The children had grown up and left the house. She spent many days alone. She told me “I don’t know what has happened to my life. The time just slipped away.” I never wanted to say that about myself.


Looking back, it was inevitable I would start and run my own business. This is not the case for a lot of good people. After all, the world needs entrepreneurs and employees. One can’t exist without the other.

Be clear with yourself before it is too late about which is the best fit for you. There is no right way; there is only the way which will make you feel successful and fulfilled.