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Three Examples of On-Again, Off-Again Entrepreneurs





Back in April I wrote about a trend I see increasingly, called the “on-again off-again entrepreneur.”

I promised I would write more about that trend, so here goes.

The on-again off-again entrepreneur is someone who moves back and forth between being employed and owning his or her own business — multiple times.

In today’s world we are almost assured of having more than one career in a lifetime, not just a single career.

Luckily we don’t have to choose between either being an entrepreneur or being employed by another company. Today more and more people will find themselves at various times as entrepreneurs and being employed, depending on the circumstances in their lives.

An on-again, off-again entrepreneur can be anyone, of any educational background, any age, any gender, just about any line of work.

However, I have observed that the on-again off-again entrepreneur tends to fall into one of three profiles:

  • 20-something or 30-something entrepreneur – This person has a strong desire to be a business owner, but faces financial commitments — because of a young family perhaps — that require taking a job. Our thirties tend to be some of the heaviest spending years, because of buying homes and raising children. So it is no surprise a person may feel financially-pressed, and feel he or she has to take a job out of necessity.

    This person may have started a business previously, and found it did not grow fast enough to provide a reliable income, or wasn’t successful for whatever reason. The lessons this person learns during an initial foray into entrepreneurship can be put to use the next time around the startup cycle. Often the aspiring entrepreneur in this situation will be putting aside money while employed, so as to have a stake for starting the next business.

    See my example of this type of on-again off-again entrepreneur.

  • Lifestyle-necessitated entrepreneur – This person is someone who was employed, but due to life commitments needs a more flexible work schedule for a period of time. Typically this might be a stay-at-home-Mom who has babies or young children. (And let’s not forget the stay-at-home Dads.) Or it could be a person caring for an elderly parent, or having health problems that make long commutes unfeasible. A full-time, high-pressure job is not compatible with their life responsibilities.

    In the past this person might have gone to a part-time job or become a full-time “housewife” for a period of time. Some still do.

    But today, attitudes toward entrepreneurship are changing. The maturation of the Internet, the availability of mobile telephones and inexpensive long distance rates, and the ready access to so many resources for entrepreneurs, makes running a business at home an ever more viable and attractive proposition.

    Just search in Google for the acronym “WAHM” which stands for “work at home mom” to get a glimpse into this world. Visit some of the sites. One site will lead to another and then to another…. You will discover an entire subculture of lifestyle-necessitated entrepreneurs.

  • Older entrepreneur – This entrepreneur may be someone who was employed for most of his or her career. Then he or she leaves employment and becomes self-employed. Often the kind of business this person runs is consulting, writing, speaking, and other skills that leverage knowledge accumulated over the years.

    More people over 50 are becoming entrepreneurs these days — see this USA Today article profiling this phenomenon.

    But retirement planning goals, need for health insurance, or an especially attractive job opportunity may entice this person back to the ranks of the employed for periods of time. In fact, the website Not Yet Retired outlines “working retirement” strategies that may involve entrepreneurship or getting a job.

    At this stage of his or her life, the entrepreneur doesn’t have expectations of being employed for a long time. A year, perhaps 2 or 3 years, may be all this person expects, fitting in nicely with certain employers’ needs. Often this person will attempt to keep the business going part-time while being employed.

I’d like to hear from others about their experiences moving in and out of being employed and being a business owner. Please leave a comment below sharing your circumstances.

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Anita Campbell Anita Campbell is the Founder, CEO and Publisher of Small Business Trends and has been following trends in small businesses since 2003. She is the owner of BizSugar, a social media site for small businesses.

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