Why You Should Never Go in to Business for Yourself

by Glenn Shepard

October 28, 2014

Category:  Entrepreneurship





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People sometimes tell me they’re thinking about going into business for themselves, and ask if I think they should.


My answer is always



In his Hierarchy of Human Needs, Dr. Abraham Maslow identified security as the second greatest need of normal people.


Self employed people are abnormal, because security isn't a priority for them.


They’re like degenerate gamblers who’ll risk their health, finances, and relationships to feed an addiction called Entrepreneurship.


These self employed gamblers ("SEGs") ignore the fact that 90% of small businesses fail, and are arrogant enough to think they'll be the 1 in 10 that succeed.


Going for Broke


Contrary to what most people think, most SEGs don't make more than their counterparts.


CareerBuilder.com reported that self employed workers in the U.S. make an average $26,921. That's less than half the $56,053 annual average of the total workforce.


SEGs would rather go broke working for themselves than make a fortune working for someone else.


A Pew Research report found that 40% of the self employed said their family either falls short of meeting their basic living expenses or are barely getting by.


Risking It All to Keep Playing the Game

When times are good, SEGs will plow every dime they make back into the business, hoping the big payday is just around the corner.

When times are bad, they'll take cash advances off their credit cards to make payroll.


And it's not limited to mom and pop operations.


I know of a SEG named Fred who once flew to Las Vegas to gamble his company's last $5,000 on a blackjack table in hopes of winning enough to pay a large fuel bill.


The Power of the Addiction


I understand how strong the addiction can be, because I've been a SEG for over a quarter of a century. When I was 24, I bought a spinoff of a small Nashville based publishing company. Within months, I expanded into Memphis but was drowning in debt. To stay afloat, I sold a 50% stake to a venture capitalist and later expanded into Knoxville, Chattanooga, Birmingham, and Cincinnati.


I was stretched so thin that we almost bought a Piper Cherokee so I could fly from city to city to manage our employees and see customers. Eventually I sobered up enough to focus on the results (bottom line) instead of the size of the organization. But I came close to losing everything, including my home, because my risk tolerance level was so high that it was reckless.




So why would anyone become a SEG, short of insanity?


Because studies have shown that while most SEGs make less, work more hours, and experience more stress, they have higher job satisfaction and are happier.


SEGs value opportunity over security, and prize the autonomy and freedom that comes from being self employed.


So why do I tell people to never become self employed? Because SEGs don't care what others think - they just do it. 


If you prefer the security of a steady paycheck and fringe benefits like health insurance and paid vacation days, congratulations. You're normal.


But if you're thinking about becoming self employed and what I just told you hasn't discouraged you, you're in for a long, hard road.


It will, however, be the most fulfilling ride you've ever taken.


Small business owners are my heroes because they believe in rugged individualism and self reliance. And because they create the majority of all new jobs. And because nearly every big corporation began as a small business.


To Your Success,



Glenn Shepard, a Proud 26 Year Veteran SEG




P.S. You may have heard of the SEG who played blackjack to keep his business afloat in the early days. He's Fred Smith, and his company is FedEx.




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