5 Questions All Aspiring Entrepreneurs Need To Ask

At some point in our lives we reach a milestone (literally: a very long stone) in which we examine our career goals. If satisfied, we continue along the road of predictability, in the vehicle of apprehension, toward the convenience store of apathy until we reach the parking spot of death. (Please don't try these metaphors at home. I'm a trained professional who reads a lot of Dave Barry.)

However, if, like me, you loathe the daily grind and would rather poke your eyes out with a rusty Swingline stapler than spend one more day in a suffocating office pushing meaningless papers around, then perhaps becoming a business owner is for you.

[Left: "Drizzled" by Dave Clark. Buy abstract expressionist paintings at www.daveclark.etsy.com]

When I decided to leave the corporate world and become a professional artist, I fortunately had my father, a seasoned business owner and CPA, to act as my mentor.

Here are 5 questions all aspiring entrepreneurs need to ask themselves:

1. Am I organized? The responsibilities of owning your own business are enormous. As a starting point, take stock of your personal financial papers. Are they arranged chronologically in file cabinets, color-coded and cross-referenced? Or are you unsure if you, technically, own a wallet? Self-discipline is essential to success. Organization is key.
   
   
2. Can I handle physical and emotional isolation? Running a business, especially a creative business like painting or writing, can be lonely. After all, at the end of the day, you're the one responsible for its survival. So get involved. Join organizations like Rotary International, which are geared towards business and professional leaders. It always helps to know people.
   
   
3. Do I know my DRs and CRs? Most entrepreneurs open up shop because they're skilled tradesmen, not accountancy experts. Do you feel comfortable researching complicated tax laws? How about complying with convoluted, and often bizarre, local, state and federal wage withholding and other tax-reporting requirements? (Not that I'm complaining. Please don't fine me.) Do you feel comfortable preparing financial statements and bank reconciliations with software like Quickbooks? If not, can you afford to hire a CPA to do it for you? Knowing someone with an accounting background is VERY helpful.
   
   
4. Do I need security? Be honest with yourself. Can you handle the psychological and financial stress of going months (maybe years) with little or no income, while watching bills pile up? If not, best to just pursue it part-time until you build a name for yourself.
   
   
5. Can I handle failure? Unpleasant to consider, sure, but it's a very real possibility. Many businesses do fail. So have an exit strategy. If for nothing else, it serves as psychological reassurance. "If I lose everything I can still: get my old job back, work construction for my brother, sell a kidney, etc." It's amazing how helpful this technique becomes when sales are slow.

Above all: don't get discouraged. It's supposed to be hard. That's what makes success so rewarding.

In the next article: "My Top Four Most Inspirational Contemporary Artists"