Thinking About Starting a Business? 4 Questions to Ask Yourself

Thursday, March 13, 2014

Do any of these scenarios hit home?

  • Like 70 percent of today’s workers you just aren’t engaged at work. You feel undervalued and like no big opportunities will ever come your way.
  • Your daughter is planning a wedding that you’ll be financing.
  • Or finally, after decades on the nine-to-five treadmill, you’re ready to retire—but a little worried about how far your bank account will stretch.

In any of these scenarios, you might find yourself thinking: “Gee, it would be nice to start that business I’ve always dreamed about. Then I’d feel like I have more control over not just my finances but my life right now!”
If you’re like most people, though, that wish is followed by a “but”:  “But starting a business is really stressful.”  “But it’s too risky.” “But I don’t have enough time.”  And so on and so forth.


All of these justifications for not wanting to become an entrepreneur are sound, but if you’re smart about it, there’s never a bad time to start a business. You simply need to ask yourself a few essential questions:

  1. What will be my motivation for running the business through good times and bad? You will not love your business every day. It’s important that you have something to focus on that keeps you motivated when times are tough. Post a visual reminder for yourself, such as photo of a vacation home, a college pennant of the school your child desires to attend, or something more tangible. Perseverance is the most common quality in successful people, so the more motivation you have, the better.
  2. What is the payoff? Is it additional income? You may need to pay down debt or a mortgage or start paying for a child’s college tuition. When we are unhappy, the grass will always look greener on the other side. So whatever your payoff is, it should be concrete: a long-term goal that equals a major personal success.
  3. Why do you think the business will succeed? Do your due diligence to find a need in your market for this product or service. What data supports your projections? Who will be your competition, and can you offer something unique that will give you a marketable advantage? Will your store offer a product or service that an online retailer cannot offer, like free set-up or ongoing training/support? This is information you must effortlessly communicate to potential customers and investors. It must be so attractive they choose your business over all others.
  4. Who will be on your team to help you run the business? This may include—but not be limited to—an accountant, lawyer, insurance agent, bank, etc. Who will you need to operate your business? Employees, contractors, and partners should add key skills and know-how that you lack.

Most of all, your team needs to include a mentor that will guide you and advise you until you succeed.

About the Author
Sean C. Castrina is a successful entrepreneur and author of 8 Unbreakable Rules for Business Start-Up Success. Learn more at
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