This is an interesting question and one probably not asked often enough by would-be entrepreneurs, which explains why so many businesses never make it to Year Five. Even the most well thought out new venture carries a certain amount of risk, which is part of the attraction. It’s one thing to risk money, time, and energy when we’re in our 30s or 40s, and quite another when we are 50 or older, for obvious reasons. So even if you have a great idea and the money to invest in it (or know how to raise it), it makes sense to put yourself through at least one assessment of your potential as an entrepreneur. Here’s a pretty good one from Monster.com, twenty-one questions that will help you get clearer about communications skills, self-confidence, how you deal with uncertainty, financial issues, partners or employees, to mention a few essentials. Fun to take. If it turns out that you don’t have the right stuff, take heart. All it has cost you is a few moments of soul-searching.

We also recommend Michael E. Gerber’s The E Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It, especially Part II, The Turn-Key Revolution: A New View of Businesses. What we learned from this book is very simple: a successful business is one that can and must outgrow its founders. It can be franchised, scaled up, whatever buzz word fits. Two other gems: “Without a clear picture of the customer, no business can succeed.” “Ask yourself: Does the business I have in mind alleviate a frustration experienced by a large enough group of consumers to make it worth my while?” Read it before you take the plunge.