Perhaps even more than the lure of money, optimism dominates the entrepreneurial mind. Whether it’s well-grounded or not, every business enterprise is fueled by it.

“During the Great Recession, more Americans have become entrepreneurs than at any time in the past 15 years,” states the Kauffman Index of Entrepreneurial Activity. Even with the nation’s economy in a persistent slump, more individuals opted for business ownership.

As history tells us, many of these fledgling enterprises will fail. Yet, even taking the step to “go out on your own” is an act of incredible optimism, particularly since others often talk about “going into business” but never act.

It shouldn’t be surprising that any talk about a downside is intolerable to the entrepreneurial spirit. Optimism trumps all challenges, including recessions.

While a positive attitude is essential in business, ignoring the downside can spell trouble and even worse — and the best way to avoid crises is to head them off before they take their toll.

Even more to the point, failing to think about the unthinkable is not a plan. Halloween, as we all know, has become the nation’s second biggest holiday event. In 2011, the Massachusetts-based 54-store retailer, iParty, was more than ready, having rented extra space in malls. Then came a major storm that wrecked sales.

Having gone through this devastating experience, it was somewhat surprising that the retailer was not better prepared for Halloween 2012 when hurricane Sandy wiped out sales. Although management evidently considered buying business interruption insurance, it dropped the idea due to the cost, as reported by The Boston Business Journal. CEO Sal Perisano said they “hoped lightning would not strike twice.” The company’s future remains in question.

One of the best ways to think about the unthinkable is to ask “what if” questions. Here are a dozen worth considering.

• What if we outlive our value?

It can and does happen. Even though we see it in other enterprises, we have great difficulty in recognizing it in ourselves. While a “nothing can stop us” attitude is both commendable and useful, it’s easy for companies to blind themselves to a creeping loss of relevance.

It’s prudent that every business ask, “What should we do to make sure we never outlive our value?”

• What if we drag our feet with technology?

It seems as if the vast majority of small- to medium-sized businesses are close to clueless about their customers. They act as if customer data is unrelated to their success, let alone their continued existence. Even though they may accumulate customer data, they’re totally ignorant of how to take advantage of it and leverage technology to better target customer preferences, buying cycle stage and sales opportunities. In effect, they send an unavoidable message: “We don’t care about our customers.”

What these businesses don’t “get” is that customers know when they are being ignored and taken for granted.

• What if a new competitor moves in on us?

Between believing “nothing can stop us” and failing to probe the competitive landscape, it’s easy to be blindsided, to wake up one morning and say, “We have a problem.”

Staying on the offensive is critical, but having a defensive strategy is equally important. Getting caught off guard can lead to negative consequences.

• What if we lose a major supplier?

You may think certain vendors love you. Perhaps. But just remember: “Love is blind.” Far too often, businesses see what they want to see — and then it’s too late. Nothing is forever, so make sure your options are always lined up.

• What if we don’t know what we don’t know?

Businesses are often “closed systems,” more akin to “solitary confinement” than they are to classrooms. Employees know the topics that are “off limits” to open discussion, while “impenetrable walls” guard against the threat of fresh ideas.

In such a stultifying atmosphere is it any wonder that companies fail to meet new challenges and opportunities?

• What if a key person leaves?

Count on it because it always happens. It will be the one who’s “indispensable,” the one “we can’t do without.” But that actually may be the person who specializes in maintaining the status quo, who impedes change, who makes it difficult for the business to make the right moves.

When the indispensable person makes an exit, the door of opportunity opens wide.

• What if our market changes?

Acknowledging change is like pushing a boulder up a mountain, particularly when it involves critical business issues. It isn’t easy. GM did it for decades and Research in Motion had to hit the ropes before admitting they were faced with a life threatening problem.

• What if we have a serious problem that impacts our customers?

Plan on it. It will occur. That’s why having a plan ready is absolutely necessary. And, by the way, denial is not a plan, neither is trying to put a “spin” on it nor hiding from the media — “no comment” doesn’t make the cut.

That leaves one option if you want to be viewed as credible and put it behind you as quickly as possible: being candid and clear, i.e., tell the truth. It’s the stuff of which trust is made.

• What if marketing and sales don’t get along?

Unfortunately, “sacred silos” are alive and well when it comes to marketing and sales. In a recent Corporate Visions survey, two-thirds of the responding companies “struggle” with collaborative efforts between marketing and sales.

One solution for overcoming this pervasive problem may be marketing automation technologies that allow flexible, response-appropriate actions based on where the customer is at the moment so data flows seamlessly from marketing to sales and vice versa.

• What if your largest customer leaves?

It may be closing its doors, being sold or moving to a new vendor. Whatever the cause, it can instantly raise doubts among employees who fear for their jobs. The effects often extend to customers and other business relationships.

Many businesses seem to rely on keeping their fingers crossed when it comes to the unthinkable rather than asking themselves a serious question: What steps should we be taking to mitigate the effects of losing a large customer?

• What if we drop the ball or mess up a customer’s order?

Let’s be clear: an excuse is the last thing a customer wants to hear when this happens. Right? Yet, we continue making excuses rather than offering explanations that make clear what we’ll do to assure customer satisfaction.

• What if we get a negative online business review?

It can happen to any business today, not just restaurants and plumbers. And the Smartphone is driving it. Consumers can “do it now” before anger cools.

If you have good reviews, a poor review should not be a problem. Customers are suspicious of 100 percent great reviews. One negative is understandable since you can’t please every customer every time. The key is to monitor sites regularly so there are no surprises.

While every business is faced with overcoming challenges, avoiding unnecessary damage is more than worth the effort to think about the unthinkable. Ironically, focusing on the “what if” questions may be the path to getting over the hurdles and reaching your company’s objective.