(FORTUNE Small Business) – Like all deep thinkers, I am consumed with the big questions of our time: Why don't cameras click anymore? How come nobody wants to swipe my identity? Why Jack Welch? I do not have all the answers. But questioning, as wise entrepreneurs know, often yields rewards. Inventive minds push ahead, unfulfilled in their quest until someone attaches a seven-figure value to their solution. Everything we depend on to live our lives--even ring tones--started as a nagging query in someone's head. (The question, in that case: Why do only ice-cream trucks play tinny snippets of "The Entertainer?")

So great is humanity's hunger for such questions that there now seems to be a growing market in providing them. You can't pick up a newspaper without reading a story that muses, IS THE RECOVERY FOR REAL? (Tellingly, the answer usually comes in the form of yet another question: Who knows?) Computers are programmed to ask us about every click we make. ("Are you sure you want to see this question next time?") Listen, there are probably questions crowding your cranium right now. Entrepreneur Maura Cassidy offers a few: "Why am I working so hard on my business and not seeing my kids? How can I let meetings interfere with dinnertime? Am I doing what I am supposed to be doing?"

Cassidy, 44, could keep rattling them off, but not because she's some kind of introspection freak. Her business, Go Ask Anyone, makes "conversation cards" with banter-building questions printed on them. Decks include Go Ask Your Father ("If you could have one superpower like a superhero, what would it be?"), Go Ask Your Grandparent ("What famous trial verdict do you wish could be reversed? Why?"), and four other varieties, all designed to spark the kind of insightful conversations that buyers are presumably too soft-headed to start on their own. This year she hopes to sell $120,000 worth of the 52-card decks, which retail at gift stores for about $9 apiece.

Lately Cassidy, who is based in Winthrop, Mass., has been approached by giant companies, including a lingerie chain and a greeting-card maker, interested in having her design custom decks for their customers. She's also been asked about producing cards for dysfunctional families (One helpful suggestion: "Why did you show up drunk at my Little League game?"), blended families (How about "When did you steal Daddy from Mommy?"), and an X-rated version (think for yourself already). Yet what Cassidy has not considered--despite admitting, "I have had many, many questions along the way"--is making a deck for entrepreneurs. The cards could help determined business builders--particularly neophytes--focus on the questions that matter. Such as:

Question for mother: You know I'm good for the money, right?

Question for father: Why did you tell Mom I wasn't good for the money?

Question for venture capitalists: Does this mean I get to keep my second-born?

Question for nanny: How many children do I have? What is my second-born's name?

Question for first hire: When you think about it, isn't every cubicle pretty much a converted dumpster anyway?

Question for classmates at 20th high school reunion: Would you buy this product from me?

Question for patent office: What do you mean, I can't patent the letter "e"?

Question for accountant: If I take business calls at home, can I write off my mortgage?

Question for tablemates at a wedding: Would you buy this product from me?

Question for first customer: What time is dinner, Grandma?

Question for first supplier: When you say you'll break my kneecaps if I can't pay, that's a joke, right?

Question for financial planner: How much would it cost to insure my kneecaps?

Question for marketing consultant: Are you sure we won't get sued for promising eternal life?

Question for nosy rival: Even if we did have a revolutionary business model, do you actually think I would share it with you?

Question for website designer: Would we get more unique hits if I changed my name to Pamela Anderson?

Question for person who stops to ask for directions: Would you buy this product from me?