If there’s been one consistent theme of this blog, I suppose it’s this: It ain’t easy working for The Man.

For this month’s issue of Money, my editors asked me to consider the question of when it makes sense to chuck the paycheck and strike out on your own. The website has turned that story into a quiz. But the straight version of the story is below. I’ll be expanding on some of the points here in coming posts.

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Not so long ago, there was a standard recipe for affluence: Start with four years of college. Add one white-collar job. (For best results, find a big corporation with a pension fund.) Carefully stir in equal measures of obedience and initiative. Wait 40 years. Retire.

Getting ahead doesn’t seem so simple anymore. Few companies are looking for lifetime relationships—many aren’t even sure what business they’ll be in a few years from now. Or if they’ll have one. A job that seems secure today could be replaced by better software or a cheaper overseas worker tomorrow. In short, you’re living with lots of uncertainty, dodging and weaving as your industry changes, and working 50 hours a week in the bargain. So perhaps you’ve wondered, “Wouldn’t I be better off working for myself?”

Tough question. Certainly if you look at your neighbors with real wealth, you’ll see a lot of entrepreneurs: Half the families with a self-employed breadwinner claim a net worth greater than $336,000, and folks who make it big push the average for such families to more than $1 million. Then again, you could meet more than a few business owners in the waiting room at bankruptcy court. In between are lots of people hustling for every buck. Unless you get past that stage, you’ll likely make less than you do now, says William Gartner, who teaches entrepreneurship at Clemson University.

But going into business is more than an expensive lottery ticket. For many who take the plunge, it’s a chance to build something of their own, to test themselves and to pursue new experiences.

Now let’s talk about the big questions every would-be business owner must wrestle with.

I have a good job. Why should I be thinking about going out on my own?
First, don’t quit your job. Not right now. For most entrepreneurs, going into business isn’t so much a life’s calling as it is a life stage—something they do when the right opportunity comes along at the right time. Even the most passionate entrepreneurs generally collect a paycheck for a big chunk of their career. Jeff Sandefer, a founder of Acton MBA, a recently opened Austin business school that specializes in entrepreneurship, encourages students to work for five to 10 years in sales or operations before they strike out on their own.

Even while you’re on the clock, though, ask yourself, “What’s next?” Economists argue about just how much job security has declined, but the unambiguous fact is that unemployment can happen anytime. Nearly 1.5 million people were let go in mass layoffs in 2006. And the rewards for being the Organization Man or Woman aren’t what they were. You’re unlikely to be walking away from a fat pension or retiree health plan if you start a business. But you can take your 401(k) money with you.

Speaking of retirement: Since you will, on average, live longer than your parents did, it may make financial sense for you to work past 65. But a recent survey from the Boston College Center for Retirement Research finds that employers are lukewarm about keeping on more older workers. And even those who don’t discriminate may not be able to offer the flexible schedule you’ll want. Not a problem if you can go it alone.

Are economic conditions right for starting a business now?
They’re never perfect, but they’re good. “The best day to start a small business is the day before a recession ends,” quips William Dunkelberg, chief economist for the National Federation of Independent Business. “We’re six years into an expansion that’s old and weary.” Still, the economy looks solid. Business owners polled by the NFIB say that credit remains easy to get. And unemployment is low—a problem in the unlikely event that you’ll soon need 20 workers, but good news if you’re cooking up a consulting practice out of your spare bedroom. “You can go back and get a job if you fall flat on your face after 14 months,” says Carl Schramm, president of the Ewing Marion Kauffman Foundation, which promotes entrepreneurship.

Keep in mind also that the big economic picture isn’t everything. Do the people in your town have cash to spend in your boutique? Can you name three local companies that would be interested in your IT consulting service? Does the world really want an even hotter hot sauce? Those questions matter more than the Fed funds rate or the level of capital spending.

Business owners seem like a different breed. Can I really be one of them?
Most of us have an image of entrepreneurs lodged in our heads: hyperactive, visionary, guts of steel. But those who study entrepreneurs say that’s an illusion. “Some have very boring personalities,” says Schramm. Part of the problem, says Kelly Shaver, professor of entrepreneurial studies at the College of Charleston, is that we tend to focus on superachieving outliers. (You could be one-53,000th as successful as Bill Gates and still be a millionaire.) And many books and magazine profiles about entrepreneurs look only at the ones who have already made a fortune. When asked to explain their success, Shaver says, people tend to think back and try to identify some brilliant thing they must have done—and maybe forget about the routine work, their many mistakes or their sheer luck.

So entrepreneurs aren’t mutant geniuses. But there are a few things that set them apart. A huge academic survey called the Panel Study of Entrepreneurial Dynamics (the PSED) found that you are more likely to get a start-up off the ground if you already have experience in the relevant industry. “You have the social networks and industry contacts, and you know the rules of the game. That’s huge,” says Clemson’s Gartner.

You also—surprise!—have to be willing to put in a lot of time. Many entrepreneurs get a business going while they are still working, but it has to be more than a hobby. “It you’re not putting in 20 hours a week, forget it,” says Gartner. And it seems better to focus your effort all at once rather than dabble for a decade. The median time to start a business is about two years, says Paul Reynolds of Florida International University.

Okay, but what about risk? Aren’t a lot of entrepreneurs really gamblers?
Risk is part of the game, for sure. A third of all new businesses with employees fail within four years, according to Brian Headd of the Small Business Administration. One study based on the PSED found that people starting businesses were more conservative than the rest of us. Business owners can also do a lot to control their risk. Most stick to their home turf. “It’s where their safety net is,” says Reynolds. And the smart ones keep their investment and costs low. “You do a lot of small, cheap tests,” says Sandefer, an entrepreneur who made his name in the oil business. “The ones that work, do more of them.”

Amar Bhidé of Columbia Business School agrees that entrepreneurs get no special kick from risk. But he thinks the most successful ones do have a high “tolerance for ambiguity,” or a willingness to make decisions in the face of uncertain odds. That’s different from gambling. Lottery players know they’re throwing money away—the odds are easy to figure—but an entrepreneur can never collect enough data to know for sure whether a product or service will be a hit. Entrepreneurs may be unusually confident, says Bhidé . But some tolerance for ambiguity can be learned: Studies suggest that we get better at it when we’re familiar with the subject we’re guessing about. So a computer engineer might be comfortable betting on software. A chef might rather take a chance on a restaurant. Again, experience helps.

If you start a business, Shaver warns, you have to be comfortable with volatility as well. This too is different from risk in the gambler’s sense. Even a successful business owner might earn $30,000 one year and $200,000 the next, and then drop back to five figures the year after that. If your lifestyle (or stomach) can’t handle those swings, stick to the day job.

How do I come up with a great new idea that investors will get behind?
Who knows? Maybe ginkgo biloba? The truth is, you don’t need a wild idea—and you can forget about investors for now. Bhidé studied firms on one year’s Inc. 500 list of the fastest-growing private companies and found that only 6% had unique products at first. Many opportunities are about being cheaper, faster or better. Or just closer to your customer. Look at today’s leaders and you’ll see no contenders for “the next iPod.” You will, however, find two companies selling iPod accessories.

As for money, at first it’s likely to be your own or friends’ and family’s. Venture capital comes later if at all. As important is making sure you can keep body and soul together for the first few years. That could mean savings. Or keeping your job for a while. Or relying on a working spouse’s salary—and health plan.

I’m not ready to start just yet. What do I do in the meantime?
Be an entrepreneur at work. Look for a new assignment or a special project—you’ll increase your odds of stumbling across an idea for a new business. Also, think like you have money at stake, suggests Neal Thornberry, author of Lead Like an Entrepreneur. Instead of spinning out ideas for projects that might work, he says, identify concrete opportunities. That means knowing how big a market is, what people would pay and what the competition would be. Or find ways to save the company money. You’ll train your mind for a future business—and might save your job in the process. “You don’t have to be an entrepreneur,” says Schramm. “But you no longer have the luxury of not appreciating that you live in an entrepreneurial economy.”