I know a man who quit his job because he was tired of taking orders. He wanted freedom. Independence. The satisfaction of making his own decisions. So he started a real estate business.

Now he takes orders from tenants, lenders, contractors, inspectors, insurance companies, and a city official who has developed a personal interest in his staircase. Congratulations. He's finally his own boss.

I've always found our idea of being the boss rather romantic. We imagine a man who answers to nobody, makes the rules, and spends his afternoons deciding which yacht to buy. In Hamlet, Laertes warns Ophelia that the prince is not free to choose as ordinary people do. He is, as Shakespeare puts it, "subject to his birth." His position gives him power, but also obligations that limit his freedom. I sometimes wonder whether we misunderstand business owners in much the same way.

The boss looks like the freest man in the room. But he's often the one who sleeps the least. Everybody else can finish work, complain about management, and go home. The owner goes home too, except the business comes with him. When the contractor disappears, the employee makes a mistake, or the bank wants its money, somebody has to answer.

The buck stops here. That was Truman's famous expression, and it's considerably less romantic when the buck is a $40,000 problem nobody knows how to solve. And here's where things get uncomfortable. The man who started his business because he hated unreasonable bosses may eventually find himself making the same unpopular decisions. He has to enforce deadlines, reject excuses, cut expenses, and occasionally tell perfectly decent people things they don't want to hear.

He didn't dream of becoming a pirate captain. But there he is, commanding a collection of ambitious, argumentative ragtags who expect him to lead them toward a better life. And sometimes he's tempted to behave like a pirate, too. Bend the rules. Take a little more than he should. Convince himself that whatever keeps the ship afloat must be justified.

Of course, responsibility doesn't excuse greed or corruption. Plenty of owners manage to run successful businesses without becoming the villains of their own stories. But perhaps the temptation is part of the job. The boss has more authority than anybody else, yet may have less freedom to walk away from the consequences.

So here's my question. When we dream of becoming our own boss, are we dreaming of freedom, or simply volunteering to become responsible for everybody else's? And how do we avoid becoming the very person we once couldn't stand working for?