I have interviewed dozens of men and women while they were in jail. A frequent topic during my conversations with them is their plans for work once they are released. Understandably, many are uncertain for a variety of reasons. Will their former employer rehire them? Will their criminal record restrict their choices? Where will they live, and what jobs will be available?

A significant number of offenders tell me they intend to operate their own businesses. And, of course, many people all over the world have the same aspiration. The criminal, however, has not the slightest idea of what operating a business entails. Most appealing to the criminal is that he will be in charge and not have to “take orders.” He knows next to nothing about startup costs and hasn’t given any thought to logistics including marketing, employee hiring, obtaining licenses, and so forth.

In the criminal’s mind, he thinks of himself as reaping huge profits from the sale of some fantasized produce or service while barking orders to employees who are his lackeys. It doesn’t matter what the product or service is. He is positive that success is assured and that he will turn a quick profit with the ultimate goal of not having to work at all. Even if he is in a position to take over an already operating business, his thinking is similar.

One man was offered the opportunity to run his family’s home maintenance business, a company that took more a decade to build. In a year, he bankrupted the company by making risky investments and unsecured loans to friends. When he assumed control of the company, he figured he’d be making so much money that he could retire after a few years. He envisioned himself relaxing on a beach, drink in hand, without a care in the world. Instead, he created a financial calamity for his family while he ended up penniless and disgraced.

This idea of getting rich overnight by running one’s own business is akin to the big score idea, enriching oneself by committing the perfect crime.

Just of out jail, Jack went to work at his father’s restaurant. Determined to learn the business from the ground up, then run it, he began by waiting on tables. His father was so pleased by his son’s diligence that he promoted Jack to assistant manager. Dissatisfied with the modest salary he was earning, Jack wanted to be the top manager and ultimately take over the entire operation of the restaurant. Knowing that his father was planning to retire, he was impatient to begin running the place. His daily routine was getting to him. Seeking excitement, he flirted with customers and propositioned waitresses who were reluctant to complain to the boss about his son. Then money began missing when receipts were totaled for the bank deposits. It turned out that the thief was Jack who explained that he was “just making temporary loans” to himself which he intended to repay. Rather than running the restaurant, Jack found himself out of work and on the street.

The anti-work attitude that criminals have before their incarceration persists afterward. They expect rapid enrichment with minimal effort. Intolerant of routine and notoriously poor decision-makers, their pretensions outstrip their effort. Whatever modest success they may achieve, it is never enough. And so they resort to shortcuts, improbable schemes, and gross deception.

The failure of many criminals as entrepreneurs and businessmen does not stem from a lack of job skills. It is because they continue to function with the same thinking patterns which, in the past, resulted in failure.

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