Question:

You're looking for a manager to run a new store you've just opened. Two people apply for the job, both honest and upright individuals, both seemingly credentialed for the position. The resumes indicate that Applicant A was until recently employed as a manager of a successful retail establishment. Applicant B was an entrepreneur who had actually owned a similar store in the past—but had closed it when it failed to show a profit.

Whom do you hire?

Answer:

If you follow conventional reasoning, you will go with the guy who successfully managed in the past. Out-of-the-box thinking, however, dictates that you give the nod to the guy who went bankrupt.

A tzaddik is an indentured employee, someone accustomed to following ordersThere is a fundamental difference between a business owner and an employee. On average, an employee's primary function is to follow orders; he doesn't take risks and he's not expected to expand the business in completely new directions. An owner, on the other hand, answers to no one. He has only one concern, and that is increasing his company's revenues. Typically, an entrepreneur is more an independent and original thinker.

And while Applicant B failed in his last endeavor, with proper direction and oversight – with care taken that these directions not quash his entrepreneurial spirit – odds are that he can take your store to levels that Applicant A cannot even imagine.

The Ben Ish Chai (Chacham Yosef Chaim, 19th century Baghdadi scholar) uses this analogy to explain the Talmudic saying (Berachot 34b), "In the place that ba'alei teshuvah (penitents) stand, perfect tzaddikim (righteous individuals) cannot stand."

A tzaddik is an indentured employee, someone accustomed to following orders. He has never tasted independence, never been on his own. Though he honestly and industriously labors in G‑d's service, he has never felt the need to take a gamble, never felt the rush experienced by someone who goes out on a limb—he's always on the straight and steady.

In contrast, the baal teshuvah was hitherto self-employed. Yes he closed up shop when he realized that his company wasn't profitable, but in the interim he had tasted freedom and independence. He wasn't following any set of rules when he was pursuing his desires and pleasures. He learned how to think unconventionally and how to drum up business when it seemed that none was to be found.

They both make for nice employees, they'll both drum up business for their Employer, but...

"In the place that the ba'al teshuvah stands, the perfect tzaddik cannot stand."