I’m often struck by the number of baalei teshuvah and geirim I know who faced serious tests not long after upending their lives —and who passed those tests with flying colors. I know nothing of the Divine calculus in these matters. But sometimes it seems as if they are being tested to prove to the world, and more importantly themselves, the depth of their new commitment.

A classic example is the wife of an acquaintance of mine. Until her early twenties, she did not even know that she was Jewish. Two decades later, she died from cancer, leaving behind a husband and household of unmarried children. A few days before her passing, she told a visiting friend, “I’m trying to work on yiras Shamayim. It’s very hard because His ahavah so overwhelms me.”

A few months ago, my wife and I lost one of our closest friends. She probably knew more about most subjects than anyone else I ever met. She was one of the early team members at one of the first Silicon Valley start-ups to hit the jackpot. Unfortunately, the exposure to fumes from copying machines to which she was exposed at that company would later trigger an onset of various medical problems.

She went through multiple “conversions” in her unceasing quest for a more authentic, closer connection to Hashem. And she was the driving force behind making aliyah with her born-Jewish husband and his decision to spend a year in full-time Torah learning after arriving in Eretz Yisrael. He went on to become a serious ben Torah, despite starting in his fifties.

For the last nine years of her life, she suffered a nonstop string of medical problems: Every time the doctors treated one threat, the severity of the treatment led to another equally perilous threat, until in the end her system collapsed. Over that period, she had lots of questions about what Hashem wanted from her, and lots of energy, at least in the beginning, for seeking further spiritual growth. But she had no doubts.

I CAN CITE NUMEROUS other such examples. But I’d like to share the story of one such test with a happy (in this world) ending. The story was not told to me by the hero (“Harry”) himself — though he subsequently confirmed all the facts — but by another new friend.

After graduating college, Harry spent a little over half a year at Ohr Somayach, and then returned to his native Chicago and became one of the first students in the Chicago Torah Network (CTN), created by Rabbi Doniel Deutsch and Rabbi Moshe Katz. At the Toronto chasunah of a friend from Ohr Somayach, he was introduced to his future wife, and they were engaged and married not long after. In the meantime, he had entered the health insurance field.

After a couple years on his own, he was introduced by a college friend to someone, who, together with his father, owned a successful insurance firm. Father and son belonged to an exclusive country club, to which no Jew had ever been admitted, and their business was located far from the Jewish suburbs of Chicago. My friend actually saw the opportunity to join a gentile firm as a plus, since he would not find himself competing for clients with the many insurance brokers in the suburban synagogue in which he grew up.

He created within the firm an entirely new division dealing in health and life insurance, and was promised that when his revenues reached a certain level he would become a partner in the business. Over time, his division prospered, while the traditional casualty insurance side of the firm began to decline. But there was no action on the promise of partnership.

One day, my friend’s chief assistant, Abby (not her real name), came into his office and told him that her life had taken a sudden turn. She had given up drinking and was in the process of becoming a religious Christian. At that same meeting, she described a seamy side of the firm involving inappropriate activities, about which Harry knew nothing.

Harry advised her that she must quit immediately, even though he had no idea how he would replace her. He succeeded in finding her a position with a devout Christian broker with whom he had become friendly, and she in turn found him an excellent replacement.

A couple of years passed, and my friend’s revenues continued to grow, but no partnership followed. The son of the firm’s founder hinted that his father simply could not reconcile himself to a Jewish partner.

At that point, my friend decided to form his own company. The father and son responded by seeking a preliminary injunction against him, and succeeded in having the case removed to a county where they were friendly with almost all the judges. If the injunctive action were successful, my friend’s new business would have been destroyed almost from the start, as his clients would have had to find other brokers. His litigation costs in the first month alone were $300,000, and he wondered how he was going to feed his family or pay the tuitions of his three young children.

Meanwhile, my friend’s attorney received a call from Abby. She had heard from the woman who replaced her about the dire legal situation, and told the attorney that she wanted to testify. She showed up at court the next day, with various e-mails and other evidence reflecting poorly on the firm.

Despite his desperate situation, my friend begged her not to enter the courtroom. He pointed out that she would be cross-examined mercilessly about topics that she would not want her children to read about one day.

But she insisted. She told my friend that the example of his family life and the way he conducted himself had been the major impetus behind her decision to change her life so dramatically. Her appearance in the courtroom and the documents in her possession so unnerved the father and son that within a week the suit was fully settled on favorable terms to my friend.

THIS STORY EVEN HAS a happy postscript. Three years later, Abby called up my friend out of the blue. She had worked her way up with a global brokerage firm that allowed her to work from home, while she raised three children. Then a new management team came in and insisted that she make the long commute to work. She felt that she could not do that and take care of her family, particularly her youngest daughter, who has a severe hearing deficit.

Abby’s husband was out of work, she had drawn down her 401(k) account to live on, and she owed the IRS a large amount. She was on the verge of a nervous breakdown. Harry responded to her call by lending her the money to pay the back taxes, offering her husband freelance work, and asking if he could cover her daughter’s medical expenses. (Abby told me, not Harry.)

In the meantime, Harry had become close friends with the CEO of a major international steel firm, whose wife was among the original students at CTN. The firm was experiencing many problems with its insurance handlers, and its major broker was under criminal investigation. The CEO asked Harry if he would take over the company’s insurance business.

Harry replied that he was not staffed to handle a 3,500-employee firm, but he agreed to take home two cartons of documents and think about the offer.

He decided to let Abby look at the cartons of documents and see what she could find. Two days later, my friend received an excited phone call from her. She had gone through the cartons and found ways to recover millions in monies fraudulently taken by the previous brokerage firm and to work around another major insurance-related problem. On Monday, Abby made a four-hour presentation at the steelmaker’s corporate headquarters, and she and my friend were hired on the spot.

Today, Abby works from her home in an office my friend built for her, and she has even brought in several other large national accounts, which the firm was formerly not equipped to handle.

My friend passed the test, when his and his family’s future was on the line, by trying to dissuade Abby from testifying on his behalf. And she passed hers by showing her gratitude for the way his example of a Torah family life inspired her to build her own family.

Originally featured in Mishpacha, Issue 732. Yonoson Rosenblum may be contacted directly at rosenblum@mishpacha.com