One might say Making It Work is a book Ari Wasserman’s been getting ready to write for a long time. Born in Fort Jackson South Carolina while his father was an army doctor there Ari grew up in Los Angeles and attended the Yeshiva University of Los Angeles (YULA) high school. After spending a gap year at Sha’alvim Ari attended the University of Pennsylvania and then after one more year at Sha’alvim took a law degree at Harvard.

It was there that he first began what has been a decades-long preoccupation with delving into halachah and sharing the fruits of his learning with others. Seeing that the break between Minchah and Maariv at the Harvard Hillel minyan was being frittered away with idle chatter Ari — ever the initiator — began delivering a shiur on halachah to the assembled which he continued for three years with barely a missed shiur.

Eventually that shiur helped find him his life’s partner too. During the very last shiur he gave before leaving Cambridge to begin his first job in New York a yeshivish-looking fellow from Lakewood was in attendance. Impressed with the shiur he approached Ari afterward to chat and two weeks later made the match between Ari who’d been looking for his zivug during the three years he was in Harvard and Miryam Nussbaum of Riverdale.

Put to the Test

As he transitioned from the university campus into the workplace, Ari began to realize just how challenging today’s work environment can be for a frum Jew looking to be faithful to halachah in all its particulars. From his very first day in the real estate department of Sullivan & Cromwell, one of New York City’s most prestigious law firms, when his firm’s human resources manager greeted him with her hand outstretched to shake his, Ari faced daily tests of his willingness to adhere to religious principles, even at the cost of great social awkwardness, in a wide array of circumstances he’d never before encountered.

Could he attend work lunches at treif restaurants, and what could he eat there? Was it a problem when his dinner was delivered to the office by the kosher takeout joint’s regular delivery boy, but without a double seal? How far did he have to travel to find a midday Minchah minyan, and was he even allowed to take off time from work to do so? The challenges he faced, and those he heard about from his friends in the business world, were complex and seemingly endless.

In 1997, after just a year and a half in New York, Ari transferred to his firm’s Los Angeles office, returning to his childhood roots and raising his family there until their move to Eretz Yisrael eight years ago. On the West Coast, he continued as before to experience ongoing conflicts between his dual personae as religious Jew and corporate attorney. (His introduction to his new colleagues came at a social gathering at the Beverly Hills mansion of the female managing partner, where the hostess greeted the guests clad in a highly immodest outfit.)

After a nearly four-year stint as a big-firm lawyer with Sullivan & Cromwell, Ari decided he’d had his fill of a life whose high pay was offset by even higher pressure. He made the move to become general counsel at a midsize marketing company and later struck out on his own, cofounding a small company that designs, manufactures, and sells consumer products, a business he continued to be involved in after moving to Eretz Yisrael.

He calls the experience of working for his first boss, Joe (Chaim) Shenker — the chairman of Sullivan & Cromwell and perhaps the highest-placed frum Jew in the American legal community — “a privilege.” Mr. Shenker, he observes, taught him many valuable lessons: “Be the best you can be, always prepare for whatever you undertake to do, and details matter — even the placement of a comma can dramatically change the meaning of a sentence.”

Obligate Yourself

Over the years, law firms, hospitals, banks, and other business venues, especially in large urban settings, have become much more accepting places for Orthodox Jews to work, as Ari Wasserman’s own career demonstrates. When he began at Sullivan & Cromwell in 1995, he was the first attorney to wear a yarmulke; now, there are dozens of such employees there.

But his years in the law firm also opened a window onto challenges that extend beyond straight-and-narrow questions of halachah into the realm of larger, meta-hashkafic questions: Should one’s life goals be career advancement and financial success, or becoming the best Jew he can be and raising a happy Jewish family? How should one prioritize and allocate the hours of the day between work and family and spiritual pursuits like Torah and tefillah?

Ari recalls one fellow at his firm “who was billing 3,000 hours a year. He was billing all the way to the bathroom, reading as he walked. Eventually, of course, he made partner. My wife’s friend was married to a big-firm attorney, and once, on a Purim that fell out on Thursday, she told my wife she hadn’t seen her husband since the previous Motzaei Shabbos, when he’d left for the office to work round-the-clock on a major deal, and didn’t expect him home for Purim. He would take short naps on the office floor before getting back to work, and she was sending clean clothing back and forth to his office with a car service. That’s the life, and it wasn’t for me.”

Long hours, of course, are a built-in feature of the working world in general, not just law firms, and even after leaving legal practice, Ari struggled with how to get enough learning into his workdays, until he realized that creating a sense of obligation could be a great motivational tool. There’s nothing quite like having a responsibility to others —whether by giving a shiur, writing a sefer, or even simply having a steady chavrusa — to bring consistency and quality to one’s learning.

Ari began giving both a weekly class at UCLA under the auspices of a campus kiruv group and a Shabbos afternoon shiur at his shul, Kehilas Yaakov, on practical halachic topics related to the weekly parshah, which continued for a decade. Another important mechayev for Ari has been authoring and publishing seforim, and his output has been remarkably prolific.

He spent eight years putting all those shiurim at Kehilas Yaakov into written form, which are now in seforim stores as a well-received five-volume set called Hegyonei Haparshah. It is graced by several warm rabbinic approbations, including one from Rav Tzvi Rotberg, rosh yeshivah of Beis Meir in Bnei Brak, to whom Ari regularly looks for Torah wisdom and counsel. That was followed by a four-year project that led to the publication of a two-volume work entitled Otzar Hakippah, a comprehensive treatment of men’s head coverings in halachah.

Making It Work, too, had its beginnings in those Shabbos afternoon discourses in Los Angeles, but the bulk of the material is based on classes Ari has been giving since 2010 in three yeshivos around Jerusalem: Ohr Somayach, Aish HaTorah, and Netzach Yisrael, the yeshivah of Rav Gustman ztz”l. As a result of these shiurim, there isn’t a sugya covered in the book that he didn’t learn at least six times. Over a period of seven years, he would learn though the sugyas and commit his conclusions to writing, then teach the sugya in shiur, and based on the questions and comments from students, he’d edit and if necessary rewrite the material.

He envisions this volume as only the first of an eventual three-part series. In fact, he’s already begun work on a second one, covering issues that the current one does not, such as the laws of Shabbos and kashrus as they relate to the workplace. He hopes to follow that with yet another book focusing squarely on the hashkafah of work as viewed through the lens of Torah.

What’s in a Handshake?

Nearly a third of the book is about monetary matters, with large sections devoted, respectively, to honesty in the workplace, reporting wrongdoing and honoring financial obligations like giving tzedakah and paying taxes. But Ari wants readers to take a broader view in which workplace challenges go far beyond issues of dollars and cents. “There’s a myth that workplace halachah is Choshen Mishpat — ribbis [interest] and ona’ah [overcharging] and bal talin [delaying wages]. But these things have no relevance for 99 percent of working people. They have to do only with business owners, but not the people who work for them, and certainly not people working in non-business professions.”

To Ari’s mind, the most daunting aspect of the modern workplace is the challenge presented by social expectations of the work environment. Oftentimes, attendance at social events isn’t just optional, but an expected part of one’s employment. A friend of Ari’s, an Orthodox Jew working at a large New York company, once told him, “I had a senior executive ask me whether my wife and I would be attending the firm’s holiday party, and when I said ‘No,’ he told me, ‘Wrong answer.’ ”

But while many people may be aware of the halachic problems involved in attending a X-mas party or a dinner in a treif eatery, far fewer people know that eating at a purely social gathering at any time of year, even at a designated kosher table, may be prohibited too. The same is true for sitting down for an alcoholic drink with a gentile colleague, and that may be the case even if done in a Jewish-owned establishment.

In Making It Work, Ari cites William Shakespeare’s The Merchant of Venice, in which the Jewish moneylender Shylock responds to an invitation to a non-Jewish dinner party by saying, “I will buy with you, sell with you, talk with you, walk with you, and so following, but I will not eat with you, drink with you, nor pray with you.” But what even the non-Jewish Bard knew in the 16th century is not necessarily common knowledge among some of today’s frum Jews — and Ari has seen the fallout, too, that Chazal had in mind in enacting these prohibitions.

He was approached some time ago by the CEO of a company who said to him, “What’s with you Orthodox Jews? I’ve got five working for me, and most of them are doing things they shouldn’t be.” He concludes his chapter on social drinking with the cautionary note that no matter “how sophisticated, aware, and in control we may feel — and no matter how frum we may be — socializing, with or without alcohol, can end in disaster, causing permanent, irreparable damage.” And he illustrates those ominous-sounding words with the true story of a marriage and family that were left broken by attendance at one office party.

The gift-giving that takes place around holiday time presents its own pitfalls. A friend of Ari’s at a large firm shared an office with a Greek Orthodox woman to whom he’d regularly pass along the nonkosher gifts of food coworkers had thoughtfully given him during the December holiday season.

One day, this office mate, having heard him make a brachah over bread, exclaimed, “I know that blessing — it’s hamotzi!”

Taken aback, he asked how she knew it, and she explained that she’d once attended a Jewish camp as a child. As they continued speaking, it emerged that her mother’s mother’s mother had been Jewish, which meant he’d need to explain to her that she was actually Jewish too. But it also meant, unfortunately, that he’d been unwittingly supplying a fellow Jew with treif food.

Shaking hands with members of the opposite gender is one area of halachah that is a constant challenge for frum Jews in the workplace, with no easy resolution. Although Wasserman concludes his chapter on the topic by citing the lenient position taken by several American baalei halachah (provided the other person has initiated the handshake and the frum person has no improper thoughts during it), he cites at length from the great majority of major poskim who prohibit it under all circumstances (the Chazon Ish goes so far as to deem it a matter of yehareig v’al yaavor). But Ari is careful to stress that the book “is not a sefer of psak — it’s a sefer for spotting the issues and learning about the relevant sugyas.”

Clean Business

Since the book’s publication last year, numerous people — including some of his students in yeshivah — have posed additional questions to Ari, and he has already compiled a whole book’s worth of material responding to these queries.

Making It Work contains chapters on how men in the working world can both maintain the motivation to learn Torah and find the time to do so, and Ari’s own life is an object lesson in applying the strategies he offers. How does a man run a business, make time for spouse and children, teach Torah several times weekly and still manage to publish seforim and books that are close to numbering in the double digits?

In Ari Wasserman’s case, it’s the result of a disciplined effort to maximize every hour of the day, and every minute of the hour to the hilt. As his rav back in Los Angeles, Rabbi Gershon Bess, puts it, “He allocates times for learning and sticks to them. He’s a living mussar sefer, because people see the results of his efforts.”

To be as productive as possible, Ari counsels doing one’s learning first, at the beginning of the day, so that it can’t get pushed aside by the pressures of the workday, the ringing phones, the never-ending e-mails, and all the rest. And he lives it. His day used to start at 3 a.m., but now he rises at four — “I’m sleeping in,” he quips — in order to begin his learning at 4:30, which continues until seven, with a break in the middle to daven with a haneitz minyan. After helping out with the morning routine at home, he picks up again at 8:15 and learns for another five hours before starting his business day.

One source of inspiration in how to strike the proper life balance is Ari’s own brother Noam, who, he insists, is “much more interesting than I am.” A professor at Harvard Business School for over a decade before his recent transfer to the University of Southern California, he “wrote the book” (in Ari’s words) on entrepreneurship with an award-winning study on business start-ups — and he’s also the head of a large family. Yet the bio on his website mentions among his accomplishments the fact that he has finished Shas, the result of an ironclad commitment to learning Torah for three hours daily.

Ari adds proudly, “And he’s as yashar as can be. Harvard Business School gave him a $5,000 annual technology allowance. Three years ago, he submitted a reimbursement request for only $240, the cost of a new computer monitor, because he hadn’t needed anything else and didn’t want to spend the allowance on anything that wasn’t genuinely necessary. And two years ago he outdid himself, spending none of the allowance at all.

“Once, on a visit to my brother in Boston,” Ari continues, “I needed to print out about 200 pages of material to read on my return trip to Israel, but his home printer was out of toner, so I asked whether Harvard would permit me to use his office printer. Noam replied that while many staff members used office equipment for personal purposes, he avoided it, and instead, he drove me to a Kinko’s to do my printing.”

Stay Focused

It’s extremely difficult to be as disciplined and consistent as Ari Wasserman is without the willing involvement of the person who shares his life, and he’s quick to credit his wife Miryam for making it all possible. “Although she initially worked in finance back in the States, my wife’s full-time occupation is in the field of chesed, whether it’s raising our kids or preparing for Shabbos starting Wednesday for our many Shabbos guests. We have a full table of guests for our meals, from every walk of life and religious orientation.

“We throw everyone together. Yeshivah bochurim, guys from Ohr Somayach bringing their kallahs or grandmothers, kiruv groups, nonreligious Israelis — although we don’t mix Hebrew and English speakers at the same meal, because that’s too difficult. As soon as the fish comes out, I’ll give a devar Torah and then ask a question about it. We go around the table, and everyone gives a response — people share the most amazing experiences and insights, and all walls come down. It’s quite amazing.”

And, yes, those divrei Torah, and the fascinating give-and-take they elicit from family and guests alike, will also soon be appearing in a book entitled Welcome to Our Table, arriving in bookstores in two weeks’ time.

Ari has one further thought on how to get a lot done in life: “One thing that’s killing people’s productivity is technology. You see it with guys in yeshivah who can’t accomplish in two years today what took one year to accomplish 20 years ago, because they’re constantly distracted. I recently saw an avel who was davening from the amud go back to his seat before chazaras hashatz to check his e-mail. So, to stay focused, I would say to put the technology away.

“The great gaon Rav Efraim Zalman Margolios, who was also a successful businessman, said that when Chazal taught that to succeed in Torah, a person needs to be meimis atzmo aleha, they meant: Tell the people in your life, ‘When I’m learning, pretend I’m dead — don’t disturb me.’ I’m not up to that point, but I don’t have a smartphone — not for halachic reasons, but just because I don’t want to be disturbed. I want to be able to learn.”

Although Making It Work sounds the alarm about the numerous pitfalls along the route of the Orthodox Jew in the modern workplace, the book also has an underlying tone of optimism. There’s a recurrent theme of the possibilities for navigating the career path successfully, with one’s ruchniyus intact and, indeed, enhanced.

In the chapter on wearing a yarmulke at work and on interviews, Ari tells the story of his friend, a recent college graduate, who decided to forgo his kippah during his job search. After more than a hundred unsuccessful interviews, he landed one more with a prestigious accounting firm, wore his kippah, and got the job.

Another fellow began business school going bareheaded for the first time in his life, uncomfortable as it made him feel. But because he spurned many of the after-class social activities, he was perceived by classmates as aloof, a distinct disadvantage in an environment where networking is seen as crucial to success. But beginning his second year, he decided to put the yarmulke back on, and had far greater success, not only academically but socially, too. Wearing the yarmulke communicated to his peers that his non-involvement in school social life was not snobbish but religiously motivated. It turns out that opting to uphold the halachah was the right thing, in every way.

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NO MIDDLE GROUND

Ari Wasserman opens Making It Work with an important insight about corporate America from Yosi Heber, a veteran marketing executive: “If an employee is a non-Jew, he or she can be perceived in the eyes of an employer in one of three ways: liked by people, disliked by people, or middle of the road ( ‘one of the boys’).

“If a person is a frum Jew, however, there are only two possibilities: Either you will be respected because you are a frum Jew (and you create a kiddush Hashem), or you’ll be disliked because you are a frum Jew (and that can lead to chillul Hashem). You cannot and will not ever be accepted as ‘one of the boys.’ There is simply no middle ground for you in a corporate environment.”

Wasserman cites six rules of thumb Heber compiled in consultation with other frum Jews in the secular workforce:

Bend over backwards to be nice to people. Be sure to express compliments and appreciation wherever appropriate, and if you’re a boss, be easygoing.

Do outstanding work. Know your field well, acquire knowledge of specialized areas, be creative, and offer guidance and help to anyone who needs it.

Be consistent in your religious conduct. Consistency earns respect. One systems analyst knew he was on the right track when a peer told him, “If only I were as consistent with my diet as you are with your religion, I would have lost 30 pounds by now.”

Be frum, but show them that you are a “normal person.” Be “professionally” friendly, talk about politics, and ask after coworkers’ families. This type of friendliness can be more powerful than conforming to the “social friendliness” stereotype that people think one needs to succeed, such as going out for drinks after work.

Be someone whom people enjoy being around. Project a positive attitude and a sense of being a happy person.

Strengthen your ruchniyus level at home. The greater the nisyonos presented by the outside world, the more extra care one must take to reinforce his ruchniyus outside of work. Have a rav whom you can consult and ask questions and maintain a regular Torah study session. Daf Yomi can be an excellent, consistent, structured program, even when traveling.

Yosi concludes that it “may seem improbable, but I have met many prominent people in the corporate world over the years who say that by merely following these types of guidelines, they have never really had a negative experience. Even in seemingly difficult situations (e.g., late Friday meetings, business trips abroad, etc.), many comment that they have always felt that they were respected for their religious beliefs and not thought of as ‘odd’ because they were so different from everyone else in their respective companies.”

(Originally featured in Mishpacha Issue 676)