Pho­to by Erik Mclean on Unsplash

In 2016, my career took a breath­tak­ing swerve. I left twen­ty years in mon­ey man­age­ment to become head of a Jew­ish board­ing school in the South. I made this unortho­dox career move for two rea­sons: to per­form tikkun olam and to teach. 

Teach­ing proved as reward­ing and enjoy­able as I had hoped. Tikkun olam, how­ev­er, was more com­pli­cat­ed. The school’s pre­car­i­ous finan­cial con­di­tion need­ed urgent atten­tion and giv­en my back­ground, I thought I could help. 

I couldn’t. 

The school’s chal­lenges proved big­ger than a bad bal­ance sheet. I left before the school closed, but took with me (along with mem­o­ries and friend­ships), a con­vic­tion and a question.

The con­vic­tion: the school set­ting was a cre­ative muse wait­ing to be chan­neled by a recep­tive author. Write about this world,” the Jerusalem stone build­ings seemed to whis­per as I crossed and recrossed the stun­ning cam­pus, hus­tling to stay on top of things. Not long after start­ing the posi­tion, I real­ized that my wife and I were liv­ing in an improb­a­ble hybrid of Tevye’s Anat­ev­ka, I.B. Singer’s Chelm, The Lawrenceville School, and Jew­ish sum­mer camp. As if those weren’t enough ingre­di­ents for an intrigu­ing nov­el, the school was a melt­ing pot, bring­ing togeth­er Jew­ish stu­dents from around the world, from Hong Kong to Pana­ma City. 

The school’s fre­net­ic envi­ron­ment, the close­ness and quar­rel­ing to which this tight-knit com­mu­ni­ty was prone, and the dai­ly cri­sis that some par­ent, teacher, or stu­dent would tell me must be solved right now—all of this was ener­giz­ing, exas­per­at­ing, and, ulti­mate­ly, inspirational.

The con­vic­tion proved out. I lis­tened to that muse — she has a quirky sense of humor — and the result is my first nov­el, The Acad­e­my of Smoke and Mir­rors: A Board­ing School On The Brink. It is a com­ic nov­el, fol­low­ing head of school Jeff Tay­lor, who wants to resign before his school fails. But Jeff nev­er seems to be able to get out the door because there’s always a new mess that must be fixed first.

I some­times point­ed out that the two great­est lead­ers of the Torah, Moses and Joseph, were both brought up away from home, where they learned to be leaders. 

Writ­ing humor­ous fic­tion is chal­leng­ing. Sure, there was that muse, but co-writer Jim Par­ry and I also sought guid­ance from two great nov­els that caught the spir­it we hoped to evoke. Those nov­els are Catch-22 by Joseph Heller and The House Of God by Samuel Shem, each famous for por­tray­ing with black humor the absur­di­ty of work­ing in a large bureau­cra­cy whose cul­ture has long ago lost touch with real­i­ty. (The bureau­cra­cies being the US Army in Catch-22 and a large New York City hos­pi­tal in The­House Of God.) Over the five years it took for Jim Par­ry and I to write The Acad­e­my of Smoke and Mir­rors, we would often revis­it those texts, treat­ing them the way rab­bis do the Tal­mud, as a source of wis­dom and a how-to manual. 

It is my dream that in that mys­te­ri­ous place where notable lit­er­ary char­ac­ters wait to be sum­moned to a sequel by their cre­ators (or reimag­ined in fan fic­tion), Samuel Shem’s Fat Man and Joseph Heller’s Yos­sar­i­an are shar­ing a laugh with new­com­ers Jeff Tay­lor and Rab­bi Ben­jamin Baum.

I men­tioned that my time as Head of School also left me with a ques­tion: can a board­ing school that seeks to be the Jew­ish Lawrenceville suc­ceed? (The Lawrenceville School, one of America’s elite board­ing schools, is famous for offer­ing its stu­dents an out­stand­ing edu­ca­tion and for pro­duc­ing many dis­tin­guished graduates.)

I think the answer is yes, and I think such a school could do for the Amer­i­can Jew­ish com­mu­ni­ty what Lawrenceville and its peers still do for Amer­i­ca, name­ly pre­pare a steady stream of young peo­ple for lead­er­ship. Before mak­ing the case, I must acknowl­edge that the track record is not encour­ag­ing. There have been two such promi­nent Jew­ish board­ing high schools, one in the US and one in Eng­land, and both even­tu­al­ly closed. 

The case for a Jew­ish Lawrenceville rests on some­thing I saw at the school I head­ed, some­thing mov­ing and noble. That school incul­cat­ed into its stu­dents a belief in some­thing greater than them­selves, a col­lec­tive mis­sion for them to serve. Now, since the school was a Jew­ish insti­tu­tion, there would have been an unend­ing dis­pute were it required to pre­cise­ly iden­ti­fy that mis­sion. But, in the end, almost all would agree that grad­u­ates left the school pre­pared and eager to devote them­selves, in part or whole, to strength­en­ing the Jew­ish peo­ple. Rec­og­niz­ing this achieve­ment, let us return to the ques­tion. Can a Jew­ish board­ing school succeed? 

I believe it can. 

And as the need for lead­er­ship in Amer­i­ca, both sec­u­lar and Jew­ish, becomes more acute, and as the search for ways to cul­ti­vate it inten­si­fies, I believe some bold phil­an­thropist will start a new Jew­ish board­ing school, one with a mod­el that avoids the weak­ness­es of its pre­de­ces­sors, while con­tin­u­ing to instill that mission. 

When I was head­mas­ter, I often heard that a school which has chil­dren liv­ing away from home is in ten­sion with Jew­ish val­ues. I some­times point­ed out that the two great­est lead­ers of the Torah, Moses and Joseph, were both brought up away from home, where they learned to be lead­ers. Per­haps there is a mes­sage in the way they were pre­pared for their mis­sions, one that should inform Jew­ish edu­ca­tion­al policy.

Alex Troy worked at two Jew­ish schools, teach­ing his­to­ry at one and serv­ing as Head of the oth­er. Before becom­ing an edu­ca­tor, he worked as a lawyer and investor for thir­ty years. He recent­ly pub­lished his first nov­el, The Acad­e­my Of Smoke And Mir­rors: A Board­ing School On The Brink. Alex is a grad­u­ate of Yale, Har­vard Law, and St. John’s College.