![](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/04\/d34979ddfaddfe1e2fff568e994d7650c3-horace-mann-2.rhorizontal.w1100.jpg\")
<\/p>\n <\/p>\n
\n The author (far right) and two classmates.
\n Photo: Courtesy of the author\n <\/p>\n
In June 1997, when I graduated from Horace Mann, one of New York\u2019s most prestigious private schools, the New York Times published a story about our class<\/a> that began as follows: \u201cThey were, by some accounts, the class of mediocrity.\u201d<\/p>\n A reporter had tagged along with our valedictorian, Loren Easton, and found the freckled 17-year-old wrestling with disappointment, a sense that we hadn\u2019t lived up to the school\u2019s expectations. \u201cAll we cared about was getting into good colleges and we didn\u2019t even do that well,\u201d Easton told the reporter. The truth was that 44 percent of us had gotten into an Ivy League school. But for Easton, who spoke for at least some portion of our class \u2014 and who\u2019d chosen the University of Pennsylvania after being rejected by his first choice, Dartmouth \u2014 it was less about the data and more about the feeling that we weren\u2019t a particularly impressive bunch. \u201cWe\u2019re not like last year\u2019s senior class, which had so many geniuses, so many stars,\u201d he lamented.<\/p>\n This obsession with achievement is familiar to anyone who has been in the orbit of an elite private school. Since time immemorial, or at least since the mid\u201320th century, affluent parents with soaring ambitions for their children have jockeyed for precious slots at schools prized for vaulting grads to the Ivy League and into illustrious careers. When the president of the class above mine got into Harvard, the only person visibly prouder than him was his mother, who immediately traipsed through the halls wearing a crimson sweatshirt emblazoned with the university\u2019s crest.<\/p>\n My father, a corporate lawyer who often reminded his sons that \u201ca man can never be too thin, too rich, or too well dressed,\u201d worked his way up and out of the middle class without the benefit of brand-name schools. When he wrote the first of a handful of $15,000 tuition checks to Horace Mann (which now costs $68,700 annually, more than a Harvard undergraduate degree), I think my dad imagined I\u2019d develop excellent posture while readying myself for a career as a Supreme Court justice, literary titan, or captain of industry.<\/p>\n Instead, after graduating from Pomona, a small liberal-arts school in California, I spent my early 20s playing in a series of ill-fated bands whose achievements \u2014 performing at Central Park\u2019s SummerStage and various Verizon Wireless amphitheaters, signing a publishing deal \u2014 were thrilling but fleeting. I also spent a few years writing screenplays no one wanted. I did manage to wrangle $1,000 from William Shatner to rewrite a comedy he\u2019d dreamed up, but he didn\u2019t like my take and the movie never got made.<\/p>\n Meanwhile, after working as a reporter at a small newspaper for a couple of years, I bounced between jobs that felt embarrassing for someone with my privileged background: copyediting a yoga magazine, tutoring distracted teenagers, headhunting hospice nurses (which was every bit as ethically uncomfortable as it sounds). To me, these didn\u2019t feel like the customary day jobs that most creative types take to pay the bills; they felt like daily reminders of my inability to make good on the advantages that had been handed to me.<\/p>\n By my mid-40s, I\u2019d built a modest career doing communications for nonprofits whose missions mattered to me but whose dysfunction drove me bananas. My daily responsibilities hardly seemed to require a first-rate education. I wasn\u2019t sure if I\u2019d failed Horace Mann or if Horace Mann had failed me. In any case, whatever advantages my elite schooling had conferred, I was pretty sure I\u2019d squandered them.<\/p>\n One day a few years ago, during a break from yet another funereal procession of Zoom meetings, I was complaining to Marc Bush, a friend from Horace Mann who\u2019d been a model student: managing editor of the school newspaper, ardent water-polo player. In his yearbook photo, he stands proudly in a blue blazer, tie, and khakis, surrounded on the page by quotes from Plato and Shakespeare. Marc went to Yale and, when he was only 22, founded a nonprofit that packaged cross-country cycling trips as affordable-housing fundraisers. Now, in his mid-40s, after a stretch of unemployment, he was a demoralized part-time consultant for an educational-strategy company. Professionally, he seemed and felt lost. Photo: Hugo Yu\n <\/p>\n Easton, our valedictorian, now works in private equity. I reached out, but he didn\u2019t want to talk. In the nearly 3,000-word Times article, Easton served as a kind of surrogate for our class, and the privileges he enjoyed, which were briefly documented in the Times story \u2014 weekends in the Hamptons, summer trips to Europe \u2014 were typical of Horace Mann students. The reporter captured plenty of the psychodrama of our senior year, including Easton\u2019s reaction to being rejected by Dartmouth: \u201cIt\u2019s not like it crippled me, but it was the first time anyone ever said no to me.\u201d I called the reporter, Andrew Jacobs, who still works for the Times, and he seemed to have some regrets about probing adolescent Easton. \u201cI think about him a lot,\u201d Jacobs said. \u201cI don\u2019t know how we would have done that story today. I don\u2019t think it was a horribly damaging story, but it probably felt like a betrayal.\u201d<\/p>\n As for the rest of our class, Jacobs recalled being impressed. \u201cAll smart kids, strivers,\u201d he said. But he was taken aback that everyone was \u201ccompletely obsessed with their grades and the school they were going to.\u201d \u201cIt was absurd,\u201d he told me.<\/p>\n Nearly 30 years later, it\u2019s fair to say our class has had no trouble succeeding in business. Ben Leventhal co-founded Resy, which was valued at $53 million<\/a> when it was acquired by American Express. Ara Katz, a serial entrepreneur, several years ago closed a $40 million series-A-funding round<\/a> for her probiotics company, which has since launched an AI-powered biological-research platform<\/a>. Katz, whom I grew up with in Westchester County and followed to Horace Mann, was also an adviser to a high-end sneaker emporium co-founded by another classmate, John McPheters, who sold the company for $250 million<\/a> and now runs a boutique investment firm.<\/p>\n Plenty of other classmates are lawyers, wealth managers, and Wall Street traders. A number have made small fortunes as real-estate developers. \u201cI guess I had faith in myself that something would work out,\u201d Scott Alter told me, recounting his decision to leave private equity in his late 20s to start a real-estate company with a friend. That company is now one of the 50 largest affordable-housing owners in the U.S. with over $6 billion in assets under management. \u201cI\u2019m really driven, and I thrive on that,\u201d he said. His three daughters attend Horace Mann.<\/p>\n As Alter and I spoke, it quickly became clear that he shared none of my burdens. He didn\u2019t feel, as I did, that Horace Mann had imposed on us a sense of specialness, creating monumental expectations that were extremely difficult to live up to. \u201cI don\u2019t look at it like that at all,\u201d he said. \u201cI looked at Horace Mann as just a great education.\u201d He\u2019d cherished our strenuous learning environment, whereas I\u2019d viewed high school as a means to an end \u2014 an end that, for me, had come to seem unreachable.<\/p>\n When I suggested that he\u2019d achieved the kind of success we\u2019d been bred to attain, Alter took issue with my definition. \u201cSuccess, to me, is finding purpose, finding community, finding ways to give back,\u201d he said. If I\u2019d heard those words from another prosperous executive, I might have rolled my eyes. But I knew Alter meant it. His company was tackling a genuine economic problem \u2014 the nation\u2019s workforce-housing shortage \u2014 and his earnest and upbeat attitude was the same one he\u2019d exuded back in high school.<\/p>\n I didn\u2019t doubt Alter\u2019s work ethic, but it\u2019s tough to credit Horace Mann\u2019s rigorous academic program for some of my classmates\u2019 business success, which often owes at least as much to family money and high-value networks. As one classmate who has dabbled in real estate told me, \u201cI mean, look \u2014 it\u2019s not that complicated.\u201d He recounted a story he\u2019d heard about another classmate of ours who\u2019s now a prolific real-estate developer in New York City: \u201cHe just put together a small fund and went to his family. He went to his parents and aunts and uncles and stuff like that and was able to pull together enough cash, along with a bunch of debt, to start buying things. If you\u2019re coming from a family situation where they can afford to cut you a check for a few million dollars for something speculative, then that\u2019s absolutely gonna get you moving.\u201d\u00a0<\/p>\n Researching my classmates, I found I wasn\u2019t all that curious about those who\u2019d taken predictable routes to success or accumulated tremendous wealth. I was more interested in the ones who had strayed from the conventional path of the elite-high-school grad.<\/p>\n \u201cI hated the place since I was 2,\u201d Ted Wallach said of Horace Mann. A gangly and restless teenager who, like most of our classmates, grew up on the Upper East Side, Wallach found the school\u2019s demands oppressive. \u201cYou can\u2019t do five hours of homework a night,\u201d he said. \u201cYou can only do three or four.\u201d To stay afloat, he haggled with teachers and did everything he could to \u201cbeat the system,\u201d as he put it. A lingering resentment of systems, he said, got him fired from his first few jobs.<\/p>\n But around a decade ago, he said, he found his calling: coaching founders and executives. \u201cMostly people who\u2019ve been really successful in round one and are trying to figure out round two,\u201d he explained. \u201cI teach people to sing the song they must before they die.\u201d Since 2020, Wallach and his family have lived in his wife\u2019s native Sweden.<\/p>\n Wallach spent a good chunk of his 20s and 30s making a documentary about kids from low-income neighborhoods training to be professional magicians. For much of that time, he relied on his wife\u2019s income. Having family help out financially was a not-uncommon theme in my conversations with classmates. When my own wife and I found a house we loved in Pasadena that was out of our price range, I called my dad to help us cover the down payment. But while some of us are a little more comfortable thanks to our parents\u2019 money, others have come to depend on it.<\/p>\n Henry Chromow stopped working in 2017 when his project-management gig at a division of Bloomberg ended. He spends some of his time helping out his aging mother, once a high-powered attorney, dividing his time between her Upper East Side apartment and house in Connecticut. \u201cIt\u2019s three acres, it\u2019s an older house \u2014 nothing fancy about it \u2014 but it\u2019s got a bunch of woods in the back, flat land, and it\u2019s just peaceful and quiet and I just like spending time there,\u201d Chromow told me. \u201cI have my computer. I have trees. I feed the birds. I\u2019m perfectly content to futz around the house.\u201d<\/p>\n Chromow\u2019s decision not to return to work seems to stem less from laziness and more from relief at having finally overcome the depression that dogged him for years. \u201cI\u2019ve always had mental-health issues,\u201d he said. \u201cWhen I was in my early teens, I felt that pressure of like, Gotta get into the right school and do well there and get the right job. That was a big part of why I ended up in therapy. I was a mess until my very late 20s. I was fucking useless.\u201d Last year, Chromow was the best man at the Lake Como wedding of another classmate, Joe Bernard. At 38, after stints as an assistant district attorney and strategy consultant, Bernard quit the white-collar world to make a go of acting. His parents, who by then had paid for high school, college, a law degree, and an M.B.A., footed the bill for a two-year acting-conservatory program. I imagined Bernard might feel self-conscious about all the career-hopping on someone else\u2019s dime, but he didn\u2019t. His parents, he said, had always encouraged him to pursue his passions. He was the one who\u2019d resisted acting. \u201cI was like, \u2018Nah, I should do something serious,\u2019\u201d he recalled. \u201cI should go to law school; I should go to business school. I don\u2019t know whether I viewed acting as frivolous \u2014 it just didn\u2019t seem like a serious long-term choice.\u201d<\/p>\n Bernard said he finds a lot more meaning in making art than \u201ctrying to move a stock price.\u201d Last year, a film he helped produce won the audience award at Cannes. His acting career, though, hasn\u2019t taken off. \u201cIt\u2019s all been slow going,\u201d he said. Regardless, over the course of a few conversations with Bernard, I didn\u2019t detect any of the anxiety that I\u2019d been lugging around.<\/p>\n \u201cThe Horace Mann\u2013ness of it,\u201d he said, \u201cthe idea that you should be excelling \u2014 whatever the fuck that means \u2014 yeah, I\u2019m sure that\u2019s true, but I separated myself from that a long fucking time ago.\u201d\u00a0<\/p>\n Given Horace Mann\u2019s intensive focus on academics, I was surprised that only a few of my classmates wound up working in academia. When I reached out to Demetra Kasimis, who teaches political theory at the University of Cambridge, I suspected she\u2019d have trouble relating to the inadequacy and disappointment I\u2019d felt for so long. But she described struggling to let go of the fantasy of building a life in New York. \u201cI think for those of us who moved out of New York, that feeling of not measuring up might be stronger,\u201d she said. \u201cI always found it difficult to disentangle what it meant to excel at Horace Mann from being highly visible and impactful in New York City. So sometimes I\u2019ve measured it in those terms: Why couldn\u2019t I have just made it in New York?\u201d<\/p>\n Kasimis was teaching at the University of Chicago when she took a sabbatical in Greece, where she has family. She bought an apartment in Athens. \u201cI thought, Well, if a job in Europe ever opens up, I\u2019m gonna apply.\u201d Two months later, one did at Cambridge.<\/p>\n \u201cI took a pay cut, but my life is now in Europe and I\u2019m happier,\u201d she said. During breaks from teaching, she returns to her place in Athens. \u201cI\u2019m making this career work in a way that suits my life rather than making my life subordinate to my career.\u201d<\/p>\n I envied these classmates for living life on their own terms, for shedding the outlandish expectations of our youth. I called others \u2014 a psychiatrist, a quantitative researcher, a school psychologist, an environmental consultant who runs a nature preserve \u2014 but none felt plagued by unfulfilled potential. Ordinary midlife malaise hung over some of them. \u201cI don\u2019t think I ever found what I love to do,\u201d a real-estate developer confessed, \u201cbut I do have things I\u2019m good at.\u201d A software engineer seemed resigned to his career: \u201cThis is what I know how to do, and this is what I do.\u201d A journalist shrugged that while his education could\u2019ve thrust him in any number of directions, \u201cthis is the direction I chose, which is fine.\u201d The classmates I spoke with appeared to have accepted where they\u2019d ended up. It seemed I was the only member of the class of mediocrity who still felt mediocre.<\/p>\n Midway through my Schadenfreudian quest for dissatisfied classmates, I left the company I was at and became an independent consultant. It\u2019s not the esteemed or exhilarating career I\u2019d once envisioned, but I\u2019m grateful for it. I can be choosy about my clients, whose causes resonate with me and who aren\u2019t mired in dysfunction. And working independently means no one\u2019s looking over my shoulder. About a year ago, Marc Bush, the demoralized education consultant, decided to launch his own travel advisory firm. Working for himself, he\u2019s more energized than he\u2019s been in years.<\/p>\n The more I talked to my classmates, many of whom run their own companies, some of whom struggled under supervision \u2014 one told me, \u201cI don\u2019t like people telling me what to do or what to think \u2026 I\u2019m a manager\u2019s worst nightmare\u201d \u2014 the more I wondered if that\u2019s another consequence of our privileged upbringing: a need to be our own bosses.<\/p>\n \u201cThe word I\u2019ll use is spoiled,\u201d Danny Mishkin, another classmate, told me from his home on Long Island. \u201cWe were told we were gonna be the boss.\u201d Mishkin wasn\u2019t bad-mouthing any of us. He\u2019s thought a lot about the psychology that shaped our adolescence, and he\u2019s built a career out of trying to remedy its ill effects. After getting a master\u2019s degree in Jewish education, he founded a surf camp rooted in Jewish spirituality. The camp\u2019s mission is simple: teach kids from high-pressure homes to chill out.<\/p>\n \u201cThe research is overwhelming,\u201d he said. \u201cTeenagers are stressed out, they\u2019re overprogrammed, the expectations on them are to be perfect. No missteps. And we\u2019re like, \u2018No. They need to learn whole-person education.\u2019\u201d<\/p>\n I\u2019m not sure Mishkin and I ever exchanged a word in high school. He traveled in a tight-knit circle of confident kids who seemed to belong at Horace Mann. Many in that circle are now CEOs, finance executives, and the like who send their kids to the school. Mishkin remains close with them, but he has distanced himself from that world.<\/p>\n \u201cI feel like I got out of spiritual poverty,\u201d he said. \u201cI don\u2019t actually think of our upbringing as a leg up.\u00a0We were around a lot of miserable people when we were kids. They were very, very wealthy, and they were pretty unhappy.\u201d This spring, thousands of anxious parents in New York City and across the country, eager to maximize their children\u2019s potential, will enroll them in elite private high schools. Even as AI threatens to decimate the white-collar workforce<\/a>, raising unanswerable questions about the purpose of elite education<\/a>, these parents will write huge checks to schools that promise to push students to become the most outstanding versions of themselves. I wonder how many of these parents will get a return on their investment. I wonder how many of their children will have to unlearn much of what they absorb or struggle to discern their own desires amid so much pressure to succeed. I wonder how many will wind up regretting the countless hours spent trudging through suffocating volumes of homework, the nail-biting SAT prep, the tireless rumination over college applications that, perhaps, are not so determinative of their flourishing after all.<\/p>\n After a few years of tracking down classmates, and decades spent wondering how I might have turned out if I\u2019d just stayed in public school, I was ready to close the book on Horace Mann. I reached one last time for the crimson yearbook I\u2019ve kept on my desk to help with my research. I flipped through it and found the note from Ara Katz, the serial entrepreneur, who\u2019d sung Horace Mann\u2019s praises after enrolling there in seventh grade, encouraging me to follow her there. On the page, she\u2019d written \u201cWas it worth it?\u201d<\/p>\n Related<\/p>\n","protected":false},"excerpt":{"rendered":"The author (far right) and two classmates. Photo: Courtesy of the author In June 1997, when I graduated…\n","protected":false},"author":2,"featured_media":196631,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[8],"tags":[40802,67,78348,9,24,55,54,56,38370],"class_list":{"0":"post-196630","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-new-york-city","8":"tag-audio-article","9":"tag-education","10":"tag-horace-mann","11":"tag-new-york","12":"tag-new-york-city","13":"tag-new-york-city-headlines","14":"tag-new-york-city-news","15":"tag-ny","16":"tag-private-school"},"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/posts\/196630","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/comments?post=196630"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/posts\/196630\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/media\/196631"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/media?parent=196630"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/categories?post=196630"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-ny\/wp-json\/wp\/v2\/tags?post=196630"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
As we commiserated, Marc suggested I revisit the Times story about our underperforming class, whose shadow seemed to be looming over the two of us. I needed to know if other classmates were similarly afflicted. Did the residue of unrealized potential linger in any of them the way it did me? I was less interested in what they\u2019d accomplished than in how they felt about their work and the lives they\u2019d built, especially when measured against the exalted aspirations of our youth. I decided to go searching for the class of mediocrity.<\/p>\n![](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/04\/5be5c149472e32d72aaf2bfe0de64d6273-horace-mann-lede.rhorizontal.w700.jpg\")
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Mishkin didn\u2019t quibble with the excellence of our education \u2014 none of my classmates did \u2014 but he felt we were groomed for achievement at the expense of our development. \u201cWe were thrust into adulthood, in some ways, way before we should have been,\u201d he said. \u201cWe didn\u2019t get the chance to be carefree kids.\u201d<\/p>\n