Had I been looking to teach Torah for the sake of teaching Torah alone, I would have had plenty of opportunities to do that.

You often hear stories about the kids who don’t make it in yeshivah — the ones who chafe in their seats during the long hours of learning, the ones who aren’t cut out for the academic rigors of the yeshivah environment. You don’t hear as often about the kids who do make it, the kids who take to Gemara like fish in water.

I belonged to the latter category. I was the smartest kid in the class, frankly, and I was also one of the hardest workers, which made for a very productive combination. By sixth grade, I was already polishing off masechtos with ease. I genuinely enjoyed every word of Gemara, and I savored every vort I heard from my rebbi’s mouth. I also liked the way the rebbi looked directly at me any time he explained a particularly difficult concept.

Naturally, I was accepted into a top high school, where I continued to flourish. I used every free second to learn, and I loved it. Some people today would say that it’s detrimental to a kid’s emotional and mental health to learn as many hours a day as I did during my teenage years, but I never found my learning schedule to be too intense. I knew I had to chill out sometimes, and at those times I would play ball and relax with my friends. My friends jokingly called me “the rosh yeshivah,” but at the end of the day I was just one of the guys. Once, I overheard my rebbi telling the menahel that I have the perfect balance of Torah and derech eretz. I felt like a million dollars.

When I was in beis medrash, some of the guys would kibitz about how I was going to marry the rosh yeshivah’s daughter and spend the rest of my life learning. I took this good-naturedly, telling my friends that I’d owe them shadchanus if the shidduch ever came to be. I certainly couldn’t deny wanting to spend the rest of my life inside the four walls of the beis medrash.

By all accounts, it seemed as though I was being groomed for Torah greatness. I was appointed rosh chaburah for my class, and I was asked to speak at any occasion or gathering. Every year, the rosh yeshivah picked me to be the student speaker at the parent orientation evening. I actually enjoyed public speaking; it came very naturally to me.

At the end of my third year of beis medrash, there was no question as to which yeshivah in Eretz Yisrael I was going to attend. Even before I broached the subject with any of my rebbeim, two of them came over to me independently and assured me that they had the right connections to get me in. Some of my friends who were considered top bochurim spent months desperately trying to pull strings in order to get into that yeshivah, but I was in after no more than a phone call or two. Not only that, but by the time I arrived in Eretz Yisrael I had my chavrusas arranged for me and a spot waiting for me in a prime dirah. I even had a seudah set up for me at the home of one of the rosh yeshivah’s relatives the first Friday night after I landed.

I’m not going to pretend that I was totally mufka. I knew that the reason I was enjoying VIP treatment was because everyone considered me one of the top bochurim — if not the top bochur — in this yeshivah for metzuyanim. While I was shteiging over my Gemara into the wee hours of the night, I’d sometimes hear arguments going on between bochurim over who was the best guy in the yeshivah. Some of the arguments pitted me against Chaim Gellerman, while others pitted me against Elimelech Strasser or Gavriel “Gabe” Harari, but I was always in the running for the number one slot. I kept a surreptitious eye on these challengers, adding to my learning schedule at times to ensure that I retained at least a slight edge over them.

The week before I left Eretz Yisrael, I made a siyum on Seder Nezikin — Gemara, Rashi, and Tosafos. The entire yeshivah came to the siyum, and even the rosh yeshivah stopped by for a few minutes, to everyone’s surprise. Not wanting to seem conceited, I acted as though I was embarrassed by all the attention that was being heaped on me, but the truth was that it did seem kind of normal for me to be up there saying over a complicated pilpul in front of hundreds of bochurim who were considered the cream of the crop of the yeshivah world. In my mind’s eye, I could just envision myself wearing the frock of a rosh yeshivah and standing at the front of a packed beis medrash giving shiur klali to bochurim who were thirstily drinking in my chiddushim.

When I came home from Eretz Yisrael, the shidduch phone calls started pouring in. There were days when my mother printed out over ten resumes, and by the end of bein hazmanim, her shidduch loose-leaf contained about 100 resumes, at least 20 of whom were the daughters or granddaughters of roshei yeshivah and gedolim across America. I took this all in stride, but my parents found it unnerving. “These people are not like us,” my mother said uncomfortably as she flipped through her loose-leaf.

The first girl I went out with was the daughter, granddaughter, and great-granddaughter of great roshei yeshivah, whose names are spoken with trepidation throughout the Torah world. The farher from her father went great, but it was downhill from there. I didn’t think I needed to marry someone very worldly, but this girl didn’t know what the word “indicative” meant! Not that knowing the meaning of the word “indicative” is important to the fabric of a marriage, but it was indicative of our inability to relate to each other.

At first, I thought that maybe the problem was that I wasn’t used to talking to females outside my family. I continued going out with daughters of roshei yeshivah, thinking that it made sense for me to marry someone who was committed to the type of lifestyle I wanted to pursue. But after I went out with a few more girls with impressive last names, I realized that I just wasn’t on the same plane as these girls. My upbringing had not been nearly as sheltered as that of the girls I was dating — my parents were both professionals, and my family was a regular balebatish family. Although Torah was the paramount value in our home, I had been raised to value all forms of knowledge, and my parents had always encouraged me to read quality literature and non-fiction.

It was hard to turn down girls from such chashuveh families, but I realized that at the end of the day I had to marry a girl, not a shver. Relieved, my mother began to look for a girl who was machshiv Torah, yet from a background similar to mine.

In the meantime, I made a siyum on all of Seder Nashim, followed a few months later by a siyum on all of Seder Moed. I knew all of the yeshivish masechtos cold, and I was asked to start giving chaburah in the yeshivah. It was weird, being single and giving chaburah to married guys, and for the first time in my life, my position didn’t feel natural. All I need is a wife, I told myself, and then I’ll be one step closer to fulfilling my dream of becoming a rosh yeshivah. Thoughts like these filled my head all day, and the quality of my learning was diminishing.

One day, while I was daydreaming during seder, my cousin Yechiel Rubin came over to tell me that he had the perfect girl for me. “This girl, Esti Birnbaum, reminds me of your sister Chedvah in terms of personality and background,” he said. “But she’s very serious about Yiddishkeit — she goes to shiurim, does a lot of chesed. She’s looking for a boy who’s going to learn for a few years before going out to work.”

I was about to tell Yechiel that I was planning to learn long-term, but at that moment it dawned on me that I’d probably learn for only a few more years before accepting a shteller. I didn’t consider that “going out to work,” though.

“Just try it,” Yechiel urged me. “She’s exactly what you need. You’ll see, this one will be different.”

He was right. From the start, I connected with Esti in a way I had never connected to any other girl. We seemed to agree on everything, and I felt as though I could talk to her forever.

Eventually, I told Esti about my aspirations of becoming a maggid shiur or perhaps even a rosh yeshivah. She paused for a while, and then said, “You know what? If I had heard that before meeting you, I probably would have said that it’s not for me, but now that I know you and I see how passionate and talented you are, I wouldn’t stop you from pursuing your dreams.”

In my heart, I wanted to hear something entirely different. I wanted to hear my future wife say, “My dream is for you to become a great rosh yeshivah as well, and I’ll do anything in my power to help you get there!” But I was 27 now, and in my head I knew that this was right.

A week later we were engaged. I was invigorated, happier than ever before, and I finally regained my energy and concentration in learning.

The first few years, things were great. I was shteiging, we had two children, and I felt very blessed. I finished Shas, I got smichah, and I earned a reputation as a talented darshan.

Around the time of our fifth anniversary, I started to feel some pressure to start earning a living. “When are you going to do something already?” my mother often prodded me. “This kollel thing can’t go on forever!” There were also a few comments to that effect from my father and my in-laws, and after discussing the matter with Esti, we decided that I should start putting out some feelers.

I had always hoped, even expected, that a shteller would fall into my lap when the time was right. I didn’t think that I’d have to actively look for a position, not after all the chaburos and derashos I’d given over the years. At the very least, I thought that if I’d mention to my rebbeim and friends that I was willing to hear of a shteller, the offers would come pouring in, just as shidduchim had come pouring in for me.

But the only offers that came my way were for elementary school positions, and I couldn’t see myself working as a third-grade rebbi, or even as an eighth-grade rebbi. I needed a more chashuveh position, one that was appropriate for someone of my caliber. I politely turned down all these offers, opting to wait for something more attractive to materialize. I was really hoping to land a shteller as a maggid shiur or shoel u’meishiv for beis medrash bochurim, but I knew that I might have to settle for a job as a high school maggid shiur. I wasn’t prepared to take anything less than ninth grade, though.

In the meantime, our finances were getting really tight, and the pressure of having to find a paying position was starting to get to me. Once again, I couldn’t learn with a clear head, and all I could think about during seder was whether to put the latest bill on the credit card and hope for the best, or dip into the chasunah money that we had put away toward a down payment on a house.

When Esti’s uncle offered me a management position in his business, I couldn’t say no. The job was eminently respectable — definitely more grandiose than a job as a third-grade rebbi, and certainly better-paying. It meant that I had to give up my dream of becoming a rosh yeshivah, but what was the alternative? To spend my days gluing arts ‘n crafts projects in a classroom of whiny kids and listen to hysterical parents at PTA? Thanks, but no thanks. I wasn’t cut out for drudgery — I had always been at the top of the food chain, and that was where I wanted to stay — even if it meant that I had to exchange the beis medrash for a boardroom.

Deep down, I blamed Esti for my failure to reach my true potential in harbotzas Torah. Had she been more committed to building me into a gadol, had she shared my vision of Torah greatness, then I could have overcome all the obstacles and found the shteller of my dreams.

Esti sensed that I held her responsible for the shift in my life trajectory, and she didn’t deny it. “I’m sure a rosh yeshivah’s daughter would have insisted that you hold out for the right shteller,” she reflected. “Her father probably could have pulled a few strings for you, too. But you can’t get stuck in a mold, you have to go where life carries you, you know what I mean?”

Yeah, I wanted to say. Life was carrying me to a bright future in the Torah world, not into a stuffy job in your uncle’s corporation.

Now, whenever I go to hear a shiur, I feel awash with regrets. As I listen to the rav or maggid shiur speak, I imagine myself standing at the podium, giving a far better shiur.

I was born to be a rosh yeshivah — everyone always said so — and there was no reason why I shouldn’t have been able to find a shteller that would have been a stepping stone to fulfilling my true destiny.

Then again, sometimes I wonder if I would have been better off without all the hype about my would-be destiny. It felt nice, at the time, but it hasn’t helped me all that much in life.

From my new perspective around the boardroom table, I see that you can’t really pursue a “career” in Torah the way you pursue a career in the business world. Had I been looking to teach Torah for the sake of teaching Torah alone, I would have had plenty of opportunities to do that. But I wanted to be a Torah CEO, so to speak — and maybe that’s why I’m sitting here in the boardroom today.

(Originally featured in Mishpacha, Issue 432)