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ICYMI: Pivoting Our Career On the Tip of a Torah Scroll

In Yeshiva – a system of advanced learning in the orthodox Jewish world, there’s a saying: “Shiv’im Panim laTorah” – which means “there are 70 faces of Torah”, but implies that there are many equally valid ways of getting to a certain point. That idea resonates with IT practitioners, because there are many paths that led us into our career in tech. In this episode, Leon speaks with guests Corey Adler, Rabbi Ben Greenberg, and returning guest Yechiel Kalmenson about how that made that literal pivot, from yeshiva into the world of IT, and what their experiences – both religious and technical taught them along the way. Listen or read the transcript below.

Leon: 00:00 Hey everyone, it’s Leon. Before we start this episode, I wanted to let you know about a book I wrote. It’s called “The Four Questions Every Monitoring Engineer is Asked”, and if you like this podcast, you’re going to love this book. It combines 30 years of insight into the world of it with wisdom gleaned from Torah, Talmud, and Passover. You can read more about it including where you can get a digital or print copy over on Thanks!

Josh: 00:24 Welcome to our podcast where we talk about the interesting, frustrating, and inspiring experiences we have as people with strongly held religious views working in corporate IT. We’re not here to preach or teach you our religion. We’re here to explore ways we make our career as IT professionals mesh – or at least not conflict – with our religious life. This is Technically Religious.

Leon: 00:48 In yeshiva, a system of a dance learning in the orthodox Jewish world, there’s a saying: “Shiviim paanim laTorah,”, which means “there are 70 faces of Torah”. But it implies that there are many equally valid ways of getting to a certain point. That idea resonates with it folks, because there are many paths that led us to our career in tech. Today I’m going to speak to people who made that literal pivot – from yeshiva into the world of IT – and what their experiences, both religious and technical, taught them along the way. I’m Leon Adato, and the other voices you’re going to hear on this episode are returning guest Yechiel Kalmenson

Yechiel: 01:20 Hey, thanks for having me back.

Leon: 01:24 No problem. And also his partner in coding crime, Rabbi Ben Greenberg.

Ben: 01:29 It’s great to be here.

Leon: 01:31 It is wonderful to have you. And sitting across from me, because he’s also a Cleveland-based Orthodox Jewish Geek, is Cory Adler

Corey: 01:39 Live long and prosper, Papu.

New Speaker: 01:41 There we go. Okay. So before we dive into the actual topic at hand, I want to let you all do a little bit of shameless self promotion. Everyone, take a minute and tell the Technically Religious audience a little bit about who you are and how they can find you on the interwebs.

Corey: 01:58 So, hi, I am Cory Adler. I am a team lead engineer at Autosoft. You can find me on Twitter @CoryAdler and I am the constant pain and Leon side,

Leon: 02:08 Literally and figuratively, yes!

Yechiel: 02:10 Well, uh, my name is Yechiel. I’m a software engineer at Pivotal. Um, on Twitter you can find me @YechielK. My blog is at, and I also co-author a weekly newsletter called “Torah & Tech” with Ben Greenberg.

Ben: 02:26 And I am that Ben Greenberg that Yechiel just mentioned. I’m a developer advocate at Nexmo, the Vonage API platform. And I also am that coauthor of “Torah & Tech” with Yechiel, and you can find me on the Twitter world @RabbiGreenberg, or on my website at

Leon: 02:44 Great. And for those people who are wondering, we’re going to have all of those links and everything in the show notes. And finally I should just to round out the four, uh, Orthodox people of the apocalypse, I guess? I don’t know.

Corey: 02:56 You’ve been watching too much Good Omens.

Leon: 02:58 Right? I just finished binge watching it. Anyway. I am Leon Adato and you can find me on the twitters @LeonAdato, I did not attend to Shiva, which is a point that my children who DID attend yeshiva are quick to mention whenever I try to share any sort of Torah knowledge. I started out in theater. I know that comes as a complete shock to folks who wonder why I could do that if I’m so shy. It’s almost as weird a path to IT as Torah is. And one that’s definitely informed my understanding along the way. But again, we’re focusing on this yeshiva path and that’s where I want to start. I want to hear from each of you, where you started out, what your sort of, growing up experience was.

Ben: 03:41 Uh sure. So I guess I’ll start. So I grew up in San Diego, California, a little far also from the center of what seems like the center of Orthodox Jewish life in America, in New York City. But I moved to New York for Yeshiva and college at the same time. And I went to a yeshiva college called in English, the Lander college for Men, and in Hebrew, or in a New York accented Hebrew, The Beis Medrash L’Talmud, which was and still is in Queens, in a little neighborhood in Queens called Q Gardens Hills. And so I was there for four years, right, that simultaneously yeshiva and college. And then after I graduated that I said, “I’m not done with yeshiva.” So I went for another four years to another yeshiva, this time to study for a rabbinic ordination. And I did that at yeshiva called – and they only have a Hebrew names so I apologize for the three words in Hebrew here – Yeshivat Chovevei Torah, which at that time was based near Columbia University in the upper west side of Manhattan, and is now in Riverdale, which is a neighborhood in the Bronx, also in New York City.

Corey: 04:55 So I guess I’ll go next then. I grew up, born and raised in Chicago. I went to Skokie Yeshivah, and that’s yeh-shivuh, not Yeshiva. Why? It’s that way. Nobody knows.

Leon: 05:07 But they beat you enough until you just stopped saying it the other way.

Corey: 05:10 You get shamed if you say it the wrong way there. After high school I went to tlearn in yeshiva in the old city of Jerusalem for two years at a place called Nativ Ariyeh. Afterwards I came back to the United States and went to New York University. Not “YU”

Leon: 05:30 Yeah, NYU, not YU. I went to NYU also, although we didn’t know each other because I’m old and you’re a baby. Okay. So that means Yechiel you’re bringing up the rear on this one.

Yechiel: 05:43 Yeah. I’ll round off the lineup. So, I was born and raised in Brooklyn, New York, center of the world. But for yeshiva, I left town. I went to Detroit, I was there for five years after which I went to a yeshiva in a small village in Israel called Kfar Chabad. Then I came back to New York and I studied, for my Rabbinic ordination at the Central Chabad yeshiva in Crown Heights in New York.

Leon: 06:10 Fantastic. Okay. So now we get to laugh at ourselves when we were young and idealistic and had no idea what the world was going to throw at us. What were your plans at that time? Like what did you think life was going to be like? You know, IT may not have been your ultimate life goal. So what did you think it was going to be? Yechiel we’ll go backwards. We’ll start with you this time.

Yechiel: 06:32 I’m glad you can laugh because I actually look back to those days pretty fondly. So back then I was of course very idealistic. My plans were to be a Chabad rabbi. For those in the audience who don’t know Chabad is a sect within Orthodox Judaism. And at least for the sake of simplicity all I’m going to say about them is that they’re very strong into Jewish outreach and bringing Judaism to unaffiliated Jews, all Jews. So back then I had plans to be, to go out somewhere in the world and be a Chabad rabbi and that’s what I was studying towards and what I was learning. And in fact after I got married, I even did live out part of that. I moved to Long Island for a few years and we helped a local Chabad house until eventually the bills caught up with us and we realized that it wasn’t paying.

Leon: 07:23 So Ben, how about you?

Ben: 07:24 So I first of all, I do want to comment on the fact that only a Brooklynite would think “moving out of town” was moving to Long Island, New York. I do just want to make that comment as we’re engaging in this conversation.

Leon: 07:39 It is definitely the New York state of mind.

Corey: 07:41 Yup.

Ben: 07:42 And I also do want to say another wonderful thing about… well *a* wonderful thing about Chabad: In my role now is a developer advocate. I do a lot of traveling and I have encountered and have had the great fortune to spend, many Shabbatot and holidays – many Jewish Shabbats, Sabbaths – with Chabad houses around the world and have truly seen the diversity of both Jews and non Jews who attend Chabba for Shabbat meals, for Shabbat services. Just a couple weeks ago I was at Chabad in Venice in Italy and saw just really like every, every type of person. The whole spectrum of human life, it felt like, was present in the Jewish ghetto in the courtyard, celebrating Friday night services and dancing in the streets for Shabbat services with the Chabad. So it was really just quite beautiful. I had such a wonderful time in yeshiva for those eight years, I decided I actually wanted to be a rabbi and so I spent about 10 years of my life actually working as one. And I worked in Cambridge, Massachusetts as a campus Rabbi, A Hillel Rabbi, which is central for Jewish student life on campus. And then I went from there and I worked as a congregational rabbi in Colorado. And then I actually did some community organizing work after that in Chicago around gun violence and immigration reform. And so I kind of got to experience both nonprofit Jewish organizational life in the latter part of my career in the Jewish world. And then also in the beginning part, more traditional forms of being a rabbi, like a campus outreach and congregational rabbinate, the synagogue / pulpit rabbinate. So I actually did it for a bit and I feel fortunate that I’ve had that opportunity.

Leon: 09:49 Wow. That was kind of the gamut. Okay. Corey top that!

Corey: 09:54 For me, actually, I’ve known since fifth grade, pouring over old Tiger Direct catalogs

Leon: 10:04 Oh that brings back…,

Corey: 10:04 I’ve known for a long time that I wanted to get somewhere into the tech industry. But I always, I imagined myself originally going into programming video games. I loved playing Starcraft and Madden and all these fun games and I wanted to actually work for one of these companies and imagined it was going to be so much fun programming video games for a living.

Speaker 1: 10:32 So, so you didn’t, you didn’t have visions of being a Chabad rabbi on Mars?

Corey: 10:37 No.

Leon: 10:38 Okay. All right. Okay, fine. So, um, along with that, along with what you thought was going to be, what was the part – because I know a lot of the folks who listen to Technically Religious don’t have a window into this world. So what was the thing that you enjoyed the most; or the most impactful thing about that part of your life that, you know, the time that you were learning in yeshiva? What was it that that really just, you know, would have drawn you back? That you would’ve gone back again? That you look back most fondly.

Ben: 11:05 So for me, I think there are very few spaces in life, or opportunities in life where you get to just sit and ask questions, meaningful questions, and engage in the pursuit of trying to figure out what… meaning: trying to figure out the intentionality behind why… why you do things, why you don’t do things? And get engaged in just intense philosophical, theological questions ranging from sometimes the most pragmatic – like, “Is my dishwasher kosher?” And all the ramifications and permutations of that; To very theoretical questions around, “Well, who possesses greater reward for doing a good deed: somebody who is obligated to do that, or somebody who’s not obligated?” And spending hours delving deeply into questions like that. Where else do you get the opportunity to do that, and just take the time? It was a precious gift to have that time and to have a carved out dedicated space for those kinds of ponderings and intellectual pursuits.

Leon: 12:15 Nice. Nice. Corey, how about you?

New Speaker: 12:19 For me it was the ability to stop thinking about the end result and focusing on those individual steps that lead to that end. Quite often we, as a society and as individual people, we end up trying to jump to the conclusion trying to find … just go straight to the end, see what happens. But when you’re learning, Talmud in particular, you may already know what the law is before you started learning a particular section. You may have read it in some law book else elsewhere before you even seen this discussion. But that doesn’t mean you’re going to know all the particulars. You don’t know what all of the edge cases are, as we would say. Arguments for and against various positions. And even on something simple like, “hey, my animal just caused damage to your animal.” Like, what do we do in this circumstance. Even that, just getting that ability to focus in and delve into the steps versus getting straight to the end.

Leon: 13:25 Nice. Okay. Yechiel anything to add to that?

Yechiel: 13:29 Yeah. For me it was actually, the fact that how yeshiva was a world where you’re totally immersed in – like people I speak to are generally shocked to find out that a regular day for yeshiva boy, or yeshiva, bochur in our parlance, would start at 7:30 AM and go till 9:30 PM sometimes. And it’s nonstop learning. You have a small break for eating, obviously for the three prayers every day. But other than that, it was just nonstop sitting and learning for over 12 hours a day. And that’s something that you don’t find anywhere else. It was, I think, a totally life transforming experience

Leon: 14:07 You know, for those folks – and again, I didn’t attend any of that, but I watch, I’m watching my kids go through it – and it’s a very different thing than sort of the secular educational system where the goal of every school child is, “how do I get out of this as fast as possible? How do I skip as much as I can? How can I just memorize the questions for the test.” This is a culture, this is a world that, as I like to tell folks, it’s almost that nobody cares about the answer. The highest praise, the highest reward you can get from a teacher is “you asked a really good question.” And that says something about the attitude that’s there. That we enjoy this, we enjoy the playfulness with ideas.

Yechiel: 14:51 And to add to that, that’s actually a big difference between studying in a yeshiva for example, or studying for a degree or for a certification or whatever. Whereas in most cases you’re studying, you’re trying to gain a piece of knowledge. You want to… you’re learning for your degree, so you want to know all that. Let’s say you’re learning for your law degree or for your computer science degree, wheatever it is – there’s a certain piece of knowledge which you want to acquire. In yeshiva it’s not about learning the subject, it’s about, like I said, it’s about the journey, not about the destination. It’s about spending the time learning. It’s not like if you can finish the tractate of Talmud quicker, then like, “okay, that’s it. You can go back to you know, to your house and go to sleep.” That’s not what it was about. It wasn’t about gaining a particular piece of knowledge. It was about the process of learning.

Leon: 15:38 And the joyfulness of… taking joy in the process. Given that: Given how wonderful it was and how exciting and fun it was, what made you decide that you are going to pivot away from it? That you weren’t going to become the Chabad rabbi, Yechiel. That after 10 years as a pulpit rabbi or organizational rabbi, you’re going to make a move and specifically into IT What, what was it that got you to that direction?

Yechiel: 16:04 Okay, so I’ll take this one. So as I mentioned earlier, for various reasons we wont’ get into, the rabbinate didn’t work out at the time and got to a point, you know, a growing family, bills don’t pay themselves., food doesn’t put itself on the table. So I started looking outside of the rabbinate for other sources of income and tech was a pretty natural choice for me. When I was a kid I was that kid in the back of the classroom with the mechanical pens taking it apart, breaking and trying to figure out how the spring worked. Or anything. I don’t know how many watches my parents bought me that ended up in like a mess all over my desk. So that was always something I enjoyed, figuring how things worked. And when computers, when I started getting access to computers, that was like a whole new world for me to take those things apart. I, I’m not one of those kids like wrote code at the age of 10, but I did enjoy figuring out like, you know, what tick, what made computers take, how they worked on what was going on under the hood. So when I was looking for something to do, my first job actually out of the rabbinate was doing tech support. Which was great for me because I was learning these different systems and how they worked and how to troubleshoot them and how to debug them. And it slowly progressed from there. Eventually programming was just the logical next step and haven’t looked back since.

Leon: 17:25 So Ben how about you?

Ben: 17:26 So I’ve always been a bit of a geek and I’ve always loved tech. In fact, so this is my second career, but in many ways it’s also my third career because when I was in high school, I founded a hacker conference with my friend and partner in crime at that time. And we actually just celebrated its 20th year of the Hacker Conference in San Diego, and it’s one of the largest infosec conferences in southern California to this day. And we had our own little network penetration, security testing company back then as well. We didn’t necessarily use those words back then because then the mid to late nineties, it was all kind of new and everything was evolving at that point. We were kind of right on the cusp at that point. And so it was actually a really exciting time to be in it. And so when I decided that it was time really to take a break from the rabbinate take a break from the clergy life – 10 years in the clergy is kind of like 40 years in another career. And I was ready for a bit of a break and it was also correlating with the desire of my family and I to think about a move out of the States into Israel. And to start thinking about ways in which we would support ourselves in Israel. And the idea of going back to a career in tech, which was something I was always interested in to begin with. And I had a bit of a history in it, albeit a very old history at that point because tech has moved and has continued to move to move really fast. So things that I was doing in the 90s like writing some code in Perl for example, would be like totally… Right?

Leon: 19:11 Perl!

Everyone else: 19:11 (general mocking of both Leon and Perl)

Ben: 19:16 So one of the conference I was at a few months ago was at FOSDEM, which is one of the largest open source conferences in the world. Totally a free conference. Unbelievable amounts of people are there. It’s in Brussels or, at least was that year. And literally every sector of the tech community is under that roof, including Perl associations and Perl groups.

Leon: 19:39 Ahhhhh. It’s my happy place!

Ben: 19:39 And it was so beautiful to see that, it brought back so many memories of my childhood. And so tech felt like a good place to go back to. And it’s a very good career and a good career path where I live now in Israel. So it just, it made a lot of sense,

Corey: 20:00 Dear God, you guys are old.

Everone: 20:01 (laughter)

Leon: 20:05 OK Corey. All right. So what about you?

Corey: 20:08 Well, I second the idea of being a total geek as you well know, Leon. But for me yeshiva was always just the first step in a journey. I knew I was going to end up in IT, but I knew that the whole yeshiva experience was something that I needed for myself in my life, it helped me become more independent. It helped me figure out a lot of things about myself along the way. So I knew I needed that. I knew what I wanted to get out of it and needed to get out of it, but it was not the permanent solution for me. I knew that eventually I was going to come back down to Earth as it were and…

Leon: 20:48 Oh yes. Come down from on high, the Crystal Tower of Yeshiva and back down to down to the dust, in the gutter,

Corey: 20:57 Which is better than the dark tower.

Leon: 20:58 Well, okay.

Corey: 20:59 Of Perl for example.

Leon: 21:01 Oh See, okay. See we had to go there. Al right. So I’m curious about this because again, it was such a pivot. Were any of you resistant to the idea at first? You had this opportunity, you each had a predilection for technology, so you saw that it could work. But was anything in you saying, “Nah, that just… Oh, you know, what will the neighbors think? What will my mother think?” Was there anything that held you back? Yechiel, how about you?

Yechiel: 21:27 So yeah, actually I was pretty resistant to the idea at first. Like I mentioned, I’ve always seen myself going into community service, going into adult education. Teaching is something that I really enjoy. I still enjoy it. I try to incorporate it into my tech career. Like the Torah & Tech newsletter and my blog and also at work mentoring, mentoring interns. Teaching is in my blood. And I always thought that I would be someone who taught, who led, who spoke. And in addition I was also, I was raised on the ideals of community service. So going off to the other direction was tough for me. Though what helped me come to terms was going again back to when I was a kid, a particular genre of stories that I really lovedwas stories from the old country, from the shtetl. There were the Jewish towns with a Jewish shoemaker and the Jewish tailor. And there’s actually like a class of Great Torah scholars who could have easily gotten a position as a rabbi or in some yeshiva teaching. But they specifically did not want to use their Torah as a means to support themselves. And as a kid that was something that really touched me and I sort of romanticized it. So now when I started looking away from the rabbinate towards working for myself and I realized that actually technology nowadays is the blue collar work of today. Today’s programmers and developers and sysadmins – those are today’s shoemakers and blacksmiths. And you know those are the people that make the world run. And the idea of supporting myself through my own handiwork started appealing to be more and more.

Leon: 23:11 It’s an interesting thought. I have met one rabbi who is also an auto mechanic, but that’s not the typical career path that you find for folks. So yeah, I like the idea that, IT is the next tradesman for, especially for itinerant scholars.

Ben: 23:27 I will say though that now having lived in Israel for about a year, this is an area where there are, I do believe there is a cultural divide between American Orthodox Jewry and Israeli Orthodox Jewry. And the fact that in my own neighborhood, I know somebody, for example, who has a Ph.d in Academic Bible from Hebrew University and works with his hands all day as a craftsman. And it just brings back to mind stories of maybe some famous Jewish carpenter from 2000 years ago that some people might have been around…

Leon: 24:03 Wow. We’re just going to throw little shade.

Yechiel: 24:07 Pretty sure this is your first all Jewish panel. So we had to, you know…

Leon: 24:11 Yeah, we had to at least take one shot.

Ben: 24:14 But I say that as a joke, but there’s so many people like that in my neighborhood and my community who have ordination or I would advance degrees in Jewish studies or both and who are not working in that field, who are not working in Jewish communal service. And yet they volunteer. They give classes at night or on weekends on Shabbat. They teach they offer sermons. Our community is basically… Our personal community, where we go to synagogue, our community in Israel is essentially lay-led. And so people take turns signing up an offering words of Torah on Shabbat and holidays and a lot of those people who do that are, those possessing rabbinic ordination. Or, if not rabbinic ordination, having spent years of their life in yeshiva and who had decided to pursue a career as opposed to making the Torah or Jewish life their career. And a part of that is just the economics of the country, that it’s just hard to sustain oneself in Jewish communal service in Israel. So people end up taking other jobs. But it’s also, I think there’s part of an ideal here of, we would call maybe “Torah v’Avodah” of Torah being combined with a job – of Torah and some kind of occupation going hand in hand. And that not being a less than ideal, but that actually being the ideal. So just an interesting reflection as I’m listening to this conversation and thinking about how I situate myself and sit where I sit now and can see both sides. And I’ve lived in both sides and the differences between those two.

Leon: 26:02 Nice. Okay. So Ben as long as you’re going, how about you? What was the challenge pivoting away from the rabbit into a career in coding?

Ben: 26:10 I think it’s a challenge that a lot of people who are going into a second career often face regardless of what their own particularities are, which is letting go of what others think; or what you think others are thinking. And for me that was a challenge. Leaving the rabbnic world was challenging because you – especially if you go to a hyper-focused mission driven rabbinical school, which I went to – there is, uh, a real sense of serving the community and that being the passion and drive of one’s life. And switching to another career can feel like you’re letting down your teachers, your mentors, your rabbis, your peers, your fellow alumni, you’re a co collegial community. But recognizing that what helped me was the recognition that all of those people that I just mentioned, they also care about you and they wants what’s best. They want what’s best for you as well. And if they don’t, they probably are not somebody you want to be invested in a friendship with to begin with and you shouldn’t be necessarily taking their opinion to heart to that extent. That anyone who cares about you, who wants what’s best for you, will recognize that maybe it’s time. Will recognize along with you, and honor the fact that you expressed the idea that maybe it’s time to switch careers and maybe it’s time to move to something else. And I think getting to that point where recognizing that others value you and care for you and are not looking down upon you or critiquing you. And if they are, it’s okay to say, “enough of you, you’re out of my life.” It’s okay to do those things and to put your life first. And what’s best for you and your family. Those were some major hurdles, but once I got over them became it became pretty straightforward.

Leon: 28:18 Nice. Corey!

Corey: 28:20 For me wasn’t too difficult because, as I previously mentioned, I knew I was gonna go into IT all along. For me, the most difficult part – was because I had grown up and been in some religious schooling system for my entire life – It was the idea, of leaving the cocoon as it were. And you know, now not everybody I’m going to meet is orthodox. Not everybody that I’m going to have to deal with in school or in work is going to be, you know, a member of the tribe as it were. You know, so there was a little bit of trepidation, but I knew it was gonna happen.

Leon: 29:12 Got It.

Leon: 29:13 We know you can’t listen to our podcasts all day. So out of respect for your time, we’ve broken this particular discussion up. Come back next week where we continue our conversations about “Pivoting Our Career On the Tip of a Torah Scroll.”

Roddie: 29:25 Thanks for making time for us this week. To hear more of Technically Religious, visit our website,, where you can find our other episodes, leave us ideas for future discussions, and connect to us on social media.

Leon: 29:38 So there’s these three rabbis that walk into a bar.

Ben: 29:40 Uh, that’s not how it goes.

Yechiel: 29:42 I think you totally ruined that joke.

Corey: 29:44 This is how that joke goes.

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