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ICYMI: Pivoting Our Career On the Tip of a Torah Scroll, part 2

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 continues the conversation 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!

Doug: 00:22 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 This is a continuation of the discussion I started last week with Yechiel Kalmenson, Ben Greenberg and Corey Adler on how they pivoted from a life of Orthodox Jewish studies into a career in it. Thank you for coming back to join our conversation.

Leon: 01:03 Okay. So, I think a lot of people are asking themselves at this point, now that they have a better sense of what yeshiva was like and how very different it is from a secular education, how very different that kind of world is from sort of a normal working situation: How did you do it? How did you go from this really intensive… Yechiel, I think you said from 7:30 in the morning until 9 or 10 o’clock at night learning constantly, with a couple of bathroom breaks and a little bit of food and maybe a nap… go from that to learning to code or learning IT or whatever it was? How did you get through it? And in fact, Yechiel, since I mentioned it, why don’t you go first?

Yechiel: 01:42 So, I guess as I transitioned to programming through tech support, so I was doing that before. Though I knew I would have to move on at some point because tech support… There was, there was a limit to how much I could grow there and how far it can get. And actually, it’s funny, before you asked, you asked like, you know, “what would your mother think?” She was actually the one who, it was her idea. She had someone in her office who went to a bootcamp, (actually a friend of mine) who went to bootcamp and later got a job as a programmer. And she was telling me, “No, why didn’t you do that? You know, you’re smart, you can do that.” And I was like, “No, that’s not for me.” You know, in my head at least “no programmers were these genius hackers who had been born with a silver keyboard in their laps. And like, that wasn’t me. And like, you know, I might be smart, I’m not that kind of smart. And I like, I just kept telling her, “No, that’s not for me. I, you know, he could do it. I can’t.” And then I promptly went home and took my first coding class and been hooked ever since.

Corey: 02:42 For the record, my keyboard was platinum, not silver.

Yechiel: 02:46 Well, Ya know, we’re talking about the layman… Lay folks.

Leon: 02:50 right, well, he’s Brooklyn, you’re Chicago, you know, there’s a whole economic strata.

Yechiel: 02:55 Right. Anyway, so I took a few free coding classes online and got hooked and saw that this actually was something I could do and this was something I enjoyed. And once I realized that I was ready to commit to it for the long run, I enrolled in a bootcamp – FlatIron School. I don’t know if you heard of it. I took it part time while I was still doing tech support. So back to our yeshiva days, I would work all day and then code all night, up too late. You know, until 2 to 3:00 AM like three or four nights a week. But it was a transformative experience. I met Ben at the same bootcamp. He went to the same boot camp as me. He’s been bugging me ever since. And then half year later I got my first developer job.

Leon: 03:38 So Ben?

Ben: 03:39 So I decided to go to the Flat Iron school, as Yechiel did for the sole purpose and aim to continually bug him about my challenges in programming for the rest of my professional life. And I and to have someone to bother on Slack forever and ever and ever. But I also chose Flat Iron school in addition to Yechiel because I knew that I needed to retool and retrain and I knew I also didn’t have a lot of time to do that. When you have already a family and responsibilities, you need to make a career transition quick. There’s no time to go back for another four year program or two year program or even a one year program. And so the Flat Iron school at that point had a self paced program. I think it still does. I’m pretty sure it does. But it has a self paced program where you basically can do the program as fast as you can do it. And I tried to do it really fast. I left my job and I did it full time over the course of a summer – a summer plus a little more. Hours and hours and hours. And I actually think that spending four years in a yeshiva/college combined was a really great prep for that, because as Yechiel mentioned earlier, that days are very long. And balancing a dual curriculum of yeshiva studies in college meant that when I was in college, I was starting my day at around seven in the morning and ending at around 11 o’clock at night in studies all day between yeshiva curriculum and a yeshiva, (Beit midrash) study hall time. And combining that with traditional college classes. So the bootcamp – which is meant to be a very intense experience because it’s full time and it’s a lot of material – actually didn’t feel that intense. It actually felt less. So it was actually a pretty relaxing experience, although intellectually stimulating and it definitely pushed me in my knowledge and learning. I didn’t feel it didn’t feel overwhelming because I had that experience from combining yeshiva and college at the same time, which is a very intense thing to do. And so, uh, within a few months of graduating from the boot camp I also found my first job, and it happened to be seated right next to Yechiel in the same company.

Yechiel: 06:07 So I thought I’d gotten rid of him

Ben: 06:08 … on Long Island. Yeah. Cause everything eventually ends up back on Long Island. So we worked together for about a year, one cubicle apart from each other in a lovely place where it felt like you walked into the set of “The Office” every day.

Leon: 06:29 So I’ve been in it for 30 years and, and it’s amazing how many environments that show evokes for folks. It wasn’t just there.

Ben: 06:39 No, definitely not. Not this just in Scranton Pennsylvania.

Leon: 06:42 Okay. Corey, it’s your turn.

Corey: 06:45 So I went to NYU as previously mentioned I got degrees in computer science and Jewish history. Afterwards I went to Case Western for only one year of Grad school, which is a story in and of itself, but it is something that my brother, who has a Ph.d and just recently got tenure at Northeastern Illinois University loves to beat me over the head with on occasion…

Leon: 07:14 I was gonna say he doesn’t rub that in your face at all? Every five minutes.

Corey: 07:17 Oh he totally does . But I get to make fun of him because I make more money than he does.

Leon: 07:22 Well, a Ph.d in history or in political science only takes one so far.

Corey: 07:27 It does. That’s really true. That’s really true. So afterwards, then after Case Western, I went into the workforce and started worshiping at the altar of Stack Overflow.

Leon: 07:39 And who doesn’t do that? I want to point out that , recently I had the privilege of taking a few folks who were sort of in the adult version of yeshiva called kollel, which is for married guys. And they had been doing this for just a very little bit of money, but were learning scripture, Torah, all day long and realized – very much like you three did – that they needed to get a job. That their time of being able to do this was sort of coming to an end. And we also realized in the community that IT might be a wonderful transition point. And so I took them, in a period of about four months, from basically being at a point where the most technically advanced thing that they used was a flip phone. You know, not even a chocolate bar phone, but just one of the old dumb flip phones into programming, network engineering, sysadmin. And a lot of people said, “How could they do that? How could you take them so far, so fast?” And one of the things I want to emphasize for the folks who are listening is that the yeshiva program is not one that’s structured to tell you the answers, (which we alluded to before). It’s not about, “do you know the answer to this test?” “Okay, I pass the test . Moving on.” It’s, do you know how to think about the material? Do you know how to ask yourself – not just “what is the question and the answer”, [but] “why is THAT the question? Why did they ask that question here? They could have asked any one of a dozen or two dozen or a million possible questions about this material. Why did they start there?” And when you start to look at information that way, why was that the question they asked? Why was that the answer they gave? Why didn’t they give this other answer? When you start to think about that, your brain begins to process information in a very different way. And what that means is that you can categorize and digest information – especially IT information – much more efficiently than folks who might’ve come up through a more traditional learning program. And we’ll talk about that in a little bit, but I just wanted to highlight that because it came out in each of your stories. So I’m curious on the flip side, what about this transition to IT do you think was harder for you three coming from yeshiva than it might have been for folks coming from a different route, from a more traditional American educational route. Yechiel, how about you go first?

Yechiel: 10:11 I guess the main point is like Ben mentioned, it applies to any career change. I don’t know if it applies specifically to someone coming from the yeshiva or from the rabbinate. The lack of formal education in the field, with me I didn’t get a computer science degree. I didn’t go to college for four years learning this stuff. And I know there are people in the field who believe that that is a hindrance. In my professional life, I didn’t find that to be the case. I mean I appreciate the value of a computer science degree. I mean it teaches you the theory behind computing, the theory behind… and it is something that helps me in my life now. But to get started, it’s like, when you’re a carpenter, you don’t have to know the theory of how the tools work, how, wood works. All you have to know is how to actually take a saw and a hammer and a nail and make things work. And that’s something you can pick up. My first job as a web developer, that was literally just banging tools and nails together. And sometimes actually did feel that way. Like Ben can attest. And even though now I’m doing more backend-y, computer science heavy stuff, that’s all stuff I was able to pick up later on. I was able to pick it up on the job as they say.

Ben: 11:29 I often imagine, or conceive of our projects together in our first job together as we were building a sukkah out of code and a sukkah is… during one of the Jewish holidays in the calendar year, we’re meant to go outside and build these temporary structures to dwell in for a week, and they’re very fragile structures, that can easily yield themselves to the wind, to rain, to cold. And that’s the intention behind them – is to reflect on the fragility of life. And so, often times, the code we’re building in that first job felt very much like this sukkah of code. Um, the fragility of code.

Yechiel: 12:14 And if I can extend that analogy,

Leon: 12:17 Of course you can! We KNOW you can.

Yechiel: 12:18 There’s a popular meme that goes around every year around Sukkot time (which is the holiday when we build the Sukkah), of a photoshop-ed sign at a Home Depot saying “Dear Jewish customers: Unfortunately, we don’t know what the thing that connects a thing to the thing is. You’ll have to be more specific.” And sometimes googling programming questions can feel like trying to figure out “what is the thing that connects the thing to the thing and does the thing, it makes the thing work?

Ben: 12:46 It’s an interesting question you asked. And I think for me the biggest differentiator there was: ultimately that the work I’m doing nowadays is not imbued with the same level of… sanctity? Uh, the same level of holiness, the same level of devotion and dedication that the work I did before was imbued with. And and I think in some ways it was both simultaneously challenging to come to terms with that, and come and reckon with that; but it also has made my life a lot easier. It both a challenging thing… I’m used to working in what I do 24 hours a day and having no differentiation between work and life, and yet getting used to having the differentiation between work in life. And having a time when I’m not working has actually been really pleasant. And discovering these things called “weekends” has been really nice. I didn’t know what they were before and now I know what they are and they’re… It almost feels like the episode of “Downton Abbey” when the matriarch of the family asks very naively and very innocently – but also from a great place of great privilege – “A ‘week end’? What is a week end?” I asked that out of, not great privilege, but out of great stress. “What is a weekend?” And now I know what a weekend is and I never want to lose it ever again.

Leon: 14:28 I just have to emphasize, again, for the it folks who listen to the show, that if you feel like you’ve been overwhelmed, just think of the hardworking rabbis who have… you know, we talk about 60 hour weeks in IT and “Oh my gosh, we have a Sev one call that went all night” and things like that… That if you wondered if there was something that was a notch higher, apparently the rabbinate is it. So just to let you know. Okay. So Corey, how about for you?

Corey: 14:56 For me the most difficult thing was just trying to find the right balance between my work life and my religious life. So in keeping those two worlds kind of separate, but kind of mingled. But then also having to try to explain to people what that meant. So try to explain to my boss, “No, I’m sorry. I understand that there’s a sprint launch coming up on Monday, but I can’t make it because there’s the holiday” Or in winter time, “Yeah. I’m sorry. I can’t be at a four o’clock meeting on a Friday…”

Leon: 15:33 …because sundown is a half hour from now.

Corey: 15:35 Yeah. The Sabbath is starting and I just can’t make it or “Yes, I’m very appreciative that you bought lunch for everybody, but I can’t actually eat this.” And “Yes, I understand. And no, this didn’t have to be blessed by a rabbi” Or “No, I can’t make a 7:30am meeting in Pennsylvania because I’ve got to attend morning services.” And also the idea that so many times – especially earlier on in my career – I would run into people who are doing 50 – 60 hour work weeks, and they’re telling me all about working on the weekend and doing some Saturday work. And for me it’s, “Well, okay, well how am I going to make myself look like I’m working as hard as they are, but I have one less day to put in the same hours that they are?” So it was really trying to maintain that balance between my work life, my professional life, and having my religious life. And where I was allowing the two to kind of coexist.

Leon: 16:41 Interesting. Interesting. All right, so we started to hit on it, but I want to take the flip side of ‘what was easier, coming from a yeshiva background’? What did you find about the transition to IT that was easier for you? Again, we talked about a few things, but is there anything else you wanted to add?

Yechiel: 16:55 So I guess like you mentioned earlier, yeshiva thinking, for those who had a chance to look a little bit at the Talmud, yeshiva thinking, or yeshiva learning really trains you for thinking in abstract concepts. When you’re programming, you’re always trying to abstract things. You have a problem, a real physical world problem and you needed to abstract it into the idea what is the problem… what’s the question behind the problem? What’s the ultimate problem? And there are layers upon layers upon layers of abstractions. And I found that my time in FlatIron… I always, like I told you I’m a teacher at heart. I was always going back and helping students. And I found that this is something that a lot of people coming in from other fields struggled with that I struggled a lot less. Just idea that like when your screen says “x”, it doesn’t mean “x”. It means the idea behind “x”. It was something that came more naturally to me and that’s yeshivas in general. Specifically. I learned in a Hasidic yeshiva, which puts a stronger emphasis on philosophical and Jewish philosophy. So they were constantly abstracting stuff. Going layers and layers deeper into the ideas. So that’s one idea which you touched upon. Another idea actually, which I found interesting, which is not universal to tech, but and my company, Pivotal, we’re very strong on the idea of pair programming. Like literally that’s all… Like all day, every day. Every bit of code is written by a pair. We don’t, we don’t work on our own. We rarely ever solo on our own. And that that’s a challenge to a lot of pivots moving into Pivotal. But actually at yeshiva, that is how we do all of our learning. Most of our learning is not done through lectures or listening to rabbis teach. There is some of that, but most of the learning is actually done in a system called a chavrusa, which is two people sitting together and learning together, trying to figure out the passage of Talmud, trying to figure out the commentary together, and delving deeper and deeper. So the idea of back and forth, exchanging ideas, thinking out loud, breaking a problem down together with someone else is something that came naturally to me and which I actually enjoyed when I came to Pivotal.

Corey: 19:10 Does that make yeshivas agile?

Yechiel: 19:11 Yes we are. We have a sprints. We have…

Leon: 19:14 Oh my gosh. Oh my gosh, you’re right! Yeshivas are the original agile organization.

Ben: 19:22 So who are the product managers in the yeshiva?

Corey: 19:26 The Mashgiach?

Yechiel: 19:27 The Mashgiach is sort of the supervisor who lays out the road map, tells you which material you’re responsible to cover over the next week or so. And then you break off. And then at the end there’s a retro where the Rosh Yeshiva, the head of the yeshiva gives a lecture on the material.

Leon: 19:44 I see a blog post – a very serious blog post on this

Ben: 19:49 In the Torah && Tech newsletter.

Leon: 19:50 This is awesome. Okay. So Ben, how about you?

Speaker 4: 19:54 Everything Yechiel said resonated and I would say just to add a little bit to that, the ability to switch back and forth between the concept and the implementation of the concepts. Between finding in the details, in the practical details, finding the conceptualization and then in the conceptualization, being able to go into the practical details, back and forth I think is very much a part of the world of programming. And I did also see it as an area that was very hard for a lot of people to come to terms with. That “I’m looking at this line of code and I know this line of code is executing this following thing, but in the execution of this following thing, it’s also demonstrating to me this programming concept. And I see the concept through its execution” – is actually just a natural part of learning in the yeshiva world. And it just makes a lot of sense, it made a lot of sense to me from the beginning. I think that’s a wonderful thing to port over from yeshiva life into IT life.

Leon: 21:13 That’s beautiful. Corey.

Corey: 21:16 For me, and I touched upon this earlier, which was the idea of having to go step by step through the thing. You can’t just jump to the end. And I’m sure we’re aware of some of the, the traditional introductions to the idea of logical coding, like the, the old “Peanut butter and Jelly Sandwich” example. Tell me how to make a peanut butter and Jelly Sandwich.

Leon: 21:43 And if you’re our friend Aaron Wolf, you actually have several loaves of bread and a few jars of peanut butter and a few other things. And you end up destroying a bunch of those as the students in the class attempt to try to tell you how to do that and do it wrong and realize the flaw in their execution instructions.

Corey: 22:00 Yeah. And it ended up destroying some students along the way.

Leon: 22:02 Well, right. But that’s just all part of the fun.

Corey: 22:05 That’s true. You gotta take your fun where you can

Leon: 22:08 Shout out to Aaron Wolf.

Corey: 22:12 So going step by step. And thinking about things logically, having to think things through – if something doesn’t work, trying to question what’s going on. Those things really ended up helping a lot when I started out.

Leon: 22:32 Nice

Leon: 22:34 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.”

Josh: 22:46 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: 23:00 So there’s these three rabbis that walk into a bar.

Ben: 23:00 Uh, that’s not how it goes.

Yechiel: 23:00 I think you totally ruined that joke.

Corey: 23:00 This is how that joke goes.

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