Shopify Distinguished Eng L10 Principal Engineering Career Story Regrets Ilya Grigorik

TITLE: Shopify Distinguished Eng (L10): Principal+ Engineering, Career Story, Regrets | Ilya Grigorik CHANNEL: Ryan Peterman DATE: 2025-10-24 ---TRANSCRIPT--- People that have to ask that question by definition are not principal engineers.

This is Ilia Gregoric. He grew to a distinguished engineer at Shopify, which is a VP level role. And I asked him what it took to get there. To be a really effective principal plus engineer, you need to have very good dynamic range. Technically, he turned down a clear path to director at Google to go back to being an engineer. This is a path that is vastly underappreciated and is actually surprisingly common for a lot of principal and then higher up roles. and his best advice might change how you plan your career. A better way, a more resilient way to build your career is to optimize for being the only person as opposed to the best person. Here’s the full conversation. You mentioned you went to Wateroo and I I I got to ask the smartest interns that I ever worked with, they came from MIT, Caltech and Singha University in China. But the best interns I ever worked with all came from Waterlue. And so I I’m curious, what is it that makes these Waterlue interns so strong? For me personally, the most important thing that uh Waterloo got right and better than most and I know that more schools have adopted this pattern, but it’s still not well well understood is their co-op program. So, what water did really well is they realized that yes, there is the academic portion of learning how to engineer and like what software design is all about. Uh but then there’s the hands-on and applied part. And instead of modeling it as hey you’re going to study for 3 years and then you have an optional kind of intermission style co-op which is what what most university operate on right you could take a year off or something like that to go and work in industry uh wateroo said you know what we’re going to just do a rotation where every semester you study you work you study you work you study you work you know what that means you don’t have a break in between you’re just constantly iterating through this loop but what it gives you is um at least six six shots on goal for trying things, right? And this actually has very positive effects on many dimensions. So, first of all, um it removes the stigma of trying things, right? Because uh many of us like we don’t know what what what’s going to stick with us. Kind of coming back to my earlier point about consulting versus something else or something else. I had so many of my peers going through university where we all started with some preconceived notion of what we wanted to do. was like, “Oh, I really want to go to Wall Street and work there.” And they they try one of the co-op terms there. And they’re like, “No, actually like this for whatever reason.” Mean like I don’t like the city or I don’t like the industry. I didn’t like the people. It like it just didn’t click for whatever reason, right? Same thing for like medicine or others or consulting. Um, and that’s really important to discover early. And the really nice thing is it’s a concentrated it’s like it’s a threemon sprint you get to try right and you have permission to try five more things at least without the stigma of looking at your resume saying hey like you you went to a role for 3 months you don’t you went to a role for 3 months you like are you really like committed are you like do I want to hire you it’s like no that’s my co-op right like that’s that’s the whole point so you could first of all try a bunch of things and get a kind of a good range of experiences under your belt um but also see the kind of the gamut of like hey here’s how a large company operates here’s a smaller company here’s a medium but like which which one resonates with me more right so it’s industry it’s uh the type of work that you do it’s the type of an environment that you’re in and I think that is really helpful on top of that you actually get exposure to like engineer things not learn the hypothetical and academic of like I know how a big onotation expresses this particular algorithm. It’s like I actually had to build the thing, right? Like and turns out this didn’t work or that particular solution worked or we had to solve it under these constraints and the whole big old thing was an issue because I was like sorting 10 items in an array. Who cares, right? It’s like pragmatic engineering. So I think that is key. um that is still a superpower of Wateroo and I wish more universities like it’s an open secret and I wish more people would copy it because it’s such a lever for success for people that go through that program. After you went through all of those iterations and all the co-op loops, I understand that you started your own company um which became Post Rank that was then acquired by Google. And I’m curious the story behind you choosing to found a company right after graduating from Waterlue. I graduated from Waterlue and as most students um I didn’t know know what to do. Um I wasn’t ready to to commit. Um so my escape uh which is which was a wellrun track for many is I’ll go to grad school. So I I applied and then got into University of Toronto actually. And during that summer in between um I had a couple of project ideas that I wanted to get off the ground. So I I had a particular itch that I wanted to scratch and the itch was if you think back to uh how Google was founded the key insight if you simplify it and boil it down that like Larry and Sergey had back in 1997 is hey um we could treat the link crap of the internet effectively as a feedback loop on what is good content. So if you and I create pages and we link to each other, that’s a mutual signal of both directions that there’s something there, right? So disconnected pages are not worth much. But in effect, it’s kind of a social currency. Links are a social currency. Right? Now, fast forward to 2010, 2011 when I’m sitting there, the web 2 revolution has already happened or like well underway. You now all of a sudden have dynamic content on the web, not static links, not static web pages, but we have comments on blogs, right? Blogs became a thing. Comments became a common thing. So my observation was, hey, if a conversation is happening on Reddit about an interview that Ryan has recorded like that means there’s something there. I don’t I can’t qualitatively say whether it’s good or bad. I just know that people are talking about it and that a signal. So what if you built a system that went out and aggregated all of these interactions and then built a better version of page rank effectively right links becomes one input but you know thumbs up and number of conversations and number of likes and all of these things become additional inputs and that was post post rank right it’s it’s kind of embedded in the name it’s it’s a was an algorithm for ranking posts based on social engagement kind of a child of the web 2 era still remember the day it was like July 8th when I released And then I didn’t sleep for 3 days because the servers were melting down. Not strictly because it was like such huge demand although there was. It was also because my code was terrible. So it’s kind of like brute force just throw more servers at the problem and then eventually you know optimize it out over the next couple of weeks to to get it back to a manageable set. So that becomes kind of this nucleus of hey there’s a there’s a feature there right and it got um it got good publicity uh which then turned into conversation hey is there a product here so I remember the juncture points somewhere late in May we’re kind of in the middle of all these conversations with investors um kind of unanticipated fork in the path right and I’m thinking what what do I do like I’m uncertain are we going to be able to close around can I do this because in a couple of weeks I’m supposed to start my my grad work and I’m looking at that syllabus. I’m like what are the courses I’m most interested in and I go through the list and it was like the the ones that immediately stood out to me about like entpreneurship and like how to do a company. I’m like wait a second. So, I could go and learn about this stuff academically and read books or I can like I’m literally having the conversations right now with the investors like I or I could just like go and like I I can read those books on my own time and I go I can go and try it which uh led me to reaching out to my adviser and basically asking hey can I take a a year time out you know I was planning to do this this year but how about I start next year and hemmed in hot and said okay I understand and you know come back to me in 6 months. Um to close that story, we did end up closing the round and that became postrank the company and uh I never did get to finish my uh so-called graduate degree. So in the process of building this company, I know eventually it was acquired by Google, but I’m really curious because I feel like a lot of acquisition conversations are behind the scenes hush hush. Um what does that kind of conversation look like like when they reach out for an acquisition? And maybe you can tell that story. It’s a lot less stressful than you make it sound to be. I remember we were actually we were building the product that I was describing and uh we were presenting at one of the conferences in the Bay Area and you know we got off stage and uh Phil Moody who was one who was the uh kind of lead PM on Google Analytics kind of walked up to us and like hey this this is cool uh do you want to have a chat? And I remember taking a train from San Francisco to Mountain View later that day, sitting in the conference room and him basically interrogating us about what is it that you build and then um ending the conversation with, hey, maybe we should do something together. It’s like, okay, well, tell me more, right? Um that’s a that’s a blank check for follow-up conversation. Um so it it was it was very friendly. There’s there’s nothing uh kind of uh more to it than that. And then uh what we learned uh after is this is right in the time span when Google and Facebook were uh like at war in terms of drawing the battle lines for social. Uh this is when Google woke up to the fact that Facebook is on a runaway trajectory and um all hands on deck. Google need. This is when Google starts working on Google+. Uh which of course has since been sunset. But it became this catalyze catalyzer with the Google for hey we we need an answer and they were looking for all the help that they could get and all the experience that they could acquire to speedrun this whole thing. Um and we became that catalyst for Google Analytics because what they saw in us is like they frankly they did not care for the uh PR product that we were building. what they cared about was uh the experience and some of the infrastructure that we we’ve accumulated that we could bring in to fast run and fasttrack this whole thing to say hey if I’m using Google Analytics I can get really good insights on how my social engagement is going and I can figure out how Google+ is helping me and all the rest um so that became the kind of the mutual point of win-win situation um that led us uh joining forces with Google Analytics in being brought in as an acquisition How do they determine leveling or compensation or any of that stuff? Google as many other tech companies run the same process. It’s usually kind of accelerated batch model, right? Where you bring in the whole team and and you kind of do a a wholesale evaluation, but otherwise um everyone on our team went through the panel through the full panel uh myself included. Uh so that that was that was the bar and really the exercise for them was to vet the quality of the team and then to figure out where kind of on the leveling uh do all the engineers stuck up. I see. Okay. So it’s it is just a normal interview process. What about in the case though cuz you’re bringing in company and assets and stuff. Is that just like a giant signing bonus or something or how’s that? it it depends on the company that that you know and then the deal of course so there there’s multiple layers to it exactly as you said right there’s the like there’s the IP there’s the customers uh there’s the people and you can treat those as kind of distinct conversations right so as so far as negotiation is concerned um are you acquiring the product what are you going to do with the customers right um is there IP there are you going to use the technology um many like there’s the aqua hire acquisition where you’re effectively acquiring the team you’re cool thing you built, but that’s not the thing I need you to be building. Let’s just put that on the shelf and let’s just focus on like rebuilding the thing um in our infrastructure. Um post rank was closer to that. It was not a full kind of aqua hire because they brought in and they used the IP, but for all intents and purposes, the thing that we built ourselves, we had to rebuild from scratch with the Google Analytics because you’re just operating at a completely different order of magnitude, right? And it was an amazing trial by fire if anything for our engineering team because we went from managing tens of thousands of analytics accounts and granted yes we were crawling the web at a fairly large scale to operating in a service that was literally executing on half more than half the internet right so like to to make a modification to a data pipeline I remember the conversations fondly um like sitting with our SR team and they’re like okay well you’re going to at this bit field right here. That’s going to be this number of exabytes of data. I’m like, “Oh my god, okay. Uh, let me think about this more carefully, right?” Because before that was not even a a conversation point for me and and my team. So um a lot of it was about the talent and bring making ensuring that they’re bringing in the right folks with the right experience and u that they’re capable of kind of hitting the ground running and and working with with the rest of the Google Analytics team. So I want to get into your career at Google and it sounds like you were placed initially in Google Analytics. I’m curious what the leveling was and the role. Were you a manager because you mentioned your you brought your team with you. Um so I was founder and CTO of Postrank and I joined as an engineering manager um because effectively that’s what my my role was um at Google and I was very invested in making sure that we build the right thing the right way and kind of manifest the vision of why we started this damn company to begin with because I strongly believed in like I want to help publishers understand that was still like me scratching my own itch of like I’m going to make Google anal analytics solve my problem. Damn it. Um and um I think we we succeeded um at that. It took us about a year to effectively rebuild our stack and the team was on a good trajectory and and that’s where I uh took us to back and looked around for hey what’s the next adventure? um I was in a really good direction uh within Google Analytics and I remember um a conversation with one of our VPs at the time where uh you know we were having one of these career sitdowns and he was like look um you have all the things you need you’re on track for director you know here are the things that I I could see I could see you take on and all the rest and like huh that sounds all exciting and like and I’m very honored that like you think I’m capable of doing this work but at the same time um I couldn’t not let my curiosity get the better of me like Google is such an amazing technical playground that even though that first year was a pressure cooker of like I need to get this thing shipped right and I’m going to work my my butt off to get it working I also was spending every free moment of time just like diving deep into various design documents and wikis uh Google is an open culture which is the thing that I loved about Google And I could approach anyone and everyone about um any piece of infrastructure, any product. And I leveraged that um and I learned a lot because you know I remember building Post rank and reading papers that were published about Bigtable this and Hadoop that and like trying to figure out how to replicate some of the magic that Google had and then I’m reading the internal design documents and I’m like oh my god this is three generations ahead of this paper that I was reading. This is amazing right? Like I wish the world knew about this right? And then I would half the time I would talk to the engineers. I’m like, “How come we never published a follow-up on this thing?” They’re like, “We’re too busy.” It’s not that it’s a trade secret. We’re literally too damn busy. Like, you know, if you find us the time and I was like, “Huh, well, that’s interesting.” Like, wouldn’t it benefit the entire world, the entire like internet if we did more of this? um which led me down some interesting conversations and I discovered this group within Google which was called make the web fast which is basically a skunk course project started by uh Sergey um around well how can we make the internet fast u and it’s a very kind of self-reerential self-motivating thing um that there’s very direct evidence that the faster the internet is the faster users brow the browse the web the more they use Google so So it’s a mutually beneficial relationship, right? So within that group, we had all kinds of fun projects. We literally built radio towers trying to figure out how to build more effective cellular networks. Uh you know, dug trenches built built towers. Uh we worked on TCP IP and trying to figure out how to reduce congestion. Uh we worked at optimizing proxies for hey, turns out that most humans write terrible websites. Could we just like optimize it out kind of dynamically as a web server plugin to um hold on a second when we say make the internet fast? What does that even mean? Like we know it when we see it and when we feel it, but if you had to put a number on it, how do you express that? Right? So if you if you walk the full dynamic range of those questions, you like it’s it’s an just absolutely amazing laboratory of like experiments to run. And I was really fascinated about about that. And I remember at that at that point in time I I I realized that I had I had an opportunity to cash in some chips and I could say look um I I see a path towards kind of career growth as a director in this and that and that that would be a great achievement. On the other hand, I could take a step back. I could take this lateral step and go and work as an IC in this field. I’m actually not quite even sure how I’m going to contribute. I just know that this is a really cool area that I’m passionate about and I’ll hopefully probably find something useful that I can do there. Um, but that would definitely take me off the career track, right? I remember that conversation. It was like, well, you know, if uh IC bar at Google is actually really high, so if anything, you’re going to be downleveled likely um and you’re going to reset your track. I was like, okay, I think that’s a trade worth having because I get to control my time. I get to work with people I look up to and I get to work in a particular on a domain that I think is just absolutely fascinating. So, I made that pivot and in retrospect it was an amazing right decision for me because um it allowed me to kind of flex my curiosity and technical muscle in a completely different direction. you turned down this more clear-cut director path which would be the clear-cut growth path for career um to optimize for other things which was sounds like intrinsic motivation in the work curiosity and also sounds like maybe you got some time back is that the math you were doing in your head and making that choice exactly that it was and there was a lot of uncertainty in that process but um this kind of a a repeating arc through my career where as a manager your time is managed by others, right? Like you you are in the service of others and I wanted to uh shift gears and and go into a mode where I have more self-direction and go pursue some like interesting research or uh projects that like where I can apply my own skill set in a unique way. So later I saw that you switched back to management and you’re director of uh developer relations at Google. So what was the rationale then switching back given what you just said? Yeah. So, I’ve seesawed um a number of times through IC to manager and I think this is a path that is vastly underappreciated and is actually surprisingly common uh for a lot of like high performing um IC’s and like you’ll find in in principle and then higher up roles and the observation is um I think as a tour of duty uh when I’m when I’m doing management um to be a really effective like principle plus engineer you need to have very good dynamic range technically right and you can you can work well at a low level of the stack you can also zoom out and look at the business requirements kind of deeply understand what’s actually necessary where can you relax constraints uh where can you where you need to hold hold the line and all the rest and once you get attached to certain projects like some projects you can execute and you call it done you’re like a great I solved that problem right but many problems that are handed to you they they become they come as nebulous statements that then evolve into huh this is actually like a team’s worth of effort like now that we’ve understood the shape of this problem and uh what often happens is you you kind of you see this pattern of um some individual doing the trailblazing work path finding where where we need to climb and then they find themselves okay now I need to recruit a team of people to help me actually build the thing like I know how to get to the top of that hill with a machete. But now we need to build a highway, right? And to build a highway, I need a team. Okay, well, let me go find a team. Before you know it, you’re kind of you’re you’re a TL, right? And you’re exercising your soft power to help direct people and all the rest. It’s not a far stretch to switch to a manager, right? Because like, well, now you’re doing performance management as well, plus a few other tricks. But often times, you’ll find kind of yourself um managing or being responsible for the direction of a broader team. And before you know it, like I think it’s a natural transition to say, well, okay, fine. I’m going to like manage this domain. I’m going to manage this as a product team. I’m going to manage this like the growth of the individuals and the rest. And that’s completely fine. That’s what happened to me with developer relations. Um, when you think back to the kind of the set of problems that I that I shared with you, um, I ended up gravitating towards the question of how do you measure performance? And I found myself doing a lot of web standards work. I got engaged with W3C and ITF and and trying to figure out hey what kind of metrics can we define in browsers such that we all have a common ground truth for how to measure performance and that was great a lot of that and that was my kind of IC contributor role um then you get those metrics into browser and then the problem becomes great how do I get community or ecosystem adoption on this thing well I need to go tell people and I need to convince them to adopt it right uh and integrate it Well, now I need to go talk to all of the analytics vendors. Uh, let me go talk to all the open source projects, right? That problem does not scale with one human. Like, you really need help of other humans. This is where the go to market and the kind of developer relations part came in. And I quickly realized that like it would be really helpful to have a team of people that can focus on this thing. And this is a thing we deeply care about. We want to accelerate the adoption of these things. It’s kind of my my um model based on prior experience was look if we just leave this ecosystem be as it is in 3 to 5 years time we will probably see the adoption that we want but I’m not happy with 3 to 5 years like my question is how can I compress it into one to two years ideally one year or less right and for that to happen we need to inject we need to inject energy into the system that energy is a team of people great fine let me switch to the my manager role. I’m going to go recruit people and I’m going to like put my organizer hat on and we’re going to go and execute this problem. So when you say tour of duty, it’s this starting as an IC doing pathf finding and then becoming a manager potentially is all in service of a mission or a problem like you you see some problem maybe em is the best way to solve that problem maybe IC is but it’s really all about the problem. Exactly. Exactly. And it’s kind of like your relationship and your commitment to the problem, right? Because not every problem has to become your mission. Um I’m often engaged in projects where I’m participating. I’m actively contributing and then I say, “Look guys, you’re you’re well on the way. Like you have the right vector. Go execute. You have everything you need. Like you don’t need me here.” And in fact, that’s my kind of measure of success as a as a principal engineer often times, right? I don’t if the team is dependent on me pro that means that I’m probably doing something wrong because my job is to uplevel the team and make sure that they can deliver this thing self-sufficiently. So if you know the uh the Homer Simpson meme where he like disappears into the bushes. Yeah. Right. Like it’s like kind of like that like if I can pull that off successfully on a project and the team continues executing in the right direction with a good velocity like that’s success for me oftent times. Now, occasionally I stumble into a problem where I’m like either I’m like just it’s in my bones and I feel like I need to be like I want to own that problem and see it to it logical conclusion. um or I have some unique position or leverage in it where like yes I’m the right person to take on the broader responsibility and kind of execution of the team to see it through completion and it’s a judgment call for which you know when you pull that off and when you say okay this is going to be my tour of duty like my job is over the next I know that I’m committing for the next two years or something to like really run this thing own this ship and that’s my responsibility and you know what at the end of it I’m gonna do the same thing I did before. I’m gonna like my success I have I need a succession plan and my succession plan is either we solve the problem and it’s done or I’ve set it on a trajectory where I can successfully pull back and focus on the next thing and to focus on next thing. I’m going to become an IC again and go find the next thing to solve. I know later the story continues with you went to Shopify, you became an IC and you went from a principal engineer to a distinguished engineer. I’m curious what is the tour of duty there that got you promoted? One of the I think underappreciated or misunderstood aspects of being a principal engineer is when people ask what what does what do you do like you know g give me give me a job description because I want to become a principal engineer like what are the boxes I need to tick and the answer is actually embedded in the question because people that have to ask that question by definition are not principal engineers right because the problems become ambiguous enough at that level where you kind of have to figure it out yourself. Like my expectation for I I mentor a lot of uh principal engineers that come into Shopify. Uh my expectation for someone coming in that level is look uh you’re basically to use an analogy here, you’re going to be dropped parachuted into foreign terrain. You’re on a reconnaissance reconnaissance mission and within the first seven days you should figure out the lay of the land and figure out where the problems are. Build alliances with your directors, VPs, whoever it needs to be. figure out what their problems are and then kind of understand the situation and figure out where you can apply your particular skill set to help them. Right? I don’t have a prescription for you. Like it it is your agency. It is your problem to figure this out. And that requires a particular kind of skill set and a toolkit that you have to develop to figure that out, right? Because there’s a lot of ambiguity in that. um going to a level above that uh kind of as a distinguished engineer it’s even more amorphous in many ways there isn’t any shared definition right but I the way I think about it is uh proof of the dynamic range of the problems that you can solve so and then dynamic range kind of goes in a couple of different directions one is technically u so are you able to have you shown a repeatable record of being able to oper operate kind of at all layers of the stack. If you’re engaged with the team, are you able to kind of go all the way down to the bare metal and understand what are the constraints, what are the problems kind of from ground truth, reconstruct the problem. At the same time, are you able to operate with the business requirements, you know, with your VP and product counterparts to actually understand what’s in their head, how it manifests in code and translate that into actionable change and like deliver the right product. That’s the technical aspect of it. Um but then there’s also the uh the execution model uh kind of in the middle where you have to be able to flex. Uh there are different types of projects that you get parachuted into. Some projects are uh working at the frontier of knowledge or product space where there’s like just fog of war. You don’t know what you don’t know. And you have to be working kind of startup mode of look, we’re going to fire. We’re going to see where it lands. Then we’re going to aim and we’re going to fire again. And we’re going to do that really rapidly, really fast, as quickly as we can, so we can figure out where the hell we are and then we’ll figure out what we’re going to build, right? That requires a particular skill set. On the other hand, you can be parachuted into kind of a slower moving pace pace layer of the company where it’s like, okay guys, we have this uh platform API problem, you know, we have a just using like a random example, right? Um, and it’s really important that we think through how we design this API because it will have second and third order repercussions like years down the road for our partner ecosystem and all the rest. So, we need to engage our slow thinking brain to really understand how this change at this layer will manifest its way through all the others, right? And that’s a very different mode of engagement. That’s like that’s much more in a way academic. But you also need to be able to take all of that divergent thinking and converge the problem to like here here’s the actual recommendation, right? So it really becomes the demonstration of your toolkit of being able to execute across all of those domains because when you talk to like the expectation for a distinguished engineer is kind of similar to a VP like it is a VP equivalent role, right? Like write me a description for a VP. The job of a VP is to solve every problem that lands on their plate, right? It’s like and by definition all the easy problems have been solved before like at layers below them so they only get the hard problems with incomplete information or imperfect decisions. So, uh, show me the volume and show me the versatility of your toolkit. That gives me confidence that I could parachute you into like I can give you this weird shaped problem next and with reasonable success you’ll be able to navigate yourself out of it. One thing that I I share often with u folks that I coach and work with is I I I have this belief that a better way a more resilient way to build your career is to optimize for being the only person as opposed to the best person. So what does that actually mean? There there are two different paths that you could take. You could say, look, I’m gonna pick a particular domain and I’m going to be the best person that will know the most about a particular thing. So I’m going to like take security as an example, right? I’m going to learn everything there is to know and that’s going to be my life life calling. And that’s great. There’s absolutely nothing wrong with that. Um you you can optimize for that. My personal philosophy is um that is one way to success but it is not the most resilient way to success. Uh because what if you pick the wrong field? What if the world changes under you? What if um your particular company does not need that particular skill set? Be the only to me is is about building a talent stack or a portfolio of skills that you can juggle and be effective. And I think this is actually um reflects back in the dynamic range conversation that we were just having, right? Were you able to say look uh and maybe this is actually me justifying my own career track because when I look back on my career, I could say like look, I was a mediocre designer. I was a mediocre um salesperson. I was okay at support, but like come on. Like that that’s not my life calling either. But you know what I did really well? I combine all of those things into a unique toolkit that other people could not do. Like I could look at a problem and I could say, “Yeah, I could sling together website. I know Photoshop well enough and I know how to host it and I know how to secure it and I can stand all that up for you in, you know, in the next two days.” You don’t have to hire a team for that and I have I have the dynamic range to do that. Now, if it turns out that um we now hired a graphic designer, that’s excellent. But great, I’m just going to take that particular skill set out of my quiver, hand it over to them, and I’m going to focus on the other things, right? And I think generally uh you can acquire very high competence like 80 90% uh competence very quickly in a domain. You can get to 80% in a matter of days to weeks and especially now with the tools that we have access to with LLMs and all the rest like the ability to acquire context is uh just amazing. you can spend the next year to get yourself to 90%. And now if you optimize for that, you have resilience because I’m able to converse with our marketing team because you know what? I took the time like I I literally remember going on Amazon and I bought 15 books on marketing and I spent a week nothing but reading marketing books so I could understand the lexicon, the jargon and and speak the right words when I talk to marketing teams. I’m also adept enough at uh working with our PR teams because like I’ve written a lot, right? And I’ve practiced that muscle. I’m also an engineer. So I now I’m able to bridge. So oftent times when I find myself in conversations at Shopify or elsewhere, I’m the translator between all of these different parts of the company and organs of the body where I’m able to kind of synthesize that information and bring it together. And that gives me a lot of versatility, right? It doesn’t mean that I’m the smartest person in in the room. Oftenimes it’s far from the uh from the truth. I’m often the most senior person, but rarely am I the most knowledgeable. And that’s actually very important because part of my skill set is to figure out who are the most knowledgeable people and figure out how to leverage them in the most effective way. Right? My contribution is I understand kind of the fundamentals of the platform and what you can do with um our APIs or our platform. I understand the business requirements. There’s a very messy middle in the middle of how you actually implement the solution with a number of variants. That’s not my responsibility. My responsibility is to help the people that know the most about that messy middle through that decision space. And I have a toolkit to help them facilitate that. But it’s not it doesn’t mean that you know the most senior person in the room knows all the answers which I think is a mistake that a lot of engineers make when they think about principal engineers like oh if you’re a principal you know everything there is to know about the web platform. It’s like well not really right like what I’ve learned is a lot of pattern matching. I’ve learned how to find answers. I know where to find answers and I know how to navigate out of tricky situations. But it doesn’t mean that I know every API and every quirk. Now, some people do because that’s what they make their life calling. And that’s I think that that’s perfectly fine. But as a general strategy, I think it’s not as resilient. Antifragile career is where you have a set of these capabilities where you can just swap out any given moment and say, “Okay, well, I guess I’m solving a go to market problem right now, so let me pull out my other quiver of capabilities.” I see. So when you say don’t be the best, be the only, you’re saying that generalists have an advantage because they can put together a bunch of skill sets, get most of the way there, and be the only because the intersection of all those skill sets is more special and more resilient because you have such a wide toolbox. Is that right? Yeah. This is this is literally probability math, right? It’s like how many people if you multiply out the probabilities of how many people know this particular have this particular skill set like you know enough about databases you know enough about graphics you know about you do you know enough about all these other components who is the person that is the only person that has sufficient domain expertise and connective tissue to solve this problem right so the being the only is about having a wide range of tools that you can reach into and say hey I can combine them in any particular way which is what makes you versatile and makes you effective in these kind of ambiguous situations where you can based on the situation adapt how you work, right? Because I can shift gears and say, “Look, I’ve I’ve been a manager before. I understand what it means to do performance management. I understand how to coach people.” Um, so I can even if I’m working as an IC, I can take an engineer aside and say, “Look, like here’s some feedback or here’s some recommendations here. I know how to conduct myself. I know what things to say, what not to say and and help them along the way, right? It doesn’t mean that I’m exercising that skill all the time, but I’m able to be parachuted into situation where I can act as that temporarily. And that’s turned out to be incredibly helpful. I had one mentor who did seesaw as well. And he said that management always appreciates an IC that understands management because it’s much easier to partner with them. Yes, absolutely. So I would absolutely encourage um if you’re an IC track and you’ve never tried management like def like being a TL is a great learning wheels um you should definitely try if it if it suits you to do management as well but don’t assume that it’s a one-way path right you can go back and forth and there isn’t a stigma I think historically there has been in some organizations because also we’ve kind of painted this picture of hey the path to success is you grow to be a manager right but That’s not like when I talk to a lot of managers in like high roles, directors and all the rest, you know, after you sit at a bar and and have a couple of drinks, they’re like you reflect back on what was when were you happiest in your career? They say, “Huh, you know, it was a couple years back before I became an ex because I had like I was really competent at that thing and I was loving it, but I was told that in order for me to like grow quote unquote, I needed to take on this other thing.” It’s like well huh well that’s that’s an interesting reflection right and at the same time they will reflect and say but I’ve also learned a lot in this new role I appreciate what it means to run a team the complexity the interpersonal dynamics the performance management and all the rest and that’s an amazing tool to have in your toolkit great now um let’s set up our organizations in a way where that is okay for people to transit between those roles you’re not penalized and let’s not as an industry positioned as some sort of like demotion, right? Because often times it’s like, oh, you’re a manager. You became an IC. What happened? What do you mean what happened? Like nothing happened. I just I I wanted to take on a new challenge. Like that’s not a demotion. When you look over the course of your career, were there any points where you have regrets that others could learn from? Don’t let the pressure of your success stop you from trying. Um, let let me unpack that a little bit. Uh, I reflected on this like as as a writer, as a blogger. I remember like when I look back, um, and I wonder if you can if you can relate to this. When I look back on my early writing, I read it now, I’m like, oh my god, that is terrible. What was it? Like, how could I have published that? That is just flatout embarrassing. I hope nobody finds this, right? Or frankly, if I go on GitHub and look at my own projects, like it is embarrassing code. But you know what? It was the limit of my ability at the time when I did it. And I’m so glad that I did it, right? Because it was those milestones like putting that work out there that gave me the right feedback, gave me the right encouragement that then led me to improve. But the challenge that you run into is as you level up and as you get like an audience and an expectation, it’s like, well, you know, Ryan’s interviews are really good. So, in the next one, like I I expected to be like an out of the park, better than ever. You keep setting a higher and higher bar where you start to filter like, you know, here’s a thing I would have published before, but I’m not sure if it’s up to my standard now. Like, is it really interesting? Do I have a unique take on it? Whereas before it was like, I don’t care. like and just a thought. Here you go. Keep publishing. Like I struggle with this all the time. Like keep putting stuff out there because don’t let that expectation become a gate and filter for the work that you put out because that feedback that you get and exposure is like that that is actually the quintessential ingredient that you need for growth. Definitely. Definitely. And yes, I can relate. I think there was uh there’s a year or two where I was writing a newsletter and every week I’d publish something and at some point the email list is growing and it’s growing and I could tell at the beginning when I’m ideulating what am I going to write this week a lot more nos coming in my mind I go oh no this one this topic’s not good I’ve seen this somewhere yeah it’s it’s that courage to be wrong to be disliked to make a mistake right it’s like Ryan I thought you’re like or Ilia like I I thought you were smarter than that. Like why did you say that thing? It’s like well that’s what came to my mind and like it’s fine. I I don’t claim to be an oracle, right? I I have I have other um expertise and and other things and this is what I thought at the time. Definitely. Yeah. And I I also wonder if that kind of similar thinking as you grow in your career, I mean it would take some courage for you to step into a new area that’s completely new to you. If everyone knows you as distinguished engineer and very knowledgeable in your given domain to step into some new area where you’re going to make a lot of mistakes that that feeling of that downgrade is is tough for a lot of people. Yeah, that’s where setting the right expectations with yourself and others is also very important. Like the the way you show up to these conversations makes all the difference, right? Because I don’t show up as hey I know all the answers. Rather, I show up as hey guys I’m here to help. I’m just I’m like really curious and I start asking why like what are the fundamentals? Help me understand this. the way you ask questions becomes very important because it’s very easy to come across as trying to question all the things as opposed to being curious right like there’s a subtle difference between them um am I trying to attack your work or am I just trying to construct a model and just setting clear expectations of that um often times when I begin these conversations I’m just very open about guys I don’t know what you what you know right and I need to very rapidly build my mental model of the space. So I’m going to ask a lot of dumb questions like excuse me upfront. I also have my expertise and I also know some other things that you don’t. um so help me navigate through this and it becomes a collaborative exercise right because I can uh clear roadblocks and do things that they can’t but they can bring all of the knowledge and this becomes the symbiotic relationship of that goes back to how do I leverage the expertise of people in the room as opposed to trying to question their work and that takes a lot of that stigma out of that new environment um in work but I think there’s uh an even higher filter for when you’re like broadcasting because there’s an expectation and an aura of like what what you’re expected to be saying, right? And I think it’s um some people do a better job of that than others in terms of staying true to their thoughts and and less filtering. Is there a top book that impacted your career? The first thing that comes to mind and this is uh this not a book but an author uh Sir Ken Robinson. uh he has a series of books um on like finding your element, creative schools and the rest. U if nothing else um go on YouTube and search for Ken Robinson and watch his TED talks. Uh it is I think 20 minutes of your time that is going to be the highest ROI if not today this week maybe this year. Uh he he’s been an inspiration to me and I think his messages needs to be continued. uh unfortunately he passed away but a key of it is we need to rethink how we think about education and it actually kind of circles back to the conversation we’re having about wateroo his messages stop we need to rethink our education system from a factoryline model where we like put people by age into a certain bin and teach them specific skills like we all spike in different ways at different points in our life right like let’s have an environment where people can choose their own adventure Now that how do you execute that turns out to be really hard and he dedicated his life to trying to figure that out like how do you reform the educational system but I think his philosophy is very much kind of in line and probably informed a lot of my thinking for hey it is about creativity you should mix things up. You should combine skills. uh let’s build a system that actually allows us to like help kids learn these behaviors better as opposed to pigeon holing themselves into like well no you’re in grade five in grade five you’re only supposed to learn this thing thank you very much and uh like please don’t touch advanced math until you like until you get to grade six it’s like well that’s that’s nonsense right like for some kids they can go all the way to grade eight math when they’re in grade five just to use one example and then the last question is if you could go back to yourself at the beginning of your career and give yourself some advice knowing everything you know now what would you say I would come back to the don’t be the best be the only um I I think early in my career had a lot of fear of hey I’m I’m mediocre at a lot of things like I I see my friends I would look up to my friends who are really good at design and I’ like oh I wish I could do that right or I look to my other friends who are just better engineers like I wish I could that could do that but the thing that I had was ability to negotiate across all those themes and that’s uncomfortable because I wasn’t sure if that would pan out and it turns out that it did um and then the other thing is exactly as we were just discussed don’t like don’t don’t filter be be braver about this stuff um it’s it’s kind of ironic that later in my career I part of like my 9 to five effectively became public speaking. Going through high school, I was deathly afraid of public speaking. I would run away from class to avoid it. Right? Like I I vividly remember those stories. And then it dawned on me later when I was doing post rank that hey h why is it that I was even through university like I had cold sweats standing out in front of a class trying to explain the thing uh but I was totally adept and fine when I was pitching uh my product to an audience and the difference is in one hand I I was trying to describe a thing that you know I didn’t have any particular investment in it was a test of my knowledge versus here’s a thing I’m passionate about and I want to like enact change in the ecosystem to move it to some new direction. So that turned out to make all the difference for me. And uh maybe that’s the key thing like if you told me uh early in my college career that my future holds public speaking, I would I don’t know what I would do. I would say that you’re crazy. I see. So to be more brave, chase your passions. Yeah. And it’s also very different when you’re chasing your passion. Kind of a a lot of things flip in in how you engage um as opposed to being told to stand up and you know and rehearse a skit. 100%. Awesome. Well, thank you so much for your time, Ilia. I’m really excited to share this one with everyone. Is there anything you want to say to the audience before we end the the recording? I think we covered a lot of ground. Um, I hope some of it is useful and um, you can find me on on the internets and please feel feel free to reach out and and have a chat. Awesome. I’ll put that in the show notes. All right. Thank you. Thanks, Ryan. Appreciate it. Thanks for listening to the podcast. I don’t sell anything or do sponsorships, but if you want to help out with the podcast, you can support by engaging with the content on YouTube or on Spotify. If you want to drop a review, that’ll be super helpful. And if there’s any guests that you want to bring on to, please let me know. I feel like sourcing very senior IC’s, there’s no wellstudied list out there on Google that I can just search this up. So, if there’s someone in your org or at your company who you really look up to and you want to hear their career story, let me know and I’ll reach out to