Shopify Distinguished Eng (L10) on Principal+ Engineering, Career Story, Regrets

People that have to ask that question by definition are not principal engineers. This is Ilya Grigorik. 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. 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 waterloo and i i gotta ask the smartest interns that i ever worked with they came from mit caltech and xinhua university in china

But the best interns I ever worked with all came from Waterloo. And so I'm curious, what is it that makes these Waterloo interns so strong? For me personally, the most important thing that 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 waterloo did really well is this is they realized that yes there is the

academic portion of learning how to engineer and like what software design is all about but then there's the hands-on and applied part and instead of modeling it as hey, you're going to study for three years and then you have an optional kind of intermission style co-op, which is what most universities operate on, right? You could take a year off or something like that to go and work in industry. Waterloo 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... at least six shots on goal for trying things. And this actually has very positive effects on many dimensions. So first of all, it removes the stigma of trying things.

Right. Because many of us, like we don't know what's going to stick with us. 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. It's like, oh, I really want to go to Wall Street and work there. And they try one of the co-op terms there. And they're like, no, actually, for whatever reason.

I don't like the city or I don't like the industry. I didn't like the people. It just didn't click for whatever reason, right? Same thing for medicine or others or consulting. And that's really important to discover early. And the really nice thing is it's a concentrated, like it's a three-month 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 three months, you jumped. You went to a role for three months, you're like, are you really committed? Do I want to hire you? It's like, no, that's my co-op, right? That's the whole point. So you could, first of all, try a bunch of things and get a good range of... experiences under your belt and 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 the type of work that you do. It's the type of 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 O notation 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 a non-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 That is still the superpower of Waterloo. 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, which became PostRank, that was then acquired by Google. And I'm curious... the story behind you choosing to found a company right after graduating from waterloo i graduated from waterloo and as most students i didn't know know what to do

I wasn't ready to commit. So my escape, which was a well-trodden track for many, is I'll go to grad school. So I applied and then got into the University of Toronto, actually. And during that summer, in between, I had a couple of project ideas that I wanted to get off the ground. So I had a particular itch that I wanted to scratch. And the itch was, if you think back to how Google was founded,

The key insight, if you simplify it and boil it down, that Larry and Sergei had back in 1997 is, hey, 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 in 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 PageRank effectively, right? Links becomes one input, but, you know, thumbs up, a number of conversations, a number of likes, and all of these things become additional inputs. And that was post-PostRank. It's kind of embedded in the name. It was an algorithm for ranking posts based on social engagement. Kind of a child of the Web 2.0 era.

still remember the day it was like july 8th when i released it and then i did sleep for three 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 and just throw more servers at the problem and then eventually optimize it out over the next couple of weeks 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 good publicity, which then turned into a conversation. Hey, is there a product here? So I remember the structure points somewhere late in May. We're kind of in the middle of all these conversations with investors, kind of unanticipated fork in the path, right?

And I'm thinking, 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 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 ones that immediately stood out to me about like entrepreneurship 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, or I could just, like, go into, like, I can read those books on my own time and I can go and try it.

which led me to reaching out to my advisor and basically asking hey can i take a year time out you know i was planning to do this this year but how about i start next year and he hammed on hot and said okay i understand and you know come back to me in six months um to close our story we did end up closing the round and that became post the post rank the company and 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. What does that kind of conversation look 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...

Well, we were building the product that I was describing, and we were presenting at one of the conferences in the Bay Area. And, you know, we got off stage, and Phil Moody, who was the... uh kind of lead pm on google analytics kind of walked up to us and like hey this this is cool um do you want to have a chat and i remember taking a train from san francisco to mountain mu 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

So it was very friendly. There's nothing kind of more to it than that. And then what we learned after is this is right in the... time span when google and facebook were like at war in terms of drawing the battle lines for social this is when google woke up to the fact that facebook is on a runaway trajectory and

all hands on deck google needed good this is when google starts working on google plus 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 speed run this whole thing.

And we became that catalyst for Google Analytics because what they saw in us is like, frankly, they did not care for the PR product that we were building. What they cared about was... the experience and some of the infrastructure that we've accumulated that we could bring in to fast run and fast track 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 Plus is helping me and all the rest. So that became the kind of the mutual point of win-win situation that let us... joining forces with Google Analytics. In being brought in as an acquisition, how'd 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 where you bring in the whole team and you kind of do a wholesale evaluation. But otherwise, everyone on our team went through the panel.

through the full panel myself included and 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 old engineers.com i see okay so it's it is just a normal interview process what about in the case though because you're bringing in company and assets and stuff

is that just like a giant signing bonus or something or how's that it depends on the company that you know and then the deal of course so there's multiple layers to it exactly as you said right there's the like there's the ip there's the customers There's the people. And you can treat those as distinct conversations, right? So as far as negotiation is concerned, 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 many like there's the aqua hire acquisition where you effectively acquiring the team you're saying 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 in our infrastructure

Postrink 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 more than half the internet, right? So like to... to make a modification to a data pipeline. I remember the conversations fondly, like sitting with our SRE team and they're like, okay, well, you're going to add this bit field right here.

that's going to be this number of exabytes of data i'm like oh my gosh okay let me think about this more carefully right because before that was not even a conversation point for me and my team so A lot of it was about the talent and ensuring that they're bringing in the right folks with the right experience and that they're capable of...

kind of hitting the ground running and working 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 pulse rank and i joined as an engineering manager 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 Analytics solve my problem. Damn it. And I think we succeeded at that. It took us about a year to effectively rebuild our stack. And the team was on a good trajectory. And that's where I...

took a step back and looked around for, hey, what's the next adventure? I was in a really good direction within Google Analytics. I remember a conversation with one of our VPs at the time where Uh, you know, we were having one of these career sit downs 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 could see you take on and all the rest. And I'm like, huh, that sounds all exciting. And I'm very honored that you think I'm capable of doing this work. But at the same time, 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 i'm gonna 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. Google is an open culture, which is... the thing that I loved about Google. And I could approach anyone and everyone about any piece of infrastructure, any product, and I leveraged that.

And I learned a lot because, you know, I remember building PostRank 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. 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. If you find us the time, and I was like, huh, well, that's interesting.

wouldn't it benefit the entire world the entire like intranet if we did more of this which led me down some interesting conversations and i discovered this group within google which is called make the web fast which was basically a skunk course project started by Sergey around, well, how can we make the internet fast? And it's a very kind of...

self-referential, self-motivating thing. There's very direct evidence that the faster the internet is, the faster users browse the web, the more they use Google. 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. You know, dog trenches built towers.

We worked on TCP IP and trying to figure out how to reduce congestion. We worked on optimizing proxies for, hey, turns out that most humans write terrible websites. Could we just like optimize it out on kind of dynamically as a web server plugin?

to um hold on a second when we say make the internet fast what does it 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 So if you walk the full dynamic range of those questions, it's just absolutely amazing laboratory of experiments to run.

And I was really fascinated about that. And I remember at that point in time, I realized that I had an opportunity to cash in some chips. And I could say, look... i i see a path towards kind of career growth as a director in this and 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. But that would definitely take me off the career track, right? I remember that conversation. It was like, well, you know, if IC bar at Google is actually really high, so if anything, you're going to be down-leveled, likely.

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 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...

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. to optimize for other things, which 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. And it was a lot of uncertainty in that process, but this is kind of a repeating arc through my career where as a manager, your time is managed by others. You are in the service of others. And I wanted to shift gears and go into a mode where I have more self-direction and go pursue some interesting research or 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 developer relations at Google.

What was the rationale then switching back given what you just said? Yeah, so I've seesawed a number of times through IC to manager. And I think this is a path that is vastly underappreciated and is actually... surprisingly common for a lot of like high-performing ICs and like you'll find in principle and then higher up roles and the observation is I think it was a tour of duty

when I'm doing management. To be a really effective principle plus engineer, you need to have very good dynamic range technically. You can work well at the low level of the stack. also zoom out and look at the business requirements currently 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 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, pathfinding, 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 a 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 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 oftentimes you'll find kind of yourself managing or being responsible for the direction of a broader team.

And before you know it, I think it's a natural transition to say, well, okay, fine, I'm going to manage this domain. I'm going to manage this as a product team. I'm going to manage the growth of the individuals and the rest. And that's completely fine. That's what happened to me with developer relations. When you think back to the set of problems that I shared with you, 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 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. I did a lot of that. And that was my kind of IC contributor role. Then you get those metrics into browser. And then the problem becomes great. How do I get community or ecosystem adoption in this thing? Well, I need to go tell people.

and I need to convince them to adopt it and integrate it. Well, now I need to go talk to all of the analytics vendors. 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 it would be really helpful to have a team of people that can focus on this thing. And this is the thing we deeply care about. We want to accelerate the adoption of these things. It's kind of my model based on... prior experience was, look, if we just leave this ecosystem be as it is, in three to five years' time, we will probably see the adoption that we want. But I'm not happy with three to five years. 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 energy into the system. The energy is a team of people. Great, fine. Let me switch to my manager role. I'm going to go recruit people and I'm going to 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 pathfinding 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 principal engineer oftentimes right i don't if the team is dependent on me

that means that I'm probably doing something wrong because my job is to up-level the team and make sure that they can deliver this thing self-sufficiently. So if you know the Homer Simpson meme where he 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 oftentimes now occasionally i stumble into a problem where i'm like Either it's in my bones and I feel like I want to own that problem and see it to its logical conclusion, or I have some unique position or leverage in it where, 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 really run this thing, own this ship, and that's my responsibility. And you know what, at the end of it?

I'm going to do the same thing I did before. 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 the 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... under appreciate or misunderstood aspects of being a principal engineer is when people ask what what does what do you do like you know 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. Because the problems become ambiguous enough at that level where... You kind of have to figure it out yourself. I mentor a lot of principal engineers that come into Shopify. My expectation for someone coming in that level is, look, you basically...

To use an analogy here, you're going to be dropped, parachuted into foreign terrain. You're in a 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.

I don't have a prescription for you. 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. Because there's a lot of ambiguity in that.

Going to a level above that, as a distinguished engineer, it's even more amorphous in many ways. There isn't any shared definition, right? But the way I think about it is... 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 so are you able to have you shown a repeatable record

of being able to operate at all layers of the stack. If you're engaged with a team, are you able to go all the way down to the bare metal and understand what are the constraints, what are the problems 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 deliver the right product. That's the technical aspect of it. But then there's also the execution model in the middle where you have to be able to flex. There are different types of projects that you get parachuted into. Some projects are 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 the startup mode of look we're gonna fire We're going to see where it lands, then we're going to aim, and we're going to fire again. I'm 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. That requires a particular skill set.

On the other hand, you can be parachuted into a slower moving pace, a pace layer of the company where it's like, okay, guys, we have this platform API problem. just using like a random example right um and it's really important that we think through how we design this api because it'll 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 that 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. Well, the job of a VP is to solve every problem that lands on our plate. And by definition, all the easy problems have been solved before, like layers below them. So they only get the hard problems with incomplete information or imperfect decisions.

So 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 share often with folks that I coach and work with is 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 are two different paths that you could take. You could say, look, I'm going to 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 calling. And that's great, but there's absolutely nothing wrong with that. You can optimize for that. My personal philosophy is... That is one way to success, but it is not the most resilient way to success. Because what if you pick the wrong field? What if the world changes under you? What if...

Your particular company does not need that particular skill set. Be the only to me is about building a talent stack or a portfolio of skills that you can juggle and be effective. And I think this is actually... reflects back in the dynamic range conversation that we were just having right were you able to say look 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 salesperson. I was okay at support, but like, come on, that's not my life calling either. But you know what I did really well? I combined 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 a 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 of 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 the dynamic range to do that. Now, if it turns out that 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. And I think generally, you can acquire...

very high competence, like 80, 90% 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 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 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 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 now I'm able to bridge.

So oftentimes 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 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 the room. Oftentimes, it's far 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... fundamentals of the platform and what you can do with 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 navigate through that decision space. And I have a toolkit to help them facilitate that.

But it doesn't mean that 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'd know everything there's 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 myself 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 I think that's perfectly fine. But as a general strategy, I think it's... not as resilient. An anti-fragile career is where you have a set of these capabilities where you can just swap out at 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 the skill sets is more special and more resilient because you have such a wide toolbox is that right yep

This is literally probability math, right? It's like, how many people, if you multiply out the probabilities of how many people have this particular skill set, you know enough about databases you know enough about graphics you know about you know 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 only 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 been a manager before. I understand what it means to do performance management. I understand how to coach people. So I can...

Even if I'm working as an IC, I can take an engineer aside and say, look, here's some feedback or here's some recommendations. I know how to conduct myself. I know what things to say, what not to say, and help them along the way. It doesn't mean that I'm exercising that skill. all the time but i'm able to be parachuted into a 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 if you're an IC track and you've never tried management, Being a TL is a great learning wheels. You should definitely try 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 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 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 at x because i had like i was really confident 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 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 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 position there's some sort of like demotion right because oftentimes it's like oh you're a manager you became an ic what happened what do you mean what happens like nothing happened i just 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. Let me unpack that a little bit. I reflected on this as a writer, as a blogger. I remember when I look back... and i wonder if you can like if you can relate to this when i look back on my early writing i read now i'm like oh my god that is terrible what was it like

how could i have published that that is just flat out 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 expect it 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 the 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 it's 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 up because that feedback that you get and exposure is like 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 ideating what am I going to write this week a lot more no's coming in my mind I go oh no this one this topic's not good I've seen this somewhere 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're smarter than that like why did you say that things like well that's what came to my mind and like it's fine i don't claim to be an oracle right i I have other expertise and other things, and this is what I thought at the time. Definitely. And 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 a 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 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 really curious. And I started asking why. 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? There's a subtle difference between them.

Am I trying to attack your work or am I just trying to construct a model? And just setting clear expectations of that. Oftentimes when I begin these conversations, I'm just very open about, guys, I don't know what you know, right? And I need to very rapidly build my mental model of this space. So I'm going to ask a lot of dumb questions. Like, excuse me up front. I also have my expertise and I also know some other things that you don't.

So help me navigate through this. And it becomes a collaborative exercise, right? Because I can 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 in work. But I think there's an even higher filter for when you're broadcasting.

Because there's an expectation and an aura of what you're expected to be saying. And I think some people do a better job of that than others in terms of staying true to good.

their thoughts and less filtering. Is there a top book that impacted your career? The first thing that comes to mind, and this is not a book, but an author, Sir Ken Robinson. He has a series of books on finding your element, creative schools, and the rest. If nothing else, go on YouTube and search for Ken Robinson and watch. his TED Talks. 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 he's been an inspiration to me and i think his messages needs to be continued 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 Waterloo. His message is, stop. We need to rethink our education system from a factory line model where we 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. Let's build a system that actually allows us to help kids learn. these behaviors better as opposed to pigeonholing 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're in 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. I think early in my career I had a lot of fear of, hey, I'm mediocre at a lot of things. Like I see my friends, I would look up to my friends who are really good at design and 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 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.

And then the other thing is, exactly as we just discussed, don't filter, be braver about this stuff. It's kind of ironic that later in my career, I... part of like my nine 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 said i vividly remember those stories

and then it dawned on me later when i was doing post rank that hey 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 But I was totally adept and fine when I was pitching my product to an audience. And the difference is, in one hand, I was trying to describe a thing that...

I didn't have any particular investment in. It was a test of my knowledge versus here's the thing I'm passionate about and I want to enact change in the ecosystem to move it to some new direction. That turned out to make all the difference for me. And maybe that's the key thing. If you told me early in my college career that my future holds public speaking, 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. A lot of things flip in how you engage. as opposed to being told to stand up and rehearse a skit. 100%. Awesome. Well, thank you so much for your time, Ilya. I'm really excited to share this one with everyone.

Is there anything you want to say to the audience before we end the recording? I think we covered a lot of ground. I hope some of it is useful. And you can find me on the internets. And please feel free to reach out 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 ICs. There's no...

well studied 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 them.