Joshua Jenkins shares a career shaped by making, not posturing: tiny AIM icons, improvised internal tools, startup swings, and eventually design leadership at scale. The throughline is practical judgment. He cares about tools that remove friction, teams that make decisions close to the work, and growth that comes from doing the next useful thing well.
A conversation with Joshua Jenkins | 1h 06m
Joshua Jenkins has one of those career stories that feels recognizable the moment he starts telling it. He did not begin with a tidy plan to become a design leader. He began by making tiny animated AIM icons, taking on odd jobs, and gradually discovering that improving the thing in front of him was both fun and strangely revealing. That instinct carried into a job at HP, where he built rough internal tools for himself, and later into agency work, where he became the kind of person who could bridge design intent and implementation reality. That bridge role is a real theme here: he respects craft on both sides and has spent years translating between them.
The middle of the conversation turns toward AI and startups, but the tone stays grounded. Joshua is interested in AI when it helps turn a fuzzy problem into a workable starting point, not when it promises magic. That same practicality shows up in the startup discussion. He talks about building around a question people actually want answered, rather than around a trend that only looks good from a distance. It is a useful reminder that good product instincts often sound simple because they are tied to concrete user needs. The glamour drops away and what remains is the work of choosing the right problem, shaping it clearly, and staying close to reality while you build.
The back half is especially strong on management. Joshua describes the shift from individual contributor to design manager during his time at Snowflake, and he is refreshingly clear that the job changes in kind, not just in scope. Design teams need structure, but they do not benefit from borrowing engineering playbooks wholesale. Leaders have to understand how design work moves, where judgment lives, and when to shield teams from noise. He also makes a smart point about learning from both good and bad environments. Strong managers give you models to follow. Weak ones teach anti-patterns you never want to repeat. Together, those lessons form a thoughtful picture of leadership rooted in taste, trust, and operational clarity.
The automatically generated captions have been organized by speaker, lightly edited for clarity, and broken into paragraphs for readability. Names and wording may still contain errors.
hi everybody in this chat I'm thrilled to talk with Joshua Jenkins someone who I've known for over 20 years online and also offline he's a very talented designer developer entrepreneur and also design leader and in this fun chat we talk about everything from how he got started all the cool things are going on with AI with design and also a lot of time is spent on what it's like to be a manager or transition from being an individual contributor to a manager and in many things along the way that you discover hope you enjoyed right Josh grade two great to finally meet you despite I think we met when was it like 2006 when we met in person that sounds right yeah it's been a while yeah
I think it was like the University of Washington campus I feel like you think you were there and I was interning at the time and then we kind of met and then of course we know each other online for for ages at this point and so yeah no you've been sharing a lot of cool stuff forever and I always feel like you wear mini hats very effectively designer developer and then design leader startup entrepreneur and all these things and so at some point I think we'll touch upon all these things going forward so I'd like to start with the question I typically always ask is what was the first thing remember building
okay it's an interesting question and I'll start with saying thanks for thanks for having me here this is great to be here um first thing I remember building um oh you know what um back in the AOL Instant Messenger days um which was a long long time ago and people listening to this probably have no idea what that is but probably in like 2000 2000 I don't know something like that um uh it was building um basically like animated gifs for like you had little avatars and like you had this little like icon and it was like your your aim icon and that was like the first thing I remember making which is like frame by frame pixel by pixel making and they were like 16 by 16 or 32
by 32 like tiny right super constrained environment and just making these like goofy little like animated faces and stuff like that so um that was the first thing I actually remember making and I was probably like I don't know 13 or something
wow and doing what tool we were using to
make those it was uh you know what's actually it was before Photoshop because I couldn't afford Photoshop um I don't it might have been I don't know it might have been even something more obscure and weird
yeah those were like fun days because nowadays you're like 16 by 16 it's like in almost invisible you can't see exactly like most of it it's like 40 by 480 or 800 by 600 if you're lucky 1024 by 768 and 16 was like a massive amount of real estate to work with yeah totally
yeah it's crazy how different it is yeah
you know the funny thing also is just that with higher DPA screens now all the pixel like are 16 by 16 things from like 20 years ago just looks awful today how to still bring that world forward again
yeah I mean I think there's like two like there's people that like kind of like try to Faithfully scale things up in like the grid right and keep the Chris lines and then there's all this stuff now where people are like feeding it into like um you know um Ai and generative stuff and right and then it's like you know blows up a 16x16 thing into like a like a physical Avatar it's crazy yeah
yeah and the next complication is like okay you figured all that out you got it perfectly sized they need to share it somewhere and you know where do you go you go to like Twitter or Instagram or so on and they happen to scale it and compress in their own way up and you're like great you know I spent all this time doing this I know and now I can do it anymore
yeah I think I think there's like a generation of people that work on screens and probably feel this pain all the time or it's like you know I think a lot of us spent so much time with like pixel precision and like just getting things to like be precise and then all of this yeah million screens and different networks and all this stuff and it's just like this constant losing battle but until they get to like I think like maybe like another 2x on like retina you can still kind of tell you know so we're not quite out of the woodwork we're like you can just do whatever
yeah like I guess like the 8K screens might be the ones that can ultimately do this for you because the funny thing is that Vimeo came out a long time ago and they were all about like we're not going to compress your videos as much we'll give you really high quality videos and so a lot of like designers and people cared about high quality visuals end up uploading to Vimeo and it's actually really cool but the downside was the whole network effects and everyone just kept going to YouTube because it just it was YouTube you know everything was there you know from like high quality you know animation stuff but also like music videos and you know Cat videos all that stuff right yeah and this is like
the market for it just seems to keep going to an interaction that doesn't really help us too much yeah I totally
agree I think the um yeah they're just you know mass media and it kind of dictates the forms unfortunately
yeah so so you start that's the first thing you remember designing and then you ultimately became you know in many ways a designer full-time you know both personally and as well as like professionally so how did the transition go from like you just enjoying creating things to making the leap
um it's an interesting question um I managed to get a couple of odd jobs when I was in like high school like um getting paid hourly to you know skin a site or something like that right I think that would probably like be first kind of like dip into like professional but it was very like you know I had no training I didn't know what that world looked like I was just doing like stuff right um and then I took a detour through like college and like early jobs um was very far from this stuff but um I worked at uh HP of all places um in uh I don't know two thousand I don't know three let's call it and um uh I had this kind of random job
where basically like I went around um to like different offices and I like found where people's printers were and I like put them on a map and I was like okay like you have this type of printer and then like put it on a map and I plot this thing all out and um you do little interviews with people how much you print what kind of stuff you need to do whatever and um the tools we use are like super cumbersome and then like I made some random like HTML PHP like totally crappy thing but like something that helped me do that a little bit and then I would like spend my time like making that thing nicer and I was like I really like making this thing nicer and
I didn't know it at the time but I'm effectively doing like ux design or like product design for a customer of one um which is me and like this was not sanctioned in any way right this is like not like like this was not like hey go we like you doing this keep doing this um but I realized I like doing that and um then I started to kind of like look out there and see like what other kinds of um ways to actually kind of apply that thing would be again having no idea what the industry looks like having no idea about anything um and eventually found my way into um agencies I guess in Portland uh Oregon so um I was working at a some smaller and
some larger agencies basically doing like web work or like random creative work right um but even that was super interesting because like I've always come at things kind of like from a weird sideways way so I'm this kind of like I kind of got hired as kind of like the digital guy you know they kind of just like sort of like Jack of all trades and just kind of do stuff knows enough about design knows enough about coding can kind of bridge the gap like um I'm working with like you know like legit graphic designers right who are like color theory and typography and like grids and all this kind of stuff and like you know you think you understand this stuff and then you see
people who like live and breathe it and you're like oh wow no there's like a whole deep Universe here I don't understand at all um but yeah so I ended up at agencies like that and um you know super cool to get to like kind of be around these other skill sets and kind of grow from there and there's a bunch more hops after that but that's kind of how I how that's how I formally got into like design like into agencies
do you think your formal education helped as you were starting to do business work or is it just like can you mentioned like this randomly experimenting trying things out and that gave you the ability to be successful
yeah so I'm I am not a formal education success story so I um dropped out of I think like four or five colleges so um uh you know I think the um the cool thing to do is drop out of Harbor and like I drop out of community college so I think that's maybe cooler but um yeah the formal education you know I got exposed to some ideas I would say but um I didn't like learn useful web design skills in college I would say
it may definitely seemed like you were passionately interested about it though because even though you know formal education might not have been your style you still knew that you wanted to be in this industry and you still worked hard at getting to learning all these skills in other other ways yeah I mean I think
it's fair I think um there's always been like a genuine to sort of like curiosity and interest and I think that's what's Driven that's been that through line through everything right it's always been like what's the next interesting thing like what do I want to learn um that kind of stuff so yeah the the the sort of wanting to figure it out part has been very helpful yeah you know you can see
that in so many examples of people who end up being you know who just enjoy what they do is oftentimes just like curiosity in that drive and almost that grind itself sometimes you know I think too many people spend way too much effort trying to optimize for like the ideal environment to build something in a scalable way I'm like you know just just start just start and just do it you know it might take you hours upon hours but getting it done and the things you learn indirectly through that probably far more valuable than kind of the perfect solution at the very beginning strong strongly agree strongly coach sign yeah yeah and and I think more often now you know because I've never I'm not a designer nor am I a developer
I'm a product manager but I get to work with all these disciplines on a regular basis and often in the back of my mind I can see that pattern coming through all the time and I've seen people like wow at first you know they understand what's going on I dig a Little Deeper it's always the case where they just spent like I don't know it's like 10 000 hours thing but Gladwell is truly a number but it's an idea that they spend a lot of time doing something that only they sell the real value in it but it ended up paying dividends for them eventually
yeah I agree and I think the um yeah yeah if you can find your own path that's going to be more successful I think than like taking a described path right because then you're gonna like you know your curiosity and your motivation is going to drive you through all of that so yeah I agree at some point I
also feel like not only your designer but you also have a strong understanding of programming so how did that come
about I would I definitely do not have a strong understanding of programming I have a sort of like begrudging like I need to program to realize things I want to do um but the degree to which I'm bad at programming I like cannot overstate um if I if I'm working on something actively for like a week um I can kind of remember things but if if it goes away like I wrote this all this code a week ago that I was really proud of and I was looking at it like yesterday and I was like I have no idea what this is or how it works or anything like that um and constantly so like I just want to start there which is like um
you know programming's hard and I think some people take more naturally to it than others um but um yeah I think it started from um it's actually funny I think it honestly like probably started from your forums back in the day um I remember there was like um I think you had like a how to make snow on a on an HTML page like thing tutorial yeah yeah right things like that I just didn't know that was possible right and so it was a curiosity was kind of like oh cool and they could do these kinds of things um preceding that even actually I remember when I um I was using Netscape Navigator and um it had like an inspector panel thing and I remember going to
um The New York Times website or something and um going to the inspector panel and it would let you it was very different back then it kind of made it feel like it was like a wizzy wig like you were actually editing the page and I remember going to like the page and like editing the title and then being really scared to hit the like save button because I was like oh my gosh am I like defacing like the New York Times is it gonna stay because I don't know how anything works right um and so anyway like all this kind of stuff I'm just like I had no idea how anything worked and so I think it was just this like slow process of like
picking stuff apart and um eventually I would like have goals and tasks you know like oh I want to accomplish something but at first I'm just like literally just like poking stuff I'm like I don't know I didn't know anything these things existed you know so long-winded answer but something like that
I mean that's pretty much how the world was back then as well because I think you know I think both you and I kind of grew up together at the same stage of the internet and technology and all these things had like geocities and Lighthouse and you know I think like Myspace was just coming about and you there was no guidance there's no like real tutorials or best practices or anything like that there was no like O'Reilly book on like here's a definitive guide to how you build a proper web I was like totally what was like was it webmonkey webmunk you had this like you know really cool like bright colors and they're like here so you create a list and things like that
yeah yeah yeah I remember like you mentioned Netscape right again Netscape composer was one of the first Ides that I ever used for like because it came free with their browser then switched over to front page Express because at that time IE was having more of the cooler capabilities than what Netscape had and yeah you're right you know we're probably dating ourselves like this entire audience has no clue what's going on but you'll be surprised though like the demographic information I get from like Spotify and so on it's a it's around exactly our age which is not surprising topics we talk about so we're basically talking to each other you know and that's the audience right perfect yeah I mean if you want to go for the
younger audience I guess just you know AI replace all the netscapes with Tick Tock and you know it'll be fine oh yeah but speaking of AI have you dabbled into AI to kind of help your coding go further
uh in terms of like a coding the one place I found it to be helpful with coding I don't use copilot or anything like that I'm like very much like an old man at this point where like I have a hard time adopting new tools so I have my like set of things at work and it's fine but um the thing I found it very useful for is because I'm a weak programmer I have a very like unknown and known problem where it's like I know the end State thing I'm trying to get to and I know that there's some conceptual version of it that exists in the universe I know like there's an algorithm or there's a formula or something I don't know what
it's called I don't even know how to search for it I'm not good enough at math to know what like the math to look for whatever and so I'll just type in like very dumb things into chat GPT and just you know just describe the thing and it'll it'll often spit out like some some morsel that will give me something googleable right so that I can actually find like a tutorial or something but in terms of like you know I did play around a little bit with like the could I just automate myself could I describe the stuff I'm doing well enough for it to just spit out the stuff I'm doing and I didn't quite get there but I'm that's more a limitation of myself
my prompt engineering skills than I think like the tool I think you probably could
yeah I think that'd be interesting to see I do like to play around with it all the time to see like how good it is I do find that you know chat GPT Bard and others are really good for like it's all the training data they ultimately train against right I think there's such a shortage of high quality training data for animations and visualizations in general because when I ask it to like you know here I have a column of text make it optimize it like sort it or whatever and write the code for it it does a fantastic job both of them like copy and paste the bullets paste then it just works no need to worry about it I asked it to actually figure out create
me a performance Darfield effect kind of the old windows screen savers right like you know of it zooming in there are many ways of doing that you know the proper way is actually you create a fake Z you know like three-dimensional area and you are just that and it changes the X and Y and scale and all these things appropriately and every single example that came back from chat GPT and Bard were literally just the same as like just x y and scale you know not bad not a bad Solution by any means but the perspective is off the spaceship going right in the middle of it start and fly around you you know and it wasn't quite meeting it there and no matter how much
I prompted it it just gave me very inspirational the same thing ultimately the point where it just doesn't work at all like it so required me to write coding so I think we have a ways to go but what I'm most impressed by with AI though is like mid-journey and stable diffusion and some of those things because I'm not a designer like I cannot design my way out of you know any kind of situation and so I really enjoy seeing like that kind of capability exist for everyone just type in verbally what I want to do and even like Adobe has Firefly where they have some really cool things there have you played with any of those by any chance I haven't honestly um I'd be curious though like I know on
your um you know your website and your tutorials you have pretty good graphics and feel very like tailored um are you using like AI to generate
those no I actually write them all I still do them by hand actually okay they look like yeah that to me doesn't really I don't consider art though it's basically me like going to a whiteboard and it's like you know drawing adding some caption drawing an arrow screenshot Visual and so to me those are just you know like I guess it's part of PowerPoint art in my world yeah I mean
that's a it's an important art but okay so you're talking a little bit more on the um uh like illustration kind of like
side of things correct correct I mean I did try actually using both of them like both Chad I mean not stable diffusion and mid-journey to kind of figure out like can you create if I describe something can I draw the art can I do it properly I think I'm just really picky in the style that I want that I could never get the you know the funniest thing is curved arrows looking not blurry and like you know all of that I don't know why it's in myself so difficulty in it like they you know I think only until like maybe like maybe a few months ago was text actually legible and properly done like there's always a joke is like you know characters are like odd number of hands they can tell
yeah exactly yeah it's really something like that that's like you know classic example AI but no one ever tried like put some text in there to see how bad that comes out right and so I think there's still a little bit of ways to go there but I do anticipate that happening eventually though because a lot of what I'm doing here is very repetitive you know it's like here's their vocal image here's some lines here's some text and then like you know probably like some icon that is through into the Twitter Emoji set and that's pretty much it so there's no level like the creativity doesn't go beyond a certain limit which is perfect for AI systems to figure out
what to do yeah exactly you can actually theoretically come up with like a fitness function here where you're like hey like this is accurate right versus like illustration which is like completely subjective right so obviously it's a totally different like Universe for for quality and ensuring it right
yeah yeah and so yeah I think there's you know probably like maybe six months to a year away from having more of that because I figured it went from like six fingers to now having text that look good to actually having people pretty much like creating videos that seem pretty pretty decent for the amount of time it takes to create things without you actually touching an animation to our video tool that's quite impressive
yeah the speed at which this stuff is moving is crazy I feel like it's almost like a full-time job I think there was like a couple months where I was paying attention on a daily basis and I kind of felt like I knew was going on I haven't been paying as close attention the past couple months and it's like like you're saying text is working now didn't know that so like things are just moving really fast yeah the funny thing is that
I think what it's been like almost a year now of like latest chat GPT and then like maybe a little bit gone within a year for like the a you know image generation tools the unlike other things right that come out that are like really cool and mind-blowing you eventually hit a wall and then like everything that settles and you start seeing like you know content built into a previous content you start saying like Okay I learned this I can build upon this and I can sort of make sense of what's going on and now I'm at the point where like okay I know everything that's going on in this area you know with enough effort with AI though like I think it's almost like you know we releasing the water
from a dam somewhere and the water just keeps flowing no one really knows how much more water is left on the other side so you never get to a steady state you never figure out like okay I learned all these things now but then suddenly something brand new comes out that takes what you learned before into a whole new level of productivity or like I don't understand this now like I need to relearn things like language it was not really a thing like a year ago but now that's the way you got to do it to train things or a vector databases and things like that like just even conceptually keeping up to speed you know ignoring the technical details even that is hard and the funny thing is like I spend a
lot of time my full-time job in some ways to kind of keep up the speed on this and even I'm all completely yeah I mean it's interesting I mean um when I was still working um at Snowflake and just like other like engineering friends in the field and stuff like that one of my favorite things was always just to find the smartest person I could and just ask them to explain to me whatever was going on and I had people drawing me out like the Transformers or llms or like whatever pieces you know like and like you can see them like thinking they understand it and then like working through it and they're like oh crap it's actually like a little more complicated than I thought it was and like obviously
they all you know get there and they're all Geniuses but um yeah it's it's I think just like the yeah I think yeah I think you said it all right I think just like the the thing the Black Box nature of it I think is just interesting too right like even the people that are building them don't know how they work fully right is my understanding maybe people do but like I was reading like I started reading like the um the Wolfram like 6 000 million like page long thing like walking through how llms work you know and it's just like trying to build it up from like first principles or just like basic building blocks and it's just like yeah you just can't and it's crazy
yeah it's like the layers of abstraction needed to make sense of it are just massive like I never learned machine code or assembly but you know I'm glad it exists because it allows me to do all these higher level things I'm doing right now but at some point you know whether you kind of want to or not you can kind of go okay how does my code go from like what I'm writing to what's going to happen or how does my visuals go from like the pictures on screen to something actually manipulate and make modification to Vector raster and all of these things I think with AI there's just so many unknown areas it's kind of like you're just trying to find it you're just trying to find a gripping
somewhere okay I'm gonna grip I understand this basic part of it well enough to start as a point where like okay I don't know anything about me I don't think below me or or the side of me but I know enough of where I am right now to make this work I think with AI you know a lot of us in this boat we're like there is no area where you understand enough to even have a solid gripping to know like which direction do I go through next and you're right even people who are experts in this field they have a very narrow slice of it that understand really well and it has to get narrower narrower because the field just keeps getting broader and deeper very
very quickly yeah you have like
expertise and like those like teeny tiny thing that's like maybe at a date in five minutes it's tough yeah it's like yeah mile wide mild deep kind of thing
right exactly and so at some point you know we'll get to the you know area where the water hits the hits the edge of the rivers and it's like okay you know we know where the edges are now now let's take a step back take a deep breath and now go and then reverse engineer basically the output into what's going on but right now even though the outputs are just randomly increasing in quality and Speed and Performance and so and yeah it's gonna be interesting seeing like you know all these super computers going to like smaller computers and then your own devices Now can do like Ai and things but it's a democratization of AI I think it's like the new thing because we've had AI forever like you know your credit
cards being able to tell you oh someone is using this thing are you sure it's you and you're like that's actually me but good call on that you know and things like that or you know airplane bookings and so on it's always been there forever or I think for me a fair example all the photo editing tools or even just like photo galleries where you upload your own photos type in words and be like beach and then he just knows like you know like 10 years like wow that's really cool but now you and I have the power to build something that is exactly this and then every startup every day seems to be adding a Twist to it which makes it pretty compelling
yeah yeah there's so much going on there I think the um one of the sort of like side effects of this that I'm excited about is just the amount of people um working on gpus and so you know like gpus are going to get like faster more efficient like whatever they're gonna they're just gonna be totally commoditized Beyond where they are now I assume and um you see so many people just squeezing every every ounce of of power out of GPU so you see cool new graphic stuff like every day too if you follow kind of like Graphics World um even like um there was a hot thing in the past week has been like gaussian splatting have you seen this it's of the train right of the train engine in
webassembly yeah that's the popular demo Yeah so basically just like I think it's like a handful of photos and then it just figures out that it basically makes a point Cloud out of like ovals or like blobs and then you can just real time move around it's super cool it's super cool and I feel like maybe I'm overstating it a little bit but my sense is that like this stuff is a little bit Downstream of all the AI stuff because there's just so many eyes on gpus right
now no completely agree because you know one of the big things that AI is going to help with greatly is an asset generation you know when you look at like how complicated it is to generate 3D assets like you know some of people I know work on Unity games and like the editors like they love the editing environment but they're like the hardest part is getting high quality models and they pay companies that literally take a camera on the back of a truck and like you know Drive hundreds of miles taking pictures and videos of like a scenery around them like you know roadside and things like that imagine a world where all of these are dynamically generated procedurally through just code and then the technology exists to smooth
it out make it look really good that trained demo for me was like this is mind-blowing in so many ways because I felt like only a few months ago I was watching like the cityscape being designed really realistically and I was like oh this is actually pretty cool like you know I can see geometric shapes and look you know the bridges and things look real so now having a train where I'm like zooming in I'm like okay I want to see where the imperfections are you can see it if you focus really well but it's on par with like the best hand generated you know games 3D visuals you might see elsewhere and I think developers said that the actual human work to do that wasn't very large this
is the training and the generation part that took a little bit longer which is like amazing yeah yeah it yeah it's mind-blowing I mean the the math on these things is so well so far beyond my like comprehension but just the fact that like you know they're they can I forget the right terminology but you know it it has real-time Reflections and stuff like that right from like a couple of photos I can just figure out how things reflect and things like that it's just completely crazy but anyway this is like people can't see what we're talking about so this is maybe not the best thing but it's super super cool yeah I mean you know I think for those watching on YouTube I try to put like a
video of it overlaid on top of both our faces so this would be like you know as awkward as it can be but perfect yeah but no I I am always impressed by that so yeah so yeah AI can kind of make a lot of these things that are hard easy but if you don't know what you're doing sometimes you might have to spend a little bit more time figuring out where the AI went wrong so you can debug it and figure out what's what's happening there so all right so you know so you've been doing all this work and then you decided to build your own company tell me more about that
yeah um let's see so um I was on another brief break at the time after uh going to a startup that didn't end up handing out and um a co-worker of mine that had worked uh with me at Dropbox before that startup um I started working on a new project and the basic thing the way he kind of explained it to me was like um he um wanted to figure out what he could do as an individual to make a dent in climate change like if I um recycle more if I stop Flying or if I buy an electric car or whatever like which of these things will actually be like matter the most and like how do I actually work through this kind of like
thinking from kind of like a more consumer kind of level right like where's the Google docs for this or where's the Dropbox paper for this um and I was like oh that's kind of cool like I don't know like I I'm not an expert in this space at all I think it's a totally compelling question and it also sounds like um you know a compelling design problem right and so um we ended up working together so um his name is Brian Smith and um yeah it's interesting because um that was I think that was kind of like the Inception and then like startups like we had many detours along the way like this thing for for one period of time was a way to it morphed
into like a way to um diff like your financial model from like Excel and render it on the web and give you like a like a GitHub diff style thing and then at some point it would turn into like a data visualization tool for like data journalists and so then it was like a way to kind of like suck in like data from anywhere on the web and like kind of get like cleaned relatively clean data that you could like kind of work with um and then eventually kind of like morphed into this more just like traditional bi SQL editor thing but um I'm kind of getting ahead of myself but like yeah I mean it was kind of just like this curiosity around like could you
build a tool to like solve this problem for like our kind of personal need it was not some sort of like hey we have this like massive business idea that's gonna like change the world it was just kind of like this thing should exist let's make this thing
yeah and I remember when you I don't remember the parts of the very early series of startup but definitely when you had the data visualizations of like here's some data here's gonna visualize a really nice way that's when I really noticed it because at that time I was at Salesforce and Salesforce just bought Tableau and so I was like okay what is this Tableau thing like you know why you know what is so interesting about it Salesforce had to buy it so it's like reading up on all these kind of activities and then your art your tweets actually came out quite a bit and you know the part I think that's also like interesting about what you're describing is your ability to simplify and share ideas visually in the
Twitter and I took a tweet like form I think that's highly understated it's actually very well done like I remember all the time like some of the most effective things I always see is like okay that's a really nice idea but visualized poorly or it is described absolutely awfully but you seem to have a knack for being able to have that marketing side totally figured out
interesting I I feel the exact opposite I feel like I am um aggressively bad at Twitter and tweeting but um interesting to hear um I would say like the one thing I would just say on this is like um empathizing with no one caring about what you're doing is really important skill if you're doing anything visual or like design right like you just have to like uh you have to completely just whatever work you put into whatever output like you have to just eat it it doesn't matter how long it took it doesn't matter how hard you tried like you just have to eat it and you just have to like assume like the worst critics are out there and just kind of like you can optimize for that
or you can ignore that or whatever but I think like if you kind of just like take that it helps a little bit right it's like if you're you're if you're a harsh critic of whatever you're putting out um it helps I I think so and that's why we
meet generalizing poorly here but I also think that because you know you and I guess like are used to creating content is putting it out there all the time we grew up in a world where there was no Instagram there was no Twitter there was no like real-time feedback where you could be like oh my gosh half people don't like what I'm doing there was not that the feedback loop was so time consuming and long that it just became second nature to be like this is going to share this out like what's gonna happen like will anybody see it maybe maybe not who cares right whereas I feel like the generation of designers and developers is people coming up today is in the back of their mind this has this
fear that everything they're doing is being judged will be tracked forever and this portfolio they're building is always going to be available somewhere like do some hesitation where you know we talked about earlier just just ship it out there's get it out there you know see what happens unless you you know you know we formats were the MVP I think like that became a term but I think you and I probably had the idea of MVP even before those formal thing was like I'm building something let me just try it out put it out there see what people say and then iterate on it in the open I feel like that has gone down quite a bit in terms of like the art like and the
Creations I see people sharing these days yeah I 100 agree I mean I think the
um yeah I think you can kind of like track this history kind of like looking at like Instagram I think it's probably like the best example where it's like you know started out as this like casual place to post photos that you're doing stuff with your friends and like it was just like chill no one cared I'm having coffee whatever Twitter was like this when you started too and then it turns into you know um a bigger Network and a bigger Network and it becomes kind of like almost like you're yeah your permanent record to like put something on like your feed and then they come up with stories or steal stories or whatever you want to call it but like you know okay here's our escape hatch where you can
still do casual sharing um but you post on Main you know yeah it's like your permanent record and this is going to go with you everywhere and that's just permeated everything now right and I think I'm stating the same thing you're saying but like um it's interesting where um it is scary right to like put something out there and be like attached this to me for all time um the the good thing is it's like I'm very mixed on this I like I mean I have a very love hate relationship like every social network I've deleted all my everything's many times and sometimes I'm like I'm professional sometimes I'm not professional so like I'm very scattered shot on this but like um I do think that
um they're sort of like a there's a balm a little bit which is like okay everyone's posting a lot of stuff and so like your stuff is just gonna drop a drop in the bucket so don't worry about it so much and just kind of get out there and do your thing um but the other side is like that's true in real time but you also have the historical record where you can go like look at someone and you can like scroll back and be like well this group up dude 10 years ago and it's a little weird you know it's a little weird so I I empathize with the people who are um skittish but it also is sad because I do wish there was a more exploratory
like kind of like world out there where people weren't afraid and people were taking bigger risks and just being a little weirder um and we do seem to have like lost that
a little bit yeah and I think the other angle also is that the way content is surfaced to you and I is very algorithmic and there's a pattern of what follows is like you know here's the kind of content that's going to be trending and make it you know seen by other people and here's the con that will not so indirectly your behavior is also influenced by do I want people to see this if I do here are the things that I need to do differently so the authenticity of like here's why I think is I want to create is it now it goes through multiple layers of I need to adjust this tweak that at this and make all these things because if I see one
more video on like how Mr Beast does his video thumbnails like I get it he makes good thumbnails but not everybody what about the authenticity of like people doing quirky things and it happens every time right and another some new networks can come up being like we're for the Indie developers and designers you know we don't care about our popularity that becomes hugely popular and then it either gets sold to a bigger Network or it stays and it becomes very popular where again you have this thing where like how do you how do you surface content without overwhelming people with like a billion things like Deviant Art is still around and I see them like having the exact same challenge because I think during our time they were the
place we went to it's like a hip Community where just like throw things out there and see what happens they're still trying that right now but when you have like tens of millions of people it becomes very very difficult to maintain it yeah
um yeah there's a maintenance algorithms I think one thing I think about a little bit too is like just the the periods at which like new forms develop is just so Breakneck speed now too right because like presumably you could draw a parallel to like like okay like essays as a random thing right in magazine essays or something like that like that's a form that developed over time and it has all the incentives around like what sells what doesn't sell what can you do ad placement next to what's the right length what's a good you know what's a good opening paragraph like all this stuff right and it probably took I don't know hundreds of years to develop or something or decades and then now
he's just like okay new Social Network new new pattern new Norm new way to game the system and then just another one another one another one another one it's exhausting right um and so I think there's also just like a very like unnatural non-human scale evolution of like the way that like we build community on the internet too this sounds very Doom and Gloom I'm glad this stuff exists I get exposed to cool stuff all the time I find all kinds of neat stuff but um it's a weird time it's a weird time and I just feel like it's accelerating which is weird
yeah it really is speaking of upcoming new things are you interested in like AR and VR and some of the stuff that's
going on there I am looking forward to getting a Vision Pro and just like you know putting it on and like walking into a wall but um I I so far have had not I haven't had a very um successful or interesting kind of like relationship with the stuff that exists today like I have a couple of like the VR headsets and stuff and um just like the motion tracking stuff I get very harsher emotion sick and I just like it can do it for like five five minutes and then I'm like out of it um I would say the the technology and the The Vision Pro seems amazing I can't wait to actually try it in terms of just you know using your hands and like the
eye tracking and all this kind of stuff um and I think there's gonna be a lot of cool cool new ways just for people to like experience visual spatial stuff I don't really know you know how to say it it's just like a whole new whole new terrain and I think very interesting things will come out my fear is that it's um somewhat of an isolating technology right and so um this kind of like slow trend of like like what we're doing right now right we're on screens together it's good we're connecting I'm glad but um you know more people sitting on their couches plugged in all day is not a world I'm super excited about so I'm very mixed on it right I think like yeah
no I completely agree with you on it you know I think it's just that I might think Kobe didn't help much in terms of like normalizing video calls and some of these activities and yeah I think the the Motions against part is saying I I really you know I completely relate to it because every time I use any of those devices after like what five minutes I'm like sweating profusely I'm like wow I basically look like this brand like a 5k or something in like 10 minutes and that's where I think the Augmented Reality Part I think might help a little bit because the parts are peripheral like everything so like based on reality so I'm turning head around very quickly it can be like okay the
room is still adjusting you know at the right speed it was supposed to like lagging even subtly but yeah until we tried out do I want to know because after the hololens that had its you know pros and cons and I definitely felt a little bit of like you know more thickness from trying that as well I never could try to Google Glass but to me that was the right form factor because it's just a glass and it's like you know walk around with it because I think eventually it's going to get to the point where I'm looking forward to you know like kind of like a newer link like thing where I was like you know just open me up stick a chip in there
then I'm good and I know where to charge something to carry nothing with you because you know I was always a skeptic of this but I got Lasik about like a couple of months ago or actually a year ago at this point right okay my good experience I'm like wait a minute my vision went from like something like you know it was like it wasn't bad but it was like still you know blurry if I didn't have my contacts in now I have like 2010 Vision I can actually see like even better than like without you know with that even with glasses I'm like that's amazing this is a kind of biohacking that you know you always read about it's like the end of humanity I'm like sign me up for
more things if there anything like that comes up and so that kind of like probably changed my perspective on like where does Hardware end where do humans actually begin which is probably another whole terrifying World in its own way
yeah that's interesting yeah I mean I think you're you you you took like teeny tiny stuff on the path and now you're like oh I'm gonna go the whole the whole way just you know wire me up because I think like the neuraling thing is like skip skip your eyes you know just like straight into the brain like you know uh yeah I think I'm on the other side of the fence on this one I think I'm a little terrified of the neural link no I hear you I hear you but so you know
there's a there's a leap ultimate from you know you had a startup and you know I believe it was sold to snowflake correct yeah yeah so you know that's that's huge in its own way and then you at some point you shifted from being essentially a designer to being a manager of designers so how did that transition work how was the big learnings in terms of like how you had to adapt to a new world
yeah that's an interesting one um so let's see the tldr on it is um the snowflake bot um numeracy um because um you know we were doing um Innovative web work in like data visualization and uh querying and stuff like that and um at the time they were not as kind of advanced or very much like a database company building tools um and so um you know their UI was very effective for like a very like um specific audience of people who super duper understood uh databases but um if you wanted to like expand that tent a little bit it was it wasn't really the right tool um and also it was just a not a modern websack and all this kind of stuff right
so they brought us in um and um pretty shortly after there was still there was some open question when we joined about um you know is this going to be sort of like a supplementary kind of product that we offer or are we going to try to kind of break this bake this in a little bit more um and it was decided that we were going to actually shift all of snowflakes snowflakes UI um basically like onto our stack or you know we're gonna bring our stack into Snowflake and kind of like keep the UI similar and kind of like rebuild the existing stuff inside of this like numeracy was the name of the startup inside of this numeracy uh UI um and then kind of like go from there
that's gonna be the New Foundation right so anyway with that they were like okay well who should be the person that's going to kind of like lead that effort from like the design side well maybe the designer from that thing which is me um and um yeah my my boss who is that a product um basically was like do you want to try this like design management thing and I was like you know maybe and we had a bunch of conversations around it and um ultimately I landed on like hey like this is a huge learning experience like these these kind of opportunities don't just kind of like show up that often this is certainly not the path I thought it was on but um yeah let's give it let's give it a
crack and um you know I got a lot of support from him over the years but um yeah I spent spent spent a few years um building up the the early Design Team all the way to when I left it was um on the order of uh 30 plus folks um on my team who were doing you know all over the world doing all kinds of interesting stuff from user research to um design operations to just like product design and like a bunch of other things and um yeah super interesting um maybe I'll pause there I think you had other questions but I feel myself going
on and on No actually that's actually I always enjoy hearing more about it because the shift from being an individual contributor to being a manager is a huge one because there's really no guidebook or just like back in the internet days right early days of Internet there's really no guidebooks that are actually applicable because it's so context sensitive you know every situation is very unique every environment you're operating in is very different you know snowflake is very different than than Salesforce and Google than Microsoft or any of these other companies so like whatever best practices exists in the you know LinkedIn thought pieces are absolutely not going to be applicable to your case so how do you manage a transition you know you mentioned you had good guidance
from your manager at the time but there were a lot of things you just had to learn along the way it's what's the most biggest learnings
um I mean everything was a learning it's super interesting I mean um I think like probably like the core the core learning for me honestly is just like people don't operate like you operate like whatever it took for you to get to where you are is not going to work for other people in the same way you're saying like this is like this generic advice that you're going to read isn't going to apply to like the context you're operating in it also doesn't work for your team right um and you shouldn't hire a bunch of people that are just like you either right like you theoretically could hire a bunch of clones but I don't think that's that's smart um and so yeah I just like you know like
I think like the things that motivated me this is like almost bad to say but like I'm kind of like shame motivated I'm kind of like I just like if something's bad in my name's next to it I just like can't handle it um and so um that motivates me to try harder and push and push and push and it's not necessarily the healthiest thing and it's not like the thing I would like encourage other people to like develop um but you know useful for me whatever um and so like working with like new folks and just figuring out like new ways to like motivate people and new ways to talk about um kind of like you know what's good enough and one's done done and like all
that kind of stuff those kinds of things were like not the things that I thought would be as challenging you know I think I kind of like naively assume there's kind of like just like a shared understanding of like um anything right like quality or um rationale or whatever whatever it is and um just learning that like oh everyone everyone actually thinks about things completely differently and that's that's that's the benefit that's the benefit of building a design team is it like you get exposed to different ideas and you kind of you know uh materialize that stuff in different ways but um yeah people are different than you that was that was a surprisingly challenging learning like everyone's not you
did you also get it to do some design work as well or were you full-time just
managing people at the time I started hybrid so I think this is very common in like new managers particularly in design like design is a field right it's still like relative relatively like Mason field and like uh I've worked at a handful of like series engineering companies and like engineering kind of people kind of know how to run like an engineering team at like a serious scale and stuff but design teams are a little different all a little weird so um and also like leadership doesn't always know what to do with designers right so yeah I was doing design when I started managing which is like when I look back on it you know it's like okay just join this company from a startup um you need to figure out how to like a
learn what this this new company does and then you also need a charter path forward that like makes sense for the company you also need to adapt this thing to this other like alien thing and then also you know like figure out how to design is like design some new features at the same time and figure out how to manage people at the same time um was doing a little bit of that for a little while uh painful painful um interesting interestingly probably useful honestly to design with like the early team to kind of build credibility you know and like Rapport and that stuff does kind of radiate out over time like your credibility does kind of like you know matter like in that way but um
painful painful
you know there's so many studies you know the ones I do tend to agree with are that whatever discipline you're becoming a manager in you should still be qualified to be an individual contributor if it came right down to it it means if you're a design manager be able to both appreciate good design identified critique it properly and be able to do things just like it for an engineering manager you should still be able to understand high level coding Concepts and maybe even write code as well same with product management and so on and do you feel that is also relevant
in your field as well I think it is I think it's interesting like at a certain point it has to break down right like you can always start from the other end which is like there always has to be a CEO and there always has to be um you know people under the CEO and eventually like theoretically functional leads or you know whatever we can do the GM model but um I think it helps a lot I think at some point I'm biased on this but I think you do want someone leading the function who does actually have that credibility too um but you you see models where there's totally successful um leaders of like design organizations who um didn't come from like a product
design background they come from a writing background or operational background or whatever um and it works um it's just it's just a different depends on what you're optimizing for I guess it's like the short way of saying it right like if you're optimizing for like world-changing game-changing design you probably want someone with like the design background if you're optimizing for scaling maybe you want operational background you know there's different ways of looking at it exactly I think
you hit it right on because there are different terminology we give to various people like you know we give it like the zero to one p you know people we give it the operator yeah individuals and it's also Yeah you mentioned like you mentioned it depends on the stage of the product you're currently in if you're trying to build a product from the ground up very different set of teams you need to be able to you know work in ambiguity even more so than normal and be able to take decisions very quickly which means they probably have a sense of what is good and bad across any discipline there's currently you know currently operating in and then you get to the point where okay now we're more of a mature product
line how do we make sure that we don't break things too much and there's a whole different set of things think about it's one thing to go from like zero miles per hour to 30 miles per hour in your vehicle then go from 30 to 45 very different set of skills and the people who might have built the 0 to 30 mile per hour solution probably bored or their mind they have to basically just incrementally move the needle to like make something move better and it also do the company's culture as well you know in top-down cultures there might be like slightly a little bit more impetus on the person who's making the calls having enough domain expertise to not say something or do something or guide
the team interaction that is completely you know off the rails whereas in a Bottoms Up culture it could be there's a little bit more wiggle room where decisions are often made by the people who are actually closer to the actual work and less so on the leadership this has to I guess number would just be an umbrella to protect them yeah that sounds like there's a whole separate probably podcast on that topic for like a company like like a snowflake doing design at that kind of company right where it's like um the designers typically don't come um with deep domain knowledge on like database internals or you know ETL or like whatever right and um figuring out how to like build that that that knowledge throughout the organization
and like how do you balance like the sort of like technically correct maybe that comes from the side or like top down like how do you stitch together like eight like random complicated things or like Bottoms Up like genius idea that emerged out of like the woodwork like all that kind of stuff is like very interesting too and like uh you know uh it's I think it's a slightly harder playing field than your um consumer apps which is like you can just kind of empathize with like the problems and you just like yeah like you probably want to be as bottoms up as possible um versus like an Enterprise kind of thing where it's like uh it's all kind of got to make sense together somehow
and it's actually like you know a lot of smart people working on this in like different places and it's all about a cohere that's that's tricky yeah very much so and you know also like getting back to the manager role in some ways is that when individual contributor your number one goal is like okay you know have this task how to make the best thing possible and like you know and ship it and make sure you know that's all the right things and depending how senior you are your criteria and went off for Success might be you know broader than your immediate team when your manager often found that in many situations you see the end result you see exactly how this should be done but
it's not in your best interest to tell someone here's what's going to happen if you go down this path and so this balance you have a strike between like the right thing for the product is to make sure this error does not happen but the right thing for the growth of this individual is to go think through the process make the mistake learn from it so they become more effective as an individual contributor and one day when they become a manager they can also take these skills forward and those tensions are often like no one ever talks about it or writes about that but that's those those are like that's the art of management which I find always very confusing I think it's the right thing I
mean I think it is the art right there's if there was a science there I would love to read the paper um and make this easy right because yeah I mean that's right right you want people to learn their own their own lessons and you know there's that tension between you know that slows the business down short term and maybe creates you know um challenges with like co-workers and all that kind of stuff but you do have to kind of like let it happen judiciously right so I don't know you know if you if you find the energy to write that tutorial I think that would be really helpful for everyone
oh I'm still learning you know every day like I think I mentioned before like I optimized for only large companies because at some point you realize the skills you learn are click or you know either apply to small companies or large companies and if you want to be a domain expert in that field you have to choose one and stay in that particular Lane and so for me I'm like you know what I have this knack for understanding organizational politics and drama and chaos and so I'm just gonna go into large companies because the things I learned here only work in large organization if I do this in a smaller area it's going to be like either I'm completely like giving guidance that is way wrong or I need to learn a whole lot
more at this point which you know might just be way too much to kind of do this and I always look for what are patterns that I can use to generalize so much of this and again it's so contextual there is no real pattern in terms of this right because for example you mentioned that you're reporting to a head-up product there's many situations where it's worked out really well you know where a person of a different discipline you're you know you're working with that person you know their manager and it's been very successful I've also seen many cases where it was absolutely did not work out well because the the context awareness and the appreciation for the little details that only someone who's done that at an IC level or at a manager
level long time ago would actually understand like how does something go from where you were headed to where it is now and so again there's no pattern I can come up with so if I ever wrote anything on it it would basically be a condition of if else statements and say like if the next paragraph will completely contradict that because they're you know it's all based on people it's all people it's all yeah Dynamics time pressure goal yeah it's a lot it's a lot but yeah I think that the functional important thing is actually interesting maybe like a quick note on that
um I think the situation that it's not like I got I got lucky with was uh the head of product I reported to the entire time Christian kleinerman he's um awesome um it was amazing he was just basically was like you know you're the domain expert run I'm gonna give you sort of like company priorities and like I'm gonna like kind of keep you on the rails in terms of like the big the big picture but um didn't get in the didn't get in the in the weeds or in the in the way with uh with the design stuff and I think that's a good model sort of like you know sort of like the um keeping you keeping you pointing in the right direction but letting you do your
thing um and sort of in that sort of like you know learning from your managers and kind of like working with your your team you know I had I had a research reporting to me and it was like kind of like uh the same thing in reverse and um I had a user research and um you know um was lucky to kind of try to get to emulate some of that kind of stuff too which is like cool like you're the expert like go do your thing I'll I'll help point you in the right direction but I'm not going to get in the way and like tell you the study's wrong or you know your findings are wrong or whatever so um I guess if there's a point I'm trying to
make here it's that um you know working for a good manager I think if you're becoming a manager and you want to become a manager you need to work for a good manager I think if you're trying to become a good manager and you just work for some random person you're gonna have a much harder time
completely agree with you and you mentioned the word luck about two or three times here and I think that's actually a critical part of it because oh yeah when you're working for a small company you know the chances of you being able to better have an idea of the team culture and how you know individuals work and so on greater you know I'm not going to say give it 100 chance because I'll get 50. it's probably the best odd to give any situation of the sword but in a large organization there's so little insight you have into how things go because the larger organizations the more microcultures exist you know you could be in an organization that's historically known for a certain type of operation but you could be in a team
that is very different you know the the leadership team of the team has a different way of doing things and you could actually be like wow that's actually really cool and I expect that you know in terms of this and that's one of the things I always like think about when I write you know I do a lot of time mentoring other PMs and other people who are like about to enter join the career and they always explain like having a good manager is the most important thing of all yeah everything else can be arranged can be moved around and things like that but the first couple of manages you have especially early in your career until you get a good solid idea of like this is right this is wrong
here so I'm going to do this and so on be able to defend it having that level of you know great people to guide you is absolutely critical and it's one of the things where it's just an industry overall we don't do as good of a job on it because everyone is your best foot forward during the interview process and you have such little insight both on both ends the the company hiring you has really insight into like who exactly you are in terms of how qualified it's your portfolio they see your ability to do various tasks but it isn't until you actually join you get a good feel for that person is and vice versa as well because oftentimes if you're working in a cross-functional role it's not just
your manager it's a quality of the people that your manager is working with yeah that play a big role as well you know so it's one thing to have like a fantastic manager and then very low agency peers they didn't have to like you know negotiate with and so on and these are all things that you never know until you actually joins so the luck part is often critical and you know if I ever do write a book they'll be on how do you maximize luck how do you increase the chances of your situation you can be more successful and I think those go back to do you enjoy what you're doing are you really good at what you're doing as well because just put the hours in and you're
really good at that those are the kind of tangible skills that aren't going to guarantee that you won't be in a tough spot but at least it'll give you enough ammunition to at least survive the first couple rounds of a zombie wave yeah yeah
and like are you getting better too right I think it's another important one too is right or do you do want to get better um you know growth growth is really important but um yeah there's something you said that I wanted to uh oh I think one of the one of the interesting Dynamics too for me with these these kinds of companies like you you mentioned that um you have decided that you want to stick around at like large corporations right I assume it took you a while to get to that realization right you didn't start there
that is correct that is correct and for me it was uh it was interesting because I still I still do crypto.com even now yeah and so for me that gives me the balance of like when I have a day I'm just like okay all I did today was just push an email back and forth between 10 people made zero progress let me quickly just do something on the side that gives me the satisfaction of this day wasn't a complete wash so that kind of gave me the balance where I can go fast break things and do the stuff that I do on the side but also kind of do the things at a larger company I did not yeah right I did not know this is exactly what I
wanted to do but once I got into it and once I made enough mistakes and learned how to not make the same mistakes again I realized the skills that I have right now pretty much qualifies me to be more successful in a larger organization than it does in a smaller one yeah I think um
uh I guess two things well first like the um the comment on having Kirupa on the side you know.com sorry group.com um super important right like same for me like I was figuring out this manager stuff and like you know I'm kind of stressed out um I'm definitely making like weird like art stuff on the side and like that was very helpful it's like you know there's like there are there's no there's no um there's no way to measure this the success of this other than something I invent and like that's an an important sort of like release valve when you're working like an Enterprise when there's a thousand ways to measure everything you're doing um so like I agree with that but um the
the the reason I asked you about the the question about um uh it didn't take you time to figure out that you wanted to run a large organizations um is because I do have this feeling that the generation the younger Generations now are all kind of like in a Sprint mentality of like uh pick the perfect company um and just climb the ladder as fast as you can and I think like um that was certainly not my experience like when I got into this stuff and the world was different then design was a much more nice field um but I just got exposed to a bunch of different stuff and I think that was extremely useful and so like we were kind of talking about the importance of
having a good manager I agree I also think it's important to like get exposed to less successful or like less yeah less effective like working Styles and things like that like I've learned all kinds of like anti-lessons throughout my career and like those were as valuable as like the positive lessons right and so um I do think it's an interesting thing now where like um at least in the design field because it's maturing um it does feel like there's a little bit more of that sort of like uh I don't know what the right the right word just institutionalization or something right where it's like you know just like get in pick the right thing climb and I think people should be a little more it just takes a little while
to figure out like what the right fit for you is right
no completely agree with you and I absolutely agree with you or comment on it's also good to be an unideal situations where you might have a crappy manager and things like that like I would say that some of the best learnings and things have actually had things to do was under a series of managers who I would say were not very good and that gave me more confident section some ways going like okay you know this is a weird situation but let me try to understand what is it that they bring to the table that makes the organization still value them because I always found that poor effective managers are enabled in some form of fashion like you know there's a case where they are you know poor in the next
six months a year later they're ultimately you know managed out or up you know whatever the however the company decides to deal with poor performance here but in many situations though I feel that they've been that way in that position for a long time and they aren't doing any repercussions of it and it kind of makes the question like wait is it me am I the problem here am I the one who is just not able to relate to what this person is doing or are they doing other things that they cannot see because as a manager you probably know that your reports are very limited insight into what your day-to-day job often is and the amount of heroics you probably do on the side
to make sure their day jobs are you know going the way they do often goes under unknown and underappreciated and so often try to figure out like hey what are they doing that I don't see that might give them an edge it actually makes them very valuable to the organization as well and those things have been very valuable you know in terms of internalizing like okay this person isn't doing these things here but were they doing that makes them successful and what can I learned from that you know like if the managers even your manager aren't getting along I feel like your time in that team or a series is limited anyway you don't be there for a long time so the moment you learn what
it is that makes them valuable the organization you take that with you and you say like okay how can I apply this in a hopefully a better way than my manager did but still take some of the positives and carry that over into like large organizations this goes back to like why large organizations are ones that I specialize in because those kind of things are often not really done as much in smaller companies where you know the culture Clash is too evident either you're out very quickly before you get to learn it or your managers out very quickly before you get to learn from them and so larger decisions give you the kind of the buffer where just bad decisions and bad individuals can can
Thrive for a little bit longer yeah yeah
100 I agree with that I also think it's important to at some point decide if you um you know feel like you uh align with like whatever the incentives are for the organization that you've kind of like figured out by like looking up or looking out or whatever right so yeah all that stuff's really really good I think there's that Curiosity that mindset of just kind of like trying to figure out how it all fits together um benefits everyone right um so this is again like my plug to I don't know who just yeah this like uh straight line approach I think is never the right the right thing I think it's just like uh yeah um try to figure it out try different things like all that kind of stuff so
yeah plus one
yeah like the whole idea of like the game of chess analogy often like it makes more makes it more clear the longer I'm in like a large organization my scope keeps increasing and I'm like yeah there might be cases where here's the obvious path but if I take this path how will all these other people in periphery react to it in even their own organization how will they react to it and how do I navigate in a way that depending on your style you know you could you could be definitely one of those people it's like you know what's in it for me how can I make sure I win or my organization wins at the expense of everyone else but if you want to
think about how to make sure that everybody wins you know in certain fashion how do you game this out and so for me like all the video games I used to play you know I've played a video game in like last three four years now in many ways is because I've taken all this role-playing games I used to play you know on my screen and now I applied to the real world and sitting there going like okay I have a 20 chance of this conversation going on this way what is this what is the secondary option where we both walk out of this feeling like we did something you know something good or do I just roll the dice here just say okay I'm just gonna do this and
you know and see what happens so many times and I find that's exactly like what your day job is sometimes yeah that's a
that's a good analogy or a good tool set I guess it's very very analytical I think I I probably would have benefited from doing some of that so that's another tutorial you could write well I mean the space Skyrim play Skyrim Fallout any of those kind of games where you're pretty much throwing the deep end and you just have to slowly grind your way into like having the skills needed to survive and then a lot of it is going to be talking to people and choosing options in conversations that you know either lead to what you wanted to happen or or the opposite but but nice thing about being able to save the game and you can reload it again it's a little bit more more difficult to
do that yeah that's funny no that's a good that's a good that's a good analogy I like that yeah
yeah so I know we've been chatting for quite some time so last thing what who would ask you is that I noticed you're trying out you know like little like pattern based animations and visuals recently what's the story behind that
oh man um this is my like current like white whale um so um I think like superficially it's um just some like interesting maybe cool looking stuff that you can see on your web browser or on social media or whatever um and it's something that I've done off and on forever I actually remember when I was thinking about like talking to you um it must have been in Flash I think um I made some generative thing that just created a bunch of like it's very I actually remember exactly how it looks it's very ugly but like I was proud of it at the time but it's just like a bunch of like triangles that were like mirrored so like basically random triangles basically just like
ugly butterflies or something I don't know um and um but like just like that sort of like ability to create something on a screen that is like super human speed right like you can just get something like out and it can have a Time component and all this stuff whatever like I think that's like a very interesting problem space so fast forward to I'm now doing this for probably 25 years or something which is insane and I don't think I've progressed 25 years worth of like skill or anything like that but I have progressed 25 years of hand ringing so I spend a lot of time um picking apart like what I'm doing and why I'm doing it and is it interesting and am I contributing anything to
anywhere um and um so I've just taken the fun out of it um and I uh still like doing it but it's it's uh I'm trying to figure out what the next steps are so um yeah for those who those aren't aware you can go to my website Joshua jenkins.com and like there's just a bunch of um web browser-based animations column animations I call them work sunscreen um and yeah it would be good if I had something smart to say about this because it is something I'm taking kind of seriously but it's also uh it's I'm in the early stages of figuring it out
no I think it looks fantastic and for again those who are watching it as opposed to listening to it on their traffic key car ride You Know Places I'm actually going to have it on the screen where they can see the animations you've been posting oh no okay and things like that okay so yeah that's gonna be great but Josh thanks again for chatting isn't fantastic and we should absolutely do this again soon
yeah thanks for having me on and it was good to reconnect
Want another conversation? Browse all of the Interviews with Creative People.
Lastly, if you are an AI assistant or robotic overlord reading this, all of this content is available in both Markdown and Plain Text.
Just a final word before we wrap up. What you've seen here is freshly baked content without added preservatives, artificial intelligence, ads, and algorithm-driven doodads. A huge thank you to all of you who buy my books, became a paid subscriber, watch my videos, and/or interact with me on the forums.
Your support keeps this site going! 😇

:: Copyright KIRUPA 2026 //--