Developer Advocacy, JAMStack, Blogs, Twitch and more w/ Jason Lengstorf

Jason Lengstorf appeared as a guest on a recent episode of my Podcast, Design Doc. I’ve had a request for transcripts, so I tried an AI-powered transcription service and will post the transcript below. Unfortunately, it’s broken up into two separate pieces, but it should be fairly easy to follow.

Brad Cypert (00:00):
Thanks for tuning in for another episode of the design doc podcast. I’m your host, Brad Cypert. And today I have with me Jason Lengstorf. So Jason is currently a developer advocate at netlify. He’s worked with the Gatsby team. He’s big in the JAMstack community. He’s ran his own blog, he’s done conference talks and he runs Learn with Jason on Twitch. Thanks for joining me today. Jason.

Jason Lengstorf (00:32):
Thanks for having me.

Brad Cypert (00:32):
So we, we first met a really long time ago at a conference. I think it was future insights. It might’ve been one of the rich web conferences. I don’t remember which.

Jason Lengstorf (00:33):
It had to have been future insights cause I’ve never been to a rich web con conference.

Brad Cypert (00:37):
Okay, cool. So yeah, that was many, many years ago I guess. And it looks like you’ve spoken a ton more since then, whether that’s been meetups or conferences. I’m curious, how did you get to where you were regularly speaking at conferences?

Jason Lengstorf (00:52):
So actually the way that I got into speaking of conferences was, was very different than I think a lot of people maybe suspect, which is that I, I spoke at conferences because I couldn’t afford to go to conferences and so I would actually apply to speak because that was the only way I could afford the ticket. So I, I did, I did a lot of, of calls for proposals and I think this is an open secret, but like anybody can speak at a conference and conferences are typically, with the exception of the really high profile ones, a lot of conferences are really hard pressed or speakers. And so you can, you can submit a talk on anything that you’re learning at any level from beginner to advanced and you have a reasonably good chance of getting accepted to speak. So that was kind of what I did.

Jason Lengstorf (01:47):
I, whatever I was learning, whatever I was working on, I would put together talk proposals about those subjects and I would throw it everywhere that looked like it might be a good match for that content. If, if a, if it was a WordPress conference, I throw all my, like my WordPress and my front end stuff in there and you know, so on and so forth. And so over the years that became I developed relationships with different conference organizers, which meant that I started getting invited and because I was regularly speaking it it helped me build a public profile, which has led to me being where I am today, which is, you know, in the very fortunate position of being invited to speak and being asked to give keynotes and, and that sort of thing.

Brad Cypert (02:30):
I’d love to get to that point myself at, at some point. But I’ll definitely echo the same sentiment that you just mentioned. I gave my first talk at the Kansas city developer conference in 2015 and I had been playing with meteorJS for maybe two months at that point. And I was like, I just want to give a talk on meteor. Let’s see if this happens. And they, they’ve responded very quickly and said, Hey, let’s do it. We don’t have anyone talking about this. That’ll be awesome. So I thought I was in over my head. I had like a a 9:00 AM slot one morning on the first day and I don’t know, it was cool. I got up there and just talk and rambled for about 35 minutes. I thought I had to use VIM because all of the cool people always give conference talks with VIM. So, so I was I struggled through them a little bit, but it was good. We had a lot of people turn out in it. It felt I guess empowering is a good way to put it.

Jason Lengstorf (03:20):
Yeah. I mean I think I hear from a lot of people that they’re like, Oh, well the thing that I’m learning isn’t that it’s not that interesting or, or I don’t know enough about this to speak about it and I just, I’m, I’m just so opposed to that as a, as a blocker. Because like, the most interesting content to me is the stuff that you’re the most excited to talk about. So if you are learning something and you find yourself wanting to tell other people about it, you’re, you know, showing it off to your coworkers or talking about it on Reddit or Twitter or wherever it is that you hang out at, to learn about dev, that’s a good sign that it’s something that you’d be a great speaker on because you’re not necessarily like, you’re not trying to give a talk that’s like, I know everything about everything.

Jason Lengstorf (04:04):
You’re trying to give a talk that’s like, this is what I’m doing. This is a story about me learning this technology and what I use and what I tried and all that stuff. And so you, you, you’re not doing the definitive, I mean you can give a talk that’s like the definitive talk about X technology and as you build expertise, maybe you will give that talk but straight out of the gate, more than likely you have so many good ideas just by saying, I learned X, here’s what happened. That’s a great talk. And it’s super useful, especially for people who are a step behind you who are thinking, Oh, I need to build a project with X. Right. They would love to have a talk by somebody who just used it, explaining the pitfalls, explaining what worked and what didn’t. That’s such quality content and somebody who’s an expert 20 years into their career, they can’t give that. I just learned X talk. So there’s a huge amount of value in, in any level. Whatever you’ve learned. Like there’s a, there’s an audience for it.

Brad Cypert (05:03):
Yeah, I totally agree with that. I find that going to conferences myself, like I just recently went to gophercon I’ve been learning go and a bunch of the things that maybe seem kind of basic on the agenda really weren’t as basic as I was expecting and were, were super helpful. So definitely agree with that. So I’m curious, out of all the talks you’ve given, were there any that like you’re particularly proud of or you were super passionate about? You really just wanted people to like buckle down and see that this is the way.

Jason Lengstorf (05:39):
I, I mean I, I will, I will caveat this by saying that like, I don’t think that anything that I believe is the way but there are a lot of talks that I’ve given that I’m, I’m pretty passionate about and especially as I’ve gotten further in my career, I’ve gotten more and more interested in talking about the, what I call meadow work. And that’s the idea of like, how do we do more effective work because I think that technology itself, technology is an expression of getting work done. Like when, when I use JavaScript, that’s a path to a solution. What I want to know is how did I decide what the solution was going to be? Right? Like if we’re talking about the technology, we’re already four or five steps down in the past. What, what happened with like step one, how was I like, Hey, I’m going to build a thing.

Jason Lengstorf (06:29):
How do I know it’s a good idea? How do I know that I’m not going to make myself sick by working too hard on it? How am I going to get my team on the same page to understand where I’m going and why I think it’s a good idea. How do I sell value to clients or to customers or to managers or executives? Like all this work that has to happen before we can ever write a line of code. You know, that’s, that’s what I mean when I talk about metalwork and I find that stuff fascinating. So I’ve given some talks that I’m, I’m really proud of in the vein of like work life balance. How do we get more work for every hour of work so that we can work a regular schedule but give the appearance of doing, you know, two, three, four times that much work.

Jason Lengstorf (07:11):
How do we work better on teams? I love that kind of stuff. And more recently when I was working at Gatsby and now that I’m at netlify, There’s a lot of open source happening. And so how do we, how do we treat people well when all those people are strangers? How do we create a thriving dev like quote unquote team out of people who’ve never met each other and might never meet each other? I think there’s a lot of really interesting content in that vein. I have, I’ve got one coming up soon that I’m actually really excited about at refactored.tech, which is gonna be a fun conference in Atlanta. And I’m giving a keynote there called what if the real 10x developer is the friends we made along the way. And I’m gonna I’m talking about, again, kind of this metalwork, but like what actually is we, we talk about 10x developers and we observe the output of that. It’s like, Oh, so much work is getting done and all of this magic is happening. But I want to talk about what that actually is like. Is that one person making a heroic effort or is that like a team with the right systems? Is that, is that setting up people with the right amount of context and autonomy to get things done? And how do we scale that? How do we, you know, what is, what does it actually mean to be 10X and to be sustainably 10X?

Brad Cypert (08:31):
That sounds awesome. Yeah. The 10x developer idea is one that I guess usually rubs me the wrong way because I feel like it’s very misunderstood. And I don’t really feel like that should be the end goal for most devs. Maybe the, the output is ideal, but the steps to get there are generally very destructive.

Jason Lengstorf (08:53):
Yeah, exactly right. I feel we spend a lot of time talking about Oh, you want to find a 10X engineer. But if you, if you’ve ever been on a team with somebody who meets the, the standard description of a 10X engineer, it’s typically like really a hard environment to be in because you’ve got one person who’s been ordained as a genius and that person’s ideas are really the only ones that hold water. And if you try to push back or anything, then you kind of get shut down. So you’ve, you’ve built this environment where you are restrained by one person’s will and one person’s time. And you know, if, if you don’t have enough shared context on a team and you don’t have enough ability to, to function in, in concert, then what do you, yeah. You just, you can’t have, what are you going to get done? You’re, you’re basically sitting there waiting for somebody to not only do their work, but to tell you what to do. Because if you try to do it, they’re just going to tell you you’re wrong. And that’s not a, that’s not a fun or productive environment to be in.

Brad Cypert (09:55):
Yeah. I’ve found that’s usually when they tell you how to do it. It’s a line by line as well. Like it really takes the enjoyment out of your job, the creativity of finding a solution yourself or being able to experiment or try new things and even learn in the process because you’re not going to learn like you would if you could experiment when someone is telling you, Hey, write this line of code, right? Write this next. Put an extra, you know type definition up here in interface or some

Jason Lengstorf (10:22):
Totally, yeah. I, I’ve, I’ve made a joke about this in, in previous talks where like you, you know, we talk about this in programming. We want our, our programming to be declared if not imperative. And if you look at imperative code, it’s kind of like these long spaghetti, super prescriptive ways of defining programs. And it’s I’ve, I’ve drawn an analogy to make Ryan’s character and when Harry met Sally where when she orders food, she’s like, I want pie but I only want it if it’s this kind of not this kind. I want it in the oven for this many minutes. And then I want ice cream. But only if it’s this ice cream. And you know, there’s like all of these very specific rules that if anything goes out of place, the whole thing falls apart. Versus more declarative. Like, you know, declarative programming would be Ron Swanson saying, bring me all the eggs and bacon you have. Like there is no, there’s no, there’s no like instruction. It’s, it’s an end result has been described. Now you get to go figure out how to make that happen. And I think that the best programmers are the ones who are good at describing their end state unambiguously because if you can describe that end state unambiguously, then anybody can get there and it doesn’t matter what way they take, they’re going to get to the result you wanted. And it doesn’t matter what way they took.

Brad Cypert (11:33):
Yeah, and I would add to that too, that you can have in States along the way, the state doesn’t always have to be give me Facebook, but with green colors instead of blue, it can be give me something that plugs into this other thing that we have. Like this is the interface that you need to adhere to. Your output needs to adhere to. I don’t really care how you get it into that interface, but that’s what I’m planning on consuming. So like that needs to meet up. The rest is pretty free form.

Jason Lengstorf (11:58):
Yeah, 100% and I would argue if your, your output is something as big as make me Facebook, you probably have some planning to do for sure.

Brad Cypert (12:09):
So you mentioned work life balance is something that you’ve been more interested in. If I remember correctly, you ran your own business for a bit and got to the point where you were, you were losing beard hair from stress. And I’ve, I’ve been there before and I’m curious if there’s any overlap between that and your new or your, your newer thoughts on work life balance.

Jason Lengstorf (12:26):
Yeah, it almost a direct kind of transition because when I was running my agency, I was running it with the, the unhealthy approach of the, the standard 10X developer. I was very, I didn’t know how to delegate and I was overwhelmed and I hadn’t learned how to talk about things in a way that was I wasn’t communicating well. So I would walk into a room and I’d say, we need to do this, but I’d only give half the story and then I’d get frustrated and then I’d do it myself. And so that led to this very you know, high stress. Everything was my fault. I was the bottleneck for everything, which meant that I was on all the time. And by the, by the end of that, toward like 2012 or 2013, I think it was, I got so stressed out that like all of the beard, all of the hair in my beard fell out.

Jason Lengstorf (13:19):
I had, I had like, if I had just let my beard grow naturally, I would have these really terrible mutton chops. And a mustache. So like what’s that, what’s that one called? The where you just shave the bottom? I can’t remember, but you know, that was like I couldn’t grow any beer, any whiskers on my chin and that led me to a, the first of two really deep existential crises. So I was kinda like, okay, well this isn’t what I want to do. Like, I don’t want to be this person. I don’t want to live this life. Maybe I shouldn’t be in tech. So I kind of hard bailed on the agency. I sold it off kind of broke down my, my interest in it and just took a single contract that, that I knew was going to be low impact.

Jason Lengstorf (14:04):
So I, I wasn’t going to make, you know, under the thousands of dollars I wasn’t destined for fame and glory. I was working remote with one client who had relatively low expectations. So I was able to work like 15 hours ish a week and make enough to get by. And I just spent a while doing that and then I hit my second existential crisis, which was I have to be doing something that means something to me because that, that client project wasn’t enough work. I wasn’t working on important enough things and I started to feel like, well, do I like why do I matter? Why am I doing anything at all? And that kind of got me to my, my, my current worldview, which is that like, you want to work hard enough to feel like you’re challenged and hard enough to feel like doing something that matters but not so hard that you’re trading off all the other aspects of your life or even more than a couple of aspects of your life.

Jason Lengstorf (15:00):
Everything has trade offs. You’re always going to say, Oh, well, I would rather, you know, eat this big fun meal with my friends, then hit my calorie goals for today. Or I would rather work on this project this weekend so that I can fully relax when I go on vacation. Then to strictly adhere to 40 hours of, of work this week. And you can always make those trade offs, but at the same time, like, you know, the, there’s a, there’s a point where it, it ceases to be a trade off and starts to be like a pattern or a lock. And I think when you get locked into that sort of stuff, that that’s when it starts to feel like you’re, you’re moving toward burnout. Does that make sense?

Brad Cypert (15:41):
Yeah. That definitely does. I’ve I’ve seen overlap in my own life there as well. I’ve generally, I guess generally for the past seven years, worked full time dev jobs but have also done contracting as well. And it’s so it feels like you never get, or at least in my case, I never get contracts when I want them, but they all come at once and then I’m afraid to say no. So I ended up pulling in like I’ll work 80 hours a week, like 40 hours, nine to five, and then like four different projects, like 10 hours a week or something. And that’s just, it’s absurd.

Jason Lengstorf (16:17):
I get that feeling though, like the, you know, especially with the contracting, cause it’s like if you say no, you might, you’ll never get that contract again. Like, and like you, you want the resume points, you want the, the cool stuff that you’re doing, you want the extra cash. Yeah, I get that. That, that’s a, that’s a stress that I am very happy not to miss anymore.

Brad Cypert (16:39):
One thing that’s helped with that is I’ve I’ve, I’ve grown a lot, not only as a developer, but just as a software, a product person, a software person maybe is the appropriate term. So I’ve started taking on some personal projects that I really wanted to see come to fruition and I get to more or less set my own hours. Actually. There’s no more or less I get to set my own hours on that, choose what we’re building in and, and all of those things. And that’s been awesome. It’s also been a really great way to, if you get fed up with work because of like, you’re working in really old versions of Ruby or something, you can, you know, have a project that’s the way you want it to be. Kind of just soak that enjoyment. Totally. The big thing for you right now seems to be developer advocacy. I think you were doing that against me and you’re, you’re definitely doing that. Netlify I’m, I’m curious are you still pushing JAMstack as we’re not pushing, but is that your main focus at nullifies JAMstack as well?

Jason Lengstorf (17:35):
Yeah, I mean JAMstack is kind of the the development paradigm that that makes the most sense to me right now. And it’s the one that Netlify is built to support. So it was a pretty good match when I’m, when I moved over. What, what I think is really interesting about the JAMstack is that it, it’s taking like, we’re not inventing new things here, right? Like the JAMstack as a, as a concept is a new way of approaching old problems using technologies that largely we’ve had that are just getting more approachable. So like what, you know, what you’re looking at is in the old days when, you know, when the internet first came around, you’d open up a text editor, you would write some HTML, you’d save that, and then you would drop it into an FTP folder or like put it on GeoCities or something.

Jason Lengstorf (18:27):
And that would become a website. And then we wanted to do more stuff. We wanted to add extra features. And so PHP came along and made that really easy. So you would, well, relatively easy, like not compared to writing HTML, but like if you want to do dynamic stuff, PHP made that pretty approachable so then you could write some PHP, but now you couldn’t just upload that to your FTP server. You needed, like you need an a server now an actual web server. So we saw the rise of web hosting, you know we, we were going up on GoDaddy hosting or, or Bluehost or you know, whatever, whatever the HostGator, and then, you know, suddenly you’re like paying for a server and then you needed a database. So now you’ve got like, Oh God, we’ve got PHP and we’ve got my SQL. And then that’s like generating HTML and all right, okay, that we can make that work.

Jason Lengstorf (19:19):
But now when you start to scale, you’ve got this problem where like if you have more than a couple dozen concurrent requests to a PHP server, it falls over. Your site goes down and like, Oh, well now you, your advertisement failed because nobody can open the website. So now you introduce this new layer of complexity. Now you need caching. And you’re doing that with varnish cache, you’re doing that with stuff it at the, you know, the server level at the Apache level, the engine X level, whatever you’re doing, trying to get the, the files that are generated by PHP into static format that then live at this cache that you can hit when you make a request to the site. Okay? That makes you a little more like, you know, add proof. If you, if you blow up, you hit the front page of Reddit or hacker news or whatever, your site’s not going to go down anymore.

Jason Lengstorf (20:06):
Okay, well why not just go back to the way things were and only serve those static files. So now you don’t have to worry about configuring the cash. You just have static files. So we just flipped the order. So if if PHP you make a server request, it says, Oh, that’s from this PHP file, which then processes and spits out some generated assets. Why don’t we just say these are all the requests that could be made. Let’s generate all those assets and put them in a folder. Right? And then you serve those folders from a CDN or from your, your favorite, like static hosting service. And that’s, so that’s basically what nullify does, right, where we are a place for you to put your static assets. And what that means is that like now you’re getting exactly the benefit that you got by dropping a text editor file into geo cities.

Jason Lengstorf (20:58):
But we’ve moved a bunch of complex like cash management stuff. So we’ve got this, this global asset delivery network and we’re doing load balancing and we’re doing DDoSmitigation and like a whole bunch of things that’ll keep your site up and scaled and, and running so that you’re always add proof. And because it’s static files, this isn’t super expensive or super complicated to do. You’re like, okay, here’s, here’s my static files. Where it starts to get complicated is, okay, now we want to do dynamic things. And then that’s where the, the, the newer part of the JAMstack, which is this idea of like serverless or if not serverless. There’s a, another thing that we’re seeing, which is still pretty new, but you’ll, you’ll see like Akamai’s got this idea of edge worker’s clouds. Cloudflare has these these cloud workers that are sort of, they’re sort of like serverless functions but they operate at the CDN level, which is kind of wild.

Jason Lengstorf (21:56):
And you know, stay tuned cause a lot. I think a lot of cool things are happening in this space right now. So I think there’s going to be some pretty exciting stuff happening there. But the problem is now we’re back to that same complexity. We’ve got like static files, but in front of those static files is a bunch of code and that code has to work every single time, even underload or else the site will crash. So how do we make that easy? How do we make that approachable? And I think that’s, that’s what attracts me to net with Phi because the, the idea behind this stuff is like all of this stuff has been possible. You’ve always been able to set up some kind of elaborate build process and put files into a folder and set up some caching layer and get your, you know, all this infrastructure and your dev ops workflows set up to manage that.

Jason Lengstorf (22:46):
But it was hard. You needed a full team on it. It was like a ton of work. So what Netlify did is they, they’re not productizing code, they’re productizing the, the, the lack of a need to write code. So I do the thing that I always did, which is write some HTML and put it in a bucket and Netlify takes the CDN and the, the service workers and the serverless functions and all these things that are hard to do, they take a lot of effort and turn it into like, Oh, if you write a function and put it in this folder, you now have serverless functions. You’re not writing config files, you’re not figuring out load balancing. You’re not figuring out how to like connect four different services in, in whatever cloud provider to get, you know, your DNS to route to the function, to route to your logging service, to route to whatever. It just like, it just works. It just happens the way you want it to. And you as a front end developer get to do what you wanted to do, which was build a website, not wrestle with config. So anyways, that’s a very, very long winded way of saying that I think the JAMstack is dope.

Brad Cypert (23:50):
Yeah. I’m still learning more about the JAMstack in general, but I’ve enjoyed what I’ve learned from it so far and what I’ve seen, I really liked Netlify as a platform. I run a couple of Hugo sites on Netlify and just a react single page app as well currently. And it blows my mind how easy it is to set everything up on that Netlify as opposed to, I mean, even just dropping it in like an S three bucket, like the process is so much more automated in the DNS set up for nullifies. Fantastic. Plus you have all the forms, the AB testing from branches. It’s really helpful.

Jason Lengstorf (24:24):
Yeah. I mean, and that’s kind of the whole goal, right? That’s, that’s what really made me love and made me fall in love with the company and why I wanted to work here is that it seems like the goal isn’t just make a thing possible. It’s make a thing accessible. Like how, how does any developer get access to this cool stuff that you can do on the web? Because all, you know, AB testing and forms and all that stuff, yeah, anybody can do it. But like, do they have time? Do they have the, the available expertise in a lot of cases? No. So how do we make that something that they can do with significantly less work, significantly less required context and less required knowledge so that they get the result they’re after without having to become an expert on AB testing or, or form handling or whatever that is.

Brad Cypert (25:13):
Yeah, I think that’s a very helpful and good goal to have. There’s, there’s definitely market and making things accessible. And I mean, once, if, especially if you can make it more accessible to entry-level devs, I don’t see any reason that anyone would want to leave. So I think it’s possibly a really good business model as well.

Jason Lengstorf (25:34):
Yeah, I mean, I, I like it as a business model. You know, when I was at IBM, I I spent a lot of time looking at ways to simplify the stack because we just, we just had these problems all over the place where we were doing stuff that was very cool, but it was really hard to manage and it required all of this knowledge and context. And so a lot of times there were two or three people in the whole company who knew how to run a given service. And if they were on vacation or they were at a conference, we just sat and waited. And this is, you know, the, the product that I worked on was over 700 devs. So there were days that I don’t want to know what 700 devs idle salary cost is, but it’s way more than it should — than we should have been spending to have people do no work because we were blocked on something being too hard. And so, you know, that’s, it’s really, it starts out as being something that was like, Hey, let’s make this accessible to beginners. But, but what it ultimately becomes is let’s remove the need to become an expert in things that aren’t core to our business.

Brad Cypert (26:36):
Sounds like a no brainer when you put it like that. So it’s, it’s really interesting to hear that that’s like an issue that very large companies and prominent ones could really face. But that does make sense. We’re going to take a really quick break get up, grab some water or anything like that if you need. And then we’ll be back in just a moment to talk about a running around site, maybe a little bit about Gatsby and the learn with Jason a Twitch stream. Great. Cool. We’ll be back in just a moment.

After the Break

Brad Cypert (00:00):
And we’re back. Thanks for sticking with us through the break. So Jason, I was curious, we’ve talked a little bit about developer advocacy. Can you tell me more about what you do as a developer advocate? I’m pretty sure the last developer advocate that I ran into gave me like 250 bucks of Azure credit and then I never heard from him again.

Jason Lengstorf (00:26):
So, well, so my job is we’re doing it a little bit differently than what you would call standard developer advocacy. So like we call it developer experience engineering. And the reason for that is that on one hand is just because like Sarah Drasner is a very good, like, she’s very good at what she does. And she pitched this when she joined nullify. But the, the goal is like, a lot of time what we’ll see happen is that developer relations or developer advocacy starts to develop a Gulf between the people doing Dev-Rel and the people doing product. And if you think about what the job is supposed to be, we’re supposed to be the people who are out in the world, both communicating the, the unique value, like what’s possible with the product. And also reporting back to the team on like what is, what could be improved, where people stumble, what, what doesn’t feel good to use.

Jason Lengstorf (01:35):
So what Sarah did when she set up a developer experience is she built in some safeguards to make sure that we are actually doing the right things. So one of the things that we do for example is we do a a three month product rotation at regular intervals in the company where I will stop doing public facing stuff or at least severely limited and work on the product. I’ll, I’ll embed with a product team, I’ll report to to an engineering manager and work with that team to build the product. And the reason for that is so that I know what the product does, what we’re working on, how it feels to work on our product, all the, all the things that are important to understand as an engineer. And it also helps me like be an engineer.

Jason Lengstorf (02:26):
Like I should be working on real products and not, not just in the the position to only ever build proofs of concept or, or to build like hello world apps to show people how things work. I should be seeing edge cases I should be dealing with, with complex things. So that’s, that’s one part of it. And then the, the other part of it is like what I would, I would consider us to be the like the interface between companies and the developers who use those companies. We are there to be paying attention. Like if you get stuck on Twitter and you’re, you’re frustrated, we should be, we should notice. And we should show up and say like, Hey, here’s a doc, or here’s an example. Or, or how can we help to try to point you in the right direction. And make sure that you don’t go from, I don’t get this to this company sucks.

Jason Lengstorf (03:18):
You know, we’re, we’re there to make sure that you succeed. We also want to make sure that people understand how things work. Like a lot of this stuff is really difficult. Understanding conceptually what the JAMstack is, especially when you get beyond the surface level and you start talking about, you know, how do you integrate serverless stuff? How are you doing authentication or, or you know, when you start digging into like these really advanced workflows, what does that mean in the context of the JAMstack? How do, what’s the language we should use to describe that? What does it enable? And like how could we fit that into a workflow that’s never really considered doing it that way? Like that’s on us. We need to come up with those analogies with those conceptual guides that help people make the, make the steps between where they are now and where they could be if this ended up being the right stack for them.

Jason Lengstorf (04:07):
Cause you know, a lot like the vast majority of us just need to build products. So when we’re doing research, we don’t have time to like do conceptual trailblazing. We need to look at like established pipelines and choose the one that meets our needs best. So it’s, it’s our, our job in like developer experience, dev-rel, whatever you want to call it, is to provide those pathways. We want to show you the happy path and show you what to do, you know, and, and really like broaden that happy path. So it’s not like, well, you can do this one thing really well. It’s like, well, how do you do this one thing really well? And then also start to expand out to cover more and more of the edge cases so that you can fit like any part of whatever business into this into this paradigm. And we do that by building stuff and by talking to the product, talking to customers, talking to our engineering teams and making sure that we’re kind of sitting at that, the center of that Venn diagram and understanding all of the concerns and trying to help match them together.

Brad Cypert (05:05):
It’s interesting to think about because in a lot of ways you’ve kind of play like a customer experience or customer support role, but also a product role and also a developer role all at once.

Jason Lengstorf (05:15):
Yeah, it really is. And I think that’s a good way to look at it because it’s it is all of those things and it, it’s also, you know, in addition to that documentation like writing and, and education. So you’re, you’re a teacher and your support and you’re an engineer and you’re thinking about product. So it’s, you know, it makes you wear a bunch of different hats. But I think that’s what makes this job so much fun for me is that it’s, there’s a variety of things to do. And so, you know, it’s, it I feel like everybody has their own tolerance for like routine and I have a very low tolerance for routine. I get antsy if I feel like I’m doing the same things over and over again. So this job is, is a lot of I guess what I would like maybe chaotic good if you were going to put in it, put it in an alignment chart. Like this is, you know, this is what it is, this is where I want to be. Like I’ve been described as chaotic. Good. And I took that as a compliment.

Brad Cypert (06:19):
I mean there are eight other spots you can fall and four of them are in my opinion, worse. So that’s it. It’s pretty good. Plus it really depends on what you’re looking for. Okay. That clears up a lot. I, I’m curious before the break you mentioned the open source work as well. Do you do much open source work as a developer experience person at Netlify or is that just kind of Jason Lengstorf thing?

Jason Lengstorf (06:45):
We do, I mean we do open source work. So like, and that, that varies in, in I think intensity. But for example you know, we, we’ve got people who are on the, the Vue core team. That’s that Sarah angular core team. It’s a terramin exec. Phil Hawksworth does a ton of, of open source work. Divya does, so I mean, so much open source work and, and that can range from building examples to managing communities. Like swigs on our team manages the, the react subreddit and does a ton of work building out. Like he’s, he’s like a, a test pilot, you know, he just dives into everything and tries it and sees what works and what doesn’t. And, and kind of reports back. So there’s, there’s open source work in the sense of we will try this and write a report so that you can get a kind of at a glance, look into what it does.

Jason Lengstorf (07:42):
There’s open source work, like submitting poor requests to documentation for different open source repos. There’s open source work Lake, you know, I think Tara and Sarah are, are straight up writing core code at certain points. I contribute to like the Gatsby core repos on not often anymore, but I I have made contributions to the Gatsby repos. I do a lot of contributions to open source examples to show people how things are built. And obviously like the vast majority of my work, I think 99% of code that I write is open source. And that, you know, that’s a choice. Like I, I prefer that all that stuff is an open book because you know, why not make it an example if I’m going to write it.

Brad Cypert (08:27):
Yeah, I appreciate that so much and I definitely agree with you. I try to make a lot of my stuff open source or at least have codepen examples or something that I can share with people where they can clone it and play around with it and tinker things and hopefully get them a closer, one step closer to what they’re trying to build. So you also run Lengstorf.com. I have some questions about that, but I guess I’d be remiss to not ask, does it run on the JAMstack? Is it Gatsby?

Jason Lengstorf (08:59):
Yeah. So langsdorf.com is is it Gatsby site? It runs on like a couple themes. It’s running on Netlify, and I think it’s backed by a lot. Like I use airtable for part of it and Markdown for part of it or MDX more specifically. We’ve got a few data sources in there and then learnwithjason.dev is also a it’s a Gatsby site powered by sanity and something else. No, just by its yeah, sanity and it’s got a little MDX in there as well also deployed on Netlify.

Brad Cypert (09:42):
So as someone who’s not super familiar with Gatsby, those are different backends that you can plug up as a data source or content source. Is that correct?

Jason Lengstorf (09:50):
Yeah. So what I would say like Gatsby’s unique value proposition is like Gatsby does a lot of things really well. But a lot of modern frameworks do a lot of things really well. And I think what Gatsby is, is currently kind of alone on is that a Gatsby does this like data source content mesh is the, the language to describe it where you’re effectively able to say, I want to use Shopify for products and WordPress for content and MDX for like legal pages and you know, Instagram for photos. All of that gets sucked into Gatsby and put into a unified graph QL data layer. So now you can, and there’s a lot of advanced use cases, you can create relationships between different nodes and all that stuff. But with the power that that gives you as a front end dev, I go into Gatsby, I install a source plugin that pulls in data from wherever I feed it, an API key and it just creates a GraphQL representation of my data.

Jason Lengstorf (10:53):
And then I put another source plugin in and in the same query I can get two disparate backends in the same like similar GraphQL shapes and in identical data accessing workflow. So the, the power there is that like I don’t need to learn how to access, like Shopify as an API. I just drop in this thing and then I get a an API or a GraphQL end point that’s like, Oh, if I query all Shopify product, I’m going to get a list of my products. It’s a really, really powerful model. And, and to me, one of the major factors in a decision to use Gatsby as a framework is it like, it completely removes that whole layer of like data munging that that gets really complex and challenging.

Brad Cypert (11:39):
Yeah, that’s, that’s really cool. I’m just trying to imagine like BradCypert.com which runs on WordPress and getting a similar experience is more or less just a bunch of WordPress plugins and, and ideally, well ideally non but likely a ton of CSS to just make everything kind of blend properly, remove all the implicit stylings that some plugin author thought that I wanted and everything like that. So that’d be nice.

Jason Lengstorf (12:05):
Yeah, I mean the, so there’s WP GraphQL is a a plugin that turns the WordPress API into a GraphQL API and Jason Ball who created that is actually working for Gatsby right now. So like his primary goal is to make it easy to build Gatsby sites powered by WordPress. So it, assuming you’re interested in doing react and JavaScript in GraphQL it could be a fun way to try it out. I know that Jason would, would love to hear your experience with that if you do decide to make the move.

Brad Cypert (12:40):
Yeah, I, it’s funny, I’ve been running into tons of issues with my theme and just kind of where I want to go with the site. So I, instead of trying to relearn how to do WordPress themes like I did six or seven years ago, I figured I would move to something different. But the, the holdup has been like getting my content out of work for us and into something else. So knowing that that’s an option I really like graph QL. I really like react. If I can use a Paulo in between, that’s even better. Unless Gatsby offers something out of the box that might be better than Apollo. But yeah, that sounds great to me.

Jason Lengstorf (13:15):
Well, the, the thing that’s interesting about Gatsby is, so like Gatsby, all of the Gatsby stuff happens at build time, so you will, you’ll access build time data one way and then if you need runtime data, you can sit Apollo right on top of it.

Brad Cypert (13:29):
Interesting. Okay. And I guess that’s how you get your, your fast load times and your static pages. Exactly. Yeah. Okay. That’s awesome. Yeah. I really, man, I should have hopped on the train years ago. When you first started talking about this, circling back to your blog I, I, like I said, I run a blog, so I’m always curious about other developers or tech people that, that blog, like what prompted you to start blogging?

Jason Lengstorf (13:55):
Well, that’s a great question. I mean I blog in two channels. I guess I have technical blog posts that learn on that live on, learn with Jason. Dot. Dev. Previously I had like, I’ve moved them around because I can never figure out where they should be learnwithjason.dev seems like where they’re going to stick because that’s like where I’m doing all of my code stuff now. Prior to that though, I, I wrote technical posts because I didn’t, I was living in Montana, didn’t really have a whole lot of you know, I had a small developer community that was great, but like there’s only so much networking to be done and in Missoula, Montana. So the conferences were one way and we, we kind of talked about that and writing articles was the other way.

Jason Lengstorf (14:46):
So the same way that I would write tech talks about what I was learning and kind of what I was excited about. I started writing articles the same way and I wrote one for CSS tricks and Chris Coyer was nice enough to just like put it up even though he had no idea who I was then, you know, I had no credibility whatsoever. He was like, yeah, this looks cool. Let’s put it up. And it, it was it was popular and so that helped me get a little bit of attention. So then I would just kind of blog, I would put together. I did little challenges for myself. Like I had this thing that I called instant tip Tuesday that I ran for like a year back in 2010 or something. And I, I would like do my best to write up a 300 word post that had like one little thing in it.

Jason Lengstorf (15:34):
That didn’t last long because I ran out of short tips very fast. But, but it was always, you know, it was like I wanted some way to collect thoughts and then like later I, as especially as I started doing more of the, the work life balance stuff, I wanted to write about the meta work. And so that’s the other channel that I blog in and that’s on lengstorf.com which is much more about how to work how to the, the different lessons and stories that I’ve learned about how to make myself happier and more effective. And you know, less of a, like less of a Dick. You know, all that stuff has been, has been very just as I go through a struggle as if I realized that I was doing something that was a pattern that like is worthy of documenting, I tried to write it down and like share the thing that I did and what I’m trying to do to be better. That, I dunno why I started doing that. I honestly just like kept, I was like, I don’t know, I should write this down. And then I just kept doing it.

Brad Cypert (16:39):
I have a friend that is doing a very similar thing and I’m so thankful that he, he does that just to, it gives me more insight into his thought process and just how his life is going. But I also, I subscribe to your mailing list and I get your updates as well and they’re always they’re super insightful and I am trying to think of the right word to use, but I love the tone that all of the messages come across with, they’re very factual, straight to the point and sincere, if that makes sense. So I’m, I’m super appreciative of that.

Jason Lengstorf (17:10):
Cool. Well, I, I’m, I’m really happy that that you enjoy them. It’s funny because when you run a, like a newsletter, you rarely hear from people. So a lot of times it’s like, am I just like shouting into the void here or like, and I don’t check my subscriber numbers, so I don’t know how many people are on the list. Like that just gives me anxiety so I don’t look at it. So I don’t know if anybody gets this stuff. I’m just like, I’ll just put it out there. We’ll see what happens.

Brad Cypert (17:35):
Yeah. Tell me about it. I have started doing some, some more focused email marketing or I guess email. I don’t, I’m not marketing anything really. I’m just communicating with people. So I guess just subscriber contact. And every single email is sent out. I add something that’s like, if you want to talk to me, just reply directly to this email. I promise I’ll read it, no responses. So yeah, I don’t, I don’t know, but I assume people are opening them and reading them. So

Jason Lengstorf (18:03):
Yeah. Like I like, I know, you know, I know that that people do, cause I do hear sometimes, you know, like right now that, that people are reading it. But yeah, it’s, it’s funny because what I found is that the stuff that I’ve written that I’m the least confident about is the stuff that generates the most discussion. And I can’t decide if that’s a good or a bad thing because I feel like what that tells me is if I launch a half-baked opinion out there, there will be a lot of discussion. And so maybe that’s a good thing. But that also points toward this idea of like, does that mean that I shouldn’t think things through and just like launch it out into the world? That seems like it might cause more harm than good. So I don’t know. I mean I, I, it’s it’s a weird balancing act. Right?

Brad Cypert (18:49):
Yeah. I think it boils down to, do you care about the number of people that are commenting on something or do you care about like the message that you’re getting across?

Jason Lengstorf (18:58):
Yeah, that is, that is an interesting one cause it’s kind of like is is a healthy discussion, a signal of good content or like is a lack of discussion, a signal that the thing that you said was like, people agreed, they’re like, Oh, I don’t have anything to add to that. Or you know, cause like if people disagree you’re going to hear about it. So I, I think like no responses is kind of the, it’s either I didn’t read this or I didn’t have anything to add. And I guess that in either case, like that’s fine. I’m not, you know, I’m not upset if somebody didn’t read it and I’m not upset if somebody read it and was like, cool. You know, like, so I guess I, it is always nice to have these discussions with people, but like, I don’t know. That’s what we’re doing now. Right.

Brad Cypert (19:48):
Absolutely. So you mentioned learnwithjason a couple of times now. So I just knew the learn with Jason show on Twitch. But it sounds like you also have a website for that that you blog on.

Jason Lengstorf (20:02):
Yeah. So the the show happens live on Twitch and then after the live episodes they get cross posted over to learnwithjason.dev where the, the episode with links and stuff like that. There’s also a schedule of upcoming shows on there and a blog with a few posts. I’ve, I’ve been trying to post more. We’ll see if I get better at it. I, I always like make myself this promise that I’m going to be better at blogging. And then what I’ve learned is I just have like, I have a rhythm with this stuff that I don’t understand where I’ll get a ton of motivation and I’ll blog a bunch and then I kinda like taper off and I don’t have a lot to say. And then I’ll like find something I’m interested in and I blog a bunch again. Chris Biscardi is actually way better this Chris, he’s a, he is one of the most consistent content producers that I’ve met. He just is always doing this. So if you want to learn how to blog more or more consistently, you should talk to Chris and not me.

Brad Cypert (21:04):
I think a, I probably go in similar swings of producing a lot of content and then not producing much at all. It usually goes with learning new technology. I blog a lot about things as I find them. Yeah. And, and not so much like once I’ve been doing it for a while, but I’m trying to change that a little bit. Also, my draft count goes up exponentially faster than my like published post counts.

Jason Lengstorf (21:28):
You know, there’s a, there’s a technique for this that that Chris and, and another friend of mine, Joel hooks talk about a lot, which is this concept of a digital garden. And they, they didn’t create this term but they’ve been really effective at, at running it where they effectively as they write notes, they just publish them and they’re, you know, sometimes they’re sentence fragments, they’re not complete. It’s more like if they were writing down notes for how they accomplished a thing, they just put it up. And if they find themselves going back and referencing it, then they turn it into a full post. So they have like this this section on their, on their sites called notes and then a section for blog. And it’s like, you know, the, the notes are basically drafts that may transition to blog posts at some point in the future. But it’s a good way to get that content out there cause it sets the expectation that like, what this is for me is like a note is a note to self. I’m, I’m keeping a record of something that I learned. It may not be polished or consumable by anybody but me. A blog post is when I realized that something that I’ve taken a note on is worth polishing up in some way. And I think that’s a really cool way to look at it.

Brad Cypert (22:34):
Yeah, there’s always a chance someone stumbles upon one of your notes as well, and then they comment and say like, wow, this was super helpful. Like, I, I’m so shocked I stumbled upon this. And then you could actually take that and run with it and say, okay, well, maybe I should put some context around this to help other people find it.

Jason Lengstorf (22:50):
Yeah. Well, I mean, think about, I don’t know if this happens to you, but I find myself Googling around for answers and I’ll get, I’ll end up on a gist, and it makes it so helpful, right? And so this is effectively a, gist that you’ve put on your own site. I needed to do X, I did X, Y, and Z , and it worked. And that’s the end of my story. That, that to me maybe has a lot of like long tail SEO value. Or maybe it’s just something that when I have to Google it later, I remember that. I already wrote that down once.

Brad Cypert (23:20):
That’s, that’s how I got started blogging actually. And if you were to look at some of my earlier posts, I almost guarantee you that the ones you stumble upon will be a paragraph that sets context, a code snippet and then a paragraph that says like thanks for reading this or something because I was like, I have no idea what to put. Yup. So, so the Twitch show, do you run that regularly?

Jason Lengstorf (23:45):
Yes. I run usually two to three episodes a week and I bring a guest on who’s an expert on something and they teach me the thing they’re an expert on. So like recently I had Angie Jones on, she is a, a testing expert and she taught me how to do visual, a visual snapshot testing. And it was really cool cause like it’s something that I’ve, I’m, I’m aware of, but I don’t, I’d never done before. So she just walked me through setting it up and, and talked through the benefits and it was great. And I’ve done this on like in so many different places. Like I had Sarah Drasner on to teach me D3 and like 3d stuff and it was amazing. I had Paul Henshall taught me three JS and react three and the, you know, the like Rich Harris came on and taught me Svelte, Zach Leatherman came on and taught me eleventy like I get to learn all these amazing things.

Jason Lengstorf (24:38):
And I always like the shtick of the show is that I show up completely unprepared. I almost never know the technology. I don’t do any research. We just start with an empty folder and we’re like, all right. Would like, where would you start? And I try not to use boiler plates. I try not to use starters. It’s just, Hey, let’s, let’s, what’s the first file I should create? And we just write it all out by hand. Cause the idea isn’t to build something incredible. It’s to build a conceptual understanding of what’s happening. Like, why does this thing work the way that it works? And you start to see that when you write the files out by hand and it, it provides a lot of room for, you know, there’s a live chat. So the chat gets to ask a bunch of questions about like, well why’d you do it like this?

Jason Lengstorf (25:18):
Or what’s the benefit of this over this other technique or, you know, those sorts of things. And, and I, you know, I’ve got a million beginner questions too, cause I’m going in as a beginner, so, you know, why are we doing it like this? Like what’s, I, I don’t, I’ve never seen it done like this. What was your reasoning here? And the, those are really, really fun, fun conversations to have. And I feel like it’s making me a much better programmer because I get all these brilliant people coming in and sharing their perspective and I get to carry that perspective back. Even if I don’t use that exact tool, I get to learn the lessons that, that informed that tool. And it it goes back to the way that I write my code day to day.

Brad Cypert (25:53):
Full disclosure, haven’t tuned into an episode yet. It’s been on my radar, but I didn’t realize that it was, I thought it was more of you teaching people things and I was curious how like how long that content stream would last. But if you have people come on and they’re teaching you things, the content stream is endless. And also like, yeah, really nice for you because you get, like you said, really smart people that are experts in something.

Jason Lengstorf (26:16):
Yeah. I don’t know. Like I, I’ve joked about this a lot, but I don’t know how the hell I pulled this off, that somehow my job became to talk to people that I admire and get them to teach me stuff that doesn’t it, it, if you would have asked me 10 years ago, what’s your wildest dream? I think it would have been something pretty close to this.

Brad Cypert (26:39):
Yeah. I similar, similar idea with the podcast. I’ve really enjoyed with some people that I admire and value their opinions on to have the same, same kind of conversations, which is why I’m super, super pumped that you joined us for this one somewhat maybe more political question but I’m curious, do you think Twitch has a future as a source of education for people that are looking to learn more about software development? Or do you think there are better avenues for that?

Jason Lengstorf (27:06):
I mean, I think like, I think that live streaming is establishing itself as a strong medium for educational content. It’s a, it’s a, a one to many approach in real time, which I think is, is super powerful. And it’s not necessarily cap. Like if you run a webinar, people have to install software. There’s, you know, a seat limit. You usually can’t get more than 50 or a hundred or 500 people in. Whereas like with Twitch, you’ll regularly see streams at 20,000 plus people watching at the same time. And that, you know, that causes issues. Like the chat becomes kind of unusable at 20,000 people, but at the same time, you, you are able to do this like one to many communication. That’s not polished. That’s not best case scenario. And I think that a unique value of something like Twitch over something like a, a prepared workshop is that in a workshop you’re going to see the happy path the instructor has done.

Jason Lengstorf (28:12):
They’ve done the work, they’ve done the debugging, they found all the, the edges and they’ve, they’ve carefully navigated around them so that in the workshop everything works and that’s a good experience, right? You’re going to learn great things and you’re probably going to get a lot further in a workshop than you will in a livestream. The flip side of that is that in a live stream, you’re going to watch somebody hit those edge cases. You’re going to watch somebody debug, you’re going to learn not how to do the thing perfectly, but how to struggle through learning new things. And I think that learning how to learn is one of the most beneficial things that we can do as, as adults really. And like, as a, as a developer, one of my favorite things is, is seeing how other people solve problems. Because it helps me understand like, Whoa, what, why did you ask that question? I never would’ve thought to ask that question. And then I learned this whole new perspective that makes me as such a better problem solver going forward. And so a lot of it is, I think that’s the value of streaming is you get to watch somebody struggle and you see the way that they unblock themselves to the way that they, they work around a challenge. And that helps you build a toolkit of like, well, I can do that too.

Brad Cypert (29:30):
Yeah. The, the live stream thing feels very real. It doesn’t feel like a stage. And generally because it’s not a stage like workshop like you mentioned. Yeah.

Jason Lengstorf (29:39):
Yeah. I mean, and like I said, you know, my, there’s reason that I go in totally unprepared, like I never wanted to feel like, like performance art. The, the performance art is the, the banter and the joking around and you know, like I’m comfortable, like ad-libbing. And I think that makes people feel more comfortable. And I think if I was just like, you know, angry and frustrated because I couldn’t get a thing to work, that wouldn’t be very fun to watch. So I think that the performance is, is being able to fail with a smile. But the, the failure is very real.

Brad Cypert (30:12):
I think it depends on how angry and frustrated you get. There’s probably a cap where it starts to get enjoyable again.

Jason Lengstorf (30:20):
I don’t know if I’ve ever been above that limit. I think I like, I’m more of a sulky, angry developer. I just like glare at my computer. I haven’t, I have yet to flip a table.

Brad Cypert (30:33):
That’s probably for the best. Usually a lot of very expensive technology resides on that table. Indeed. Indeed. Ucool. So this question’s a little odd, but it’s probably one of my favorite ones. It’s kind of stuck with me through the Design Doc episodes so far. Uso everyone seems to run into issues on something from time to time. And I’m curious if any of their PR, like with any of your projects, if you ever thought maybe I shouldn’t be doing this, like maybe I made a wrong choice.

Jason Lengstorf (30:59):
Like with the, with the technology or, or just kind of in general.

Brad Cypert (31:04):
I would say in general. But if you need to go to technology, that’s fine too. I feel like those are more common though.

Jason Lengstorf (31:10):
I mean, I, so we talked about this a little bit earlier when, when I was running my agency where I, toward the end of that agency, I was working like 90 hours a week and I couldn’t see a way out. I was, I was realizing that I had painted myself into this corner where I didn’t have the bandwidth to train people or to build processes or to go out and hire a, I wasn’t charging the margins that I needed to charge to be able to have employees that I couldn’t afford employees. I couldn’t afford to pay contractors the rates that I needed to be charging them to be able to keep them around. And so I, I was in this very, what felt like a completely hopeless state. And so at that point in time, I remember very seriously sitting down and looking at the, the want ads in the paper and thinking I could just go be a barback.

Jason Lengstorf (32:11):
Like I wouldn’t make very much money, but I would go to work and then I would clock out and then I would be done and I would just get to live my life. And and I spent probably a full year, like very seriously considering dropping out of tech entirely because I didn’t know how to handle the stress. And you know, it, it took, it took me making a pretty catastrophic personal decision to more or less like abandoned everything that I’d built in favor of starting fresh to reset. And like I, you know, I was lucky enough that I had that option. You know, I could get that contract that would let me in. Like, granted, I took pretty extreme measures. I moved to Thailand so that this contract would, would cover my needs. It wasn’t like somebody was just like, here’s a bunch of money to do very little work.

Jason Lengstorf (33:02):
It was like, no, we’re going to give you a little bit of money to do a little bit of work. And I was like, cool. If I live in Thailand, I can survive on that. And so I, you know, I took, I was like, okay, I’m resetting. Like I want to be reset. And and it was, it was a huge jump, but it, you know, it gave me the distance to realize that it wasn’t technique. Like the mistake that I’d made wasn’t working in tech. The mistake that I’d made was the way that I built my career to that date, which was to use me as a linchpin. Instead of like, instead of being a force multiplier for people around me, I was, I was trying to make myself a center of gravity where everyone had to move around me. And, and what I should have been doing instead was figuring out how to make sure that everybody else could move faster with or without me. You know, the, the idea isn’t to become a dependency. The idea is to become independent and and you should be like the, the most effective developers, the ones who get promoted are the ones who make themselves redundant. Like you’ve built your process in your team to be so effective that they don’t need you anymore. That’s when you get promoted to do that again somewhere else. Right. You don’t want to be completely indispensable because that means you can’t leave, you can’t go anywhere. You’re stuck.

Brad Cypert (34:15):
Yeah. It always sounds nice on paper when you say like, Oh, I’m indispensable if I try to leave, you know, they’ll offer me three grand more a year to stay or something. It doesn’t happen generally from experience. And then yeah, like the, the idea is exactly what you said. You get promoted because now instead of doing that with an engineering team, you’re doing that across an engineering department. And then maybe across like an entire tech department or software product department or whatever it is. And that’s, that’s growth.

Jason Lengstorf (34:44):
Yeah. And like in every, every healthy engineering organization or every healthy company they’ve got a career leveling doc where they can show you the ladder and the ladder is typically gonna go across like multiple facets of your job. And what you’ll see is that like when your early career, mid career so you know like engineer one engineer to engineer three those levels are largely concerned with your skill, your ability to do the work, your ability to like learn and execute on things. But once you hit senior and beyond, so like when you go from senior to principal to staff to whatever the next layers are, you, you start seeing that like the ladder is not about your skill anymore. The, the ladder that functioning orgs is going to talk about your ability to make everyone around you more effective. So you, you know, in, in my experience like that’s what makes a senior engineer is, is when you, you raise to the level that you’re able to do your work. Sure that, but that’s table stakes. Like if you can’t do your job, you’re of course you’re not a senior engineer. But being a senior engineer doesn’t mean you can do more of your job. That means that you help the people around you who aren’t senior get closer to senior, you know, your, your, you’re lifting everybody else’s productivity, you’re lifting everybody else’s velocity by being a resource and being a force multiplier for them.

Brad Cypert (36:06):
I’ve been in companies that don’t have a very well defined career ladder and some that do. Linkedin was one that I worked at that was extremely well-defined and I really appreciated that. I don’t think I, I don’t think I did as much while I worked there, but in hindsight, like after experiencing some companies that don’t have one, didn’t have one, it’s really, really nice.

Jason Lengstorf (36:26):
Yeah. I mean, it can feel a little like stiff and corporate to, you know, Oh, here’s the checklist about whether or not you’re going to get a promotion. I think that kind of sucks, but it’s also kind of nice like, Hey, I checked these boxes, give me the money.

Brad Cypert (36:39):
That’s exactly how I felt about it at the time. And with the company I work for currently TeamSnap they’re working on restructuring that and part of their restructure involves like all those checkboxes and I’m so thrilled.

Jason Lengstorf (36:52):
Yeah. I, I do love like laddering I think is something that is like getting levels right makes all the difference in a team. Cause it’s, that’s also how you avoid things like underpaying minorities and women. That’s, that’s how you like avoid under leveling people. Like, you know, Oh I feel like you’re a senior versus I feel like you’re not, it’s like, no, let’s, let’s run through the list. You are obviously a senior and you are not doing the stuff that’s on this list. Like you get the job and you don’t it, it just helps like at a certain level it’s always going to be subjective. Like, you know, it doesn’t matter how well-defined something is. Somebody is going to still be in a position of power to be like biased but removing at least the, I feel like you did a pretty good job. Let’s give you, let’s give you a promotion. Like, I think that if you can get rid of that in a company to, to the furthest extent that’s reasonable it, it gives everybody a much better chance of, of working in a functioning like fair org, which is, I think that’s, you know, the best we can hope for it.

Brad Cypert (37:55):
It’s interesting how many companies are so obsessed over numbers when it is product focused, but as soon as it comes to employees, it’s like a very subjective, it’s not empirical evidence or anything. So that’s interesting to hear your thoughts on that.

Jason Lengstorf (38:11):
Yeah, it’s kinda, it’s like that scene in in Monte Python where they’re trying to decide if somebody is a witch, right? Like, it’s like a good is a, they’re made a wood, right? So does, does she float?

Brad Cypert (38:28):
So I guess we’ll wrap up really quick. I have two, two small things to wrap up on. So I’m curious if you have anything else planned for you anytime soon. And how do you get ideas for what to do next?

Jason Lengstorf (38:43):
Huh. Ooh, so things that are planned for me. So I’ve been having an absolute blast doing the live streaming and I’m trying to find ways to play with that idea a little bit more. And that ranges from trying to find ways to make the stream more interactive. Like one of the, one of the things that we do to play is you can trigger sound effects from the chat. So if you, you know, if you think I’m doing something that’s taking too long, you can play elevator music or if something works and you, and you know, we’re all stoked, then we’ve got a sound effect that’s like me, like saying something excited. And so I’m building more of those and building ways to play even further. And that, you know, maybe that’s like, I don’t know, I found this really cool AR projector so that we could actually control the screen behind me and show stuff in, in my actual office based on the chat.

Jason Lengstorf (39:36):
I don’t know if I’m actually gonna do that cause it’s super expensive, but like the ideas like that or figuring out how to live stream different things. Like my partner is an excellent Baker. What if I could live stream learning how to make a sourdough or you know, live stream, how to make a good cocktail. Like I love making cocktails. Maybe that would be a fun thing to do. So I’m also looking into options for how I could do that without converting my entire house into a studio, which is both impractical and I’m pretty sure something that would get me into a lot of trouble with my partner. But yeah, trying to try to play more with those concepts and then also just trying to do more creative stuff. I’m not very good at having hobbies if I don’t think I can monetize them. So I am trying to have more useless hobbies and I, I think that cause I who said this, somebody said this and it was, it was incredible. I think it was Charlie Gerard said, useless is not worthless and that’s, that’s good advice.

Brad Cypert (40:45):
I like that advice. I guess regarding anything that we’ve talked about today including starting a business, the live streaming developer excellence, any of that type of stuff. Do you have any tips for people that are interested in learning more about those avenues?

Jason Lengstorf (41:02):
I mean for learning more, there are, there are so many like brilliant people that you can follow. Laura Hogan has a ton of information. April Wensel has a bunch of information about working on teams. There is a book called, what’s it called, an elegant puzzle, I believe. That’s written by an engineering manager at Stripe. I think it’s a, a really good book about that sort of thing. I also think just like recognize that the, the, the highest value thing is not code or understanding code. The, the highest value thing is understanding the way that people interact with each other and the way that people learn. Because if you can figure those things out, you can get anybody to understand and use any technology. It’s, it’s not about, it’s not about the code, it’s about getting everybody to a point where they can agree on what to build. And and I think that’s like those are the skill sets that they really start to make the difference in what will take you from, from being in a like a mid career to the senior beyond.

Brad Cypert (42:19):
Cool. I really liked that last tip, but not to say you’re targeting anyone, but that feels super practical to me.

Brad Cypert (42:29):
Cool. Well if people are interested in following you or your work work and they do that

Jason Lengstorf (42:34):
I spend the most time on, on Twitter. My, my handles Jason Lengstorf, I also post, there’s a full schedule up on learn with Jason. Dot. Dev. I have a newsletter full of, of tips on metalwork and discussions of, of kind of career things on Lengstorf.com. And that’s, those are, that’s really, that’s where I hang out the most is those those places.

Brad Cypert (42:59):
Well, cool. Thanks for taking the time again to talk with me today, Jason. I really appreciated it and I feel like we have a ton of insights. You’re an extremely quotable person.

Jason Lengstorf (43:08):
Well, thank you so much for having me on. I appreciate it. And you know, I, I, I hope that this is useful to your listeners.

Brad Cypert (43:15):
Yeah, I hope so too. So I’m, I guess this wraps it up for this episode of the design doc podcast. As always, I’m your host, Brad Cyprus. You can find me on Twitter at B R A D C Y P E R T and bradcypert.com. Thanks for tuning in.

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