Changelog & Friends – Episode #43

Motivated by play

with Annie Sexton

All Episodes

Annie Sexton has been on quite a journey since she was last on the show back in early ‘22. On this episode, Annie takes us on that journey, shares her new-found perspective & tells us about how she’s approaching her side project this time around.



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Notes & Links

📝 Edit Notes


1 00:00 Let's talk!
2 00:38 Sponsor: Tailscale
3 02:23 Resets & Friends
4 06:34 Define "out of money"
5 16:36 Being a "YouTuber"
6 17:34 A sweet setup
7 24:23 Sponsor: Sentry
8 28:10 Workin' 9 to 5
9 31:44 Freelance (bad) clients
10 35:39 Side project moderation
11 39:13 Doing it for the love
12 40:59 On gratitude
13 46:31 Typist & Obsidian
14 53:48 Obligatory AI mention
15 55:04 Sponsor: Coda
16 56:21 The maps analogy
17 1:01:45 Neurospicy lookups
18 1:04:18 GenAI boundaries
19 1:12:51 Back to paper maps
20 1:19:03 Arists being replaced
21 1:28:35 Prompting AI art
22 1:34:32 Bye friends!
23 1:36:00 Coming up next


📝 Edit Transcript


Play the audio to listen along while you enjoy the transcript. 🎧

So we have Annie Sexton back on the show, from the famed Git Your Reset on episode…

Oh, yeah.

…a couple years back, where we nerded out about our Git flows for way too long… But people seemed to like it. Welcome back, Annie.

Thank you. It’s great to be here.

I guess you’ve got a different kind of reset on this time. I didn’t even plan that, but it worked out, didn’t it? I mean…

[laughs] Oh, yeah. That’s good fun. Yeah, it’s been a ride…

It’s been a ride. So you were with Render back when you were on the pod, I think ’21, ’22… What year was that, Adam?

’21, yeah.

That’s right.

And then a lot happened in 2021 and since then. I mean, in the tech industry, it’s been a roller coaster; and mostly downs, more than ups, I think… But how’s it been for you? I mean, we’re mostly on the sidelines. Of course, we felt it financially as well here at Changelog, but we aren’t employed traditionally; Adam and I don’t do the traditional job search things, although maybe we’ll have to at some point. We just haven’t had to. We wondered for a minute there, “Might we have to go get real jobs here soon?” But we seem to be surviving. What happened from your perspective, Annie? Help all of us catch up.

Well, let me just say, if I could go back and talk to myself, I would advise myself that 2023 is not the year to be unemployed in the tech world, and to take a break from the tech world… So at the end of 2022 I was feeling really burned out on the tech world for a lot of different reasons, and I really wanted a break. I think part of it was – actually, I would say a lot of it had to do with my own adaption of the side hustle mentality and how many years I had gone through that, and let that be a huge part of my life, and how damaging that became. I hit a point where I really just needed to stop altogether. And I thought that at the end of 2022 that was the end. I’m done with tech. And I actually went on to pursue something completely different. I actually took a course in interior design, I got certified. I wanted something wildly different. And it was great for a time. There’s also a lot to – I took away some notes, being in a very female-dominated industry for a short time.

Better or worse?

Better, better. Definitely better.

Okay, that’s good.

But that brought a lot of thoughts back to the tech world when I finally did return. I did find that just even though I love interior design, I love design, I love art in general, I don’t want to be in that world. I don’t want clients; I don’t want to be a freelancer for one thing. And it’s also really hard at – I think I was 34 at that time. It’s really hard to start over in a new industry, starting those low-level jobs, where they’re really quite unfulfilling, I’ve found… And you’ve just got to. You’ve got to pay your dues. And I realized I did not want to do that, and I also wasn’t excited enough about where that would have taken me.

So anyways, it didn’t work out, and I decided I would – “You know what? I’m kind of running low on money. I’m going to get myself an engineering job again.” And so I started to search in the summer. And granted, I was not looking for traditional engineering jobs; I was trying to look more for product work, and then later into developer relations, which is where I am now… But I did not anticipate how long it would take in 2023 to get a new tech job. I know I was making things a little more difficult for myself in not looking for an engineering job specifically, and looking for something that was engineering tangential… But it was very difficult; very, very difficult. And I ran out of money twice. And it was terrifying. And it was terrifying, and I think part of the worst part is that it was nobody’s fault but my own, and me just underestimating how scary the market was at the time. Because the last two jobs that I had gotten, I had gotten because of referrals… And I knew somebody, or I’d met some people at meetups, and within like a month and a half, I had a job. So I was like “I know tons of people in the industry now. It’ll be fine.”

[06:32] Right. Can you define “run out of money”? What’s run out of money look like? define what you mean by “run out of money”? literally zero in the bank? How close to the terror were you?

Zero in my bank, not zero in my – I had a 401-K that was still fine. So that’s good. But I had to dip into a Roth IRA, drained that… So unless I was going to touch my retirement accounts - which I’m very, very, very, very grateful to have that… But in terms of money that I could touch without worrying about losing my retirement funds - gone. I had to borrow money from my parents; it was really not a high moment in my life. It was really kind of – it was really scary, and I didn’t have anyone to blame but myself. That was very humbling.

Was that while you were doing the interior design freelance, or that was while you were looking for an engineering role, or both?

Both. There was a period of time when I was working at a showroom, and I very quickly realized it was not for me.

What were the indicators? I can kind of empathize. I’ve been in zones like that. What were the indicators of like “This is not for me”?

Yeah, let’s hear it, because this is interesting.

Yeah, so I was working at a tile showroom in town… This is how a lot of interior designers will start; they’ll start at a showroom, where they sell furniture, or maybe fabric, or tiles, or materials, maybe they worked in a stoneyard, whatever. And then they work their way up from there, and gain some sort of industry, niche-specific knowledge. And so I started in tile. And it was a sales position. And I’m a people person, so I thought “Sales. That’s great for me.” I only lasted a month, not because the sales side of things was bad, but rather because I did not have anything to do. And when I say “I did not have anything to do”, I’m not being hyperbolic. I literally sat at my desk for eight hours a day, doing nothing, because they didn’t have clients for me yet. I could occasionally talk to people who came in; that’s not super-frequent. But when I asked my manager, my boss, “Please, can I help organize something? Can I do something? Please, give me a job. I don’t have anything to – you’re paying me to do nothing right now. I want to be helpful, I want to be useful.” And he said “You can look at the vendor websites. You can read up on our vendors.” So I was basically asked to look at tile websites for eight hours a day, for weeks on end. I’m sorry, I can’t. I can’t do that at all. After going from a much more intellectually stimulating job in tech, and going to that, was very hard for me. And I also don’t want this to sound like in any way that I’m talking down about people who do work in that industry, who do perform that. I want to acknowledge that that was early in that particular career, and so as a salesperson, that’s how it starts out in any new sales position, is that you don’t have clients, and so you kind of don’t have a lot to do. It was too much for me to handle to be sitting on my butt for eight hours, staring at my computer, doing nothing. Nothing. It was very, very difficult, and I had to get out.

Did you ever have an itch to like bust open a text editor and just start coding at something?

So you say that…

[laughs] That’s what [unintelligible 00:09:50.07]

Let me tell you how I spent my day. Let me tell you how I spent my day.

[10:00] They had an inventory system that was so old. It’s one of those really old inventory systems that I think they’re paying like thousands and thousands, maybe hundreds of thousands… I’m not going to – I can’t speculate too much, but they’re spending thousands of dollars per year on this piece of software that I swear is stuck in 1995. And I was like “This is terrible. There’s so much room for human error here. We’re losing money, not only because this is very expensive software, but also because it’s so easy to make a mistake.” This is a reason why UX is so important, is because of things like this. There are just enough no-code, or at least low-code tools out there. I think Zoho offers some stuff like this… Stuff that just gets the job done, where you can build forms, and workflows through these low-code tools, that would be sufficient for any small business. And so I started putting one together, and the reason I went for a no code tool was because I knew that they’re not actually hiring me as an engineer, but I have nothing better to do, and I just want to build something… And so I put together a complete system that would replace what they already have, because I had nothing to do for eight hours a day. And I built this system for them. Nobody asked me to; this is just what I – this is just what I do. And I knew that it could have been rejected, I knew that. But I was “I really don’t even care. I just need a project. It’s fine if it gets rejected. I just want something to do.”

And so I built this thing from scratch. And again, I think there were maybe like a couple of places, where I had like a couple of lines of – I don’t know if it was actually JavaScript, but it was pretty much JavaScript. So I said “Here, this is like a starting point. I want to be useful. You guys have an ex engineer on your staff. Please let me be of good use. I want to be useful to this company.” And the response I got was like “Thank you for being excited. Calm down, we don’t need this right now.”

That’s a bummer.

“Please, don’t put too much energy into this.”

At least you tried…


You gave it a shot.

Yeah. Which - I won’t say the disappointment of that was surprising at all; it was just the staleness of every day. And I also want to say that many people would kill to have a job like that, where they just get paid to do nothing. And I think that’s fine to want that, and I don’t want to say “Oh, I’m just way more intellectual than other people. I’m just different.” I don’t want to come across that way. I want to acknowledge that I’m very lucky to have had a job in the first place, and so I’m grateful… I was very, very grateful for that income, but it was no good for my mental health. So I’m only speaking about my personal experience, and I don’t want this to turn into commentary of people who have types of job like that… Because having a job is a wonderful thing. Having income is a wonderful thing.

That’s okay to acknowledge that particular job is not for you, though. And I think that’s what’s important, because here on this particular show we’re not necessarily digging into this interview style, but more like topically. I think people come to this particular kind of show to think “Wow, what were their experiences? How did they experience it in life? And they made a change, they saw something different, and they wanted to sort of reject”, like you had done. And I think it’s okay to acknowledge that that particular job is just not stimulating for you. That’s totally fine. Like, masonary. That’s an amazing job. People do that. I mean, for me, I don’t lay tile and build walls and stuff like that, or even retaining walls in my backyard. I’m thinking about that, by the way, building retaining walls in my backyard. So I might become a slight masonry kind of person. But it’s okay to acknowledge that that’s not for you. Totally cool.

[13:47] Yeah, absolutely. And I would also say – so I quit that job, because it was… I can remember very few times in my life when I was that low. And also just realizing that I had taken a risk, I had taken a leap, a financial leap, a creative leap, trying to get into an industry that I thought would be fulfilling, and then realizing as I was slowly running out of money that this was not the industry for me. Very, very humbling, very scary as I started to see my savings dwindle. That was around the time that I had to withdraw from my Roth IRA – I had to drain my Roth IRA, and then later I had to ask my parents for money… And you know, at 34 that’s a bit humiliating. That feels really humiliating. And I was able to carve out some amount of compassion for myself, but it was still not great. It was not a great feeling.

And I managed to land a couple of - let’s say, I landed a job, a contractor position with They’re fantastic. They are a WebRTC company, and I was doing some dev rel for them. I did a couple of videos, working with my old buddy Chad from Heroku. I think he’s their dev rel person. I don’t know his exact position… But finding – again, it was my connections that eventually landed me that first waypoint on my journey back to tech. And I was very grateful for that. And that was a really fun position, because I had never done video content for tech companies before, I had never had that level of creative freedom before… And I really excelled at it. So I was very, very grateful to have that stop, to work for them for a couple of months, and do a bit of video developer relations work.

Those are well done, by the way. I saw those on YouTube. So and - those are the same company?

I don’t know. I’d have to double check this. Let’s –

I think is like a news portal…

No, I messed up.

Nah, is what you’re talking about.

Yes. How offensive…? I’m so sorry to the…

Too many Daily TLDs out there. It’s all good., yes. They just say Daily anyways.

Yeah, Daily is there.

I’m talking about the WebRTC company.

There you go.

So sorry for the people at Daily, forgetting the URL… [laughs]

Well, I thought I prepared well, and then you said that and I’m like “I did not prepare very well.” Those are two really well done videos, by the way. I think both of those were very spot on. I loved seeing your face speak Spanish, basically. Like, your whole – like everything was cool. And then you said you’d done that in minutes. That was kind of cool how you used that – siv I believe was the API to make that possible. But that’s just kind of cool stuff. Your demos there - if you haven’t done that much, you should keep doing it, because that was really good stuff.

I’ve actually taken – I’ve put a lot of my videos to private, but I used to have a couple of YouTube channels that got a few thousand followers… So I’ve done the YouTube thing for a bit, but it never was a full-time gig. And granted, it still isn’t a full-time gig; I was technically working as a contractor for Daily, but…

It takes a special person to want to be a YouTuber.

We’re on YouTube as part of clips, but we’re not YouTubers. I think it takes a special kind of person. And not negative, or necessarily positive, but just a special kind of person to do that kind of video work, and be on video, and be that candid, and be that vulnerable, I suppose, to a camera. I’m on video now, but at the same time, I am more of a radio kind of guy. While this is also podcasting, it’s not radio necessarily, but… Better in this case, where it’s conversational, rather than…


Yeah, performative.

Great. Thank you, Jerod. Yeah.

[17:36] Well, I mean, life is different strokes for different folks… And there’s a diversity of ways that you can make a living. So many different ways. Part of the fun and sometimes painful part of life is like figuring out what fits you, and what you’re good at, and what you like to do… And it’s easy to think that the grass is greener somewhere else. I mean, we all romanticize, I think, real world jobs, because we deal with digital things so much. I was just linking up in Changelog News an article about a guy who’s doing woodworking… And he goes through the stuff he’s building, but also what he’s doing with woodworking as a hobby, and how like “Could that become a thing that replaces a substantial part of his income, so that he could be a woodworker and not a software developer who woodworks?” And there’s a giant leap between those two things… But you don’t know until you try.

I think interior design has always sounded like a really awesome thing. I went to your website, I think it’s still linked up from your LinkedIn, the… And I’m looking at this and I’m thinking “This looks awesome.” I’m sure you’re really good at it. But the reality of the business of things is often way different than the idea of doing the thing. I mean, I was going to be an architect when I was younger, and I started going down that path… And then I saw what the business of architecture was, and I was like “This is massively different than the idea in my head of what architecture is.” But sometimes you don’t know that until you get into it and you realize “Oh, I’m gonna sit here for eight hours a day and do nothing. And this could last years until I actually build up a client base…” It’s not easy. It’s not easy. So I’m sure it was very difficult, and like you said, humbling. Thankful that you have a good relationship with your parents and everything worked out okay. But I mean, it wasn’t for nothing. You learned something, I think, very valuable through the process. And you’re still breathing on the other side, so it sounds like not all was lost.

Oh, definitely. And I would say that having gone through that scary time where I really didn’t know for months on end how I was going to eventually pay the bills - I think it’s actually a very privileged thing to say that I had never been in a position like that before. So I want to acknowledge that. But it was still scary, and now that I have a job that I absolutely love, and I have the biggest salary that I’ve ever made, and I have a type of freedom in my job that I’ve never had before, and then contrasting that with what I had just experienced at the end of 2023, there’s this very freeing sense of play and joy that I seem to be able to take to my job in a way that I hadn’t before. I think part of it just has to do with the fact that I in no way have any desire to build a side hustle. Maybe a side project every now and then, but not a side hustle. And I’m not saying I won’t ever again, and I don’t think there’s anything wrong with that. But it is very refreshing to no longer feel that pressure to do something extra on the side to have even more freedom.

I think that especially millennials have been - maybe not so much anymore, but my generation was very sucked into this idea of a side hustle. And I don’t think there’s anything wrong with it, but I do think that we need to be a little self-aware and understand where that’s coming from… Because a lot of that came from - for me - a place of wanting complete financial independence, complete control over my schedule, making good money and having complete control of my life and complete freedom. And I know that there have to be some people who are either doing that through freelance, or running their own business who are chuckling at that idea, because they’re like “Oh, you think you’ll get freedom when you run your own businesses? Oh, that’s cute.” It’s not all rainbows and puppy dogs.

I think the underlying problem with the mindset I used to have is that I thought that I was seeing all of the value in “If I can find a project that earns money, then it is a valuable project to do.” And frankly, that’s capitalist brain worms… And I lost my ability to play. And that is very detrimental to learning, to living a good human life… To be clear, I don’t think side hustles and the ability to play are mutually exclusive at all, but I do think that it’s something I’ve forgot to be aware of, of this value in play. And when I say “play”, I mean doing something for the joy of it, and that’s the only reason. That’s the only reason.

[22:18] In my new job - so I work at now - I am effectively in developer relations, although that’s not exactly my title. It’s a little confusing. I’m like JavaScript-specific developer relations… I actually have a ton of freedom in what I focus on. Sometimes it’s testing out new technologies, sometimes it’s writing blog posts… The fact that I get to write is so fulfilling. The fact that I get to go to conferences, and interact with people… I can even, to some degree, work on the platform, making it better for people deploying JavaScript apps on Fly. I have so much creative freedom in my job, and I feel very fortunate that not only was I able to find a tech job again, it happens to be one that pays better than anything I’ve had before, and with a level of freedom and space to play more than any other job that I’ve had. And I feel so, so lucky to have stumbled upon that, because it’s exactly the kind of job that I really needed, was “If we’re going to get back into tech, we have to approach it with a sense of joy. We have to like it”, as groundbreaking as that statement might sound… [laughs] You have to like it.

Yeah. Well, I mean, I think there’s a lot of disillusioned tech workers right now, for good reasons, and probably for some bad reasons… And you don’t really care about something or consider its value sometimes till it’s gone. And then you realize, “Oh, I had a really good thing, and now it’s gone. And now I know that I had a good thing. Even though I didn’t know it before, now I know it acutely.” And for you, getting to come back to that good thing and actually have a better thing on the other end is awesome. So I’m over here getting little bit jelly of your job. It sounds like a sweet setup. I mean, come on…

It’s a sweet setup. I love it. Yeah.

Break: [24:07]

Do you ever want to just go back maybe and do a nine-to-fiver? Because some of my friends, they have a traditional nine to five; they go to an office, they work eight hours, nine hours with a one-hour lunch, then they go home. And then they just get a paycheck, and then they go back… You know, I’m describing typical things in extreme detail. And sometimes I’m like “That would be nice.” And other times I’m like “That would be awful.” But what about you, Adam? Do you ever desire just the traditional life?

I mean, I would be remiss to say no… But I think when you start to exercise the actual doing of that kind of thing or think about that, it’s like well, we at the same time may see, as you alluded to earlier, the dip in 2023, which is pretty clear for a lot of people in or adjacent to the software industry… Which we are in, as well as adjacent to, which is strange…


I think you can look at that and say, “Well, sure, I can go get a job at a phenomenal place like Fly.” We love Fly, by the way. Fly is one of our partners and sponsors, we have to say that, but… I do love Kurt and the team, and obviously the fact that you’re there, and I’m sure that it’s amazing. I’ve always been a fan of what they’re doing. And Jerod and I get to be fans of so many Fly’s, and Renders, and Retools, and Cloudflares, and Fastlies, and all the people out there that are doing amazing things, but we don’t get to work there; we get to work with. And in a lot of cases we get to dream with them, but never get the experience… And maybe more so me, Jerod, that I get to deal with them more frequently than maybe you do… I mean, we do in podcast form, but I’m working with these folks pretty frequently, and dreaming with them where their future may go, and never actually walking the walk with them. And there are definitely times when I’m like “Man… It’d be so cool just to work on one team and do that one thing…” But like, we get to work on one team here. So there’s a double-sided thing, where sure, it could be, as you said, sunshine and - did you say puppies? Puppy dogs?

Yeah. I assume you get puppy dogs.

Oh, I’ve got a pup.

Is that not part of the contract? I don’t know…

I didn’t get a puppy dog.

Oh, okay.

Rainbows is the other part that you missed out on.

Rainbows, yeah. Maybe some rainbows here and there. But I think at the same time, we have a level of freedom as well in what we do, that we get to be agnostic free agents of the tech world, in a lot of ways. We get to be the dev rel for everyone in a lot of cases. We get to choose what we dev rel for. And I mean, there’s freedoms we have… When you choose a team, it’s like “We’re Team Fly”, beyond any rationale of anything being better potentially, Team Fly. Whereas we get to be team “What is the best? What is what people should focus on?” And I think there’s some true value to that that is really challenging to quantify, until you’re in Jerod and I’s position, getting to do what we do for 15 years or whatever the number of years are, steeped deeply like we are, so deeply like we are. I think there’s a lot of value we have that it just changes things if you choose a team.

Annie, what were your side hustles you were doing prior, the stuff that burned you out? Were you just taking freelance gigs, were you trying to build a product?

No, definitely no freelance. I don’t like freelance at all. I don’t like kissing up to people.

I like how confidently you know what you like and you don’t.

Oh, yeah.

You don’t cut corners. You’re just like “Nope, not for me.” A lot of people hem and haw about certain things, but you seem to know, and you just come out and say it, “I don’t like freelance.”

Yeah, I definitely don’t like freelance. I tried that early on in my career and I was like “Oh, people are awful.” And I did work with some clients that were wonderful, and…

[31:52] Yeah, that side of the thing is – the right client changes the equation; the wrong client… I mean, everybody has a little bit of both. So I did freelance for many years, and one of the things that I’ve found was you have to price yourself into the right clientele. Because there’s like a correlation between the people that are hiring cheap, and the people who are not the people you want to work with. And the people that value even – you just price out some of the worst clients… Now, there’s still people who will pay good money and are still bad clients. I’m not saying it’s 100%. But that was one of the things I learned, was like “Oh, I don’t want to find somebody who doesn’t value my time, because they already don’t value my time, and so it’s not gonna go well from here.”

So there are ways you can kind of like hedge around bad clients, but for sure, there are people that are terrible, and working with them is terrible, and it makes your life a living hell. One thing that many freelancers say is if you leave a nine to five to go freelance, or to go contract, you go from having one boss to having ten bosses. And it’s actually less freedom and more headaches. Anyways, I cut you off… You were saying how you don’t like it.

Oh, yeah. In fact, I think my last freelance client was – granted, I was very early on in my career; I was only a couple years in. And her business was a coupon business, and it may not shock you to learn that she didn’t have the biggest budget… But I was not being picky. And she specifically gave me the advice of like “You’re starting out, you need to price yourself as low as possible.” That was the advice I was given. I was like “Okay, great. Wonderful.”

Yeah, that’s pretty self-serving advice, wasn’t it?

Yeah. But I won’t go down that rabbit hole, talking about that client. But what I was actually doing was working on a note-taking app called Typist. And it was just the note-taking app that I always wanted. Both of the applications that I had attempted to turn into profitable businesses were just things that I wanted and didn’t exist yet. The first one that I built was a translation app for building vocabulary. I originally built it for learning Japanese, because that’s what I was doing at the time… And then, once again, got burned out on that, because I had let it become my whole identity. Any kind of spare time that I had, I was like “Time to work on that side hustle”, and that became very toxic.

Same thing happened when I was working on Typist, which I built and I actually used every single day. It’s basically Apple Notes with a Markdown WYSIWYG. Really easy, clean to use. It wasn’t perfect. I had a couple of – I had a few dozen users, but it was definitely buggy enough that it wasn’t ready yet. And I really loved it, and I really saw a future for it… But I just happened to burn out. I’ve actually recently picked it back up again, but I’ve set some ground rules for myself, which is if “I’m going to re approach this, I’d like to redo it in –” First of all, I’m rebuilding it because I’m a software engineer and that’s what we do… And ironically - or maybe not ironically at all - I’m rewriting it in the most common… “Oh, I want to rewrite this in Rust.” I feel like it’s almost become a meme now, of people who learn about Rust and are just like “Oh, I’m gonna rewrite everything in Rust.” And I say this – I’ve barely learned Rust. The only reason I’m considering this is because of - I think it’s called Tauri. It’s like an Electron alternative. Rust is very intimidating to me, but I’d like to learn it because one of the big complaints about Typist was that it’s massive, because it’s an Electron app. And I had many people who were like “Please, not again. I already have too many things that are Electron on my computer”, so I was like “Alright, okay, let’s try it.”

Tauri is awesome. It’s probably – if I was going to learn Rust, that would be the reason as well. It would be Tauri. It wouldn’t be any other reason. So I agree with you there. So are you just starting fresh? What are the kind of rules? You said you have some ground rules. Is this like X hours per week you’re gonna do this, or what do are you thinking?

Not even. So one thing is whatever I build, I want it to be open source, at least for the foreseeable future. Monetization is off the table.

For the love, for the joy?

[35:57] For the love. Do it for the love. Because I genuinely – the reason I decided to pick it back up again is I’ve been doing a lot more writing, and I’ve been learning, and I wanted to take notes, and I was like “Dang, I’m in this place again where I don’t like any of the note-taking apps out there, or the writing apps.” They’re all either way too simplistic, or they are like giant, complex beasts that I don’t actually want. So I wanted something in the sweet spot; you know, what I would consider a sweet spot. And so I was like “Alright, I guess I’ve gotta pick this thing up again”, because I actually do want the thing.

So open source, no monetization, not until it seems like a serious attraction… But even then, I’d say that I’m being very strict about “Don’t even think about it, Annie. Don’t even think about it. Because the moment you get a whiff of that and you’re like “This could be big!! Oh, man! This could be my whole life. I could build like a lifestyle business around that!” Toxic! Toxic for me. “Don’t do it, Annie. Don’t do it.” I just know myself well enough. I’ve gone after that dragon for so many years, and I need to pivot.

So the other one is I have to document my progress… So I’m gonna write about everything as I go, and I’ve just started… And then I have to have fun with it. And so there’s no number of like hours per week; I just have to be constantly checking in of like “Am I enjoying myself?”
There’s a sense of – I don’t even know what the emotion is. There’s this sense of exhaustion driven by passion that I have to be very careful of, because also I have ADHD… So that’s my jam, is just getting sucked into something that I love… Because that’s how you burn out a flame. And I don’t want to do that again. I want to do something to a small degree, enjoy it, then move on. Go hang out with friends, do a hobby that’s not in front of a screen, and enjoy my life. Because that is what ultimately will keep up the momentum to do other side hustles. But I am constantly keeping tab of “Am I getting sucked into this too much?” Because that’s very important to be aware of… Because number one, it just doesn’t feel good. And also, it often comes to at the detriment of other aspects of your life. And I don’t want to do that again.

For sure. I always tell my children with simple things, like treats, let’s just say. Moderation. If you only ate that, you would not sustain. And it seems easy to have that advice. I’m not saying like “Oh, yeah, you’ve got it. Moderation.” But to be in a place where you can have a process to document and self-reflect and be self-aware of how you feel - those are guardrails that are very healthy, very mature of you to have. Whereas in a past Annie moment, you had less of that maturity, less of that discipline, and it got you into places where you were less comfortable. So that’s awesome. Moderation seems to be obviously the key, but at the same time, self-awareness is so key for most folks. Like you mentioned earlier, Jerod, people that are disillusioned. I think those are people who are maybe less self-aware than they should be or could be, and if they were, then they would be less disillusioned. Yeah, good spot to be in, Annie. Good for you.

We’ve talked with hundreds of people about their software creations, maybe thousands, and so many perspectives around why they do what they do, and then what usually informs how they’re doing what they’re doing… And one of the things that we care about is the sustainability of the software ecosystem, and of the software community, the people building the ecosystem. And so we often asked them about things, and one of the things we asked them about was “Well, how are you going to make money with this? Because you’re going to do it for a long time, and it’s gonna drain you, and so part of sustainability is offsetting that time, offsetting that cost.” And some people have plans, and they’re trying to do the thing, and “This is a side hustle”, or they start it off as a passion project, “Now I’m monetizing…” And other people have just been like “No. It has to be for the joy. It has to be for the love.” And they’ll say like “I already have a job, and now I have a hobby I love and I care about. And if I turn it into a hustle, now I have two jobs. And the thing I love is now something that I work for.”

[40:21] And sometimes that’s just the answer for certain personalities. It’s like “Nah…” So I like that you’re saying “Guardrails now. No monetization for now.” You’re not saying this is a law, forever and all time, because then you go breaking your own law and feel bad about it… But you’re already making a living, the best living you’ve ever made. And so why take something that you love, and that you’re passionate about, and that you enjoy, and then start toiling at it in a way that it has to be changed into some sort of money-making endeavor? It seems like that could just very easily for you destroy all that joy.

Absolutely. And you know what I just thought of? I think what burned me out on having a side hustle was this underlying belief that until that side hustle is my full-time gig, and I am doing that fully – and it was obviously a thing that I love to do. I actually love building businesses, I love building brands, I love all of the aspects that go into it, because I’m a very multifaceted person, and I think I’m exceptionally well-suited to that type of work. I like wearing a lot of hats. I like my current job because I’m wearing a lot of hats. But I think when I let myself get so sucked into the image of what my life could be, the reason I was so driven to work on my project day and night was this belief that I’m not going to be truly happy until that becomes my full-time job, and I just need to get there, and then I can be properly happy. And that is a nasty, nasty cognitive distortion that we all need to pay attention to if that gets into our brain. I think that’s what often drives this obsessive burnout culture on side hustles, is that people – I mean, this is true for even outside of side hustles. Anything that we believe like “If I just do this, and I get to this point, then I will be happy.” And a lot of the times it doesn’t come across – those thoughts in our mind may not be…

It’s not that clear.

It’s not that clear, it’s a lot more subtle. But when you boil it down, it’s really that thought that’s driving a lot of it. And at least it was for me. And that was the part – that’s the part that I am warding against, is the reason I’m so, so focused on joy and play and gratitude is that I do not want to lose sight of what I already have, and know that I have full capacity to enjoy everything fully right now. Because I have so much, and I also know how easy it is to lose… So I am squirreling away all the gratitude that I have, and all the joy, and sucking it up as much as I can, because it’s not guaranteed, at all. It’s not guaranteed. So yeah, gratitude is a big thing for me right now, especially gratitude for joy.

Yeah. No, I mean, thankfulness is huge. That is an antidote to resentment and discontentment. Like, if you’re thankful or have gratitude for the things that you have and do and are, then you are de facto not discontent with those things, right? And so if you acknowledge that and think about it and say it… Because things that go out of our mouth come back into our own ears, and they’re more clear when we say them. That’s going to ward off all kinds of bad things in your life. Discontentment, like I said, is a huge problem. And I tell people this all the time, if you’re discontent right now, whatever that thing is that you’re chasing, when you catch it, you’re going to be just as discontent then as you are now. You think it’s going to solve your problem, but it’s not going to. Trust me, I’ve chased a lot of things, and I’ve caught some things. And I catch it, and I’m like “Okay, what now? What next? What else can I catch? Because I’m still discontent.” So that’s a bad cycle, but it sounds like you have landed on one of the key aspects of life, which is gratitude.

[44:16] Yes. I also want to call out, you’re right that if you’re constantly chasing this thing, and like “Well, then I’ll be happy”, that can be very dangerous. But I also want to hold a little bit of space for people who are in the job market, who don’t have a regular income, especially people who are new in their career who are trying to break into tech, how scary it is to get that first job. This is particularly on my mind because I saw this huge wave – it’s still happening; this huge wave of people who are sort of early in their career and they decided to get into tech because of the pandemic, and they wanted a way of having better income, a better life for themselves, and to be able to work from anywhere. And that’s amazing. Not that all tech jobs are like that, but…

But I get that allure. And so we have this huge wave of people doing bootcamps, and sometimes self-educating, getting into this… So I will say, it is okay to just keep striving for a job, and the likelihood that if you don’t have a job right now and you don’t have income - yeah, having an income will make you happier.

Oh, absolutely.

That will happen. But when it comes to side hustles at least, or anything that has that sort of like toxic draw, that makes you believe that you’re not going to be happy until you have that thing - that’s something to be aware of.

Yeah, I’m not advocating for people not to try to improve their lives or their circumstances. I’m saying if you can find contentment even without, then you’ll just be more content when you have. But if you’re discontent and think that catching something, whether it’s a raise, or a job, or a side hustle that turns into a business, or a YouTube channel that blows up, and you think that just that one thing is going to solve all your problems - that’s just a fallacy. It’s just not true. And so many people have caught the thing, or found the celebrity, or the millions of dollars, and they are still unsatiated, unsatisfied. Empty. And it’s sad. So that’s what I’m talking about. Now, absolutely, go get the job. Go get the money. I’ve got no problem with any of it. But it’s your attitude along the way that I think matters so much.

Truth. You’ve got to be careful chasing them dreams.

What’s your to-do app called?

It’s called Typist. I might rename it…

I’m pretty sure we talked about it. Didn’t we talk about like getting your reset on? I think we touched on it briefly…


Oh, maybe. Yeah. The site is up…

It rings a bell.

Yeah. If you look up, it’s – I think if you download it, it’s gonna break, because I disconnected all of the MongoDB Atlas clusters that were storing the notes… So it don’t work, but eventually it will. [laughs]

Is it open source yet? Is it out there yet?

No, no, no. This is a thing I decided in like the last week or two, so…

That’s cool. That’s exciting.

Have you used Obsidian?

Yes. That’s one of those beasts that I just – a lot of it has to do with… I haven’t used it in a while, but I have tried Obsidian, and I’ve found it to be a little too bells and whistles. I also have a thing for things that have too much metadata that you can set on a note… Because what I want is to do Command+N and then just start brain dumping. If I have to click in between like a title and a body tag - I don’t want any of that stuff; that is too much friction. My brain moves too fast. I need to just get my thoughts out. And maybe Obsidian is different now. I don’t know.

I’ll tell you, that’s exactly how I use Obsidian. I want you to build your thing. I’m not saying don’t build your thing. I’m just curious, when you talk about – I mean, everybody has their way of doing notes, and to do’s, and that’s why there’s so many apps. And most of them don’t map onto too many people’s workflows, is what you find. So that’s why, again, there’s a diversity of them. Because you just can’t find one that you like. And so the only one that you’re going to like is probably the one that you’re going to build. And that’s great. It makes it hard to make a business out of it, because there’s so many of them… And it’s hard to find so many people that work just like you do. And so people tend to make note-taking and to do apps that have all the things, because they’re trying to appeal to a large enough audience to get enough sales to continue to do the thing. So I’ve long despised most software in this space… And we have no commercial relationship to Obsidian, but they probably should sponsor us at this point…

[48:44] They should sponsor us.

…I’ve found it to be – if you like to just take notes in Markdown… It’s got tons of stuff; I don’t use any of that stuff. I just use it, Command+N, write some stuff…

Or Command+L.

…switch between notes… I don’t do any tags, I don’t do any folders. Well, I’ve got one folder for the Today Note, because the Today Note will automatically go – Nick Nisi taught me this; you can have a Today Note that will just go into a folder of like 2024/march, /whatever. That’s kind of nice. Otherwise it gets this kind of gnarly in your home directory. But anyways, not an ad for Obsidian, but I’m just a guy who’s found one that finally I can ignore all the things. And it’s still fast, and it still does Markdown rendering… And I like it.

That’s really cool. I actually am just looking at the website and it looks different than the last time I tried it. I think I tried it a few years ago.

Yeah. My fear is it’s going to change, because they have kind of become big now, and they’re adding more things, and I’m sure there’s AI in there, and there’s product roadmaps, and all the things that businesses have… And that’s usually when I start to dislike products over time. And I’m like “Ah…” I liked the 1.0, you know?

Well, the good thing about it is even if they do change it, I suppose for the most part, unless you’re like knee-deep in plugins, is that in the end it literally is just a .md file.

Yeah, portability is amazing.

That’ really good.

It’s not a database somewhere. There is syncing if you’re using iOS and whatnot, of course, but that’s why I thought “Well, I can buy into this even if it does change”, because at some point someone’s gonna say “The new Obsidian”, or whatever it might be.

Oh, yeah.

Obsidian version one, that stays there, versus version two that adds the AI, or adds the bells and whistles. Because I think the challenge is that these things - they start out simple, and that’s probably why you have the passion for Typist, is you want to keep it simple, and you also want to satiate that engineering side of your brain to kind of like tinker and have fun and have those boundaries on a side thing; not even a side hustle, just a side thing, just something you do for yourself. And then at some point it just turns into something else, and it’s not the original thing anymore. But my experience is very similar to Jerod’s, is like Command+N for New, obviously, Command+O to find things… I put everything in there; literally, everything that I can ever think of goes into Obsidian because of how fast it is and how simply it’s just driven on type, whether it’s docs, code, anything. Not like literally code, but code blocks, and stuff like that… Just sort of like mostly Linux stuff, like “How do I set up a new Ubuntu machine?” or “How do I do this or that?” I document my own processes and refer to those documents for various things.

So that’s a lot of how I use Obsidian personally… But it’s been very, very, very, very organizing, whereas it’s been disparate; things have been in iA Writer, or at one point Dropbox Paper, or just various places that were not fast. And obsidian is just fast.

That’s what I’m looking for. I’m gonna give this a try, honestly. The fact that it is a little bit different, and not what I remember –

Gosh… Obsidian, pay us! We’ve sold one. [laughs]

This is great. It does look a lot cooler.

Can you use our affiliate link when you click on that? No, just kidding.


Yeah, I’m kidding as well… But I’m a big fan.

[52:02] But we don’t want to crush your dreams just because Obsidian exists, you know?

Well, what dreams…? It’s just for fun.

I’m looking at Typist the old version, and it looks beautiful.

Thank you so much.

So I will give you that much. More beautiful than Obsidian even, which is a pretty, pretty good-looking app. It’s not like the most amazing-looking app, but yours already looks nicer.

It could be improved. There’s a lot about Obsidian that could be improved to increase efficiency, increase speed, a lot of different stuff like that. But I think mostly it’s just like distraction. There’s a lot of things that can be distracting with the interface. If you’re somebody who likes, when you do prose and you’re writing, everything else goes away… Maybe there’s a plugin for that that I’m not aware of, but Obsidian default does not disappear into writer mode, where there is no obstructions in your view, and distractions around you to shiny-object you, or whatnot.

Do you guys write in writer mode? Are you writer mode people?

No, I just know it’s pretty common for folks probably like Annie, who want to build their own tools, to be like “I want it as simple as possible.” And that’s often like - when I want to write, don’t distract me with the sidebar that has all the notes ever… Which is like - I’m looking at my sidebar, and it’s like literally all the notes ever, it’s there. So…

Yeah, the sidebar is ridiculous.

It is ridiculous.

I’ve never been a distraction-free writer though. I’m also not a writer, writer, so… I did try the distraction-free style, where it’s birds chirping, and coffee, and macOS full-screen mode on iA Writer. Just a cursor, and me, and the keyboard. I can’t write like that.

It feels lonely.

I just stare at it. I’m like “What am I going to do here?” and then like “Ah, I’m gonna go check Twitter…” [laughs]

There is nothing more intimidating than a blank piece of paper, or a blank screen.


It’s very intimidating.

It is very intimidating.

Which I think is probably the one use of language models that I’m still appreciating… Because I’m pretty much disillusioned about everything, because I’ve used it for so long now that I use it in disgust… But just not giving me a blank – mostly with code; just write this function for me. It’s going to be wrong, I’m not going to like it, but I’m going to copy-paste it and change it to be a function that I would have written. And for some reason, that’s faster than just me writing the function myself. Because I’ll just sit there and think “What should I name this thing?”

Oh my gosh, yes.

Same thing with prose. Just give me some copy… It’s going to be generic, but I’m going to make it not generic, or I’m gonna throw it away… It just gets rid of that blank page problem.

Yeah, it’s a lot easier to – well, for me at least it’s a lot easier to edit than it is to start afresh. I do think that there’s a muscle to build of just completely turning off your editor self and just learning how to braindump… But having that extra little foothold of using an LLM to just like “Just write me an intro paragraph.” I’m gonna rewrite every word of it, but… Give me something. It’s nice to get you started. I use that, too.

Break: [54:59]

Let me throw out a topic here then, since we’re on this LLM kick. And it’s not deeper into AI necessarily, but I’m just curious… When you drive or you travel, do you pretty much mostly use a map application to get there? Even if you’ve been there 1,000 times.

A lot of the times, yes. Some places, if I’ve been there enough, I don’t. But…

Right. For the most part though you use the map application, because there might be traffic, right?

No, not in the city… Unless I want to know my ETA, or something like that.

So you drive just free?

In most cases. Okay. So I went to my men’s group this morning, I did not map there. So that’s an example of not. But if I’m gonna go from Dripping Springs to Austin – I live in Austin, by the way, Annie. If I need to go into town - that’s 30 minutes away, 25 minutes away - and it’s downtown, I know how to get there. I’m going to map it. So my shtick here is not maps. It’s that the world, when the maps became ubiquitous on our phones, in our cars, a part of the operating system driving basically, we became people who, even if we’ve been there before, we’re mapping it. I wonder if the same might happen with generative AI, and the way we’re leveraging it for prose… Can you actually function that first step without having the generative, you know what I mean? Will we get there? That’s my topic I’m going to bring up, is like –

Well, you did it this morning and it worked out for you…

Right, right. And I recognize that it’s not always there… But at the same time, if I need to go into Austin, into town, I’m probably gonna use a map, even if I’ve been to the literal same parking garage. I’m probably gonna map it, just because that’s what you do.

Yeah, because why not. Because it’s there.

Right. So I wonder if we’ll become so seemingly dependent in some way, shape or form to safely drive to a place as we may safely drive to a prose, to an outcome in our possibility of writing down our thoughts, or like you had said, having this discipline of brain-dumping, but like, you just mentioned blank screen; can you just generate or give me a function? You want to start from a generative state and work backwards, and that somehow faster.

Yeah, maybe.

So I’m just curious if, because now this is state of the art, if we’ll get to a place where it’s like “Well, I can’t really begin until I’ve been assisted into the beginning.”

Well, extending your metaphor… When I’m mapping, and my wife makes fun of me constantly, I just do whatever it says. I’m like Michael Scott, driving it right into the water, right into the lake…


“Make a right turn.”

“Wait, wait, wait, wait. No, no, no, no. It means bear right. Up there.”

“No… It said right. It said take a right.”

“No, no, no, no. Look. It means go up, to the right, bear right over the bridge, and hook up with 307.”

“Make a right turn.”

“Maybe it’s a shortcut, Dwight. It said go to the right.”

“It can’t mean that. There’s a lake there.”

“I think it knows where it is going. The machine knows…!”

“This is the lake! This is the lake!!”

“Stop yelling at me! Stop yelling!!”

“No! There’s no road!!”


And I don’t want to be that way with my words. Maybe I shouldn’t be that way with my driving. But a lot of times you’re using it, like you said, even if you know where you’re going, because you want to know the fastest way right now. And maybe there’s a lane closed on this road, and it may know that, and you don’t know that… So I understand all that. And I do use it sometimes in the city for those reasons. And my wife definitely uses the map every time, even though she knows Omaha inside and out and doesn’t need to… But she just does. She likes it. But man, if Siri says “Take a right”, I’m taking a right, you know?


And I might take a right into a phone pole, but I’m gonna do it. And so that sounds like a dangerous thing for generative AI and me…

[59:59] Yeah, I think - when it comes to prose, I see what you’re getting at, and it’s something I’m concerned about, in myself at least, is I like the foothold and I’m gonna use it, but I also really want to be aware of making sure that it’s not too much of a crutch. I like it as a buddy to get started. That’s really helpful. But I also want to make sure that I’m still cultivating this skill of – it’s a very vulnerable place, in my opinion, to start writing on a completely blank page, because the first thing you write will probably be awful, and you’ll want to change it to some degree… And I think that it is a good habit to get into, to learn to overcome that.

And so that’s something that I try and be aware of; if I’m feeling that writer’s block, at least for the first few minutes, I will try and just write whatever comes to my mind; even if it’s very conversational, said really poorly, just start with something. I think that’s a really healthy skill to cultivate. There’s nothing wrong with occasionally using AI to help you with that a little bit… Because that’s essentially what you’re doing; you just need to get something on a page, so you can start to mold what you’re trying to say. But I think it’s a skill that we need to make sure we maintain, because that’s really valuable.

Yeah, motion creates emotion and momentum, obviously. Motion creates emotion is a sales term. I’ve been in sales for a long time. It was a term from Boiler Room, the movie. Ben Affleck, a few others were in there…


“Get on the phones. It’s time to get to work. Move around. Motion creates emotion.”

Well, I wonder if it even like a progress blocker. So here’s an example… I’ll reveal a little bit. So I know that in your Twitter bio you still say your neuro-spicy, which I think is cool… And I don’t really know what that means necessarily. I think I might have an idea when I think about what neuro-spicy means… I think you’re kind of a spicy person generally; we’ve spoken to you before. I thought maybe it was an Annie thing. No, it’s a real thing. This is a thing that’s emerging with folks that I think are neurodiverse. I’m not well steeped in it, you can certainly school me on it… But I went to the LLM and say “Just define neuro-spicy”, because I know if I take that same idea, or that same prompt, and put it into Google, the result I get is way different than a single paragraph that gives me just enough to have a non-embarrassing conversation with Annie about being neuro-spicy. It doesn’t have to give me all the resources ever, all the Wikipedia entries and every blog post ever, or whatever it might be. It gets me right to the nugget, which is “What exactly is it?” So this is an example of like progress blocking. Now I’m sort of hooked in a way that this response from the thing, the magic box, gives me something just enough. Like, “What do I do in the future if this doesn’t exist? I cannot map my way to the quick definition.” I don’t know.

Yeah. I think like low-risk, non-controversial knowledge, information. It’s a great way just to like quickly come up to speed on something. “Did they have real animals fight in the filming of Where the Red Fern Grows?” That would take a while to Google that. I don’t know if you guys have seen that movie. We watched it the other day… From the ’70s.


“He’s a boy, Jenny. The boy ought to have a dog.”

“Sometimes I think God don’t want me to have any.”

“If you ain’t doing your fair share. How long you’ve been saving it?”

“A long time.”

“You’re gonna get them dogs.”

You know, at the end this mountain lion attacks his dogs… And it’s like a scene where the mountain lions and the dogs are really going at it, and wife’s like “They didn’t have CGI back then. That looks pretty real. I wonder if any animals got hurt.” And so I just asked it real quick. But that’s like low risk. If it’s wrong, then I’m just like, I’m informed about something that doesn’t matter anyways. It’s non-controversial… Maybe it was controversial back then; maybe it could be. But that kind of stuff, I quickly get an answer and move on with my life. That kind of stuff is useful. But high risk, “How do I concoct this particular medicine?”, I don’t know, will be high risk. Lots of things are high-risk…

I don’t use it in any sort of email… I think ChatGPT in a tab is my current wall around it, where it’s like, I have to go – even when I’m coding, I don’t do the inline stuff, because a) Zed for some reason still isn’t working for me with their assistant, and I don’t have Copilot… And so I go over there and say “Write me a function that does this” and come back and copy and paste, or just look at it and write. And so I’m not like writing my emails with any help; I’m not writing anything with health unless I go over to it and say “Help me.”

And that feels like a good barrier for me, where I might be more tempted just to like tab-complete an email out and become a robot, you know?

Yeah. A lot of like “Thank you for allowing us to apply to your esteemed company.”


For some reason the term “esteemed company” is like the red flag that I’m like “Absolutely not. No, thank you.”

Yeah, the spammer emails have gotten slightly higher quality in the last year and a half, you know… It’s like, “Oh, this is definitely not a human that wrote this”, but it’s better than the gobbledygook they used to send.

Mm-hm. It’s good for writing bull***t.

[unintelligible 01:05:26.17]

Not that we need more of that. Not that we need more of that.

That’s destroying the web as we knew it, but… It sure helps me when I’ve got a blank piece of page, so…

I don’t know what your practice is, Annie, if you concur, but I’m with you, Jerod. I have to go to the tab and explicitly conjure the magic box. It’s not in my everywhere, and at this moment I don’t want that to be in my everywhere… Because I think that you become - again, back to the maps, you become reliant on this thing to get to a place. And I still want to invoke my own cognitive behavior, my own ability to think, but I don’t mind the momentum that it can give you to help you get through. Like “Hey, I’m thinking about a topic. Can you give me five ways or five ideas that just kind of helps me think more?” And it’s not like you’re using that to copy and paste into something else and you’re selling it as a book, or something. It’s more like “Give me something – prime my pump; prime my brain on some things.” But even that is kind of a crutch, right? Like, if you can only positively think in the future about hard things by getting primed, you kind of lose that opportunity to self-prime. And then again, back to the maps, you’re kind of crutched to this thing… And I want to be aware as I move forward with how it works, and how it’s coming more and more into our lives in different places to have that awareness, I suppose.

Yeah. I’ve thought about this… For many, many years, I don’t know how long – how long has Copilot been around?


Only two? Oh, my gosh. It feels –

No, it predates Open AI, ChatGPT, for sure.

Yeah, I was really – I wouldn’t say against. It just didn’t appeal to me for the longest time, and it wasn’t until this year that I’ve started to use it… And I’m fully on board with it. I’m very skeptical of a lot of AI things. Copilot is not one of those… I think because I learned that it was really just fancy autocomplete. I don’t even like – I tend not to give it prompts, of like “Write me a function that does blah-blah-blah.” I find it especially useful when I’m trying to debug things, because I can just type like C, and it knows that I want to log out the variable that I just wrote, or something, as I’m debugging. It’s very great for when I don’t want to write a long object for like defining headers, and the methods for a particular post request, or something. I love that feature. I really, really love that feature, and I find that I don’t use it – when I use it for autocomplete and not for writing new code… And it’s just – it’s the repetitive work. I love that it’s smart enough to know that.
[01:08:09.04] Sometimes I think it’s a little terrifying how well it knows what I’m thinking. I remember one time I looked at a screenshot of some code, and somewhere else, like in Slack or something… And then I go to Copilot and I start typing like two letters into it, and it gives me the exact – because I wanted to test out that code, and it gave me like verbatim everything that was in that screenshot. I was like “Wow, this is a little haunting.” That spooks me a little bit, but I do like it as an assistant that’s just doing sort of the drudgery of programming. That’s fantastic. That’s what we need robots for.

Absolutely. It clears up headspace. Don’t memorize that API anymore. Just know that there’s an API, and then ask it for the code that’ll use the API, and then you’ll look at it and then you’ll decide whether or not that code is good or wrong. And don’t write it in Elixir, it’s gonna be wrong.

Also, who memorizes things in programming anyways? Obviously, there’s some degree…

I certainly had like jQuery APIs memorized when I was a kid.

Right. There are certain things that you use frequently enough that you obviously memorize. But so often – I mean, can you do your job without Google? All of us…

More and more so, yes. [laughter]

That was very good. Well, without looking up, without asking for help, right?

No, because of ChatGPT, not because I’m getting smarter.

Right. Exactly. So our jobs are not difficult because we have to memorize a lot of things.

That’s not the difficult part. So if I’m getting help on the “What was that one method on this thing, that and the other?” I love that it remembers it for me. I love that.

I wrote a Node.js-based server, starting Friday, coded a little bit over the weekend… And I wanted to use Puppeteer, which is why I use JavaScript, not TypeScript, like Nick Nisi [ahoy-hoy] I don’t use TypeScript, I use JavaScript. But I haven’t written like a Node server for probably years, so I was very ChatGPT-influenced on this one… And it was so easy. It was so nice. Modern day Node is actually kind of nice. I mean, async/await everything, and ESM imports, and… I mean, it was a pretty simple screenshotting thing, but we’re talking like under 100 lines of code. Deployed it to Fly today, by the way, so I used your guys’s stuff… I was not sponsored to say that, but…

But thank you.

…I have a sponsored Fly account, so maybe that was one reason. Easy button. So nice. But yeah, ChatGPT made it so much easier… Just because I know JavaScript, and I’ve written Node, but - how many years has it been? And what’s the API for this thing? And how do you write a file to temporary disk, and then delete it later, and all that kind of stuff? Who wants to know that? Not me.

I’m actually curious to see, as we progress, as we see more early-career developers use things like Copilot, whether that’s for a net good or a net bad. I feel kind of mixed on this, because I know that when I’m in a codebase in a language that I’m not as savvy as JavaScript, such as like a Go project, or Python - I don’t know those languages as well, so having something like Copilot helped me out with a lot of the syntax is really helpful. And I do find that I’m learning, and eventually I don’t need Copilot to suggest things… And so I think it can be a good learning tool, but I also don’t know - you know, we’re reviewing applicants, and I can sometimes see when I think this has just been generated. First of all, it doesn’t work. That’s one thing.

Well, that’s one thing…

It’d be great if it worked…

[laughs] That’s not on Copilot, that’s on the applicant, right?

Well, yeah, that’s what I’m saying, is if you’re solely relying on generated code…

Then you’re not a programmer.

[01:12:07.06] We cannot be shipping code – yeah, we can’t be shipping code that’s just been generated, that we don’t understand at all. That’s no good. That’s no good.


And so that’s where I feel conflicted, is – I think time will tell, if we have new developers that heavily rely on generated code, what is the long term effect of that. Because on the one hand, I think it could be helpful in teaching… But on the other hand, I think it could be a really bad crutch. And I don’t know which way it’s going to swing right now. I think we need more time and more people using it to see what kind of programmers is this outputting.

Let me throw one more out there, just to go back to my maps analogy. Could you imagine somebody out there, navigating with this gigantic piece of paper in front of them? And then maybe they even ask you “Where am I at on this map?”, how foreign that would look to somebody in today’s age. But back in the day, I remember having a map in my car. Like a literal paper map.

For sure. That’s why you’d have a copilot that would literally sit next to you, and they’d read the map; they’d get the map out. And they had to fold it back up when they’re done.

Well, yeah, a literal copilot. I mean, that’s not that long ago. That’s like ’90s.

I remember doing it with my brother in law. We drove to Chicago for a Chicago Cubs game… And I had to be in my 20s. So we’re talking to the 2000s. And I remember having the map on my lap. And that was the last time I ever used a map. But it probably was like 2007, 2006, 2005…? Because – I mean, even the first iPhone… Unless you had a Garmin - I mean, the first iPhone didn’t have maps. The App Store allowed Google Maps to come on to it, and that was probably the start. But did that have turn by turn? I can’t remember. Anyways, that’s 2009-2010 time range. So yeah, as late as like 2006, so 20 years ago, we were just folding maps into the glove box, and unfolding them, and literally looking up and trying to see where you are, and then looking at the map again, and… It was crazy. But we did it.

So if you can go back and be that person, talking to the person now embracing map technology… This is the same person, like the pre-LLM not embracing LLM technology or generative technology… How do you think that person would say “No, no, no. Use the maps. They are amazing, on your phone. Whatever that is, that magical device - don’t stop using that.” I don’t even [unintelligible 01:14:36.03]

Yeah. I mean, I think the analog there is not the person who’s using an old map. It’s the person who already knows the way, because they’re an expert. And so they don’t need it. Like “I don’t need a map. I know where I’m going.” And they get lost anyways, because they’re just arrogant, and don’t know where they’re going.

Right. Right.

I think that’s more like that. Because I don’t think anyone’s saying “No, let’s use like a compiler from the ’90s…” You know?

For sure.

Or “Let’s write an assembly code.” No one’s really saying that, but they are saying kind of what Annie is saying, which is if people are just going to completely turn themselves over to this and just ship code that way, then they’re going to be like Michael Scott driving himself into the lake.

True. Yeah.

And they’re gonna take other people with them. I mean, Dwight was also in the car.

You know this very well, Jerod. What episode was that? What season, what episode?

I don’t remember, but it was a hilarious moment.

Well, I do agree with the sentiment that you shared, Annie, like “Who would want to remember all that? Who memorizes this stuff?” Because if you’re using ChatGPT to query the docs, let’s just say, that’s no different than navigating the docs on your own. You’re speeding up the process, and kind of boiling it down to the real thing you really care about in the docs, not reading all the theory, or the whys and the hows. Just literally to the tutorial, or the code block, or the function car, or whatever it might be… It’s just the high speed way to reading the docs more fastly. Who wants to memorize docs…? That’s what they’re there for, it’s to not memorize. Right?

[01:16:07.22] Yeah. And I think what it comes down to is – I think it’s a useful tool. If you know what you want to build, and basically how to build it, it’s just a matter of syntax. Syntax is the least important part of programming. You should know it, because if you don’t do it, it will break. So you need to have the right syntax, obviously.

[laughs] Yeah, it’s almost weird. It makes the better programmers better…

Right. Exactly.

…but the new ones not necessarily good.

Exactly. So that’s why I feel comfortable using it, because I know what I’m gonna build; I also know how I’m going to architect it. That creative work is still a part of the process, and so I don’t feel like I’m cheating in any way. I just feel like I have an assistant. So that’s sort of my metric of “Am I going to use this AI tool?” Is it an assistant, versus is it doing my work for me?

And they’re gonna get better. I mean, one of the things we’re seeing in the music world is generate a song in the style of… Blank. And I think we’ll get to a point where you could say “Write this function in the style of blank.” And if blank is a very good engineer – like, what have you said “All C code must be written in the style of Daniel Stenberg”, who wrote and maintains the Curl library, and has some of the most battle-hardened, and long-lasting C code in the world, deployed in the most places in the world? And every time somebody needed some C function, the LLM would write it like Daniel Stenberg would write it. That’s gonna be better than 99% of humans, because he’s better than 99% of humans. I’m just giving him massive props here. I think he deserves them. He’s a very good programmer, over a very long timeframe. And so what if we have our tools not just trained on all publicly-available, liberally-licensed or permissively-licensed open source, but also then curated from there and said “This is good software. Write it like this guy, or this gal”? That’s going to be better.

Right. Because we run into the problem of - there’s a lot of code out there. It’s not all good code. If we’re just pulling from all of GitHub…


…especially if our LLMs are drawing from Stack Overflow. If you’re listening to this, you can’t see my face, but it’s like a “Ugh. Oh, gosh. Gotta be careful.”

Yeah. So I think the people who are doing the training and stuff, and the fine-tuning and all this stuff, they are working on that problem. They are highly incentivized to make Copilot, and AI Codex, and Cody, and Tabnine, and all these tools way better. The people that do that have a lot of money to be made, and so I think it’ll get done. The question is how much better can I get from here. And I still think it’s going to be assistive and not replacement, but I’ve been wrong before. It happened once in 2022.

I mean, there are people who are being replaced by AI, and that’s really depressing.

Where at in particular that you’re aware of?

Artists. Many of them have completely lost their business, and are dramatically affected by this. And it’s even more grim when giant companies like Disney are using AI to generate graphics. When they have the money to throw at artists. They have some of the best artists in the world, and they’re using AI to generate some things. I think that has more to do with them jumping on a trend than anything… At least I hope. And I hope that is not a trend that sticks. One thing I’m very proud of at Fly is that we hire an artist - her name is also Annie - and she does basically all of the art for our blog posts, for our website. She’s phenomenal, and I’m so, so happy that we actually hire a human artist. But I feel it is a much more bleak situation for anyone in a creative field… Because most of the time – like, none of them consented to this, to their art being used and copied so blatantly, much to the detriment of their own careers. So I feel very bleak about that. So anytime people decide to actually pay a real human artist, that’s awesome in my mind.

[01:20:33.23] That’s such a tough one, really… I mean, obviously, the bleakness for those particular artists, but it’s such a tough one, because - I can’t recall the newsletter, but I just stumbled upon somebody who was a UI designer, and they’re like “I’m all-in on generative stuff. I want to use an LLM and all this assistive stuff to make me a better designer, to move faster and do more things.” And I’m paraphrasing some of the things I heard, but I was like “Wow, I want to follow this newsletter.” And it’s a new one, so I’m like “This is literally a UI designer, someone who’s not brand new, they’ve been in the industry for a while, and they’re leveraging this stuff to be a multiplier, versus a replacer”, so to speak.

And then you’ve got those cases where that’s not literally taking this wall art, or whatever this art might be and saying “Well, let me be Disney and generate new graphics, because we’ve got the old stuff, and we’ve fired the person who created the old stuff, and now we have this GPU that generates the new versions of it” [unintelligible 01:21:29.24] That’s not the same thing. That’s a tough one, really… Because it’s just so hard to map your mind around the long-term effects of this generative state of art in particular, and how it will replace, augment or just remove folks. And then some places where it’s a multiplier; it’s like, how do you navigate that? It’s just really a big problem to navigate.

But as you said, when it’s an artist who is in the field, and knows how to use that as a tool, that’s a very, very different thing. I have a friend, she’s been in the game industry for over a decade, and she is a concept artist. She’s easily the best illustrator I’ve ever met. She’s phenomenal. And she’s used AI in certain companies where they use it to generate a lot of – again, doing a lot of that grunt work. So if you have a particular style of tree, or item in the environment that you just need to have like a lot of varieties of… Like, “Give me 12 varieties of this type of tree drawn in this style, so that we can use that throughout our level design.” That’s amazing. That’s amazing, and that saves a lot of just grunt work. But when it comes to like character design, something that’s got to be more inventive, and isn’t just repetitive work… In fact, artists using physical mediums will often do this. I don’t know if people know this, but a lot of great artists have artistic assistants that go in and if they’re working on a giant canvas, and maybe they just need like a giant sky scene, and they just need to draw – they need to paint the sky, do thousands of little dots to do the stars, they will often just like pay a younger artist to do a lot of that grunt work. It’s the same kind of thing with AI. And I think that having that as an assistant can be really amazing in doing big, complex projects. So that’s an amazing tool to use it as such. But when it starts to replace people and mimic their work without their consent, that’s where we have a problem. It’s the replacement of people that I’m the most concerned about.

Yeah, I concur to that.

Yeah. I think the second part of what you said is where it gets really dirty… Whereas the first part is kind of what technology has always done, is replace people. Because it’s deflationary. That’s what it does. But replacing people by using art that they put into the world and didn’t consent for you to use to train a thing to replace them - that’s when you’re like “Alright, this is wrong.” But just to use an advancement technology to replace a worker with the technology, that’s the way that the world works.

[01:24:22.18] So we would be stuck with paper maps, we would be stuck with the old school printing press. All the things that have advanced humanity have also taken people out of their work. So that’s less what I – I mean, so it’s a little bit more nuanced. I do agree with you. That’s so gross though, when you use –

That’s so gross… [laughs]

Isn’t it? Like, you’re using their work to create a thing that no longer needs them, and they didn’t say you could do that.

Yeah, you capture their essence.

Yeah, exactly.

You literally steal their essence. The thing that makes them uniquely human and uniquely powerful and creative as an artist, you take it.

Right. Like, you no longer want this person’s art.

It’s like Trolls 2, or the most recent Trolls movie. Have you seen this movie?

What’s the latest Trolls movie? Gosh…

7? Trolls 7?

Well, it’s Trolls, like the animated version of it… Give me one second.

Well, Troll 2, that was the worst movie ever, wasn’t it? There was a movie about how bad that movie is. But that’s not the animated version. That’s Troll 2.

Band Together. Tolls Band Together, this latest one.

They’ve done so many that they’ve quit numbering them. They just have subtitles now.

Well, yeah. I mean, I don’t even – yeah, I think it’s like three, to be honest. I think it’s the third one. But I’m gonna spoil it real quick, so blow the horn.

Alright, blow the horn.

And Annie, tell me if I shouldn’t spoil this for you if you haven’t seen it. If you’re that concerned about it, okay.

Oh, go for it. I’m not gonna watch it probably.

Yeah, you can’t spoil Trolls Band Together.

Well, maybe…


Well, in there there were two characters that bottled up, literally took a troll - and trolls are known to be musically inclined.


And Justin Timberlake, JT is obviously part of this movie, and he’s a character in there called Branch… And we know JT from N’sync, and then now he’s simply Justin Timberlake, and he’s transcended his original boyband scenario… And N’sync is a part of this movie. It’s really cool. If you’re a fan of N’sync, you should go and get into this. My kids are into N’sync right now, so I can’t help it. I’m a dad. I’ve gotta satiate their curiosities. But anyways, they took one of these trolls and put it into this perfume bottle, and they would spray it onto themselves, and they would now extract the talent from this troll, that could sing. It was part of the in movie N’sync band, could sing all that good stuff, had very good talent… And they were not good. But they sprayed the troll onto them basically through this perfume bottle, stealing the essence, like we just talked about, and now they can sing. It’s the same thing that we’re talking about. It’s literally a version of that in metaphor in movie. It’s the same. It’s like you’re stealing the essence from somebody.

Yeah. AI trolls.

Yes. And I have a couple of comments about this… Because at least when it comes to replacing people, and that’s how technology works - I totally get that. I think that there is something a little more sinister about replacing artists, because of just the nature of art. It is a deeply human act…

Since the beginning of time. Yeah.

Well, art has never been commercially viable in a sustainable way.

Not for many people.

Yeah. So people don’t make art to make money. They make art to make art. And you can’t replace that, and you won’t replace that. But keep going. Sorry.

Well, and so the people who are able to make a living off of it - I cannot tell you how hard those people have worked to get to that point… And to now know that they can easily be replaced is very depressing. So I’ve heard this point a little bit, but not as often as the “Technology just replaces people. That’s the way of the world.”

I’ll also point out that artists – what’s the phrase, “Good artists copy…”

[01:28:07.08] Great artists steal?

Yeah, great artists steal kind of thing, which is very true. But there is a very big difference between artists that borrow from and are inspired by other artists, because they still put in their own creative energy into their work, versus artists who plagiarize. So the major complaint is that AI has created a very easy way of plagiarizing, and to very, very sinister effects in the real world. So…

You don’t believe that prompting an LLM is a skill set? I’m being facetious here when I’m saying this, but…

Yeah, I was gonna say… [laughter]

You don’t believe it takes talent to prompt an LLM?

It’s pretty easy.

I would say no. No, it’s not a skill, especially compared to – I know some people will disagree with me on that… Come at me.

I’m kidding with you. I don’t believe that either. I was joking.

I hear you, I hear you. But there are people who genuinely believe that “Listen, creating a very unique prompt is equivalent to putting in God knows how many hours to get good at a skill, and creating a piece of art from that.” Not even remotely comparable. And the fact that there are people who like to compare those things is laughable to me.

Yeah, it is not the same. At the same time, I’ve got a good friend… I don’t know if he still listens to the show. Jerod, I think you met him at least once, Ben Gillan. Remember Ben Gillan?


He did some work with us at GopherCon a while back. Now, my friend Ben is an artist, and he will create. And I think it’s really interesting watching his particular journey, just from afar. I’m not really even steeped in all of it, but I know that he’s deep in this generative AI art world. And he has done some really, really cool stuff as a result of being an artist, knowing what good art is, and leveraging it to create uniquely better art, that leverages other people’s art, while also being an artist.

And while he may be doing these prompts and conjuring things, and connecting things, and leveraging the latest APIs that might be out there, and whatever it might be, I’ve seen him from afar, and I’ve watched some of the stuff, and it’s really astounding. I’ll link it up in – you could check out his Instagram. And I would say after the show, Annie, go check it out and tweet about it if you like it… Or whatever. I know you do a lot of tweeting, and you share your opinions a lot on there, so I figured if you have post show, not in real-time opinions about our friend Ben, and how he leverages this… I think it’s really interesting.

So that’s why I say it’s challenging, and a really hard problem to solve, because we see loss now… And I don’t discredit, by any means, an artist losing their possibility. What we don’t see is the future. And hindsight is 20/20, and we don’t see the future and what changes as a result. And there’s always pain in change, there’s always discomfort, disruption, displacement even in change… And that is not ever really a good thing to go into as a first person, second person or third person, like to watch somebody go through that. So I’m not discrediting that, by any means. But I’ve seen what Ben has done with some of this stuff, and I know he’s an artist, and I know he’s a very passionate artist. He lives, eats and breathes art in every way he can. And he’s a very creative thinker, and I see what he’s doing with it, and… That’s kind of what gives me a hope, like maybe there’s something happening here… Because I see what an artist has done with the possibility, not just somebody who’s like “Well, I’ve learned how to conjure these things and prompt these things, and there you go.” He’s literally an artist, leveraging his own style, leveraging other people’s styles, and leveraging all this stuff that’s available, and doing some really, really, really cool stuff, honestly. I’ll link him up in our show notes, on Instagram in particular, and I would encourage you to check him out and see what you think.

Yeah, I will. And leveraging is the key word there. And that’s amazing. Leveraging is the key word.

[01:32:01.13] He’s not replacing anybody, that’s for sure. I mean, maybe he is, insofar as that maybe he’s not like “Hey, so and so famous artists, will you collab with me?” It’s maybe an unsolicited/non-solicited, whatever the term is, collab, through the LLM gobbling up their essence, that troll essence out there; just leveraging that essence. That’s why it’s tough.

Well, every podcast…

…does have AI in it. Yes.

…devolves into a conversation about AI. And this was no different.

Should we have a new sound effect for when we begin to talk about AI? Like a digital sound? I don’t know –

A trigger warning.

It’s kind of like a spoiler alert, but it’s like a –

Yeah, it’s like “Here comes the AI.”

Just a warning. Just an alarm bell, like “Oh, here it comes.” It’s hard not to talk about it. It’s perhaps the most disruptive thing in digital workers worlds in the last 20 years… And maybe not, also. It’s strange to have a topic that’s so divisive amongst people of otherwise like minds… There’s very smart people that are completely on the doomer side, and completely on the – what’s the EAAC thing? I don’t know what it’s called anymore. Effective Altruism… Like the altruistic side; the opposite of the doomer side. And they’re brilliant minds, completely disagreeing on where this is headed. And so none of us know where it’s headed. We see of it, we see what it can do now, and we see that at least on the prose and code side has been overhyped to make people believe that it’s better than it actually is… But then also to see in our own lives that it’s still super-valuable in the small ways, or maybe in some big ways.

Certainly, we haven’t been hit as hard as artists have, as software developers… But we’re right on the edge of that, and potentially – it doesn’t have to go very far from where it is to be able to do all the things they’re promising that it can do, like write entire programs, even though it’s not doing that today. That’s the kind of thing where I’m like “Could it get there in three to five years?” I don’t know, maybe it could. At which point you’re just hiring less devs, or you’re just doing more work. I don’t know. So it’s hard to talk about it, because there’s so many facets and opinions, and more questions than answers at this point. But… Hey, ChatGPT, how do you end the podcast?

You ask Annie “What’s left?”

Yeah, what else, Annie?

What’s left, Annie? What have we not talked about, that we can close out this show with, that’s important to you?

I hope to see more people spend time in their craft as engineers, motivated by play. I’ve said it before, but I want to see more of that, and a little less seriousness… Because I think that’s kind of all we have. I don’t know what the future is going to hold with the future of AI, how that’s going to transform the job market… No idea. And what we can do now is enjoy what we have, which - I hope that doesn’t sound too bleak. I hope that sounds optimistic, but I’ve found it to be really transformative. It is what has enabled me to learn even more, and much faster than I have before. And that’s what we need to do, we have to keep learning.

Always good talking to you, Annie. Good to have you back. Glad you’re back to well, glad you have some good discipline in your life to keep you guarded and guided. Very proud of that fact, that you’ve put it down there, you’ve written it, you’re following it, and you’re here on the podcast, sharing it with others too, to be inspired by your guidance for yourself. That’s the good stuff. Alright, bye, friends.

Thank you.


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