Debugging - The Heart of Great Sopher

It's Steph and Chris' last show.

Steph found a game, and if you've been following the journey, all of the Test::Unit test files are now live in RSpec. JWTs really grind Chris' gears.

They wrap up with things they've learned, takeaways they've had, and their proudest podcasting moments. They also thank all the folks who've helped make The Bike Shed happen.

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Microservices

Transcript:

CHRIS: One more round of golden roads, our golden. So here we go.

STEPH: Oh, one more round of golden roads. Okay, maybe that's going to get to me today. [laughs]

CHRIS: [singing] Golden roads take me home to the place.

STEPH: [singing] I belong.

CHRIS: Yeah, there you go.

Hello and welcome to another episode of The Bike Shed, a weekly podcast from your friends at thoughtbot about developing great software. I'm Chris Toomey.

STEPH: And I'm Steph Viccari.

CHRIS: And together we're here to share a bit of what we've learned along the way, at least one more time. So with that [chuckles] as an intro, Steph, what would you say is new in your world?

STEPH: Hey, Chris. Well, today is the big day. It is the day that you and I are recording our final Bike Shed episode, which we have all the feels about, and we will definitely dive into. But to ignore some of that for now, I have another small fun update I can provide about a new game that I found. So one of the things that's new in my world is I started playing a new board game with Tim; it's called Ticket to Ride. Have you heard of that?

CHRIS: I have. I don't know if I've played it. I feel like it's a particularly popular one now. But I don't know if I've ever had the pleasure.

STEPH: It's a very cute game, so we have the smaller version of it. For anyone that's not familiar, it's essentially a map. And then there's a bunch of spots where you can build trains and connect them, and then you get tickets. So your goal is that you're going to connect one location to another location. And then you get points and yada yada, but it's so much fun and especially the two-player version. It's like this perfect 20, maybe 30-minute game.

I'll be honest; I'm not really a board game person. I always enjoy it. Once I get into it, then I'm like, this is great. I don't know why I was resistant to this. But every time someone's like, "Do you want to play a board game?" I'm like, "Not really." [laughs] I first have to get into it. But I have really enjoyed Ticket to Ride. That's been a really fun game to play. And it's been a nice way to, like, even during the day, we'll break for lunch and squeeze in a game.

CHRIS: Well, I love good two-player games. They're hard to find. But when you find a good one, and it's got that easy pickup and play...I believe I'm going to now purchase this. And thank you for the tip.

STEPH: Yeah, this is definitely one of those where it's easy to pick up, and then you can get the expanded board. So there's a two-player version, but then yeah, you can get one that's a map of the U.S. or a map of Europe. And I think it accommodates up to five players as the maximum, so not a huge group but definitely more than two.

On a slightly more technical note, I have something that I'm very excited to share. It is a journey that you have been on with me, that everybody listening has been on this journey with me. And I'm very excited. I see you nodding your head, so I'm guessing that you're going to know where I'm headed with this. But I'm very excited to announce that all of the Test::Unit test files now live in RSpec. So that is a big win.

I'm very, very excited for that to be a previous state of life and not an ongoing state of life. Because I have certainly developed too much niche knowledge around migrating these tests, and that became apparent to me when I was pairing with another developer that works with the client because they had offered...they had some time. They're like, "Hey, do you want help migrating a test file?" And I was like, "Sure." I was like, "But this is wonky enough, like, we should pair and work on this together because I just know some ins and outs. And I don't want you to have to learn a lot of the hard lessons that I've learned."

And the test that we happened to pick up was very gnarly. It had a lot of mystery guests. And we spent, I think it was a good two hours. And we only migrated one of the tests, so not even a full file but one of the tests. And at the end of it, I was like, I know way too much about some of the oddities and quirkiness of this. And we got through it, but we decided that wasn't a good use of their time for them to go at this alone. So that's why I'm extra excited and relieved because I didn't want this task to carry on to someone else. So, hooray, we did it.

CHRIS: Hooray. Just in time. You're Indiana Jones grabbing your hat right as you roll out and off to [laughs] be away from the project for a bit. So you stuck the landing. Well done, Steph.

STEPH: Thank you. Thank you. So that's some great news. And then also, everything else in life is pretty much focused around getting ready for maternity leave. That's about to happen soon, and I am so ready. I have thoroughly enjoyed a lot of the things that I'm doing, [laughs] but goodness, being pregnant is hard. And I am very much ready for that leave.

So also, a lot of the things that I'm doing right now are very focused on making sure everything's transitioned and communicated and that I just feel really good about that day of departure. That covers all the newness in my world other than the big thing that we're just not talking about yet. How about you? What's new in your world?

CHRIS: Well, continuing to skirt the bigger topic that we will certainly get to in the episode, what is new in my world? I'm actually quite excited workwise right now. We have a much larger body of work that finally we got the clarity. All the pieces fell into place, and now we're sort of everybody rowing in the same direction. There's interesting, I think, really impactful code that we're writing for Sagewell right now. So that's really fantastic. We've got the whole team back together on the engineering side. And so we're, I think, in the strongest and most interesting point that I have experienced thus far. So that's all really fantastic.

On a slight technical deep dive, you know what really grinds my gears? It's JWTs. JSON Web Tokens and I have never gotten along. It's never been a match made in heaven. And we have a webhook that comes from Plaid. Plaid is a vendor for connecting bank accounts and whatnot. And they have webhooks like many people do. So they can inform us when things change, lovely feature of how we build web apps these days. But often, there's a signature that says, "This is definitively from us, and you can trust us." And usually, it's some calculated signature, HMAC, or something like that.

For some reason, Plaid's uses JWTs, and more than that, they use JWKs. So there's JWT which is the signature. That JWT itself is signed with a JWK. You have to fetch the JWK from their server based on the key ID in the header of the JWT. But how do you know if you can trust the JWT before you've gotten the JWK? All of this broke in a recent upgrade.

We went from Heroku-20 to Heroku-22 to the new platform with Heroku, which bumped us to OpenSSL 3.0, and it turns out JWT doesn't work with it. And so that's sad. It's a no. It's going to be a no. It turns out the way that OpenSSL 3.0 works is incompatible with some of the code paths in JWT. And so I was like, wait, we just can't do this? And it's low-level cryptographic primitive stuff that I'm not comfortable messing around with. I'm not going to hop in there and roll up my sleeves.

And even just getting to the point that I understood what was broken about this took like an hour and a half just to sort of like, wait, which is okay...so the JWT signs and encodes. And this will be a theme that we come back to later, but I think web development should be simpler. I think we should strive for simplicity. And this is a perfect example where I'm guessing Plaid uses JWTs and that approach to communicating security things often, but I've not seen it used much for signing webhooks. And, oof, it led to a complicated day. And it's unfixable now as far as I can tell.

There is a commit on the JWT Ruby repo as of five days ago, but it doesn't build in our system. And it's not released. And it's just a mess. So yeah, engineering is complicated. I'm both wildly excited about what we're doing at Sagewell, and then today was this local minimum of like, oh, JWTs again. Again, we find ourselves battling. And you won today, but hopefully not for too long.

STEPH: Oof, how did this manifest that you first noticed? So is it because a webhook suddenly stopped working, and that was like the error that rose up, and that's what helped you dive into it?

CHRIS: Yeah, we have a little bit of code in the controller for where Plaid events come in. We calculate and verify the signature of the webhook to make sure that it's valid, and we reject it otherwise. And we alert ourselves via Sentry, and then we also have a Datadog scan that can show what's the status code of the response. Because these are incoming HTTP payloads or requests, and so we can see there were 200 up until this magical day when suddenly everything changed. And that was when we switched Heroku stacks.

And then we can see it also in Sentry. So we're able to look at it, and we're like, why are none of the Plaid webhooks able to verify the signature anymore? That seems weird. And so then Datadog confirmed that it consistently was broken from this point in time. And then we were able to track that back. It was also pretty easy to guess because the error was "pkeys are immutable in OpenSSL 3.0," and that was the data. And I was like, oh, cool, that sounds fun. Let me go figure out what that means.

STEPH: [laughs] Well, it's a nice use of Datadog. I remember in the past you were talking about adding it. And I was excited because I've never been at that point where a team has just introduced it; either a team doesn't have it, and they wish they had more insights, or they have it and don't use it. And nobody ever checks the board. So that's a nice anecdote for Datadog helping you out. Yeah, I'm not envious of your situation, friend.

CHRIS: I do love the cup half full take [laughs] that you have on the overall situation, but that's nice how Datadog worked out for you. And you know what? It was. Thank you, Steph, for once again being that voice of positivity.

STEPH: I appreciate that you enjoy it because there are times that when someone points it out to me that I do that, I have to be like, "I'm sorry, I'm not trying to be toxic positivity over here. [chuckles] That's just how my brain works."

CHRIS: Oh, you are definitively not toxic positivity. That's a different thing. Because you ended with but also, I feel bad for you, and I'm glad that I'm not in your shoes. So you are the right level of positivity. I don't think I could have talked to you for three and a half years as co-host on a podcast if I didn't appreciate the level of positivity or the general approach that you bring to thinking about stuff.

STEPH: Okay. Well, to borrow a phrase from Matt Sumner, who has been a guest on the show, cool, cool, cool, cool. I'm glad my positivity has been well calibrated. And I was about to say I'm interested to hear how this turns out for the team. [laughs] But we're in an awkward spot where I mean, you and I, we can still totally chat. But listeners won't get to hear the rest of that particular saga. I mean, you can share. I mean, you do you. I'm setting all sorts of boundaries for you right now.

Okay. And now I'm just rambling, and I'm getting weird with it. Because the truth is that, you know, we won't be back. And this is our final episode together. So I think let's just go ahead and rip off the Band-Aid. Let's dive into it. Let's talk about it. Given that it's our last episode that we are recording, we thought of a couple of things that we'd like to talk about. You brought up a great idea that I'm excited to dive into. Do you want to lead us in?

CHRIS: Sure. Well, if we go back all the way to Episode 172, that is the first episode that you came on as a guest. I actually continue to really love the title of that episode, which is What I Believe About Software. And it both captured that conversation really well, but also, more generally, it's actually become the tagline of the show when we do our little introduction. What do we believe about building great software? Et cetera.

And I think that's been the throughline of the conversations that we've had is what remains true. What are the themes? Not necessarily the specific technologies, although we certainly talk about that. But what do we believe about building great software? And so today, I thought it would be fun for us to talk about what do we still believe about building great software? It's roughly three and a half years or so that we've been doing this. What's still true?

STEPH: Oh, well, I have the first unequivocal one, the thing that I still believe about building great software, and that's you should hire thoughtbot. That's definitely the way to go. We'll help you get it done, not that I'm biased in any way.

CHRIS: No. I'd say collectively between us; there's zero bias with regard to thoughtbot or any other web development shop out there. But thoughtbot is the best.

STEPH: All right, perfect. So we've got the first one, the clutch one of hire thoughtbot. And then I also really like this topic. And I still think back to that first episode that I recorded with you and how much fun that was and how that really got me to start thinking about this. Because it was something that, at the time, I didn't really reflect on a lot in terms of what does it take to build great software? I was often just doing the day-to-day actions but then not really going high-level think about it. So I'm excited this is one of the topics that we're revisiting.

So for the next one, this one is, I don't know, maybe it's a little cutesy, but I was trying to think of an alliteration that I enjoyed. And so this one is be an assumption assassin. So what assumptions are you making? And then how can you validate or disprove them? And that is something that I find myself doing constantly. And it always yields better work, better questions, better software, better code, better code reviews. And that's my first one is be an assumption assassin and identify what assumptions you have.

And I had a really good example come up today while I was having a conversation with Joël about something that I was looking to merge. But I was a little hesitant about it because there are some oddities that I won't dig in too deeply. But essentially, there's a test that I migrated that highlights an existing concern in the code. And I was like, should I go ahead and merge this test that documents it, or should I wait to fix that concern and address it?

And he brought up a good point. And he's like, "Well, we're assuming it's a bug and an issue, but it may not actually be depending on how the software is being used." And so then he was encouraging me to reevaluate that assumption that I had where I'm like, oh, this is definitely a problem to, like, I don't know, is it a problem? Let's ask somebody.

CHRIS: First off, I love that as a theme, as one of the things that you still believe about software. Second, I believe you correctly said that you were looking for an alliteration, but my brain heard acronym.

STEPH: [laughs]

CHRIS: And so then I was like, B-A-A-A. Is it BAAA? What are you going for there? Oh, you just wanted a bunch of As. Okay, I got it now. Secondly or thirdly, I think I'm on my third now. Apparently, within Sagewell team culture, one of the things that I'm most known for is... there are two phrases: one is just to name it, and the other is to be clear. And these are the two things that I do apparently constantly so much that it's become a meme within the team.

It's just like, okay, everybody's been talking. But I just want to make sure we're on the same page here. So just to be clear, or just to name it, here's what I'm seeing. But I agree; I think taking those things...what are the implicit bits? What are the assumptions? And making them more explicit. Our job as developers is just to yell at computers all the time and make them try and do human stuff. And there's so much room for lossy conversions at every point in that conversation chain. And so yeah, being very clear, getting rid of assumptions, love it. It's all great stuff.

Actually, in a very related note, the first on my list is that code is for humans to read. This is one of the things that I believe most deeply and most impacts the way that I write software. Any given piece of functionality that we want to author in our code feels like 10, 20, 50, frankly, almost infinite different versions of the code that would produce nearly identical functionality. So at the end of the day, the actual symbols and strings of text that we bring together to write the code is all about other humans, other people on your team, you five months from now, you a week from now, frankly, or me. I'm going to say me, me a week from now.

I want to do future me and everyone else on the team a solid and spend that extra 10% of okay, I have something that works now, but let me try and push it around and try and massage it into a shape that is a little more representative of how we're actually thinking about the code, how we talk about it as an organization. Is that the word that we use to describe that domain concept? Maybe we could change that just a little bit. Can I push more of this into the private API? What actually needs to be known here?

And I think that's where I'm happiest is in those moments because that's where all of the parts of the job come together, the bit where I trick a computer into doing what I want and simultaneously making it so that that code is revisitable, clear, expressive, all of those things. So yeah, code is for humans. And that's true across every language, and framework, and domain that I have worked in. And I've only believed it more and more so over time. So yeah, that's mine.

STEPH: Yeah, I love that one. That's one of the things that comes to mind when people talk about disliking code reviews. And I can imagine there are a number of reasons that people may have had a poor experience with a code review process. But at the end of the day, if you're not getting that feedback or validation from fellow humans, then how do you know that you've been successful, that you've written something that other people can follow up on? Which goes back to the assumptions in terms of like, you're assuming that you have written something that your future self or that other people are going to be able to read and maintain down the road. So yeah, I love that one.

One of the other things that I still hold really true to building great software is prioritize early and often. So always be checking in to understand with your users, with your tech concerns, with data that you may have, new insights, and then just confirm that yes, you and the team are constantly working on the thing that has been prioritized and that is the most important.

And also, be ready to let go. That can be really hard. I have definitely had those moments in my career where I've spent two weeks working really hard on something. And then we've realized that the thing that we were pursuing isn't that valuable, or it's something that users don't need or actually want. And so it was better to let go of it than to pursue it and ship it anyways. So that's one of my other mantras that I have adopted now is prioritize, prioritize, prioritize.

CHRIS: Unsurprisingly, I agree wholeheartedly with all of that. We're still searching for that thing, that core thing that we disagree on other than Pop-Tarts and IPAs. But I don't know that today is the episode that we're actually going to find that. But yeah, prioritizing is such a critical activity. And it is this interesting collaboration point. It gets different groups together. It's this trade-off. It's this balance. And it's a way to focus on and make explicit the choices that we're making. And we're always making choices. We're always making trade-offs. And so being more explicit, being more connected and collaborative around those I believe in so, so, so much. So love that that was something on your list.

Let's see, next up on my list is reduce complexity, just sort of as an adage, just always be reducing complexity. It is amazing to me in my time, particularly as a consultant, but even now, this is something that I hold very true is just it's so easy to grow a system in anticipation of future complexity or imagine that the performance concerns that we're going to run into will be so large that we must switch from Postgres and a nice, simple atomic database into a sharded, clustered Kafka queue adventure. And there are absolutely cases that make sense for that sort of thing.

But at a minimum, I beg of you, anyone starting a new system, don't start with microservices. Don't start with an event queue-based system. These are wildly complex versions of what often can be done with so much simpler of an application. And this scales through to everything. What's the complexity of an API? Do we need caching in that API layer? Or can we just be a little bit inefficient for a little while and avoid the complexity and the overhead of caching?

Turns out caching is a tricky thing to get right, just as an aside. And so the idea of like, oh, let's just sprinkle in a little bit of caching. It'll be easy, and then we'll get better performance, like, yeah, but did you get it right? Or did you introduce a subtle bug into your program that's going to be really hard to debug later? Because do you cache in development? Well, maybe, I'm not sure, could be.

So over time, this is something that I've sort of always felt, but I've only ratcheted it up. It's only something that I've come to believe in more and to hold more firmly to. I think earlier in my career, it was something that I felt, but I would more easily be swayed by aspirational ideas of the staggering amounts of traffic that we would be getting soon or the nine different ways that the data model will expand. And so, we should code the current version in anticipation of that. And I have become somewhat the old man on his lawn yelling at the clouds like, "Nah, we don't need it yet. We can grow to that."

And there's a certain category of things that are useful to try and get out in front of and don't introduce additional complexity, but they're a tiny, tiny list. And so, for most things, my stance is what's the simplest thing that we can get away with right now, that still provides a meaningful experience to our users, that doesn't compromise on security or robustness or correctness but just solves the problem we have right now? And over and over and over again, that has served me incredibly well. So yeah, keep that complexity at bay.

STEPH: That is one that I've definitely struggled with. And frankly, it works in my favor, that idea of keeping things simple. Because I'm terrible when it comes to predicting the future or trying to build things in a way that I just don't have enough information to really drive the architecture or the application that I'm building. So anytime I'm trying to then stretch and reach for the future in those ways unless I really have a concrete understanding of I am building for these particular scenarios, it's really hard to do. So I very much like keeping it simple and not optimizing before you need to.

And it reminds me of I think it's Mark Twain, who has a quote, "Worrying is like paying a debt that you don't owe." And that's something that comes to mind for me when also writing code and building features and software is that I tend to be someone who will worry about stuff. And I'm like, oh, is this going to be easy to extend? Is it going to be what it needs to be six months from now if we need to add more features to this and build on top of it? And I have to remind myself it's like, well, let's just wait. Let's wait till we get there and we know more.

One of my other ideas that couples nicely with the one that you just shared in regards to keeping things simple and then waiting for those needs to arise is that mistakes are going to happen. They are a part of the process. As we are learning and growing and we're stretching our skills and trying things out, things are going to go wrong. We're going to introduce bugs. And to take those opportunities, that's when we start to use that feedback to then improve things like observability, like capturing logs, and how we handle error reporting or having a plan for emergencies.

So maybe that's the part of worrying that can pay off is thinking through, all right, if something does break, or if something gets shipped that shouldn't, then what is our plan in how we handle that? How do we roll back? Or how do we get things back to a stable build?

CHRIS: It's funny. I was actually visiting with a friend this past weekend, and we were chatting more generally about life things but the idea of worrying and anticipation and trying to prepare for every bad outcome. And there's the adage of an ounce of prevention is worth a pound of cure. But increasingly, both in life, depending on the context, and in code, I've found that I've shifted to the opposite of it's impossible to stop everything.

There are going to be bugs that are going to get out there. There are going to be places where we code things incorrectly. And I would rather...I still want to try as hard as I can to get things right, to be clear. I'm not giving up on trying. But I'm all the more focused on how do we know and how do we recover when those things happen? So it's interesting that you just described exactly that, which, again, is a very human life conversation, and yet it applies to the code.

STEPH: I love that rephrasing of it. Instead of the mistakes are going to happen, it's, like, how do we know, and how do we recover? I think that's perfect. I've also found that by answering the how do we know and how do we recover, that really helps you build trust with clients as well. Because again, things are going to happen, things are going to break.

And the more prepared you are for that and then the better plan that you have, and then they can watch how you execute that plan, and it’s going to establish a lot of deep trust with other engineers and also the team that you're working with, that you have been thoughtful and that you have ideas on how are we going to address this? Instead of waiting for that moment to happen.

That's going to happen too. You're going to make decisions in the heat of the moment. But I have found that to be a really useful way to establish yourself with a team in terms of I care about this team and these processes and this application. So how do we handle the bad times, not just the good times?

I do want to circle back because you alluded to the fact that you and I, we've tried to find things that we disagree on. And so far, Pop-Tarts and beer have been the two things that we disagree on. But I do have a question for you that maybe I will disagree with you on. But I need to know some more about it first.

You have alluded to there's the Brussels snack, (Oh, I'm going to get this wrong.) Brussels sprout snack hour or working lunch, something combination of those words. [laughs] And it's the working lunch that has stuck out to me, and I've wanted to ask you about it. So here I am. I'm asking you about it. What's a working lunch? What's the Brussels snack happy hour, snackariffic working lunch look like?

CHRIS: This is fantastic. I love that you waited until the last episode that this was rolling around in the back of your head. And you're like, are you making the team work through lunch? And now, on this final episode, we get to address the controversy that has been brewing in the back of your head. Spoiler alert, no, this is just ridiculous nomenclature. These are two meetings that we have that are more like, let's get the dev team together and talk about stuff that's in our platform sort of developer experience. Or stuff in observability often is talked about in this context because it doesn't quite impact users, but it's how we think about the work.

And so there are two different meetings that alternate every other week. So every Friday afternoon, we do this, but it's one of two meetings depending on the day. So there's a crispy Brussels snack hour that was the first one that was named, which was named purely for nonsense reasons because we don't have anything else that's named nonsensically in our organization.

And so I was like, oh when we name this meeting, we should make it nonsense because we don't have any other...We don't have, you know, an SOA microservices fleet with Barbie doll and Galactus and all of the other wonderful names. Those are references to the greatest video ever about microservices; if you've not seen it, that will be in the show notes. It's required reading.

But anyway, we don't have that. And so we thought, let's be funny with the name of this. So the crispy Brussels snack hour is one, and the crispy Brussels we wanted something that was...the first one is a planning meeting. The second is like, let's actually sort of ensemble program. Let's get the four of us together, and we'll work on some of the stuff that we're talking about here but as a group. And so I wanted the idea of we're working, and so I was like, oh, this will be the crispy Brussels work lunch. But it's purely a name. It's the same time slot. It's 3:00 o'clock on a Friday afternoon. [laughs]

So it is not at all us working through lunch. I don't think we should work through lunch. I'm concerned that you thought that for a while, and you were just like, I'm a little worried, but I'm not going to bring it up. But I'm glad we got to cover this before we wrapped up this whole Bike Shed co-hosting adventure together.

STEPH: I feel relieved and also a little robbed of an opportunity for us to have something that we disagree on because I thought this might be a thing. [laughs]

CHRIS: We can continue searching for that thing. But maybe it's okay that we agreed on most stuff for the run [laughs] of this fun, little show that we did together.

STEPH: Yeah, that's gone on quite a time. We've got like three years together that we have managed to really only find two, I mean, very important of course, two things. But yeah, it's been pretty limited to those two areas. And each time that you'd mentioned the work lunch, I was like, huh, I need to ask about that because I have feelings about it. But then, you always would dive into very interesting stories of things that came out of it, and I quickly forgot about it.

So this feels good. This feels like very good important closure. I'm glad that this finally surfaced. But circling back, since I took us on a detour for a little bit, what are some other things that you still hold deeply about building great software?

CHRIS: I've really got one last thing on the list. It's interesting, there's not a ton technically in this list, which I think represents broadly how I feel about software, and I think how you feel about software. It’s like, it's actually mostly about how the people interact at the end of the day. And you can program in any language or framework, and you can get the job done. We certainly have our preferences and things that we enjoy.

But the last one really rounds us out, which is think about the users. I always want to be anchoring the conversations that we're having, the approach that we're taking to building the software in what do the users think? Who are our users? What do we know about them? What do they care about? How are they using this technology? How is it impacting their lives? We've talked a number of times about potentially actually watching the sales demo as an engineering team, trying to understand what's the messaging that we're putting out into the world for this piece of software that we're building?

Or write along with customer support and understand what are the pain points that people are hitting? And really, like, real humans, what are they experiencing? Potentially with a name attached. And that just changes the way that you think about the software. There's also even the lower-level version of it. As we're building classes or modules, what are the public facets of that, and what are the private API? What's the stuff that we're hiding away? And what's the shape that we are exposing to the outside world for varying definitions of outside?

And how can we just bring in a little bit of empathy to try and think about, again, in the case of like the API for a class, it's probably you on the other side of it, but it's future you in a slightly different mindset with a little bit less information and context on the current problem that you're working on. And so, how can we make things easier for ourselves in the code, for our users at the end of the day?

How can we deliver real value that is not mired in the minutiae of technical complexity and whatnot but really is trying to help people live better lives? That's a little too fancy as I say it out loud. But it is kind of the core of what I believe, so I'm not going to take it back.

STEPH: I love how you've expanded users where more traditionally, it's people that are then using the software. But then you've expanded it to include developers because that is something that is often on my mind and something that I just agree with wholeheartedly in terms of when you're writing software; as you mentioned before, software is for people. And so we want to include others.

And it does improve people's lives. People show up to work every day, and if you've been thoughtful if your past you has been thoughtful, it's either going to give you your future self a better day, or it's going to give other people a better day. So I think that's a very fair statement, improving lives by being thoughtful in regards to focusing on the users, people consuming software, and working in the codebase.

CHRIS: I know we've talked about this before, but I was having a conversation with one of the developers on the team at Sagewell just last week, and they were mentioning how they really loved working on admin features. And I was like, oh, that's interesting. Let's talk more about that. And it was really it's that same thing that I think you and I have discussed of like there's that immediacy. There's that connection. These are actually colleagues, but you can build software to make their day better. You can understand in detail what the pain points are.

What's the workflow that as you watch it, you're like, oh, I could put a button up in the corner of the screen that would automate almost all of this and your day would be that much faster? Oh, let me do that. That's exciting. And so I love that as another variation of it, like, yeah, there's for other developers. There's also for the admin team or other users in the organization of the software. There are so many different versions of users, but I think I think we build a better thing if we think about them more.

STEPH: I have definitely worked with teams where I can tell that certain people are demoralized, and it comes down to they feel frustrated and often disconnected from the people that they are building for. And so then you really feel isolated. I'm pushing code around, but I don't really see the benefit or the purpose of it. And I think that's very hard for developers who typically want to build something that's going to be useful and not feel like it's just going to be thrown away. So connecting your team to those users, I certainly understand. Getting to build something for your colleagues and then they get to say how much they like it is an incredible, rewarding experience.

You also touched on something that I really appreciate, where you highlighted that a lot of the technical decisions that we make are important, but they're not at the center of the things that we believe when it comes to building great software. And that's something that I will often reflect on. Like, as we were thinking through these particular ideas that we still hold true today, how mine are more people and process-focused and rarely deep in the technical weeds. And there are times that I think, well, shouldn't there be something that's more technical, something that's very concrete? Yes, you should build your code this way or build your application or use a specific technology.

But after all the projects and teams that I've been a part of, that's just usually not the most important part. And so I appreciate that you highlighted that because sometimes I have to remind myself that, yes, those things can be challenging, but it's often with people and process. That's where the heart of great software lies.

CHRIS: That's a fantastic phrase, I think, that really encapsulates all of the conversations that we're having here.

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CHRIS: Actually shifting gears a little bit, so we've just talked about what we still believe about building great software. I'm intrigued. We've been chatting for a number of years here on this microphone, these microphones. We have separate ones because we're in different states. But I'm interested; what have we changed our minds about? What have you changed your mind about, Steph? I got a couple of ideas, but I'm intrigued to hear yours.

STEPH: Nothing. I've never been wrong. I've stuck to everything that I've ever thought.

CHRIS: That must be boring.

STEPH: [laughs] Yeah, that's totally not true there. There are definitely things that I've changed my mind about. One of the things that I've changed my mind about is that people who know the most will ask the fewest questions. That's something that I used to consider the trademark of someone who is a more experienced senior developer in terms of you really know what you're doing. And so you typically don't ask for help or need help very often. And so, I'm going way back in terms of things that I have changed my mind about.

But I have definitely changed my mind where people who know the most are actually the ones that do a really great job of constantly asking questions and asking for feedback. And I think that is still a misconception that people still carry forward. The idea that if you're asking a lot of questions or asking for help that you are not as skilled in your work, and I view it as quite the opposite, that you are very good at what you do and that you know precisely the value of your time.

And then also reaching out to others for help, and then also just getting validation on things that you may have concerns around. So that's one I've changed my mind on is that I think the more experienced you are, the more questions you tend to ask.

CHRIS: Oh, I love that one. It's a behavior that I know...I think we've talked about this before. But as consultants, we try and model it just the like; it's totally fine to ask questions. And because we often come in with less context, it makes sense for us to be asking questions, but I will definitely intentionally lean into it in those contexts to be like, everybody keeps throwing around this acronym. I don't actually know what that is. Let me raise my hand.

And my favorite moment is when people disagree on what the acronym or what the particular word or what the particular project is. Like, I ask the question, and people are like, "Oh, it's this," and someone across the room is like, "Wait, that's what it means? I thought it was this totally other thing." I'm like, cool, glad that we sorted that out. Glad that we got that one up in the air.

But I actually remember many, many, many years ago, at this point, there was a video series of...PeepCode was the company, and there was the Play by Play series. And so there were particular prominent developers, particularly in the Ruby community. And they would come and sort of be interviewed and pair program. And it was amazing getting to watch these big names that you had heard of, like Yehuda Katz is the one that stands out in my mind. He was one of the authors of merb, which was a framework that was merged with Rails, I want to say around the 3.0 time.

And just an absolute, very big name in this world and someone that I looked up to and respected. And watching this video, they had to Google for particular API signatures and Rails methods. They were like, "Oh, how does that work? Is it link to and then you pass the name?" I forget what it was specifically. But it was just this very human normalizing moment of this person who has demonstrably done incredible work in our community and produced very complex software still needs to Google for the order of arguments to a particular method within Rails. I was like, oh, okay, that's good to know.

And with complete humility in the moment, I was just like, yeah, this is normal. Like, it's impossible to hold all of that in your head. And seeing that early on shook me off the idea that that's the thing to do is just memorize everything. It's like no, no, get good at asking the questions. Get good at debugging. Get good, yeah, asking questions. It's a core skill rather than a thing that you grow out of. But I definitely shared early on I was like, not allowed to ask questions, that'll be scary.

STEPH: I love that example. Because counterintuitively, to me, it demonstrates confidence when someone can say, "Oh, I don't remember how this works," or "Let me go look it up." And so I just very much appreciate when I see someone demonstrating that level of confidence of let's keep going. Let's keep making progress. I'm going to ask for help because that is totally fine, and we are in a safe space. Or I'm going to create a safe space for us to do that.

One of my favorite versions of this where you shared like if you ask about an acronym and then people disagree, one of my favorite versions is to ask about a particular area of the codebase and be like, what would you say this code is doing here? What do you think users do here? Like, what is the purpose? What's the point of this? [chuckles] And then having people be able to say, "Oh, yeah, this definitively does this thing." Or people are like, "You know, I'm not sure. I don't even know if that code is getting run." That's one of my favorite outcomes of asking questions. How about you? What's something you've changed your mind about?

CHRIS: I made a list of a couple of things like remote is on there. I didn't know if I'd like remote. I wanted to try it for a while. Tried it, turns out I like it a lot. It's complex. You got to manage it, whatever. But that I think everybody's talked about that a bunch.

I think probably the most interesting one is deadlines. Initially, in my career, I didn't really feel anything about them. And then I experienced the badness of deadlines. Deadlines are bad. Deadlines are things that come down from on high and then you fail to hit them, and then you're sad. And maybe along the way, you're very stressed and work long hours to try and get there. But they're perhaps arbitrary. And what do they even mean? And also, we have this fixed scope, and they're just bad. And then there was a period of my time where, like, deadlines are bad. The only thing that we do is we show up, and we make the software as quickly as we can.

But in reality, there are times that we need that constraint. And in fact, I have found a ton of value in deadlines when used intentionally. So we can draw a line in the sand, and we can say, at this point in time, we will have a version of the software. We have a marketing campaign that we need to align with this. So we got to have something at that point. And critically, if you're going to have a deadline, you've now fixed a point in time. You need to flex other things.

And critically, I think the thing to flex is the scope. So we need to have team management. We have user accounts right now, but now we need to organize them into teams. That is like a category of functionality. It's not a singular feature. And so yeah, we can ship teams in the next quarter. What exactly that means is up in the air.

And as long as we're able to have conversations essentially on a day-to-day at least weekly cadence as to what will make it in by that deadline and what won't, and we're able to have sometimes the hardest conversations but the very necessary conversations of the trade-offs that we have to make as we're building that software, then I find deadlines are absolutely fantastic tools for focusing and for actually reducing scope but in a really useful way.

And getting something out there in the hands of users so that you start to get real feedback so that you start to learn, is this useful? What are the ways that people are using this? What should we lean into and do more of? What maybe should we roll back, actually? So yeah, deadlines. First, I didn't know them, then I feared them. Now I love them but only under the right circumstances. It's a double-edged sword, definitely.

STEPH: I, too, have felt the terribleness of deadlines and railed against them pretty hard because I had gone through a negative experience with them but have also shifted my feelings about them where they can be incredibly useful. So I really liked that's one of the things that you've changed your mind about.

It also reminds me of one of the other things...I'm going to circle back for a moment to one of the things that I believe about creating great software is to not wait for perfection, and deadlines are a really good tool that helps you not wait for perfection. Because I have also seen teams really struggle or sometimes fail because they waited until there was something perfect to present, and then you realize that you've built the wrong thing.

So I do want to transition and talk a bit about the show because it's our last episode, and we should talk about it, and the fun adventures that we've had and some of the things that we've learned or things that we're feeling in the moment. So given that it's been a wonderful three years for me, it's been four years for you since you've been a host on the show. How are you feeling?

CHRIS: I'm feeling a bunch of different things sort of all at once. I am definitely going to miss this immensely. Particularly, I loved when I started, and I got to interview a bunch of thoughtboters and other people from the community. But frankly, three-plus years of getting to chat with you has been just such a delight. There's been an ease to it. We kind of just show up and talk about what we're doing. And yet there are these themes that have run through it. And it has definitely helped me hone and shape my thinking and my ability to communicate about what I'm thinking.

I've learned that you have a literal superpower to remember the last thing that you were talking about. Listeners, you may not know this, but we are not quite the put-together folks that we may sound like in these recordings. We have a wonderful editor, Mandy Moore, who makes us sound so much better than we are. But we'll often pause and stop and then discuss what we want to talk about next. And Steph always knows the exact phrase that she or I left off on. And it has been so valuable to the team.

But really, it's been just such a pleasure getting to have these conversations. It's also been something that has just gently been in the back of my mind at all times. And so, I'm observing the work in any given week as I'm doing it. It's almost like meditation in a certain way, whereas I'm working on something, like, oh, this is actually really cool. I want to take a note about this and talk about it on The Bike Shed with Steph.

And having this outlet, having this platform to be able to have those conversations and knowing that there are people out there is fantastic, although it's very weird because really, every one of these recordings is just you and I on a video call. And so there is an audience, I'm pretty sure. I think people listen to the show; I don't know, occasionally they write in, so it seems like they do. But at the end of the day, this really just feels like a conversation with a friend, and that has been so valuable to have. And yeah, I'm definitely going to miss that.

It's been a wonderful run, you know, four years is a long time. It's about as long as I've done most things in my career. And so I'm very happy with what we have done here. And there's a trite saying that isn't...yeah, whatever; I'll just say it, which is, "Don't be sad that it's over. Be glad that it happened." And I guess I'm still going to be sad that it's over. But I am so glad that I got the opportunity to do this, that you joined in this adventure and that we got to chat each week. It's been really delightful.

STEPH: I really liked how you refer to this as being a meditative state. And that is something that I have certainly picked up from you and thoroughly enjoyed that I have this space that I get to show up and bring these ideas and topics and then get to talk them out with you. And that has been such a nice way to either end the week or start a week. I mean, it doesn't matter. Anytime that we record, it's this very nice moment of the week where we get to come together and talk through some of the difficulties and share our stories.

And that's been one of my favorite moments is because you and I get to show up and share everything that's going on. But then when someone writes into the show or if they send a tweet or something and they share their story or their version of something that happened, or if they said that we made them laugh, that was one of my favorite accomplishments is the idea that something that we have done was silly enough or fun enough that it has brought them joy and made them laugh. So I, too, I'm very, very much going to miss this. It has been a wonderful adventure.

And I thank you for encouraging me to come on this adventure because I was quite nervous in the beginning. And this has definitely been an aspect of my life that started out as something that was very challenging and stretching my limits, and now it has become this very fun aspect and something that I get to show up and do and then get to share with everyone. And I do feel very proud of it, very much in part to Thom Obarski, who was our initial producer and helped us have that safe space to chat about things. And now Mandy, who keeps the show running smoothly and helps us sound our best week to week.

So it's been a wonderful adventure. This is going to be hard to let go. And I think it's going to hit me most. Like, this was one of those things as we're talking about it, it's, like, I'll see you next week. This will be fine. But I think it's going to hit me when there's something that I want to talk about where I'm like, oh, this would be great to talk about, and I'll add it to The Bike Shed Trello board. And I'll be like, oh yeah, that's not a thing anymore, at least not quite in the same way that it was.

CHRIS: So what I'm taking away from this is that you're immediately going to delete my phone number the minute we hang up this call and stop recording. [laughs]

STEPH: Oh yeah. I preemptively deleted. So that's already done. Friendship is over at this point.

CHRIS: That's smart. Yeah, because you might forget otherwise in the heat of the moment as we're wrapping this whole thing up.

STEPH: [laughs]

CHRIS: But actually, on that note, in a slightly more serious vein, again, there's this weird aspect where the audience is out there. But we're very sort of disconnected, particularly at the moment in time where we're recording. But it has been so wonderful getting various notes from listeners, listener questions, but also just commentary and the occasional thanks and focusing; oh, you pointed me in the direction, or you helped me think through a complicated piece of work or process a problem that we were having. And so that has been just so, so rewarding.

And one of the facets of this that has been so interesting to me is being able to connect to people and basically put out there what we believe about software, and for the folks that resonate with it and be able to have that connection instantly. And meeting people, and they're like, "Oh, I've listened to The Bike Shed. I like all these things." I'm like, oh, cool, we get to skip way further into the conversation because I've already said a bunch, and you say you like that thing. So, cool, we're halfway through our introductory chat.

And I know that we agree about a bunch of things, and that's really wonderful. And frankly, I'm going to miss that immensely. So for anyone out there who's found something valuable in this, who's enjoyed listening week to week, or perhaps even back to Upcase for things, I would love to hear from you. I'd love to connect to folks. Send me an email, Twitter. I'm on all the places. I'm Chris Toomey in various spots or ctoomey.com on the internet. Chris Toomey on GitHub. I'm findable, I think. Chris Toomey developer will probably get you there.

But I would really love to hear from folks, to connect to folks, you know, someday down the road; I think I'll be hiring again. And that'll be fun. I would love to work with some of the folks that have listened to this show or meet you at a conference, or if I happen to be traveling to a city or you're traveling to Boston. Really for me, so much of what this show is about is connecting with people around how we think about building great software. And so, I would love to continue that forward into the future. So yeah, say hi, if you're interested.

STEPH: I agree. That's been one of the most fun aspects of being co-host of the show. And I'll be honest, you are welcome to contact me, but I am going to be off-grid for probably six months. [laughs] So just know that there will be a bit of a delay before you hear back from me. But I would definitely love to hear from you.

I also want to say a very heartfelt thanks to a couple of people, just folks that have made this journey incredible and have made it so much fun. One, in particular, is everyone at thoughtbot for their continuous stream of knowledge. I mean, frankly, my software opinions wouldn't be half as interesting if it wasn't for everyone at thoughtbot constantly sharing their knowledge and being a source of inspiration. So I deeply appreciate everyone that has contributed to topics and ideas and just constantly churning out blog posts because those are phenomenal.

And I also want to give a shout-out to my husband, Tim, because he has listened to The Bike Shed for many years and even helped out with a number of show notes when that was something that you and I used to do before Mandy made our life so much easier and took that over for us. And has intervened a number of times when Utah mid-recording would decide it's time to play. So I want to give a very special thank you to him because he has been a very big supporter of the show and frankly helped me manage through a lot of the recordings for when I had an 80-pound dog that was demanding my attention.

CHRIS: I think continuing on the note of thanks; similarly, I'm so grateful to thoughtbot as an organization for everything that is represented in my career. It's a decade-plus that I have been following and then listening to the podcasts and then joining the organization, and then getting so many wonderful opportunities to learn about this thing called web development. And then, even after I left the organization, I was able to stay on here on The Bike Shed and hang out and still chat with you, Steph, which has been really wonderful. So thank you, thoughtbot, so much.

Thank you to Joël Quenneville, who will be the continuing host of the show. This show is not going anywhere. And, Steph, you and I aren't really going anywhere, but we won't be around anymore. But we are leaving it in the very, very capable hands of Joël, and I'm super excited to hear the direction that he takes it and Joel's incredibly thoughtful and nuanced approach to thinking about programming and communicating. So I think that will be really wonderful.

And lastly, I definitely want to thank Derek Prior and Sage Griffin, the two original hosts of this show, who really produced something wonderful, and for many years, I think it was about four years that they hosted together. I was an avid listener despite actually working at the company the whole time and really loved the thing that they produced and was so grateful that they entrusted me with continuing it forward.

And hopefully myself and then with the help of you along the way, we've...I think we've done an okay job, but now it is time to pass the torch or the green lantern. That's the adage I've been going with. Gotta pass the lantern, pass the mantle on to the next one. So, Joël, it's going to be in your hands now.

STEPH: Yeah, I'm so looking forward to future episodes with Joël Quenneville. They are going to be fabulous.

So I've been thinking in terms of this being our finale episode and then a fun ending for it, so there's a thing called the 21-gun salute, which is the military honor that's performed by firing cannons or artillery. Not to be confused with the three-volley salute, which I definitely confused earlier that is reserved and used at funerals, which this is not. So using the 21-gun salute, I was like, hmm, it is The Bike Shed, and we have this cute ring ring that goes. So I think for our finale, we should have a 21-bell salute as we exit the shed and right off into the sunset.

CHRIS: I love it. I couldn't imagine a more perfect send-off. So with that, what do you think? Should we wrap up?

STEPH: Yes, but I have one more silly thing to add. I've thought of a new software idiom that I'm excited about. And so, this may be my final send-off into glory that I'd like to share with you. And I think that we should make like a shard and split.

CHRIS: [laughs] I so appreciate that in this moment, this final moment that we have together, you choose to go with a punny joke. It is so on brand for the show. It is absolutely perfect. And I think with that note, shall we wrap up?

STEPH: Let's wrap up.

CHRIS: The show notes for this episode can be found at bikeshed.fm.

STEPH: This show is produced and edited by Mandy Moore.

CHRIS: If you enjoyed listening, one really easy way to support the show is to leave us a quick rating or even a review on iTunes, as it really helps other folks find the show.

STEPH: If you have any feedback for this or any of our other episodes, you can reach us at @_bikeshed or reach me on Twitter @SViccari.

CHRIS: And I'm @christoomey.

STEPH: Or you can reach us at hosts@bikeshed.fm via email.

CHRIS: Thanks so much for listening to The Bike Shed, and we'll see you next week.

ALL: Byeeeeeeeeee!!!!!!!!

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