365: Career Progression

Episode 365 · December 13th, 2022 · 37 mins 55 secs

About this Episode

Joël has been thinking a lot recently about array indexing. Stephanie started volunteering at the Chicago Tooele Library, a non-profit community lending library for Chicagoans to borrow tools and equipment for DIY home projects!

It's the end of the year and often a time of reflection: looking back on the year and thinking about the next. Stephanie and Joël ponder if open source is a critical way to advance careers as software developers.

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

JOËL: And I'm Joël Quenneville. And together, we are here to share a little bit of what we've learned along the way.

STEPHANIE: So, Joël, what's new in your world?

JOËL: I've been thinking a lot recently about array indexing. I feel like this is one of the areas where you commonly get confused as a new programmer because most languages start array indexing at zero. And what we really have here are two counting systems, either an offset so how many spaces from the beginning of the array, or a counting system where you count 1,2,3,4. At first, it feels like why would computers ever go with the offset approach? It's so illogical. Counting 1,2,3,4 would feel natural.

But then, the more I think about it, the more I've started seeing the zero-based pattern show up in everyday life. One example, because I enjoy reading history, is how we talk about centuries. You might talk about the 19th century is the Victorian age, roughly. But you might also refer to the 19th century as the 1800s. So we've kind of got these two names that are a little bit off by one. And that's because when you're counting the centuries, you count first century, second century, third century, fourth century, and so on.

But when we actually go by the first two digits, you start with the zeros, then the 100s, then the 200s, 300s, and so on. And so we have a zero-based counting system and a one-based counting system, and we sort of have learned to navigate both simultaneously. So that was really interesting to me to make a connection between history and programming and the fact that sometimes we count from zero, and sometimes we count from one.

STEPHANIE: Yeah, I will have to admit that I always get confused when we're talking about centuries and making the mental connection that 19th century is the 1800s. It always takes me a bit of an extra second to make sure I know what I'm hearing, and I'm attributing it to the right year.

I think another example where I get a bit tripped up is the numbering of floors because, in the U.S., we are counting floors using the one-based counting system, whereas I think in Europe and places outside of North America, to my knowledge, the first floor will be considered the ground floor, and then the second floor will be the first floor and onward. So that is a zero-based counting system that I can recall.

JOËL: I never noticed there was a pattern. I just thought every building was arbitrary in where it counted from.

STEPHANIE: Yeah, I do think it's a cultural thing. I would be really curious to know more about the history of how those counting systems get adopted.

JOËL: So that's a fun thing that I've been exploring recently. What's new in your world, Stephanie?

STEPHANIE: I am really excited to talk about a new real-life update. I started volunteering at the Chicago Tooele Library, which is a non-profit community lending library in my city for Chicagoans to borrow tools and equipment for DIY home projects. What I really like about it is they use a pay-what-you-can model so everyone can have access to these resources. It reduces the need for people to buy new things all the time, especially for little one-off projects. And they also provide education to empower folks to learn how to do things themselves, which I thought was really cool.

And another thing that I think might be a little relevant to this audience is that I actually first encountered the Tooele library through its open-source software, which is a Ruby for Good project called Circulate. So the Tooele Library had previously been using this software that was built by community members to do all of their lending. And I got to see it in action when I saw a librarian use it to rent out tools to community members. And then I also interfaced with it myself as a member of the Tooele Library.

I've borrowed things like saws, cooking appliances like air fryers that they also had. And when I was first a guest on this show, I borrowed a microphone from them to do this podcast because I was just a guest at the time and didn't want to commit to buying a whole new microphone, so that was a really awesome way that I got to benefit from it.

JOËL: It's a fantastic resource for the community.

STEPHANIE: Yeah, I love it so much. If anyone is in Chicago and wants to check it out, I highly recommend it. And even if you're not in Chicago, if the idea of a lending library interests you, you can check out the software on Ruby for Good. And it's no longer being used by the Chicago Tooele Library, but it would be really cool to see it be picked up by other people who might want to start something similar in their own hometowns.

JOËL: So you mentioned you're volunteering here. So this means you're going in person and helping people check out items from the library.

STEPHANIE: Yeah, I did my first volunteer librarian shift about a month ago, and right now, they're in the middle of moving from one location to another, so they've had a lot of in-person workdays to get some of that done. But even before that, I had contributed a little bit to the open-source repo, which is just a pretty standard Rails project, so I felt super comfortable with getting my feet wet in it. And it was, I think, my first open-source contribution.

I find that some of the other open-source software, especially developer tooling, is a little scary to get into. So this was a really accessible way for me to contribute to that community, just leveraging the skills that I have for my day-to-day work.

JOËL: Would you recommend this project for our listeners who are looking to maybe get their own first contribution in open source?

STEPHANIE: The Circulate project is actually on a bit of a hiatus right now. But I would definitely suggest people fork it and play around with it if they want to. I also know that Ruby for Good has a bunch of other projects that are Rails apps and have real users and are having an impact that way. So if anyone wants to get into open source in a way that feels accessible and they're building a product that people are using, I definitely recommend checking that out.


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JOËL: So, as we're recording this, it's the end of the year. It's often a time of reflection and looking back on the year and maybe even thinking about the next year and progression. I'm curious since you said this was your introduction to the world of open source, do you think that working on open source is a critical way to advance our careers as software developers?

STEPHANIE: That's a good question. Honestly, I think my answer would be, no, it's not critical. I think it's one avenue for people to explore and increase their impact on the community and increase their technical knowledge, especially if it's in an area that they are not quite working in in their day-to-day, but they're really interested in diving deeper in.

But I do think there's sometimes a lot of pressure to feel like open source is this shining beacon of opportunity for you to dive into and that it'll bring a lot of meaning to the work that you do. And people, obviously, and for a good reason, talk about how special it is that open source is part of the industry that we work in, but I don't necessarily think it's critical.

I do certainly feel inspired by people who create open-source tools or contribute to Ruby or Rails. But I don't necessarily think that it's something that should be a rule and that everyone needs to get into it or contribute to it. Because there are many ways that people can have an impact having influence on the community, and that way is one. But there's also a lot of value, even just focusing on the team that you're on and your company internally.

JOËL: I appreciate the nuance there because I think like you said, we often view open source as the main thing that everyone should be doing to get ahead. And there are a lot of different ways to improve your skill and then to get ahead in your career, which are not always correlated. One kind of really basic way that I was shocked at how much it helped me was I was learning a new language, Elm. I joined their online Slack community and just hung out in the chat room and answered the most beginner questions because I barely knew the language at the time.

And most of these could be found just by looking up the documentation or by opening up a REPL and experimenting with a thing and giving an answer, which are skills that, as a programmer who's got some experience, I take for granted but that not everyone has that as a reflex. Because Googling, searching documentation, crafting experiments in the REPL those are all skills that you have to learn to build over time. But answering those very basic questions over and over over the course of a few months actually taught me so much about the language, and I'm not doing anything fancy.

STEPHANIE: That's awesome. I have a friend who, during a time when I think she was struggling with her confidence in her technical skill and was feeling a bit stuck at work, spent an afternoon answering Stack Overflow questions on basic Ruby and Rails, and that gave her a lot of joy. Because she recognized that she was the person Googling those questions and needing to find answers many years ago, and that was one way that she could pay it forward. And I think she had a lot of empathy, like I said, for those people who are needing a little help, and it felt really good for her to be able to provide it.

JOËL: It's a way to have an impact on other people while also solidifying your own knowledge.

STEPHANIE: Yeah, exactly.

JOËL: So we've mentioned a couple of different ways where you can level up your skills, that might be through helping out other people online, that could be through open source. But I'd like to zoom out a little bit and look at not just improving your technical skills but thinking about career in general when you're looking out over the next 10, 20, 30 years. Do you have an approach that you like to take when you're thinking that broadly?

STEPHANIE: For me, I have had trouble thinking about a five or 10-year plan because things often don't turn out the way that I envisioned them. And so I think I've come to realize that leaning into how I feel about things in any given moment is more valuable and oftentimes more accurate to what I really want. Because I can have an idea of what I want my career to look like, but the things that ring most true are what I'm feeling in the moment.

And so you mentioned we're releasing this episode at the end of the year. I do tend to do a little bit of recap about how my year went if I spent it doing things that fulfilled me and made me feel good, if I grew in the ways that I wanted, even separate from any performance review. I know that this is a time of reflection for a lot of people. And I don't personally ascribe to New Year's resolutions, but I do like to think about themes or intentions. And those are things that ground me rather than setting particular goals that I may or may not achieve; I may realize I want to change.

So yeah, I really recommend just sitting with yourself and spending time thinking about what you want, and that could mean a promotion, but that could also mean a more interesting project using new technology. It could mean more responsibility and decision-making power. It could mean a move into management. I think it's different for everyone. And so when people have asked me about advice or what they should do in terms of coming to a crossroads between jobs or between projects, I think that you really can't tell anyone else what is the right move for them; only they can decide.

JOËL: And tech, it's such a broad field. There are so many different roles and paths you can take through it. Well, there's junior engineer, engineer one, engineer two, engineer three, that's just the same everywhere. And there's only one way forward; it's up or stagnation, and that's it. Like you really get to choose your own adventure in this industry, and that's exciting and maybe a little bit terrifying.

STEPHANIE: Oh yeah, for sure. I like that you brought up the different levels and roles that you could have because I have found companies that provide a career ladder or engineering ladder that has been useful for me in the past in figuring out if the next step at the company that I'm at is what I want. And it's helpful. It's very clear to me, okay, these are the skills that I need to get promoted into this next level. But other times, that description describes something that I'm not interested in, and that is also really helpful information.

JOËL: Was there ever a moment in your own career where you had to navigate some of these decisions to decide what path you wanted to take as opposed to just following a ladder up?

STEPHANIE: Oh yeah. I was presented opportunities to start getting a feel for management or overseeing a team as a lead. And people had really great feedback for me that that was something that I had shown leadership in, and they thought I would do a great job in that role. But I actually decided to kind of hit the brakes a little bit on that particular route because what I realized I wanted at the time was to focus more on being an IC and deepening my technical knowledge. And that was really tough.

I do also think that a lot of women are pushed into management because they end up doing a lot of the glue work that comes with unblocking people, supporting people, and project management and those are all skills that, like, quote, unquote, "lend themselves towards management." But just because we do that work doesn't necessarily mean that that's the direction that we want our careers to go in. And so that was a really tough thing that I had to do was to make it really clear that I wasn't quite ready for that yet. And I might be in the future, but in that moment, just standing my ground and being like, actually, I want to focus elsewhere instead.

JOËL: That's really valuable, knowing yourself and knowing where you want to go, what the next step is. Are there any exercises you like to do to try to figure that out for yourself? Because I know something that I've struggled with sometimes is not being quite sure what I want.

STEPHANIE: I journal a lot in my personal life and also about work. I think I tend to revisit that in my notes, especially about things I've learned or things that I felt excited about in terms of projects and what I've been unlearning, and just going through all of the things that I've collected over the year and synthesizing that information.

I also really like to lean on my friends and peers. So I really enjoy a good one-on-one when we just talk about those types of things, you know, dreams, hopes, goals. I like to lean on my manager a lot, too, because oftentimes, they're able to see things about my work over the past year that maybe I was just too in the weeds to be able to have that higher level perspective about.

As a third-party observer, they see a lot of things that you might not be able to, either on your current project or even opportunities for you to step into at a higher level in the company. So yeah, I think that, in some ways, it's a solitary activity, but it doesn't always have to be.

JOËL: I remember having a really good conversation with my manager as well, at some point, talking about that decision of am I interested in maybe moving into the management track? Do I want to stay on the IC side of things? And that was a really good conversation to have.

STEPHANIE: So after having those conversations and kind of figuring out what direction you wanted to go, were there times when you had to actively make that choice or advocate for yourself?

JOËL: Yes. One of the things that I realized that I care about is investing in other people, and sort of the mentoring, supporting side of things which you might think is kind of a management activity. But management is a little bit different than that. I prefer the coaching aspect than the management aspect. And so what I wanted to do at some point once, I realized that that's what I wanted and that a management position would not fulfill that desire, I started looking to see is there a way to craft that role within the company?

A common thing that happens, I think, in workplaces is that you are given roles or titles for things that you already do. Clearly, if there's something that I care about, I needed to be doing it already in my day-to-day work, and I needed to be doing it at a fairly high level. And so I focused efforts there, trying to say I want to get better at this. I want to do this in the opportunities that I do have in my current role.

And then eventually, I did go to my manager and said, "Look, this is what I am looking for in the next step." Had a discussion about whether or not management could be a fit or if we could customize a management role for this, and eventually decided that an IC role would be a better fit for that. And among other things, we introduce at thoughtbot the role of principal developer, which is kind of the next step on our career ladder. It can be a little bit different emphasis for different people on the team who have that role, but, for me, a big part of that was putting more impact on the broader team as its focus.

STEPHANIE: That's really cool. I really appreciate that you were able to come to the table with what you wanted and able to have a discussion about, okay, so management might not be the right fit. But how can we create this new role that not only benefited you but also benefited the rest of the company because that hadn't been an area that they had quite figured out yet. But by doing that, you essentially did exactly the kind of coaching and making an impact [chuckles] that you had also shared you had been wanting because you just opened this new door for others to also eventually work towards. And I think that's really awesome.

That reminds me a lot of the idea of being directly responsible for yourself and your career. There's a really good blog post by a woman named Cate, who is an engineering director at DuckDuckGo. I'll link it to the show notes. But she writes a lot about how you have to own your own career and find opportunities to have that agency. And you can always ask. Like, you might not get everything that you want, but by asking and by bringing it up, you at least can start the conversation rather than expecting or just hoping that things will turn out the way that you want without having said anything.

A couple of things that she says in the article that I also really like is the idea of expecting less from your job and more from your career.

JOËL: Hmmm.

STEPHANIE: At any given point, your job might not check all of the boxes, but maybe they check some, and that is worthwhile. And once you get to a point where maybe the job is not really doing anything towards the direction you want your overall career to go, that might be time to reevaluate. And then she also mentions learning from feedback and asking for feedback, and making sure that beyond the things that you're able to identify, learning from others areas that you can work on to have a better impact on your team is also really important in progressing your career quickly.

JOËL: So how is this mindset of owning your career path maybe different than the default that a lot of people might assume in our industry? It sounds like it's a much more proactive approach. We talked already about doing the work to figure out what you want out of a career, what you care about, as opposed to just being told what you should care about by others. Are there other aspects that you have to sort of own as part of owning that career?

STEPHANIE: I mean, I think it's just vital to having a work experience that is fulfilling and brings you joy and doesn't bog you down. I know we all have to work, but we also all have the capacity to exercise our agency there.

I know we did talk a little about management earlier, and I wanted to also plug a book, "The Manager's Path" by Camille Fournier, which is about management. But she has a really excellent first chapter about how to be managed and what you can expect from having to be an employee with a manager but also what power you have in that dynamic. She says that while you can be given opportunities and have areas of growth pointed out to you, your manager can't read your mind, and they can't tell you what will make you happy.

And so I have seen a lot of people spend time worrying about if they're doing the right things to get to the next level. But oftentimes, we just haven't really talked enough about how that next level is really totally different. And there are so many routes that that could take, whether that is becoming an open-source maintainer, or producing content like blog posts or podcasts even, or speaking at conferences, or management.

Once I realized that there were so many different opportunities available to me, I did feel a bit liberated because it does seem like, oh, you're just supposed to level up your technical skills until you've become this superstar coder. But that's not what everyone wants, and I think that's okay.

JOËL: And, like you said, there are so many different areas where you might choose to focus or invest time into, and you don't have to do them all. You don't have to be the super prolific open-source person, and also keynoting at conferences, and also publishing the book, and also, you know, whatever you want to add in there.

So once you know your goals, how do you make those goals a reality? We've been talking a lot about know yourself and have some goals. But at some point, you have to translate those goals into actions that will take you one step at a time towards those goals, and sometimes that translation step is hard.

STEPHANIE: It is hard. I think this is another place where I would work with my manager on, especially if I'm on a project where I'm not quite seeing those opportunities. Like I said, usually having another perspective or another set of eyes on what you're working on can make it clear, like, specific and concrete aspects that you can spend your energy on.

So if it's wanting to get better at testing, it's like, okay, what does the current test suite look like, and what are some opportunities that you can provide new value to the test suite to make an impact on the team? Or what are some refactoring opportunities you can make if you are wanting to have more of that experience outside of the regular ticketed feature work that you have to do?

JOËL: I think it's interesting that you mentioned impact on the team because not only do you want to level up some skills, but if nobody knows about it, your odds of getting that promotion or getting recognized for it are very low. So not only do you have to get good at technical systems, you have to get good at social systems as well.

I was recently reading an article about the role of kingship in medieval Europe and how it's very much a role that needs to play out in public in order to build legitimacy so that people will do what you say. You need to be seen to do the things that everybody has in their mental kind of checklist are things that a good king does.

And some of those are somewhat divorced from the reality of what actually is effective governance. It could be various public rituals that you do that people see and are like, oh yes, you're doing this parade every year. You're looking the part of a good king; therefore, I think of you as a good king. It could be military campaigns because there are a lot of those in the Middle Ages.

And there's this interesting cycle where kings that have long and effective reigns then get to influence what the next generation of kings are going to have to do in order to look legitimate because people will point back at you and be like, well, Stephanie was an effective ruler, and she did X,Y,Z. And so, in order to look the part of an effective ruler, you should be doing those same things.

STEPHANIE: That's fascinating. In some ways, I struggle with the idea that you have to prove that you're, you know, doing the kingly things and worthy of that title. But I do think that there is some degree of truth to that in your career as well, where you want to make sure that the work you're doing is visible.

And you also just, in general, bring up a really good idea about the importance of leadership in career progression. And I think that in my experience, and from what I've observed, that is a vital way to progress your career is to just start demonstrating leadership qualities, and that could look like reaching out to new team members and helping them with onboarding. That could mean updating the documentation, just taking the initiative, and doing that.

That could also mean starting to voice more of your opinions about risks or red flags about a certain technical implementation or a project because you have amassed the experience to be able to make those decisions and put in your two cents and then making sure that the choices that are made are the right ones.

JOËL: Additionally, I think even when you're doing things that are a little bit more inward-focused, like learning something new, you can generally find some kind of artifact that you can take and share more broadly with a team. So maybe you experimented with something, and you wrote up a small code example to showcase the thing that you're trying out; make a Gist on GitHub and share it with your team. If you learn something new, maybe write a blog post about it. Maybe even just start a thread in Slack and start a conversation on something that you learned recently.

These can be really low effort, but I always look for opportunities to take things that I have learned, things where I'm sort of working a little bit more inwardly on myself and see how can I share that with the rest of the team? Both because it benefits the team, they get to benefit from the impact of some of what you've done but also, it helps a little bit with making sure that your work is visible.

STEPHANIE: Yeah, absolutely.

JOËL: So we've been talking a lot about improving ourselves technically, but there's one question that we've danced around that we haven't actually addressed, and I'm curious about your thoughts here. For someone who's early career, do you think it's more valuable to be a specialist, someone who goes all in deep on one technology and becomes great at it? Or is it better to go more broad, become a generalist, and know a little bit about a lot of things? From the point of view of what will help move my career forward.

STEPHANIE: I personally do think there is an aspect of being a generalist for a little while, a few years maybe, to get a taste of what is available to you. I think that is valuable before really committing to decide, okay, like, this is what I want to specialize in. Honestly, as a generalist myself, I still do feel a bit like I don't know what I want to dive deep into and commit myself a little bit to being like, okay, I'm going to have to sacrifice learning all of these other things to really focus on this one aspect.

So I have found that being a generalist also kind of gives me the flexibility to work on different projects that might require learning a new language, or at least one that I am less familiar with. And I know that that's a skill in and of itself, being able to move on to different things and gather information and the skills you need to start contributing and working effectively quickly. So, honestly, I think I can really only speak to that experience, but it has served me well and is, for the most part, enjoyable to me at this present moment. What about you? Do you have any thoughts about generalist versus specialist?

JOËL: I think, in a certain sense, there's no right answer. Like we said earlier, there are multiple paths to a career in tech, and you can go through both. I think something that I've seen be less effective, especially very early career folks, is trying to go too broad, jumping on every new language or framework every couple of weeks, every month, and just dipping your toe in it and then moving on to something else and never really learning deeply, or synthesizing, or building a mental model of things. And so you're kind of stuck in the shallow end forever, and it's hard to break through into that initial level of expertise.

So I think, especially very early career people, I tend to recommend pick one language or technology and focus on getting good at that and then branch out. And, of course, you're never doing everything in a vacuum because there are a bajillion dev skills you need to learn beyond a language or framework.

So I often categorize three areas to focus on that I like to recommend for people; one is pick a primary language or framework and get good at it. Two, learn some evergreen skills, these are things like version control, so Git, SQL, using the command line. And these are not things that you need to master on day one because you're going to use these your entire career. So learn a few things, move on, come back to them next month, learn a few more things, and just keep coming back there every now and then over the course of your entire career to deepen those skills, and that will serve you very well.

And then, finally, some random thing you're interested in. I find that I learn so much faster and so much more deeply on topics that I'm interested in or passionate about. And that interest can be very random sometimes, and it can also be fleeting. It can be, oh, I was interested in a thing for a little bit, and I dug into it, and then I moved on to something else.

If I have a career or learning plan, I like to leave that room for spontaneity to say there will be things that are maybe not strategically important as my next step, but I can learn them because I'm interested in them because they bring me joy. And then later on, maybe that will actually be the foundation of something important two years down the line where I can draw on that knowledge.

STEPHANIE: You bring up a really interesting point. I do think my interpretation of generalist did line up more with the idea of those evergreen skills. So I think also about debugging and testing, and those are just part of the things that you're doing every day. And that might look different from project to project depending on what language or framework you're using and what testing philosophy people on your team abide by.

But yeah, those are areas that I do think investing in will serve you well across projects and help put you in a position where you can jump into anything and be like, okay, I have these core foundational beliefs and skills about this work and now, okay, let me figure out how to apply them to the task at hand.

JOËL: Are you familiar with the metaphor of the T-shaped developer?

STEPHANIE: I don't think so.

JOËL: So the idea is that you want to balance out a broad set of skills that you're a generalist at, that you know a little bit about them with a few things that you are a deep expert in. So you have that horizontal bar, but you also have a deep area of expertise which creates a kind of a T shape. In a sense, maybe that's just trying to say, like, do both.

But I was recently reading an article that was advocating for not only a T-shaped developer as a sort of starting point but then also beyond that, over the course of a long career, you have plenty of opportunities to develop more than one specialization. And so now you start having a very broad base of general knowledge as well as multiple areas that you have spent significant time becoming an expert in. And this article referred to this idea as a comb-shaped developer, and that's something you work up to over the course of years or decades in tech.

STEPHANIE: That's very cool. I love the idea that you might start out as a T-shaped but what you're doing is kind of like adding to your harness of skills and it being an additive process. You'd have more teeth in your comb [laughs] rather than it replacing something or a set of skills.

On that note, shall we wrap up?

JOËL: Let's wrap up.

STEPHANIE: Let's wrap up. Show notes for this episode can be found at bikeshed.fm.

JOËL: This show has been produced and edited by Mandy Moore.

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

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

STEPHANIE: Or reach both of us at hosts@bikeshed.fm via email.

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

ALL: Byeeeeeeee!!!!!!!!!

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