Beyond Writing Code

Category: career

  • Don’t do this: my career path

    Don’t do this: my career path

    Folks who are new to software development sometimes ask me about my career path. The first time I fielded this question, I told my story in a straightforward way. Hearing myself talk, though, I realized: this way of telling my story is probably not a good idea.

    This is not an actual illustration of my career path. Photo by Jack Anstey on Unsplash

    People who ask me this question are often actually asking me about their own career path. They see where I’ve landed, and perhaps they imagine they want to land somewhere similar. They might be comparing their path to my own, perhaps to see if they might make some of the same steps that I’ve made along the way.

    And my route is almost certainly not the route for someone else.

    Step one: pay a utility bill

    First and foremost: my story starts with my first tech job, in 1996… or maybe before that, with my undergraduate major in English… or even before that, with my first computer experiences as a kid learning BASIC on Commodore 64s and TRS-80s.

    I may have been using computers since I was a kid, but I sure wasn’t carrying one in my pocket until well after I graduated from college. If you were carrying a smartphone when you were single-digit age, we have grown up in very different times. That’s significant. If I wanted to learn how to program a computer, I had to go somewhere that had computers and take a class.

    Also, my first job in tech WAS in 1996 — during the “dot com bubble” days. I stumbled into it by trying to pay my gas bill online. The gas company didn’t have a website, so their URL went instead to the small local internet company that was hosting the domain. I poked around the site, discovered that the internet company was hiring for tech support, and I applied. As my boss from that company later told me, “you had the customer service skills, we could teach you the rest.”

    You may be starting to see why I don’t recommend that you follow my path. Getting a job by trying to pay a utility bill online and inadvertently stumbling into a company that will train you is not a great career plan.

    Step two: impulse buy an education

    I moved from tech support to abuse handling (canceling spammer accounts, yay!) to network engineering. Then 2001 happened, the dot com bubble burst, and I got laid off, along with a lot of other people.

    I quickly discovered that nobody was hiring the sort of network engineer I was, at least not at the junior-to-intermediate level I was at. They wanted people who could route network traffic within an office building. I only knew how to route network traffic between major cities.

    One fine Sunday, while still unemployed, I started to toy with the idea of going back to school. Maybe not for a full degree, but just to get some other interesting tech experience. Worcester Polytechnic Institute offered a several-months-long graduate certificate program in UNIX, C, and C++. I knew some UNIX, and I had a lot of time on my hands. I submitted the “request more info” form.

    Later that day, I was out on a bike ride when I got a call back (on my flip phone!) from WPI. The nice lady described the program. It sounded interesting. I explained my background, she thought it was a match for them. I asked when it would be offered next. I could hear her typing. The next round would start [clickety clickety]… on Monday morning. Less than 24 hours later.

    I told her I didn’t know how I’d pay for it. She said we’d figure that out when I got there, and if I could arrive early, I could complete the paperwork then. So yeah, I impulse-bought a graduate certificate program while on a bike ride. If you weren’t already convinced that you shouldn’t follow in my footsteps…

    To be fair, it worked out. I rediscovered that I still loved programming. But you could perhaps do a bit more research than I did, to better effect.

    Step three: work somewhere for a year or sixteen

    I was tutoring a fellow classmate during that program, so when he got a job somewhere, I thought “hey, if he can, and I was tutoring him, then I can…” That company had proprietary software, written in a proprietary language, on a proprietary operating system. I was pretty sure I wouldn’t stay longer than a year.

    I didn’t stay for a year. I stayed for sixteen years.

    I started as a service programmer, which mostly meant troubleshooting problems and fixing bugs with manual code patches. I got promoted. I went back to school, doing an undergraduate certificate in Computer Science. It was perfect — all the coursework I had missed from being an English major, without having to get a full bachelor’s degree again. It was also entertaining, as a senior programmer, to tell my boss I was taking an intro to programming class. 😉

    I moved on to being a developer, which was more about working on new features for an application (but still troubleshooting and fixing bugs with manual code patches). I got promoted again. Eventually, though, I really wanted to learn mainstream technologies.

    So I went back to school, again.

    Step four: go overboard

    You know, if you want to be a web developer, even a full stack developer, I’m not at all convinced that you need a master’s degree in software development. Some places will hire you without a degree, some will insist on a bachelor’s degree, but a master’s degree? It’s debatable whether or not I went overboard with that.

    I had tuition reimbursement, so work paid for about half of it. And that — plus 16 years as a dev — probably did enable me to come to my current employer at a higher level than I might have otherwise. Also, I am not great about sticking with a self-driven program, but put me in an academic setting, and I’ll slay it (I had a 4.0).

    However, if I wasn’t already cringing at telling you my bizarre and improbable story, I’m definitely cringing to tell you about the master’s degree. I don’t want people who are just starting out to think “OMG, to get to where I want to go, I need 25+ years in tech and a master’s degree?? I’m never going to get there.”

    But “there” (where I am) isn’t where you want to go. Because here’s the ultimate reason why you shouldn’t follow my path: you’re not me.

    Step zero: take your own steps

    My path has given me a unique combination of skills, perspectives, and experiences. Do they make me extremely well-qualified to do what I do? I sure think so.

    But here’s the secret: I’m doing what I’m doing because I enjoy it… and I’m qualified to do this job that I enjoy because, for 25+ years, I’ve just kept doing, and getting better at, what I enjoy doing.

    I didn’t know “what I wanted to be when I grew up” until my late 20s, when I impulse bought that graduate certificate and remembered that I loved programming. Even then, I didn’t know what I wanted to focus on. I tried stuff out. In the process, I discovered what isn’t for me, like network engineering, low-level programming languages, and CSS.

    The chances are slim that you want to do exactly what I do. You can see my experience or my title and guess what I do, but unless you’re my manager, you likely have inaccurate guesses about what I actually do. If you do think you find my role appealing, answer this: what do you imagine that I do? What most interests you about that?

    Just like how my own starting point is probably not like yours, my own current role is probably not your true target. Therefore, how I got from my “Start” to my “Here” — while perhaps a fine story — is not nearly as useful to you as working out your own path to get from where you are now to your own destination.

    “Follow your heart” isn’t quite what I’m recommending here. I’m suggesting something more down-to-earth. Try stuff that appeals to you. Figure out what you most enjoy doing — and, ideally, how you can get paid to do it. Then, do more of that, for as long as you continue to like it. When you get annoyed or bored (or laid off), stop and assess where you want to go next.

    Don’t follow me. Your own path awaits.

    Originally posted 12 September 2023 on Medium.

  • Choosing a mentor (updated)

    Choosing a mentor (updated)

    I’m happiest in a job when I’m learning from someone who knows more than I do.

    Last year [this post is originally from August, 2023], I started a new role on a team of engineers who all know boatloads about stuff I don’t. That by itself was a dream come true. Just after I started, we learned that one of my teammates would be going on parental leave in a few months, and it was decided that I would pick up his responsibilities while he was out. So, lots of knowledge transfer was about to happen. Better yet, he’s a great teacher, great to work with, and he works on things I’m interested in.

    Luck is not a strategy

    Let me clarify before we continue: I’m not telling you to get a mentor by changing jobs to one where everyone could be your mentor and the person who would be the best match from among them just happens to be going on leave half a year later. Nice work if you can get it, but that’s not a strategy, that’s mad luck. And it’s just the preamble to the story I want to tell you.

    The downside to this magical plan of knowledge transfer galore became painfully obvious about 5 months later when joyful news of the baby’s arrival meant my new work BFF was suddenly not available.

    Side note: it was less than 24 hours before we had a question that only he could answer. 😂😭

    I was too busy adjusting at first to notice, but it wasn’t long before I could see I was adrift. I needed a new mentor. But who?

    Start with the obvious

    First question I asked myself was an obvious one: “who do you know who might be a good mentor?” A worthwhile question, but for me it only generated some names who didn’t seem like good matches. People whose focus was different from mine (including most of my team). People who were probably too busy. People whose skills were too much like mine.

    Photo by Desola Lanre-Ologun on Unsplash

    I suspect this is where some people get derailed. I can’t think of anyone, or I don’t dare ask because I doubt anyone has time for, or interest in, working with me. And what would I ask them about anyway if we did work together?? The “who do I know” question was getting me nowhere, but it’s worth a shot, maybe someone leaps to mind for you.

    Decide what you want

    I thought about asking my manager, but then I realized he would probably ask: “what do you hope to get out of mentoring?” Huh, I hadn’t thought of that, beyond “someone to learn from.”

    There’s an important distinction here between “mentor” and “sponsor.” A mentor is a guide who can teach you, advise you, help you get unstuck. A sponsor is someone who can advocate for you in rooms you aren’t in, look out for opportunities for you, help you make connections. Identifying a potential sponsor is a whole other post. In this case, I wanted a mentor.

    I was looking for someone knowledgeable in topics I was interested in, someone who could answer questions or offer advice I had when I got stuck on those subjects. Someone who could give me a perspective from a vantage point different from my own.

    The next question that arose from this was: “what are you interested in?” Again, I hadn’t really given that much thought. I was immersed in this world of NodeJS and Kubernetes and cloud migration, but was that something I wanted to keep focusing on?

    I thought about the things I had been learning about recently, and DevOps came to mind. I know that term means different things to different people, so a few examples would be useful here. I had recently read The Phoenix Project by Gene Kim, Kevin Behr, and George Spafford (great book!). I had read some writing my new-dad colleague did on the mindset shifts needed for a devops transformation. I’d read a few items from our Enterprise Architecture (EA) team about it, and I’d been to a few architecture “community of practice” meetings where one of my EA colleagues had presented about that. That same person had written the “getting started with DevOps” article that recommended The Phoenix Project.

    As you might be guessing, this gave me an idea for who I might ask.

    You might also be thinking: great, Leaf, that you thought of someone. What if nobody had come to mind? That’s where I would have reached out to my manager. Having decided what I was looking for, I could start to tap my manager, or other people who have been at the company a while, to see who they knew who might be a good match.

    Deal with the doubts

    I had a name that seemed like a potential good match to me, but I still had doubts. Would he have time? Interest? Could I even set this up? He was in a completely different part of our tech org. And what would I say?

    I decided to deal with most of those doubts by ignoring them. Why cancel an opportunity before you even try for it? There was no way to know what would work unless I asked. I happened to have a 1:1 meeting with my boss’s boss around the time I was thinking about all of this, and I realized he might have the insight into whether this cross-org match would work. I brought it up.

    Sure enough, his first question was about what I was looking for from mentoring, so I was glad I had an answer ready. He offered to talk with my potential-mentor’s manager about it, and a few days later, I got the go-ahead.

    We scheduled our first chat. That left me faced with the question of what to actually say.

    Arrive prepared…ish

    I already have a rough framework for how I introduce myself to someone. It’s kind of a mix-and-match set of phrases about me that I tailor for my audience, omitting things they already know and focusing in on what’s relevant. I’ve been a developer for 20 years, I became a tech lead in 2020, I got to help an application grow from empty repository to serving users in production… that sort of thing. It situates me in time (how long I’ve been doing what), space (in the org chart sense), and experience (dev-turned-architect, learning devops). Pausing to invite the other person to share anything from their background or current interests is probably a good idea here, although I don’t think I actually did that, oops.

    I also had some ideas of how I was hoping this mentoring thing would go. Maybe meet once a month for half an hour, I’d batch up any questions I had about things I was learning. It was almost a “hey, let’s try this and see if it’s useful.”

    Other than that, though, I didn’t arrive to our first meeting with an agenda other than introducing ourselves and setting a cadence. I think that’s fine. I mean, if you have questions to bring already, bring them, you never know… but the first meeting doesn’t have to be a teaching session. It can just be an introduction, especially if you have not actually talked with this person before (I hadn’t).

    Bonus points (“wow, I wasn’t expecting that”)

    Let me just say that I had no idea what I was getting into with my new mentor. In a good way.

    Photo by Marcel Smits on Unsplash. That’s not me, but I did have curly hair like that as a kid.

    First? He was actively listening, even taking a few notes as I talked. It was clear that he didn’t want to interrupt me, but he was noting items he wanted to circle back to when I was done. Okay, I haven’t even finished introducing myself yet, and I’m already learning. Win.

    Second, I didn’t realize just how experienced a colleague I had picked. Checking someone’s LinkedIn profile first might be a good idea, no? I did not. In this case, my error was only in my favor, as I picked someone with decades of experience working with developers. He’s an astute advisor not just about devops and the tech we work with, but also about interactions with others. I’ve brought him some interpersonal work dilemmas and he’s had helpful insight.

    The biggest surprise for me was that this mentoring relationship turned out to be way more of a “two-way street” than I expected. What could I have to offer him, given that he has no particular need to troubleshoot a Jenkins build problem or learn how to use kubectl? Well, I’ve been a developer, a tech lead, and an architect, both doing the work and helping other devs do the work. That gives me a lot of visibility into and perspective on how dev teams in my area operate. And he’s outside of that area, so this is valuable to him. (Don’t fret if you don’t have that kind of experience, though – the perspective of a newer person is more valuable than you may realize.) We’re also working in partnership with each other, because with two different management chains, we have different sources of information, spheres of influence, and organizational contacts. We’re working out ways our teams can support each other’s efforts, and we’re introducing each other to people who can help.

    Ask, ask, ask

    Start by asking yourself the questions to determine what you are looking for from a mentor and how you imagine mentoring might look. Ask around to find a potential match, and ask for an introduction – if they don’t have time or interest, you’ll find out, and no harm has been done by asking. Keep an eye open for what you might be able to provide for your mentor in return (like sharing an interesting article or introducing your mentor to a colleague). You could ask your mentor outright if you can be of service in some way. Curiosity about yourself and others will serve you well on this quest.

    Many thanks to both of my mentors, I can’t imagine the last year and a half without you. Thanks to our management for making the connections (and for being great mentors in their own right). And thanks to “baby G” for disrupting the status quo and opening up doors for me in the process – happy first birthday.

    Originally posted 26 August 2023 on Medium.

    Epilogue

    It is now April 2025, and I am fortunate to continue to have both mentors as friends. I have also stumbled my way into a few other mentoring relationships as well. I wasn’t looking. I’ve simply crossed paths with a few more people whose knowledge and perspective have made them great teachers, whether or not they realize it.

    I’ve come to treasure those professional relationships where we can have a once monthly half-hour meeting on the calendar, with no prepared agenda, and we’ll invariably find more than half an hour of useful stuff to discuss. “Hey, I wanted to get your opinion on this…” or “so here’s the dilemma I’m facing…” or “do you have any advice for how I might approach…” or even “is it just me, or have you also noticed that…”

    I’ve also been able to be a mentor myself for a few others, folks who have sought me out directly or through their management. But whether I’m someone’s formal mentor or not, I see it as a key part of my role to just listen and be present with others, and to offer anything from my experience that might be useful in response.

  • Cloud Resume Challenge

    A piano keyboard, glistening with light effects.
    Photo by Ebuen Clemente Jr on Unsplash

    DevOps Enterprise Summit 2022 closed with a great talk from Forrest Brazeal. As a cloud architect, musician, writer, and cartoonist, he’s got an impressive resume of his own, but he also has a project to help aspiring cloud engineers improve their skills and their resume.

    Forrest’s Cloud Resume Challenge is a set of steps for building oneself an online resume using a variety pack of cloud technologies. It’s enough guidance to tell someone what to do, and not too much guidance on how to do it, which suits me just fine. There are a lot of good tutorials online to fill in any gaps. Forrest’s work gets people past the “I have no idea where to start” point, onward to the “hmm… how would I do that?” point, where curiosity can take over.

    I learn best by doing. Watching someone demo or listening to a lecture only gets me so far. I need to twist the knobs and see what they do, break and fix things several times, go down a few dead ends and have to retrace my steps back. Granted, it can be frustrating — for example, breaking my site that WAS working, and not being able to spot what I’d done to make AWS unhappy. It’s also reminding me just how much I’ve forgotten (CSS…) in a few years of disuse, which is humbling. But it’s all overshadowed for me by how satisfying it is to try out a technology I’ve never used before (like CloudFront) and make it work.

    Here’s Forrest’s talk from the Summit: Transformed! A Musical DevOps Journey. (Registration is free and will get you 10 free videos per month from past conferences — the videos are great, well worth getting on a mailing list.)

    My Cloud Resume Challenge website so far: developerleaf.com

    And yes, it’s back up… for now…

    Originally posted 19 August 2023 on Medium.

  • Why Everyone Else Knows More Than You Do, and What To Do About It

    Why Everyone Else Knows More Than You Do, and What To Do About It

    The developers you work with know stuff that you don’t, and you know stuff that they don’t. Obvious, right?

    So why does it seem like everyone else knows more, and you’ll never catch up? Why does it seem like you’re a little kid on a tricycle, trying to pedal faster while the big kids zoom by on their bikes?

    This is how I feel sometimes. Not shown in photo: all the big kids on their big kid bikes. Photo by Tommy Bond on Unsplash

    The answer is that it’s true: everyone else you work with does know more — collectively. Taken all together, everyone else knows more than any one person does.

    The mistake you’re making is the subtle assumption that if one person in the group knows something, everyone else — or at least most people, other than you — must already know it too.

    Let’s say someone asks a networking question, and you don’t know the answer, but one of your colleagues does. Then you’re having trouble getting API authentication to work, and one of your colleagues advises. Another developer helps you with a thorny NodeJS issue. Someone else teaches you how to fix a build failure. And another colleague whips up a quick script to get you some data you need. After a while you start to worry if you are the least knowledgeable person in your group… your company… maybe ever.

    Everyone else is on their tricycles too

    Here’s what you’re not seeing: Your network-savvy colleague might have been the only person on the team who could field that question. It’s not true that just because one person knew that, everyone else did. Also, that network pro might not have a clue about API authentication, or Node, or build failures, or scripting.

    Even harder to see: you definitely know things others on your team don’t, and I’m not just talking about your bank account password or the name of the imaginary friend you had when you were little enough to ride an actual tricycle. You have job knowledge, industry knowledge, business knowledge that others around you do not.

    For many years, I had a hard time seeing this. I assumed that everyone around me must already know all the things I do, for some reason. But again, it’s not true that just because one person (you, in this case) knows something, everyone else does.

    The person who helped you with the API might not know React like you do. The developer who solved the Node issue might not write clean code like you do. The script-writing whiz might be totally lost if you start talking about code security.

    Sometimes you’re the big kid on the three-speed bike, and one or more of your colleagues are on their trikes, wishing they could zip around like you do.

    You can DO that?

    Years ago, I worked with an experienced developer named Nick. Knowledgeable, skilled, kind, thoughtful — Nick was a role model for me. He’d written a lot of the code for the application I was working on.

    One day, when I was still new to the team, we were in a staff meeting. The boss started talking about some technology I’d never even heard of. I was just a little kid on her tricycle, trying to keep up with the knowledgeable big kids, so I decided it was best not to interrupt the meeting to ask.

    I was making a note to myself to ask someone later, when Nick politely interrupted the boss and said:

    Photo by Marcos Luiz Photograph on Unsplash

    “I have no idea what you’re talking about. What is this?”

    Yep. In a room with some super-knowledgeable peers, Nick had just admitted to not knowing something. The world did not end. Nobody rolled their eyes, or hinted that Nick should know this already, or otherwise had any judgmental reaction. In fact, a few people looked relieved. I’m sure I was one of them.

    The boss apologized for getting ahead of himself and took a verbal step back to explain what he was talking about.

    You know, I don’t even remember what the technology was. I don’t think anyone even mentioned it again after that meeting. But, twelve years later, I remember being floored that someone who I thought “knew everything” could just state calmly, in front of his colleagues, that he didn’t know something.

    Ask, and ask publicly

    In that moment, I saw that it was part of the role of a lead developer to speak up and ask when you didn’t know something, because your newer colleagues might not have the courage yet. Since I wanted to be a lead developer, I was going to have to get used to speaking up.

    Photo by Brett Jordan on Unsplash

    Later, I saw that the pressure to appear knowledgeable is universal, no matter what your experience level. If you’re new, you might feel you have to prove to your team that you know what you’re doing. If you’re more experienced, you might feel like others will judge you for not knowing as much as they thought.

    Let’s smash the stigma around asking questions or asking for help. There’s no shame in not knowing something. The problem arises when you don’t take action to try to find out — either you don’t try at all; or you do try, but when you get stuck, you don’t ask for help.

    How do we smash the stigma? Ask questions, and ask in a way that others see it. I know, it’s less intimidating to message a trusted colleague privately. When you keep it quiet, you maintain the illusion for others that everyone around them knows everything. When you model the behavior of humbly asking for help, you teach others that it’s okay to do the same. When others start to join you, you’re changing the culture for the better.

    Photo by Mars Sector-6 on Unsplash

    Pro tip: modeling good behavior, teaching others, and changing the culture for the better are things leaders do. When you speak up, you’re not highlighting your weakness, you’re demonstrating your strength. No joke. My boss told me recently that one of the key factors in hiring me was that I was not afraid to ask questions.

    Furthermore, when you ask your questions publicly, others can benefit from the knowledge transferred. Someone else, when they encounter the same problem or question, will get stuck just like you did. When you ask in a more public way, everyone else benefits. When Nick asked our boss for more information during our staff meeting, the whole team learned.

    Change that culture

    So, raise your hand in that staff meeting, post that question to your team, or use (or establish!) a Slack channel specifically for developers across teams to ask questions and help each other out.

    When a colleague asks something you don’t know, add a comment that you’d like to know as well. They, and others, will see that they’re not the only one with that question.

    Photo by Randalyn Hill on Unsplash

    When a question comes through that you do know how to answer, share your knowledge! Some days, you’re the big kid on the bike, and someone else is calling out to you from their tricycle, trying to keep up.

    Above all, always be kind, regardless of the question or who is asking. A question might seem basic or obvious to you, it might be answered by a simple web search, it might be better asked in another forum, it might have been answered two days earlier in the same forum… it doesn’t matter. Be kind. Establish the norm that questions are always responded to with kindness and without judgment.

    That’s what a leader does.

    Do you feel like that little kid on the tricycle sometimes? What do you do to help the people around you feel more comfortable admitting when they don’t know and reaching out for help? Let me know in the comments.

    Originally posted 13 June 2022 on Medium.