Rushing Labs

Owning My Career

Recently, I went through a layoff, and it left me reflecting...

It was my first AppSec role. And it was quite different than I expected. So, after spending over a year questioning my role, seeking job opportunities, then forced through a layoff, and then finally landing in a new role after said layoff...

I felt like I needed to take inventory of where I'd been, and where I want to go with this sticky, messy no-good thing called a career. I'm hoping to reflect, make sense of it, and come away with practical knowledge I can apply going forward.

Note: I'm hoping this post is an observation and reflection of the path I've chosen and experienced. Not anything prescriptive of what anyone should do.

Some reflection

I've been bored for a long time. Roughly 7 years ago I was happy to graduate from college with a Comp. Sci. degree, and convert to full-time work from the internship I was already working. felt good. Four and a half years of work. Payoff.

Endless studying, dubious tests, and the constant churn of assignments were traded for work in the form of stable, practical applied knowledge. Great, right? Thinking back on this, I think I see what happened: endless studying was constant engagement; those dubious tests were feedback via direct progression markers; and churning assignments were new curiousities being entertained.

The work I hoped for became a shift to the mundane. Five jobs later—five teams, five environments—still the same. It was all business software development though. Admittedly, I was trying to stay in my local area (this was before the current remote work trend), and always answering recruiter messages instead of questioning the environment around me wasn't the right call.

That's always the answer we prescribe though, right? A new job should fix it—especially if it comes with a pay bump! This was the bias I had (even if I didn't want to admit it), because nothing felt why stick with what you know is wrong—right?

I had been interested in infosec for a while afterall. So yeah, my first AppSec role sounds great!

Nope. Now, having left this latest role (or been separated? layoffs are weird), I feel like I should admit...I didn't expect so much project management to be a part of application security. After sitting in front of code every day for most of the past 7 years, and all of the assumptions for anything security, or infosec related, is constant technical felt alien to be pulled out of my IDE and dropped in Outlook. Well, it was: meetings, documentation, tickets, project boards, reports, and brainstorming enterprise governance—so not only Outlook.

The perfect environment for a "developer", right? I had worked hard to find myself through all of the jobs, and thought I was moving towards a specialization that made sense. So, what went wrong?

I feel like I need to look within.

Reflection Thoughts: "Bored People Quit"§

There's an article floating around the online tech circles, and it's aptly named "Bored People Quit". (You may see why it piqued my interest.)

It was written by Rands, circa 2011, and is one of the most insightful articles I've come across in the
times I was evaluating my career. In fact, it has sort of become this meta-checkpoint I return to almost annually, to re-evaluate where I'm at; how I'm feeling. Often it's been a telling marker.

It's addressed to managers and leaders, but it's still interesting reading from the perspective of a software engineer. It speaks to "chronic boredom", how it can creep into a team, and how to identify and combat it. It may be easy to let such an article lead to a hyper-critical view of whatever the current team situation is, but that is perhaps short-sighted.

Through each remedy Rands suggests in the article, the engineer (team member) still plays a key role in solving the problem. The article points to a certain responsibility the leaders have, but it never sits on their shoulders only. Rands highlights how leaders can detect boredom, spotlight it, present it, but ultimately they're helping the team members work through it.


So, what am I doing about it—It's nice to discuss these things, but what to do?

Start with catharsis§

For a while I’ve kept a “work journal”. It’s about like journaling, but specifically for work. A place to record how things are going. Anything notable. A clever observation. Or just venting about bad days.

Constructive catharsis 🙂

For me, this is an easy, natural place to start. Open a Google doc, and start typing. This also doubles as a way for me to track how things are going at a job. It's also let me revisit specific thoughts about previous jobs while in a job search. It also helps usher some self-awareness in areas where my judgement was clouded by the day-to-day. You’d be surprised how much your perception changes over time.

Alright, then what?§

After so many jobs, the common denominator was me. So, I had to ask myself, “What’s the point?” And then proceed from there. What's the point:

  • in working?
  • in writing software?
  • in working for a medium/large company? in a startup?
  • in seeking higher pay?
  • in seeking a company with purpose?
  • Which companies share my mission?
  • ...go FAANG, maybe?

These questions just led me back to the typical career guidance inquisitives, like: “What did you always want to be when you grew up?”, “If you could not fail, what would you do?” Those sorts of things.

The harder question for me, was: “Is what I’m doing now bringing me to where I want to be?”

It was easy to underestimate how deep some of these questions can be, even if they feel like platitudes. I had to spend time with them over multiple days and weeks. Writing my answers down and revisiting them helped immensely. Was there a trend to my feelings or were they passing moodiness? Also, taking note of which questions I had a sure-fire answer for, and which I was less confident in, showed me areas that were ripe for more work.

Considering the tech field’s apparent attempt at meritocracy (for better or worse), this series of questions led me to some striking answers to wrestle. Like,

  • I want a Ph. D., but why?
  • Why do I find compelled to seek meaning in certain interests but not others?
  • To the more practical: Are there any companies at all that build what I want to?

Turning those questions into actionable steps§

I'm still trying to answer those questions, but in the meantime what to do?

“Find a curiosity and follow it” is probably the best, memorable advice I stumbled across while trying to find my way through work that bored me more and more each day. I realized my continued attempts to follow a specific path, or determine which study track I needed to follow wasn’t working. And I let myself just go do what I wanted for a while.

Starting small, I’ve consistently been interested in building PCs for the past 15 years—Alright, let’s research and build one. And I made sure it was fun!—not just for work. Overbuilt a bit.

A few weekends getting back into gaming, I wanted to try filming some Let’s Plays, and this led me down a rabbit-hole of screen capture, GPU performance, video encoders, file containers and x264 options. Not to mention this unlocked a whole new set of creators and Twitch streamer-types to my YouTube feed, demonstrating how much can be accomplished with OBS.

Then a funny thing happened. This new injection of distractions brought me back to software engineering, in a new light. I still stopped to build the small ideas that bugged me, but I also found myself thinking I should share my work in new ideas—with a YouTube channel. Ultimately, this led to developing new skills, too: video editing, lighting, some basic photography, a focus on presentation/speaking, and social media management.

Before long, these distractions and ideas had me back at new code projects, like wondering if I could automatically transcribe videos with Python. ...A new type of project, with a new language and a new idea, completely outside my norm.

There has been much more to this little journey, and it wasn’t completely full of sitting in front of a screen. Spending time with these thoughts, and finding the energy to jump back into my own tech interests couldn’t be had without trying other things too: volunteering in my church, cooking new recipes, going for a run or some other adventure. Sometimes you just have to get away.

So, where did I land?

I'm not sure a normative tech-worker track—through software engineering or AppSec/infosec— is good for me. I continuously find myself at wit's end with the typical business software development, and I'm learning AppSec has a lot more to do with software assurance and management than I naively stepped into the field with. These aren't detriments to the work though. They must be done; just not by me.

Instead, this diversion into digital creation is showing me I have a need for creativity in my work. I need to be able to walk away having built something I could look at. But it doesn't have to be a visually artistic thing, lately I've found myself trying to blend systems design, AppSec, and the more technical aspects of computer science with more approachable presentations.

My hope is that I could build new systems, for a new audience, without the normal limitations. Security and infosec still interest me, but I need to find a way to blend this field and building systems and software. Things like ad-hoc networks, decentralized peer-to-peer systems, automation, and providing avenues for data privacy ping around in my head chewing up my curiousity. Maybe keeping that YouTube channel around to share these things will be important.

It's okay to go slow.