Thoughts on Shifting Careers

I feel like half the battle of life is just turning up, and the other half is finding the way forward. This isn’t a very philosophical understanding, but it feels pretty real to me.

After 9 or 10 month of voluntary unemployment, I’ve finally made the decision to shift careers. Despite being a software developer, I’ve spent very little time developing any software on my own, and I find this amusing. I did get my hands dirty with the C language, which has been educational, if not painful, and did write a few lines of C# to help process the thousands of pages I scanned for various antique catalog uploads. But otherwise, I’ve had absolutely no desire to build applications or websites of any kind. And it’s not that I don’t sometimes enjoy doing that, but it’s not something I spend time doing without somebody else’s infrastructure (via a job).

Many years ago, I actually tried to transition into cyber security, which was always kind of fascinating to me, but I had so little experience in software that it was painfully clear I didn’t have much to offer in the first place. I sometimes feel like my career has been something of a trainwreck as I’ve been tossed to and fro by some really weird tech stacks and seem to always be behind from where I would like to be. But I guess I can’t argue with the pay.

And I think intuition plays a big role in this picture. I’ve always known what I wanted to learn in the industry, but I’ve often lived in denial of this. One of my supervisors at my first job actually kind of laughed at me when I said I wanted to learn curl, HTTP, and regular expressions. He said that regex was just something you did and largely forgot about later, and cited a personal example, and then kind of shrugged HTTP off, saying, “It’s just a protocol”. As it turns out, though, regex is stupidly involved but extremely useful. I was actually able to break a senior developer’s expression one time, not because they were a bad senior developer, but because most developers in general never really learn regular expressions that well. But even though I broke it, I had absolutely no suggestions on how to fix it. I’ve always wanted to know regex well. As for HTTP, well, if I had learned how to get things done in HTTP, learning .Net Core MVC would have been so much easier; in fact, learning multiple web frameworks would probably become a breeze. Once you know what needs to happen in the underlying protocol, all you have to do is figure out how the framework implements such an activity. If you knew HTTP inside and out, you wouldn’t have to guess how to do something, you would just need to find the right methods to do it.

Said supervisor is now working at Amazon (which for some reason is one of several gold standards in the industry). He’s not by any means unintelligent, but I still kind of resent him for discouraging me from learning those things. I always knew they were valuable, and looking back, I should have followed my interests and my gut.

Which leads me to cyber security: I know what I have to learn. The real challenge is…time. And commitment.

For example, a lot of people disparage the Network+ exam as being “basic” or “for network engineers only”. But computer security is almost completely predicated on networks and the ability to exploit communication between computers. Sure, there are clever ways to attack air-gapped computers, but most companies aren’t paying you to spend 40 hours a week finding ways to protect those, they are paying you to secure networked infrastructure and manage incidents. So although getting such a “basic” certification doesn’t give you a one-way ticket in cyber security, it’s foundational knowledge for the role and quite frankly, it would have been really useful for software development, too. Well, maybe around 30% of the study material would have been useful. A lot of that stuff is well abstracted away.

The challenge of making this career shift, though, is that while my experience as a software developer gives me a great background for understanding computers and being able to program, it’s not the same as experience in the field. And knowing application development is not the same as knowing application security, though I’m pretty familiar with SQL and know about parameterizing database calls to help prevent SQL injection vulnerabilities. Etc.

It’s easy to become overwhelmed by the job descriptions you don’t qualify for. It’s also easy, at least for me, to confuse specialization with competence. I’ve been tempted to buy a $300+ Cisco switch so I can learned about managed switches and security features, the enterprise network environment, etc, and while learning some of that might be really valuable later, it simply isn’t very valuable when my goal is to get an entry-level position. You really have to triage your priorities. I’m not (necessarily) trying to be a network engineer, but the CCNA and other Cisco certifications are just a step beyond where I really need to be right now. The Network+ exam might not be most valuable certification to have from an HR perspective, but that doesn’t mean it can’t be used to demonstrate your willingness to learn and help push the boundaries of your knowledge.

I reached out to some close friends to see if they might receive words from God on what I should study. One friend actually received an amazingly relevant vision related to my career shift, but there still hasn’t been any clear direction on what to study, even despite having quite a number of dreams all related to making this career shift. And it almost seems like God is saying, “You already know what to study”. Not to mention, the last time I was out in the waters, hunting for jobs I largely didn’t qualify for, the one job that came through was the one that technically didn’t require me to know anything more than I knew before, but I certainly would have benefited from focusing on a few key technologies, rather than trying to take everything on at once. I learned a ton from that experience, and now I need to live those lessons out. Focus on the few things that really matter: don’t sweat all the acronyms, technologies, and descriptions that you don’t yet know. It turns out, some employers don’t really care for those, they just want to see you know the basics well enough to be effective.

It is, of course, terrifying, especially with planning to move relatively soon and just not knowing that the future looks like. And that’s why I say, half of life seems to be finding a way forward. But what is the way forward? How can we know?

Well, I think that’s kind of a mystery.

At the end of the summer, I made my way back to my favorite valley to do something conventionally stupid. I was going to head back to the Bowl, go exploring, then come back on the opposite side of the valley, which requires navigation by GPS because alpine bushes (often referred to as “willows”) don’t mess around, especially when they are sometimes taller than you. I don’t claim to hear from God all the time, but I felt like this was opened to me, that God had a way. And to be fair, everything went according to plan at first. I actually successfully navigated those willows (with a few setbacks) to the point where I wanted to cross. I even saw some ruins on the other side of the valley that probably nobody has seen for 100 years! When I got to the crossing point, I felt like God told me to put my rain jacket on, even though there were only a few sprinkles in the air from a passing cloud, and to put my binoculars away. What happened next was terrifying, as I started across the old way I had once found only to realize that over the past 6 years since I had been this way, beavers had been busy damming up the water routes, causing the original “path” I made to be water logged.

I don’t even have right words for the experience. Well, ‘terrifying’ is one word. A few times I melted into a panic, and other times I calmed myself down and tried to consider my options. Going back was possible, but would have taken at least an hour, and the sun was definitely on its way down, while the destination was only maybe 100 feet forward, just through awful terrain. I snapped at a certain point. Something just switched in my head. I plowed ahead through the willows, skirting the water as best I could by basically tromping on and through the branches. I almost sunk my boots once or twice, but the willows actually held much better than I though, and those dams are actually pretty strong. I guess that makes sense – if they can hold thousands of pounds of water back, several feet above the original water line, they can support an extra 180-200 pounds pretty easily.

And I made it. But the whole way back after that, as the sun sunk behind the mountains, I struggled to understand what had just happened. I really thought I had had God’s favor, up until that crossing. And oddly enough…I still had. I made it across. I wasn’t even wet from the experience. And putting my rain jacket on helped keep my skin from getting scratched to hell. Putting the binoculars away meant less to get tangled up in all that. But what did it mean? Had God really brought me to that point? Had I made it up in my head?

And I just couldn’t help but maybe wonder if it was a taste of things to come. Not for the sake of dreading the future (which can sometimes harbor pain and struggle), but for the sake of saying, “The path won’t always be clear, but that doesn’t mean you won’t make it through”. And I don’t want to over-spiritualize things; I know I try to look for lessons in everything, and those lessons aren’t always lessons from God (sometimes things just happen, there doesn’t have to be some divine purpose to everything, despite the modern church often claiming this), but this one was weird. Very weird. It still makes me uncomfortable. I guess if I had stopped to think about how strong those dams must be, I might have put a bit more trust in them, though to be fair, the general area was still super sketchy.

How am I going to pull this career shift off? I have no idea. But I do know where I have to go. I may just have to push through, and maybe the path is more solid than I think.