How The Heck Did I Get Here?

It seems like a lifetime ago, but I started my first technology job in August of 2020. At the time, my goal was very straightforward. My wife and I were fairly newly married and we had an infant child. I was working as a machinist (which can actually be pretty cool), but wasn’t making near enough to support my family. So the first order of business was to get our financial legs under us.

From there, things went in directions that I never expected and that I didn’t think was realistic at times. That first technology job was part-time in a NOC at a local dotcom. I got hired full-time fairly quickly and become a junior systems administrator. Since then I’ve had the following roles:

  • Systems Administrator
  • Security Engineer
  • Instructor
  • Penetration Tester
  • Podcaster
  • Threat Hunter
  • Security Researcher

Over this time, I’ve had the chance to learn a lot of lessons. Some where easier than others, but they were usually valuable. Many lessons came in the form of horrifying experiences that I chose to learn from and resolving to try to do better next time. Most are much more positive and have huge impacts on the opportunities that have come my way. Here are a few.

Make Friends

I have been extremely fortunate to make friends with some brilliant people. These people amaze me with what they know and are able to do. For some reason, they seem to like having me work with them. They have invited me into projects and jobs that have been incredible opportunities. These invitations may have come years after I met them.

So make friends and keep in touch. You get to work with people that you enjoy being with and they help you grow beyond your expectations. This is probably the most important lesson I’ve learned.

Get Good at Communication

I can be a technical master in my area of expertise and I would always be able find work because of this. But if I could not communicate with others, then my career would have had an hard limit on it. Communicating with others effectively is definitely a skill that needs constant work. There are three skills that we need to develop; listening, speaking, and writing.


Listening is first because it’s the hardest for me. I have to shut up and focus on what someone else is saying. What do they want me to understand? Where are they coming from and what are their needs? It’s so tempting to just sit there waiting until I can start talking again, but I’ve been working hard at developing this skill.


Next is speaking. This one can take a variety of forms. If I’m trying to persuade someone of something, I better know what my message is. Except in rare situations, we all talk to others regularly. I decided to take this one up a notch and started submitting proposals to speak at conferences. Candidly, I stumbled into this. I wanted to go to a local tech conference and we were too broke for me to spend the money on the ticket. I saw that speakers get a free ticket, so I kicked around some ideas, submitted an idea for a presentation, and it was accepted! My presentation was on building an open source security tool kit. It wasn’t that I was an expert, but I was willing to share what I had learned. And it was fun!

If you are willing to put yourself out there, I strongly recommend speaking at conferences. You learn a TON in the preparation. Then when you are in front of the room, you have an immediate place of authority. Everyone in the room is there because they want to hear what you have to say and they want you to succeed at it. Because of this, you get recognized publicly and have more credibility than your resume can communicate on it’s own. So speak at conferences.


Finally, I recommend practicing at your writing skills. We rely heavily on this in technology, particularly since many of us are inclined to be introverted. Writing is a “safe” way of engaging with others. Or at least we feel safer doing it. I’ve had to do a ton of writing in penetration testing reports, company blog posts, and even high impact public reports. It’s not always enjoyable, but it has made a difference for me and those I know.

Writing is another really valuable skill to have in your tool kit. On my last team I was interviewing someone for a senior role on the team. We talked about something that the person wasn’t really familiar with. I got an email the next Monday. They had spent time researching the topic, wrote up an excellent blog post on it, and made sure to share it with me. I pointed this out to my manager and the person had an offer the next day!

Learn to Learn

The need to learn new things is probably obvious to most folks in technology, but I wanted to mention it as a final lesson I’ve learned. The skills I needed to get my first job have a limited impact on my life today. There’s not much Windows NT4 or Windows 2000 out there any longer. My interests have changed a lot too. Fortunately, I find learning new things a bit rejuvenating and that has opened up opportunities that I can’t believe I’ve had. My current position is a bit of a dream job and is one that I never could have seen coming. Similar things can happen to us, but only if we do the work and learn the new stuff that’s developing around us. Have fun with it and learn how to learn new things!