From the classroom to tech.

Before tech

I studied political science and Spanish at the University of Wisconsin-Madison, but I didn't have my career mapped out. I worked at a bank, then spent four years teaching Spanish and coaching cross-country and soccer. I loved teaching and coaching, but I was still figuring out where I wanted to go.

I also built Idiomas con Jake, sharing language lessons on YouTube, TikTok, and Instagram. The channels grew, but the moments that really mattered were the live streams with a hundred people watching and the online classes full of people who wanted help learning English. Something I'd made was becoming useful to people beyond my classroom.

I wanted to keep building, keep learning, and create more opportunities for myself. Tech had always interested me. Eventually, I decided to stop wondering about it and make the move.

Starting over in IT

I earned my A+, Network+, and Security+ certifications and landed a tier 1 support job. My days became a mix of phone calls, password resets, offline devices, phishing emails, and VPN troubleshooting. Almost everything was new.

The certifications helped me get started, but they hadn't prepared me for all of the actual work. I didn't even really understand what a domain was yet. Going from teaching a subject I knew to learning the basics of a new profession was humbling.

I threw myself into it. For months, I took on more tickets, worked long hours, and deliberately put myself in situations I didn't know how to handle yet. It was uncomfortable, but the gap between passing an exam and doing the job began to close.

Four months in

A system administrator position opened up just four months after I started. I went for it, even though I didn't feel ready. At first, I was told I hadn't gotten the job. That weekend, I earned my CCNA and posted it on LinkedIn. The hiring managers noticed. On Monday, they told me the position was mine.

I can't say whether the CCNA changed the decision. I do know that I'd given the interview everything I had, and I was ecstatic to get the opportunity.

On my first day, my mentor recommended me for a priority 1 ticket. A bank was dealing with persistent slowness and dropped sessions in its core software. What started that day turned into weeks of troubleshooting with our senior network engineer, engineers on the vendor side, and the bank itself.

I found myself leading meetings with people I didn't feel qualified to lead. I was scared, and the imposter syndrome was very real. We eventually got the issue resolved together. The praise felt good, but the bigger thing was coming out of that experience feeling like I belonged in the role.

Learning in public

I'd started Jake's Tech Journey back when I was new to IT, with a few day-in-the-life videos. About a year later, while I was working as a sysadmin, one of those videos was still picking up a few hundred views a week. It made me take the channel seriously.

I decided to go all in on documenting the journey. I made videos about real tickets, the tools I was using, certifications I'd taken, and the things I was figuring out at work. That grew into career advice, interview preparation, resume help, and well over a hundred videos.

Teaching had found its way back into my work. This time, the lessons came from the problems I was solving and the career I was still building myself.

A new kind of teaching

Those videos led to an opportunity I hadn't planned on. My now-boss at Infisical reached out after seeing me explain real IT work online. He thought I'd be a good fit for developer advocacy.

The role brought me into a software startup working on infrastructure security. Infisical's work spans secrets, certificates, and privileged access management, and I've been able to go deeper into both infrastructure and AI agent security. It's given me more to learn, build, and teach.

In my first few weeks at Infisical, learning Kubernetes put me back in that uncomfortable beginner's seat. It was difficult, but it helped connect things I'd been trying to understand: distributed systems, how software is built and deployed, and the software development lifecycle. Working through Kubernetes secrets brought the security side into focus, too.

I wasn't just learning another tool. I was starting to understand how the pieces of a software system fit together. That early learning curve gave me a much stronger foundation for the work ahead.

What keeps me curious

Lately, I've been digging into how AI agents actually work: their harnesses and sandboxes, the boundaries around what they can access, and how companies put them to use. One area I've spent a lot of time on is credential brokering through an HTTP proxy.

That work took me to PlatformCon in New York City, where I gave a talk about Agent Vault, an open-source credential broker. I got to go deep on how it works and how it can run in high availability. Exploring something this new has been a lot of fun.

That's what I love about tech. There's always another problem to understand or something new to build. I don't share the doom and gloom about this career. Starting over was hard, and there have been plenty of moments when I felt out of my depth, but I'm genuinely excited about the work. I want other people to see that side of it, too.