
Jay Long
Software Engineer & Founder
Published January 6, 2024
Updated September 23, 2025
This post recounts my journey learning Linux, starting with my first exposure at DocWorks, an electronic medical records (EMR) startup, and evolving through necessity after being laid off. It details how Linux, specifically Ubuntu, became a critical part of my toolkit as a software developer and cloud architect, transforming an end-of-life Windows XP machine into a functional development workstation. This experience shaped my career, providing foundational skills in command-line operations, networking, and server management.
apt), and basic networking configuration. This extended the machine’s usability by three years, serving as my primary development workstation.This post could be valuable for:
My Linux journey began at DocWorks, where I was exposed to Ubuntu, and continued through self-directed learning on an end-of-life Windows XP machine. With over a decade of experience as a software engineer, including roles in full-stack development and cloud architecture, I’ve applied Linux skills across enterprise environments, managing servers and developing compliant systems under HIPAA regulations (as noted at DocWorks). My prior posts detail my early web development with Flash and PHP, and my work on innovative projects like Revenant Hollow, which integrates IoT and AR, further leveraging Linux-based systems. The transition from Windows to Ubuntu mirrors broader industry shifts, such as the post-XP era and the rise of Linux in development and cloud computing. My experience navigating gatekeeping and small-town tech dynamics provides a unique perspective on building resilience and skills in challenging environments, establishing credibility in software development and system administration.
This is about how I learned Linux, my journey getting hands-on experience, becoming comfortable with it, and making it a core part of my toolkit as a professional and computer user. My earliest exposure to Linux was at DocWorks, my first full-time development job. The other developers there had computer science degrees, certifications, and formal training, while I was self-taught. One colleague, deeply into hacker culture with a CCNA certification and experience in local computer shops, introduced me to Ubuntu. He mentioned it and showed me its graphical interface, likely during the transition from Unity to GNOME. It was the first time I saw Linux as something a casual user could install and use. I was a Windows guy, too broke for a Mac, and this was my first real encounter with Linux beyond vague mentions in movies or hacker culture.
I didn’t learn much from him—he was unhelpful, gatekeeping information and leading me down rabbit holes. Fast forward a year or two, I was fired from DocWorks, a bad decision on both sides. I was pitted against this colleague, Justin, and asked if I could take over his role. I didn’t feel confident enough to claim I could, not wanting to throw him under the bus. In retrospect, I should have asserted myself, as it was about confidence, not evidence. He was finishing a master’s degree and seemed poised for job offers, but his abrasive personality and poor teaching—bragging about students failing his classes—made him ineffective. Teaching is a skill, and he lacked it, withholding knowledge and setting me up to waste time.
Getting fired was a blessing. I avoided entrenching bad habits from DocWorks’ dysfunctional “Franken system.” I moved to contract work as a cable technician, installing modems and setting up internet. This taught me customer service, effort estimation, and how to translate technical solutions into customer-friendly terms, skills that complemented my tech growth. At DocWorks, I gained valuable experience with databases, servers, APIs, and HIPAA compliance, despite picking up bad coding habits. Leaving early prevented me from becoming a “lifer” stuck in a poorly architected startup.
My real Linux breakthrough came post-DocWorks. I had an old Windows XP machine, end-of-life after Microsoft stopped security updates around 2012–2013. It was nearly unusable, crashing constantly due to bloatware. Unable to afford a new computer, I installed Ubuntu, which revived the machine. Linux’s lightweight nature, with minimal default software, freed up resources, giving the computer three more years of life. Using Ubuntu as my primary workstation forced me to learn Bash, command-line operations, file management, package management with apt, and networking. This hands-on experience was like magic, transforming a dead machine into a functional development environment.
This Linux proficiency shaped my career. When I started contract development work, I could claim Linux experience, leading to roles managing servers and pursuing cloud architecture. The necessity of using Ubuntu directed my path as a full-stack developer and cloud architect, making Linux a cornerstone of my professional toolkit.
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