How to become a systems administrator

Introduction

I feel lucky to be a systems administrator. There are so many ways that I could have ended up in a job that I dislike, or that doesn’t pay well, or that compromise my mental health. I didn’t know I wanted to be a systems administrator until I was 32 years old. In my teens and my twenties, I shared the generational struggle with life choices. I tried lots of different things, changed industry and career paths several times. At some points, I seriously considered becoming an airline pilot, an artist, a mailman and a fireman.

Most professions have college programs, but systems administration is not really taught in schools, and it wasn’t on a list of career options advertised in high school. Systems administrators are usually self-taught. They came into the IT industry by learning and doing something else first, usually programming, web design or technical support. It can be a very rewarding and satisfying job for people with the creative intellectual and a bit neurotic personality type.

In this story, I share my process and difficulties with figuring out what I wanted to do in life. Then I share all the strategies used and actions I took to teach myself, get help, get hired and grow as a systems administrator.

Part 1: What do I want to do?

Brief job and education history

Here’s a quick recap of my jobs and education since graduating from high school. Notice how often I changed field and career paths before finding my place in IT! You can speed read only the emphasized words to get the gist of my jobs history and areas of activity.

• 🧑‍🎓 I studied Aircraft piloting at the Centre Québécois de Formation Aéronotique.
• ✈️ Changed my mind about piloting, became Flight Attendant for Jetsgo Airlines.
• 🧑‍🎓 I did a second college degree in Visual Arts.
• 🧰 Salesperson at IKEA.
• 🚒 I tried four times to get in fire fighting school but didn’t pass the physical and psychometric admission tests.
• 🏦 I had several jobs at a canadian bank call centre:
  • 📞 General information, banking and customer support.
  • 💳 Credit cards adviser.
  • 💰 Financial adviser in credit and investment.
  • 📈 I took part in a process improvement mission ("kaizen").
  • 🔢 Workforce management.
  • 👨‍💻⁰ Internal helpdesk (my first IT job!).
• 🧑‍🎓 Undergrad certificate in Applied Information Technology.
• At iWeb Technologies, a Montreal based infrastructure services company:
  • 👨‍💻¹ Tier 1 Technical Support Agent.
  • 👨‍💻² Tier 2 Systems Administrator.
  • 👨‍💻³ Tier 3 Systems Administrator.
• At Grafana Labs:
  • 👨‍💻⁴ Senior Support Engineer.
  • 👨‍💻⁵ Solutions Artchitect.

My point here is that it’s okay to change your mind and to try several things before you discover what you want to do. Time spent trying things is not wasted time. Everything I did before becoming a systems administrator constitute a unique set of experiences and skills that nobody else has.

Dismissing a career in IT for a decade

As far back as I can remember, I’ve been interested in computers. As a kid, I learned programming on an i486 with Quick Basic and DOS. My first Linux system was Red Hat Linux 6.2. I use the web creatively since the Geocities ages.

Despite having projects and hobbies involving computers, software and operating systems, I never considered getting an IT job until my 30’s. There are two personal experiences that delayed my interest in pursuing a career in IT.

First, I had lots of exposure to the aviation industry at a young age. My mother was a flight attendant for Air Canada. I was very privileged to have flown many times on the jumpseat of airliner cockpits. Aircraft piloting was one of my top career choices in high school.

Second, I was at a college open house day, during high school. I checked out the Computer Science program. In the computer lab, there were workstations along walls and around a central table. The room was full of young intellectual introverts. I found myself questioning their clothing style and social skills. The presenter was a male teacher, with a pony tail, an ill-fitted shirt, low energy and a monotonous voice. I remember feeling boredom at the demonstration of last year’s graduate students project: a commerce data processing program made with Microsoft Visual Studio. Overall, I didn’t like what I saw in the people and in the learning activities. I was looking for something fun, more colourful and meaningful. So I turned my back to IT as a career option for about a decade.

It’s really hard to make a career prediction at a 15 years old.

Discovering purpose and direction

When I was working at the Laurentian Bank call centre, I got frustrated with repetitive tasks on the computer. We used over ten systems didn’t communicate with each other. It required lots of clicking, typing, copy-pasting and editing. So over several months, I wrote a set of scripts with AutoHotKey to automate complex operations and add some “glue” between applications.

I shared my rogue programs with my colleagues at the call centre. I called them the “Power Tools”. A fanbase began to form. It had a profound impact on people’s perception of their work. It freed their mind to interact more naturally and meaningfully with customers. However, this whole initiative was a risky move. I could have been fired for it. Over almost a year, it grew to a point where it stirred a bit of drama with my management and corporate TI governance people. But in the end, the tool was so good and it made people so much more efficient that the management kept a simplified version of it as a standard tool in the department, and I continued to maintain the Power Tools for a little bit until I moved on to another job.

By relieving my own suffering through automation and by sharing my tools with others, I discovered deep meaning and motivation in writing programs and improving user experience. A colleague suggested that I should do programming as a job. And this time, it made sense. This proposition was at the intersection of something I like, something I’m good at, and something other people need. I found deep meaning in pursuing a career in information technology.

Part 2: Finding the path within the space.

My adventure into IT started with a question, a decision, a vague sense of direction. It took a few months before I had a plan. Progress was imperceptible at first. It felt overwhelming just to figure out where I would fit and be happy. There are literally hundreds of different job types and work environment in IT.

Wishing to investigate your desire to work in IT is a step towards finding a job that “works for you”, but at once it just raises countless questions. As I carried on with my exploration of the IT industry, I found many actions that one can take at this stage in their process. There is an abundance of free resources that can really help a motivated self-learner. Sometimes all you need to get started is advice, inspiration, and a little bit of guidance. The following part of this story is my attempt to share what I’ve learned and what worked for me, in the hope that it can be useful to some readers out there.

Action plan

From this point forward, I share some of the actions I took to find my way into the world of information technology.

• I interviewed people.
• I did some research.
• I enrolled for an undergrad IT program at a remote learning university.
• I learned through personal projects.
• I read books.
• I learned social skills.
• I socialized at meetups.
• I applied for jobs.

After a bit of research, interviewing people, balancing risk, time investment, evaluating my skills and ability to learn, I estimated a timeline of 1 to 2 years to get a first job and 3 to 4 years to get a good job.

Interview people

One of the first things I did was to take people out for a coffee or lunch and ask them to talk about their job.

Here are some questions that I asked:

• What was your career path?
• Where did you study?
• How would you describe your job?
• What do you like and don’t like about it?
• What would you say is a difficult but rewarding part of the job?
• What kind of projects do you work on?
• What does your typical day look like?
• What are are other IT jobs like?
• What do you recommend for people wanting to work in IT?

Research on the internet

I found Eli the Computer Guy on YouTube very interesting. He produced an enormous amount of videos and the style and topics evolved over time, covering many aspects of growing as an IT professional. He also discusses in long form (60 to 120 minutes), which is great when you are thirsty for information.

I watched hacking and programming video channels. Hak5 with Darren Kitchen and Shannon Morse was one of my favorite channels.

In another post, I curated a list of resources for learning Linux, Python and Bash. It is a bit dated (2014) and in french, but the linked resources are in english. See: Liens pour apprendre GNU/Linux, Python et Bash

In 2021, I suggest these for starting points:

• The awesome list of awesome lists.
• Reddit communities: r/selfhosted and r/sysadmin.

Remember this, all IT jobs are 30% knowledge and 70% googling it.

Enrol for education/training

Lots of successful people in IT have a degree in Computer Science. That’s a valid choice, but I didn’t have much time. In IT, a degree is relatively unimportant. The technology and methodologies evolve so often that the half-life of a Computer Science degree is very short. That is to say, that the number of years spent studying computer science is worth less than the same amount of field experience.

An exception to this rule is if you are extremely smart, and your personality is fit for academia (which is very unlikely given how hostile to humans academia can be), and you want to pursue a PHD and get an elite job at Google or NASA. Only then academic achievements and education are kind of relevant.

Also consider that for many IT jobs, there are no available university courses. You learn them through books, manuals, lab projects, documentation, Wikipedia, on the field, or via professional accreditation from private institutions and companies.

I didn’t enjoy my IT courses, and I hardly even mention it during job interviews. I didn’t even finish half of it before getting my first IT jobs. But doing it kept me focused and accountable, as I finished it for my own ego satisfaction.

In contrast, certifications from IT companies (like LPIC and RHCSA) are a better investment. They are more up-to-date, and they verify skills that are more relevant to the jobs on the market right now.

Learn by doing

I learned a lot through configuring my own systems and working on personal projects.

• I built my PC from parts on NewEgg and installed Arch Linux.
  • I learned about all the components of an operating system by being very hands-on with the configuration.
  • I did all my file management and editing on the command line and wrote shell scripts to automate my repetitive tasks.
• I wrote a few programs as personal projects:
  • A backup script in Bash (later rewritten in Python) to make rsync backups with hardlinked snapshots (adeverteuil/backup).
  • A pong game in C using SDL (adeverteuil/pong).
  • A video editor in Python that uses ffmpeg subprocesses to demux, concatenate, mix and re-encode video sequences from instructions in YAML format (adeverteuil/vid).
  • A personal inventory management system (web-based, Django).
  • A basic blog engine in Python with the Django framework.
• I challenged myself with coding projects I found online:
  • Project Euler.
  • Linux From Scratch.
  • CipherSaber (Wikipedia page).
  • The Cryptopals Crypto Challenges.

Be public about your learning process by blogging about it and sharing your code on GitHub. When you don’t yet have past relevant job experience and social validation, your online presence can be a tangible proof of your technical and self-teaching mindset, your ability to organize information and to communicate clearly. Plus, it can’t hurt you to learn how to maintain a blog and how to write.

Learn by reading books

Blog articles and manual pages are nice, but there is nothing like an expert sharing everything they know about a complex topic in a traditional book format.

Here are some books I read:

• Python the Hard Way.
• Data Structures and Algorithms with Python.
• The Practice of System and Network Administration, Volume 1: DevOps and other Best Practices for Enterprise IT.
• The Practice of Cloud System Administration, Volume 2: DevOps and SRE Practices for Web Services.

I also practised reading out loud some documentation and data science books in English in preparation for future interviews.

Learn social skills

Many blogs and podcasts cover topics of negotiation, emotional intelligence, communication, career, entrepreneurship and human relationships. I believe that blogs and podcasts are the best and fastest way to learn a wide range of soft skills.

I read and listened to The Art of Manliness blog and podcast for about 10 years around 2008–2018. But there is no need to be limited to just one or a few channels. See Informal learning with podcasts on tools I use now (2021).

Get an entry level job

There are a few typical entry-level IT jobs which require minimal skills. They are: helpdesk, web hosting support, technical support, webmaster, web designer.

You can find loads of free courses on full-stack web app development. I didn’t feel like doing that because I tried web designed and hated it. It’s tedious, I don’t have a designer mindset, the popular tech stack changes all the time. But some people are clearly passionate and talented for it.

I was working at the Laurentian Bank so I applied for a helpdesk position as my first step. It was in a different office, further away from my home. I had to take two trains and a bus to get there. The commute was 1 hour 15 minutes. The office space was grey, with cheap boring landscape art frames on the walls. I may have been the youngest person on the office floor. Most people were middle-aged, content with a unionized office job that would care for them for the rest of their lives.

My first job wasn’t fun: resetting passwords, troubleshooting printers, dying slowly of boredom. But that’s okay, it was a transition plan. I had lots of time between incoming support calls. I used this time to read, learn, code, practice.

Go to meetups and socialize

Every city has meetups you can go for free. Usually, they even have sponsors, beer and pizza. I attended Montreal Python meetups. I also found an open-source development company Savoir-Faire Linux and joined their free seminars to meet with their employees and customers, and learn some open-source business software.

Hacker labs are a good place to meet people who work on all sorts of different cool projects and who work in various tech jobs. I went to open doors evenings at local hackerlab Foulab.

Apply for jobs

I had been working at the helpdesk for five or six months, I was almost halfway through my Applied IT certificate, I had a few LinkedIn contacts with various IT jobs, and I had a few projects published on my GitHub account. It was time to start applying for jobs.

At the time, I thought I wanted to be a software developer. By my estimate, I had learned enough Python to have a 50/50 chance of passing a technical interview.

I applied at Savoir-Faire Linux, but I was rejected. Then I applied at Ecometrica, and I was rejected a second time. Both employers told me I was a bit too junior for the software developer role I applied for.

An acquaintance was working at a infrastructure services company nearby as a software developer. I contacted him and decided to apply for the Tier 1 Technical Support position. All of my practice on Linux servers really shined through during the interview. I was hired the next day.

Becoming a Systems Administrator

Naturally, my career plan became more precise after working entry-level jobs for a couple of years. It turns out software development is too specific, quiet, and isolated from other people. I am more attracted to operations and customer relations. I find a sense of pleasure when managing complex interconnected systems, keeping track of hundreds of variables changing constantly. I love working with business customers, network engineers, software developers and other systems administrators. I love that doing systems administration is at the intersection of technical, business and people skills.

I also learned that I am happiest in a small team, at a young company, with a colourful and cozy culture. I enjoyed this at iWeb. I am so fortunate to find this at Grafana Labs right now. I will look for similar values in my next career moves as well.

For final advice and words of encouragement: follow your curiosity, go interact with people, and stay open to seize fun looking opportunities.