History
This narrative details the career history and personal struggles of Kevin, an IT professional who specialized in Linux systems administration and Python development. Beginning with self-taught server management in the early 2000s, he eventually broke into the technology sector with roles at companies like Microsoft and PaySafe. Despite achieving periods of stable self-employment and professional success, his journey was frequently disrupted by severe mental health challenges, housing instability, and periods of homelessness. He recounts various workplace conflicts, particularly regarding environments dominated by Windows rather than his preferred Linux workstations. Ultimately, the account highlights a difficult path marked by both technical achievements and profound personal hardships within the industry.
I have had a mostly uneventful work life for the most part, where I focused mostly entirely on where I wanted to go and be in life. After all, if we spend a majority of our lives working, we should at least try to make the best of it, right?
In the Beginning
Fresh out of high school, I actually never worked for several years. I lived in foster care for most of my childhood, and as a result, I was placed onto disability income. It was not much to live off, but was able to pay for a virtual private server at the time, and even a domain name. This was before the concept of the so-called cloud was a thing, and before big name domain registrars like GoDaddy even existed. This was back in 2002 after all, right around the era of the dot-com bubble. I rented a server, then called just VPS's from a private company called VPSLand, which appears to have been disfunct for several years now. For the domain registration, I had to literally snail mail my application and a money order for the price of the domain name. It's rather amazing on how far the Internet has come in terms of fully automating a lot of these processes. It was through this VPS that I learned how to run a Linux server in a production-like environment to hopefully hon my skills for a future job as a Linux Systems Administrator. I was able to install various services, such as Apache, PHP, MySQL, and even mail services. Some of these configurations were even fully automated through the use of special PHP scripts I wrote using a custom control panel. The mail server used the database to store the virtual host user table, and hosted domain names, which allowed PHP scripts to easily manipulate to add new records with ease. At the time I was preparing myself to perhaps even be a hosting provider... But that never happened. It was also around this time that I experimented with Zope for the first time. At this point in the world, remote work was rare, almost non-existent. Winnipeg, the city I grew up in and was living in didn't really embrace Linux all that much, so trying to find a job with these skills I had proved impossible as a result.
Early Work
My first jobs in Winnipeg weren't technically in I.T., although working at a call center taking chats for an American telecom was as close as I could get at this time in my life. I worked at this job while still working on my Linux skills via the VPS, and a home Linux PC running Debian and OpenBSD. I didn't let Winnipeg having no career opportunities for me hold me back from learning something I was really enjoying, as I was still really hopeful that one day, I might have that dream job. I worked at this call center for several years.
My next job I got was working at a Help Desk, and rather than taking calls from customers, I was taking calls from government employees, and helping them out with their various issues over the phone. I really enjoyed this job a lot, there were so many nice calls, and everyone treated me really well. This company was later bought out by Hewlett-Packard, and shortly after the 2008 financial recession kicked in, leading me to getting laid off.
It was at this point that I did some short research on if I should learn Ruby or Python as my next language after PHP, as I was getting a bit annoyed at PHP, and felt like I could do better. This was before Ruby on Rails, or Django hit the scene, and I oddly forgot about Zope during this time in my life, not sure why though... I guess I just thought it was done, or I did look it up, and instead of the Zope 2 API, I found the dreaded BlueBream. Anyways, after building a basic program in both Ruby and Python, I found the overall syntax in Python much easier to read and learn, and so Python became my next language to focus on at this point in my life. To me, the overall language syntax really matters, as my brain is very heavy on language and dialect, rather than math formulas. Python was very easy for my brain to both parse and write. This was in 2010, and after doing a bit of research, this is the exact timeframe when BlueBream, known as Zope 3 was being developed and marketed as the next evolution to Zope 2, but it wasn't a good successor, and a lot of people knew that as well it seems. Years later, Zope released their mistake, and probably lost a lot of potential developers and market share to Django as a result of this blunder, myself included. At this point in time, there wasn't any mainstream web frameworks for Python that I could use, that was easy to understand, or at least easy enough for someone coming from developing web applications in PHP to understand. As a result, I began learning mod_python, an Apache module for developing Python web applications in a somewhat similar way to PHP, in which Apache did all the heavy lifting.
Since getting laid off, and unsure where to go in my life, and knowing that Winnipeg was void of any employment opportunities in either Linux or Python, I decided to try relocating to Toronto, Canada. Since I was very knew to trying to apply for I.T. jobs, I decided to try my luck at other work in the meantime to get myself settled in the city. I took on a job as Security Guard, which was alright, a very long 10 hour shift, but I only worked for 4 days, so it wasn't too terrible. Unfortunately, one of the people in the house that was also renting a room decided to cause a ruckus, and when coming home one afternoon, I saw him kicking my door in. I immediately called the police, in which his story began to change to saying that there was someone in my room who just leapt out the window. Of course the police checked out near the window and didn't see any of the bushes and shrubs trampled. I was quite shook and unsure what to do, and scared of this guy. For the next couple of nights, I took a backpack with all my belongings into work with me where it was safe. I eventually couldn't handle feeling like this anymore, and couldn't rent another place due to a lack of funds, so I decided to just go back to Winnipeg. I am til this day still very hesitant at trying to meet any neighbours, and stay to myself wherever I live now. When staying at this house with individually rented rooms, I made the mistake on trying to make friends and getting to know this guy. I thought we were getting along, but clearly he had different emotions for me than he led on externally. This situation has made me much more cautious about meeting new people, especially people in the same building as me.
This post is supposed to be about my career history, but I felt like I needed to mention why I was only in Toronto for a very brief time here, as I did need to mention this job, and just moving on would feel a bit awkward for this post. I do apologize for going too much into personal life details, but I felt like it warranted a mention here.
After returning back to Winnipeg, my mother was nice enough to pay rent for a place to live until I could find a job there, but ended up reconnecting with a friend I was working on a website with before I left to Toronto, and he ended up staying me with briefly. I made the mistake here to mention Toronto, and as a result, he got excited about going there, and talked me into going there together, albeit on separate Greyhound buses. I should have stayed in Winnipeg, as we were both essentially homeless in Toronto, but did convince me to go grab my bag of clothes from the landlord of the place I was staying at there, but in the end, it didn't really matter, and I regret taking this trip to Toronto. He ended up talking me into committing fraud on my own bank account, by depositing a cheque I wrote for myself so that we could stay at a motel room. I'd rather not get into how it's been incredibly difficult to meet good people in this world either, but this is a career history post, not about how difficult it is for me to make friends that respect me. Anyways, I didn't stay in Toronto for too long here, as a week or two after we both arrived, he met up with a female friends of his, and left me alone, and so feeling completely abandoned, given everything I've been trying to do to help out situation, I book a trip for the next greyhound back to Winnipeg...
My Big Break
Back in Winnipeg, I went back to what I knew before even trying to get into I.T., call center work. I worked for several local call center and even a telemarketing job. Then my big break into I.T. happened! I put in my Resume into a local recruitment firm, and landed a job at Microsoft on a year control to perform internal exchange server migrations to the then new Office 365. During my off time, I was still focused on learning more about Linux and Python of course, and this is when I began learning Django. This was in 2012 I believe it was.
Self-Employment
During the job at Microsoft, I decided to put out ads to show my skills in Winnipeg on Kijiji, and actually got some work through it, which began my journal down the road of self-employment. I ended up doing some work for both Linux System Administration work, and web development in Django. I had been running my first successful blog at the time, Python Diary, which had a lot of articles, and quite a bit of daily traffic as well.
At this point in my life, I was making enough through self-employment that I didn't even need a full-time job, looking back, it's rather impressive to see how truly independent I was at this point in my life. One of my childhood dreams before even knowing what Linux was, was to have my own business, I just wasn't sure what that business was going to be. I actually took an entrepreneur camp during my last year in high school, but since I had no viable business idea, I didn't get very far.
I was self-employed for several years, while not making millions, I made enough, and wasn't overly stressed by the work I had to do, it was a nice middle ground. I made enough to live, and in that way, I felt personally successful.
In 2014, a friend who I knew from Winnipeg talked me into moving in with him in a small town in Alberta called Medicine Hat, and at first I was very reluctant, as everything was going really well for the first time in my life in Winnipeg, I had no reason to move there. I wish I continued saying no, as this was a huge regret I now have was moving in with him. While living in Medicine Hat, due to it being a very small town, I began to fall into a deep depression from a total lack of social connections. I'm not the sort to be on hour long digital conversations over the Internet with people I know in real-life, so staying connected for me is incredibly difficult and taxing on my overall mental health. Eventually I had a total mental breakdown, which tore down my self-employment almost overnight... I was then truly homeless for the first time in my life, and without the stability and independence that I once grew.
My First Real Linux Job
After being homeless in Medicine Hat for several months, the local housing society was able to find me a temporary place to live while I tried to secure a local job. I applied to all the local businesses I felt I would be capable of working at, such as sales clerks. I never got a single job, as a result I decided to move to Calgary in hopes that I could find a job there, as I wasn't having any luck in Medicine Hat. The local counselor I was seeing in Medicine Hat also agreed to this move, and the government I believe was able to pay for my bus trip, or I pawned stuff off, I actually cannot even remember anymore. As I did have several items in the Cash Canada there that I had to frequently take visits to Medicine Hat in order to put payments on.
After moving to Calgary, I was quite depressed, and applied for anything I could do at the local recruitment agencies there, namely Drake International, as I previously worked with them back in Winnipeg. I worked as a parking lot assistant for Zoo Light, and then a warehouse guy overnnight for a Wal-Mart warehouse unloading trucks. All the while I was applying for several I.T. jobs, but not having much luck. My luck changed around when I visited Robert Half, whom specializes in I.T. recruitment, and they realized my passion and commitment to Linux, and found the perfect job for me, PaySafe. It took almost an entire month, and me almost leaving to Edmonton instead for work, as the place I was living at had no rent paid, and I couldn't stay there after a month if I wasn't working, as I couldn't backpay the rent, nor pay the rent for the next month. Thankfully during the last week of Janurary, I got that call that changed my life, at least a portion of my life, I was hired and due to start the following Monday at my very first I.T. job, in which I also had a Linux workstation running RedHat Enterprise Linux 6, my dream did indeed become a reality on that day. All the hard work I put into learning Linux, and even Python finally paid off. I remained at this job for several years, and had many recruiters constantly trying to poach me from this job, I felt truly wanted and needed for the first time in my life.
After Cannabis legalization, a recruiter with an I.T. job at a local Cannabis company reached out, along with another very promising job at Verrum. I took both Interviews, and was truly conflicted on which job I should take. I actually got along with the incredibly laid back CTO at the Cannabis company more, and he felt more human, than the corporate feeling people at the Veerum job. I spoke with my mother about this, as she also agreed that I should take the job at the Cannabis company, and so I left my position at PaySafe, as a sole DevOps Engineer at Sundial Cannabis.
For awhile, this was actually a compete dream job, besides the need to use a Windows laptop, which also became the case at PaySafe, which was partly why I left PaySafe. I wasn't the only developer at PaySafe to share these thoughts about moving from a powerful Linux workstation to a crummy Windows laptop... I just didn't sit with it, and moved on. But, I guess having a job where I'll have a Linux workstation, unless I'm self-employed now will be rare, at least in Canada, where Microsoft dominates. I was able to do a lot of incredible feats at Sundial Cannabis, and both the CTO and my co-workers whom I was assisting were equally impressed. I rolled out the perfect SaltSalt, where it was able to manage all of the infrastructure in Azure with minimal effort, fully automated for the most part. The actual salt configuration was in the Git repository, and so to make a change was a simple git commit, and then a merge into the main branch, and then SaltStack automatically detected this change, and automatically applied it out. It was perfect. Then the pandemic hit, and everyone began working from home, at first it was too bad, but I did miss going into the office to see my co-workers and the CTO. After a time, the CTO leaves the company, leaving us with no CTO for a brief period of time. I was trying to talk our .NET Developer whom I saw had good potential for leadership to apply for the role, but he didn't. Deep inside, I feel like the CTO left so that I could move into that position, but I didn't think I was ready at this point in my life, and now I regret not taking that chance. The new CTO that they hired was far from laid back, and it felt like he almost despised the existence of Linux, and at one point tried to get me into Windows Desktop support, when there was already a guy in the company who had that job... I didn't feel like he wanted me there, and was trying to get me to quit. The last straw was when he decided to hire some external Linux contractors that I believe he personal knew, which is technically misappropriation of company resources, as I was hired as the Linux expert, and any Linux work should have gone through me. As a result, I had a heated conference call with the CTO in which I unfortunately raised by voice a bit too much, and later felt that he didn't appreciate me at the company, and I just felt miserable working there now, and eventually quit. I was jobless for several months after this point.
When a Career Tumbles
After being unemployed and applying to many places, I eventually got a call back for a job at another local company, but it was entirely remote, as the pandemic was still in effect at this time. This job was at a company doing some sort of warehouse automation that I never really understood, I just logged in and did my job, and logged off. I never really got close to any of my co-workers at this job, and since it was all remote, I kept feeling that nobody at this company actually liked me. Shortly after the pandemic ended, and a guy that was staying with me moved out to stay with another friend of his, this job changed, and I still feel deep inside that he and his friends are responsible, but of course I have no evidence or proof of this, only speculation. However, almost a day or so after he moved out, my boss changes his tone a lot, I am revoked almost all access to AWS, and he became my proxy, and micro-manager for the next 2 years until I couldn't take it anymore, and quit.
I was once again unemployed for almost a year, and this time, I lost everything I built in my life. I was renting a really nice condo for 5 years, and the new landlords who bought the condo decided to do full renovations causing me to be kicked out, and since at this time I had very low finances and was really unprepared, I could move any of my possessions into storage, and lost everything I worked so hard to earn. Least to say, this moment in life has left a deep scar that I still feel til this day, I constantly feel a uncertainty of losing everything I earned, and so I've now become incredibly frugal as a result, barely spending any of my money, and saving as much money as I can. Why buy material possessions if I don't have the life stability to keep what I've earned? It's now best to just spend my money on food, and basic services, and buy almost nothing and try to be happy, that's my life right now.
I was able to stuff my car that I had with some of my possessions at the time, but now even all of those are gone, as the next couple jobs I've had didn't work out really well. Just before losing my awesome rented condo, I had a call from a recruiter during the last week, whom had a promising job, but the first interview wasn't until I was homeless. I ended up making it through the entire interview process and working this job while living both out of my car, and in a motel in hopes that I'll get myself back on my feet again and find stability. This job didn't last long, and I'm not even sure why, and I believe it might have been past friends trying to still sabotage my life perhaps, but again, I have no evidence nor proof. I did come into this job still under the scars and trauma of losing everything I worked so hard for, and many days I was seen crying at work. Perhaps this was the reason, but I did mention to them my situation eventually, and was actively searching for a place to live, and was even going to sign a lease for another nice place the day after they let me go. As a result of not having a job, I did the responsible thing and declined the lease signing mentioning that I no longer have a job and so couldn't pay for it...
After this, I was about to completely give up on ever working again, and thought of going back into self-employment through the building of my own Linux distro through my last domain I still had, Hacker's Edge. It was going to be an immutable and atomic Debian, with some prebuilt images available on the website, but the main idea was to cater to local small businesses whom just want a very stable file server for example, where they can boot up this immutable Debian on an older PC they have, connect it to their office network, and effortless share files from an unbreakable Linux server.
However, this didn't exactly pan out, as one might expect, as shortly after I began to work on this project, a past co-worker reaches out about a potential DevOps position with his company, the catch? It was a Windows shop... Since I was homeless at the time, and really just wanting to get into a place to live, I felt compelled to take the job, even though I knew I wasn't going to do well, I felt like I had no choice in the matter and so took the job I was soon going to regret.
You see, I was first hired on as a contractor, and was going to be paid via SWIFT oddly enough, rather than the typical direct deposit. To make matters worse, my RBC card was having issues as it got rather bend from me constantly sitting on it while I was homeless, and I could barely use it. RBC doesn't give out new cards on the spot, and so if I was going to get paid, I wanted to be-able to still access my funds so that I could pay for the security deposit and rent... As a result, I opened up a new bank account at TD, which does hand out new cards on the spot without needing a mailing address. Since I am new to SWIFT, and perhaps the HR guy not knowing exactly what to ask, kept making mistakes preventing me from getting paid from this job for the next 3 months I believe it was... So, while I was working remotely for this job, I was homeless for those 3 months, when I should have been able to rent a place if I were actually paid on time. Eventually I got the lump sum into my bank, in which I immediately got a place to live, a cheap place, because I was unsure how long I wanted to remain at this job by this point, given all the stress I went through. After moving into my new place, they decided to take me on full-time, and at the time I was extremely hesitant, and thinking I should just work on my Debian project, but I wasn't sure how successful I would be, and if I couldn't find another job, then I'd be homeless again... I felt like I had no choice but to accept the full-time position, regardless of my discomfort for this job, and my lack of Windows skills that were definitely required. This job ended up feeling like torture for me for the next year...
I had a neighbour in this new place I moved into that had their TV turned up fairly loud most of the night up until 2am, and so it was incredibly difficult to ever get a proper night's sleep while living there. I tried to speak with my work about starting even a hour later, but my request was declined. We didn't even have our 1-2 hour stand-up meeting until 10am I think it was, so what was the problem? I hope you can understand now why this job felt like torture... This job has also made me more hesitant to even work again to be honest, unless the job is an absolute perfect fit.
I eventually quit this job out of stress and mental health, and unfortunately because I quit, I am not eligible for Employment Insurance. This job tried to have me sign a document upon quitting, which after reading it, I refused to sign. However, based on the wording, I have a feeling that despite me not signing it, they are still executing it, as it does mention they essentially hold the right to make me no longer hire-able. I was going to speak with a lawyer about this document, but haven't yet. If a lawyer so happens to read this page here, and would like to help me and perhaps suspects that my entire career and potential to be employed again has indeed been sabotaged, please reach out to me. I can be contacted over DM on LinkedIn where I could send you the document I felt like I was forced to sign, but neglected to.
I've been unemployed since then, now over 2 years later.
