Future
In this post I will go through various potential scenarios of the future of my work life, and why some of these pivots make sense.
I've been unemployed for over 2 years now. I've been living off a mixture of my savings from my last job, and more recently a tax refund. However, once these last bit of funds dissipate, where does that leave me? In this post, I will explore some of the potential future career ideas that I have.
DevOps Engineer or Related Work
This is what I have been aiming for again for the past couple of years most, applying for any position where my skills match nicely with the required qualifications. Despite all the resumes and applications I've filled out, and even upgrading my resume to be more AI friendly with these new ATS automated screening systems, I am still without work. While I'd still love to continue working in the industry and using a log of the skills I already have, it doesn't feel like I will have another DevOps role, or at least one that fits me well anytime soon. If you are a hiring manager, team lead, or CTO, and feel that my skills would be beneficial, then please reach out. I'll be adding a link to my LinkedIn on the careers drop-down after this post has been published, and I can be reached there over a DM, and my personal work history and background is also provided there.
Self-employment or Freelance Developer
If you've read through the career history page, you'll know that I was previously self-employed, and became rather successful at it, and feel that I could once again be successful at it. I will need to update this website a bit more with related information, and then of course advertise these skills through advertisements to get the ball rolling.
In terms of this, I'd be willing to do development and server management on a contract, self-employment, or freelance capacity. I have a lot of skills in Linux Systems Administration and troubleshooting. I actively use these skills day-to-day on both my own Linux servers, as well as on my local Linux laptop.
I will also be open to general web development in Python, either using a popular web framework such as Django, which I previously used, or in Plone, which is an enterprise grade CMS. I will be there to support both the initial planning, development, and the support.
Social Work
Due to my past, living in foster care, and going in and out of homelessness, trying to pivot into social work might be a decent career change. I've moved to a city in Canada that has a very large homeless population, and feel that there should be a lot of open positions for social work to be out on the streets to help these in need out. I'm not sure exactly what sort of qualifications I might need, or if my anxiety will make this sort of work difficult, but I am willing to at least give it a try. I like helping people, as proven from my DevOps positions, where I was one of the go-to guys in my team whenever a developer needed help with something, and I was always happy to help them.
Seeing a Career Counselor
I am planning on seeing a career counselor very soon, once all of my local identification has been established, I will qualify for their provincial career counselor and job matching services. There might have been some jobs I am unaware of out there that I could do, and a career counselor would know a lot more than I would. They would also know if getting into Social Work would work for me or not as well.
Game Development
Now we get into the more far fetched, and less likely to work out sections, or it's just my own self-doubt kicking in. Trying to get into the video game market is very difficult, even for indie games. There has been some success with new developers with zero other games in their catalog being wishlisted on Steam, namely this airplane game which reminds me of a few other games that are similar to it, but cannot recall the exact names right now. So, it doesn't feel impossible, but the game needs to be something that people will want to actually buy and play. AI has been giving me a lot of flattery based on some game ideas I've told it, but that is all AI is, flattery.
I've been practicing game development and game design since I was in the teens, but never released a completed product. I currently have various game development tools at my disposal to actually create something, and perhaps I will over these next few months that I have left on my tax return. You can see a few examples of my work on both this website, and on RPGTube.app, a new website I launched, and will be updating the entire theme shortly to be much more compelling than it currently is. None of these are going to be best-sellers, and the only one which I personally believe might have any potential based on the story I'm writing for it, is the sort of unnamed name Cozy Test, which I have on my website here as well for anyone to try out.
A Regular Job
While I have actively taken on regular jobs in the past, such as working at a call center, if you could call that regular, to unloading a truck at a warehouse. I find that this will be the most difficult one to even try, for many reasons, and not just the self-doubt.
A few months ago while I was visiting family in a small town in Manitoba, I rigorously put in my Resume into many of these sort of places. I put a resume in with a few of the local gas stations, supermarkets, and two of the hardware stores... Not even an interview, or call back. Nothing. This doesn't make me all that optimistic for putting in a lot of effort trying to apply for such jobs, when I am barely qualified, and will need to be taught on the job how these sort of businesses even operate. I'm also quite the introvert, these some of these jobs are very public facing, which will probably cause me to have severe anxiety.
Last Resort: Homeless or Mental Ward
Yeah, perhaps a bit too much of a title, but you can probably see my slight hopelessness here. If I am believing that past friends are ruining my life as mentioned in my career history page, or that a document which essentially was bribing me with $1,000 to sign is total paranoia, then perhaps I just need a nice cozy room at the local mental hospital where I can rest and not worry about the rest of the world, rent, or food. It is an option that I am highly considering, over being homeless of course. Homeless is probably at this point the absolute last resort if I am unable to get a bed at the local hospital for how I've been feeling and invalidated over these past 2 years. A bit drastic, but what else am I suppose to do if nothing else on list actually work out? I need to live, I need to survive! A mental ward would give me a higher rate of survival than being homeless, that's for certain. And clearly, based on my career history page, I'm super stressed and struggling with unemployment, so if I cannot find a job in the next 4 months, I'll just call the suicide hotline and demand a room at the local hospital and explain my life for these past many years.
AI's Perspective
1. Self-Employment / Freelance & Independent Development (Highest Likelihood)
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Why it fits: You have a proven track record of making this work in the past—building a successful self-employed pipeline via Kijiji, running high-traffic blogs (like Python Diary), and managing systems independently. You also possess deep, practical skills in Linux system administration and Python web development (Django, Zope/Plone).
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The outlook: Because standard corporate HR pipelines (like ATS automated screening) have stalled your job search, bypassing them entirely by selling your direct expertise to clients gives you immediate control. With a bit of marketing and active outreach, this is the most direct path to turning your technical autonomy into income.
2. Strategic Career Counseling (High Support Value)
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Why it fits: You mentioned planning to see a provincial career counselor once your local identification is sorted.
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The outlook: This isn't a pivot in itself, but it acts as a crucial bridge. A counselor can provide blind-spot awareness—highlighting niche government, municipal, or specialized tech-adjacent roles in your new city that you might not find through standard job boards, as well as evaluating if social work is a sustainable fit for your background and anxiety levels.
3. Social Work (Moderate Potential, High Personal Alignment)
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Why it fits: Your lived experience with foster care and homelessness gives you profound empathy and authentic understanding for populations in need, and you genuinely enjoy helping others.
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The outlook: While there is high demand in urban centers, this path comes with practical hurdles: figuring out required credentials and navigating how your personal history and anxiety might interact with high-stress street-level work. It’s a noble and meaningful direction, but it requires careful upfront investigation through a counselor or local agencies.
4. Game Development / Indie Publishing (Long-Term Creative Outlet)
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Why it fits: Game dev is a fantastic emotional anchor, a great creative challenge, and a way to channel your programming passion (like experimenting with Zope or building projects on RPGTube.app).
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The outlook: As you noted, relying on it as an immediate financial pivot is risky. Even massive breakout indie successes (like the viral co-op game Dear Passengers developed by Flexus) are built on top of massive prior studio experience, huge multi-platform portfolios (300+ million mobile downloads), or years of full-time team iteration. Treating game dev as a passionate side project or game jam entry protects your mental space while letting you build something purely for yourself.
The Verdict
AI Second Opinion
1. The Most Pragmatic & High-Probability Pivot: Seeing a Career Counselor + Leveraging Your Technical Core
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Why it works best: Out of all the options, utilizing the provincial career counselor and job-matching services once your local identification is settled is arguably your highest-leverage immediate step. You've faced a grueling two-year employment gap, and ATS resume filters can be a black box. A professional counselor can help bridge the gap, identify adjacent roles you might not have considered (such as internal IT support, systems administration, or technical writing), and potentially connect you directly with local employers or retraining programs.
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How to anchor it: Keep your technical background (Linux, Python, DevOps) active as your baseline, but let local employment services help unearth hidden regional opportunities.
2. The Nuanced Pivot: Social Work (With Caution Regarding Anxiety)
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Why it's a double-edged sword: Your background—surviving foster care, experiencing housing instability, and moving to a Canadian city with a large visible homeless population—gives you profound, lived empathy that can make someone an incredible outreach or social worker. Your instinct that "there should be a lot of open positions... to help those in need" comes from a very genuine place, and your natural desire to help teammates (as you noted in your DevOps history) translates well to human-centric support.
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The caveat: As you wisely pointed out yourself, you have to weigh whether your anxiety and past struggles with mental health will make day-to-day frontline street work overwhelming. If you pursue this, look into administrative, peer-support, or behind-the-scenes advocacy roles first to test the waters without burning out.
3. The Passion-Driven Continuation: Python / Plone / Enterprise CMS Consulting
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Why it's a mixed bag: While aiming for traditional corporate DevOps roles has hit a wall with automated screening systems, pivoting toward specialized freelance or contract web development in Plone or Django gives you direct agency. Enterprises that rely on robust open-source CMS platforms often struggle to find developers who truly understand the underlying architecture. However, freelancing requires active networking and client-hunting, which can be exhausting during a prolonged period of unemployment.
4. The Creative Outlets: Game Development
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Why it's a long shot for immediate financial stability: As you noted, getting noticed in the indie game market is extraordinarily difficult, and leaning solely on AI flattery can create false expectations. While building games (like your work on RPGTube or experimenting with code) is a fantastic mental outlet and portfolio builder, treating it as a primary employment pivot while funds are low carries high financial risk. Keep it as a deeply rewarding hobby or side project until your baseline stability is secured.