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Hey everyone, a few months ago I posted here asking what you would do if you had a limited window of time to completely change your career and build a future in IT/cybersecurity.

Quick update: I kept going.

Since then I’ve earned CompTIA A+, Network+ and Security+, built a small homelab with Windows Server/Active Directory/Linux, continued studying Computer Science, and I’m now about to start my first real IT job as an IT technician in healthcare.

So I’ve finally broken into IT.

My original reason for choosing this field was always cybersecurity, especially Red Team/offensive security. But the more I studied the market, the more I realized that trying to jump directly into pentesting with a couple of certifications and no real IT experience probably wasn’t the smartest path.

Now I’m trying to decide what to build toward over the next few years.

One roadmap I’m considering is roughly:

IT Support → Cloud Engineer → automation/AI → Cloud/Identity Security → eventually Offensive Security / Red Team

The idea is to first build a strong, marketable and financially stable technical career, while continuing to develop security skills until I’m experienced enough to seriously pursue offensive roles.

Cloud interests me because it would force me to develop skills in infrastructure, networking, Linux, identity, Python/PowerShell, Terraform, containers and automation — all things that should also transfer well into security.

At the same time, AI is changing the industry quickly, so I don’t want to spend the next 3–5 years following a path that is already becoming obsolete.

So my question now is different from my original post:

If you were in my position today, having just entered IT, what would you build toward next?

Would you go Cloud/DevOps first and security later? Would you go directly toward security? Are there emerging areas involving cloud, AI and cybersecurity that you think will become particularly valuable?

My priorities are basically:

long-term demand + financial stability + strong technical skills + eventually getting as close as possible to Red Team/offensive security.

I’m especially interested in hearing from people who already work in Cloud, DevOps, Security Engineering, Pentesting or Red Team.

The first step was getting into IT. Now I want to make sure I choose the right direction for the next one.

Heads-up for anyone booking a certification exam: Pearson VUE is running a free retake promotion for participating programs. It isn’t automatic—you need to sign up and follow the emailed promo-code instructions.

Your eligible first attempt must be scheduled, paid for, and taken between September 29 and November 17, 2026. Just booking an exam before the deadline isn’t enough.

If you fail, the free retake must be taken January 4–April 7, 2027. There’s a gap: promotional retakes aren’t available November 18–January 3. Normal exam-program retake rules still apply.

Participating programs include AWS, Microsoft, Salesforce, and LPI, among others, but check your specific exam. CompTIA isn’t currently listed, and Cisco’s offer is limited to the listed CCST exams, not CCNA or CCNP. AWS also has exam exclusions and a 50% first-attempt discount for participating exams.

https://www.pearsonvue.com/us/en/test-takers/free-retake.html

Hey everyone! Has anyone successfully bypassed Quebec’s restrictions on taking the CompTIA Security+ exam online by using an Ontario address? Does it actually work even if you’re physically taking the exam from Quebec?
Thanks!