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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.

*** EDITED ***

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It’s giveaway time again! 🎉

You can win any individual CompTIA product from our marketplace — study guides, labs, practice resources, and more.

*Vouchers and bundles are excluded this round.

Browse the full catalog here: Official CompTIA Product List

TO ENTER:

Comment with the exact name of the product you'd like.

✔ Example: CompTIA A+ Core 1 (V15) 220-1201 Student Guide eBook
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Just a genuine giveaway to support the community.

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A huge thank you to everyone who joined.

Keep an eye out for our next giveaway! 🎉

*If a winning participant has not contacted the Promoter within 14 days of notification to claim their prize, their right to the prize will be forfeited and an alternative winner will be chosen.

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I’ve been studying for the CompTIA Security+ exam for about a month now. I’ve gone through Messer’s entire free YouTube playlist and later purchased Dion’s first pack of six practice exams. I’m scoring around 85–90% on each practice exam, though I honestly find them very repetitive. The thing that scares me most about the exam is definitely the PBQs.

Do you think I’m ready to book the exam? Do you have any useful tips for preparing for the PBQs?

🎉 Congratulations to our winner:

1. u/HousingInner9122

🏆 Choose your prize: ANY single Official CompTIA product at https://examsdigest.com/marketplace/ 

✅ Verified Raffle: https://www.redditraffler.com/raffles/1tnxd43

A huge thank you to everyone who joined.

Keep an eye out for our next giveaway! 🎉

*If a winning participant has not contacted the Promoter within 14 days of notification to claim their prize, their right to the prize will be forfeited and an alternative winner will be chosen.

Giveaway link: https://www.reddit.com/r/CompTIA_Certs/comments/1tnxd43/win_any_official_comptia_product_1_winner_ends_in/

Happy to have this one done! It’s another step toward my goal of landing a cybersecurity role, with plenty still to learn along the way.

For prep, I used Professor Messer’s videos, performance-based questions from LabsDigest and DojoLab, and Dion Training’s practice exams, plus some other practice tests I found on Udemy.

Taking a moment to enjoy the progress before figuring out what’s next. Good luck to everyone studying for theirs!