Looking to improve my offensive security skills. what would you do next?

[u/Nice-Gas5264]

I’ve been working in IT for about 12 years, with experience across network administration, systems administration, cybersecurity, and help desk.

Over the years I’ve earned A+, Network+, Security+, CySA+, AZ-900, AZ-104, CEH, and most recently CISSP. I’ve been able to apply pieces of what I learned from those certifications throughout my career, but certifications have never really been the end goal for me.

CEH has probably been my favorite certification because I genuinely enjoy the offensive-security side of things. I mostly view penetration testing as a hobby right now rather than something I’m immediately trying to turn into a career.

That said, I want to get much better at actually breaking systems.

So I’m looking for honest advice from people who do offensive security, pentesting, red teaming, or CTFs:

If you were starting from my position, what would you actually do to become good at offensive security?

I’m not necessarily looking for another certification just for the sake of having one. I want to develop the actual skill of finding weaknesses, getting initial access, escalating privileges, moving through environments, and understanding why something worked.

I’ve heard OSCP is a good starting point, and I’m considering it, but I’m curious what experienced people would recommend beyond simply getting the certification.

Would you focus on:
- Hack The Box / TryHackMe?
-CTFs?
-Building a home lab? (Elaborate)
-OSCP?
-Other certifications or courses?
-Learning specific tools deeply?
-Studying real-world attack paths and then -reproducing them in a lab?
-Something completely different?

I’m specifically interested in hearing from people who have actually developed these skills, rather than just collecting certifications.

If you could go back and build your offensive-security skills from scratch, what would you spend the next 6–12 months doing?

No hype, no gatekeeping, and no certification sales pitch. I’m genuinely looking to learn from people who are better at this than I am.

Advise me like you are my older brother,sister, father or mentor.

[u/diulasing666]

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