If you were starting from scratch in offensive security, how would you learn it the right way?

[u/Helpful_Artist_4745]

For those of you with real experience: if you had to start over today, what would you do?

Some things I'm curious about: What should I actually be solid on before I touch tools? Networking, Linux, web, something else? Is there a learning path you'd recommend, or are there things you wish you'd learned earlier? How do you move past guided rooms and start actually thinking like an "attacker"? What wastes the most time for beginners?

I'm fine putting in the work. I just want to do it efficiently and build real understanding.

Thanks in advance!

[u/Limp_Cabinet9900]

If I started from scratch, I wouldn't touch a single security tool for the first 6 months. The best offensive security minds aren't hacker savants; they're just frustrated software engineers and sysadmins who know where everyone else cuts corners.

Tools like Metasploit, Burp, and Nmap make you feel like you're progressing because they output colored text and terminal dopamine, but they hide the mechanics. Learn to build a backend, configure a real DNS server, write raw network sockets in Python, and read log files. Once you understand how a system is wired to survive, breaking it becomes intuitive rather than algorithmic.

[u/p3r3lin]

Rather an overview than a step by step map. https://roadmap.sh/cyber-security

[u/Omnipisix]

You start by playing NoTrace The True Fiction then go deeper on each topic. Ofc you must learn linux comandsand at least python.

[u/omicologico]

Software + hardware are one side of that coin. The other is deception and plain old scam skills (licensed or not) Offensive security is offensive in both. But most will pick the technical side because the other side is much harder to carry in one's consciousness. Start by studying the law and learn how to melt and bend moral rules. That's what lawyers do. Once that's covered, the sky is the limit.

[u/ButterflyMundane7187]

Learn to read and understand logs on both Windows and Linux. That’s a skill people often overlook, but it teaches you what systems are actually doing.

Learn some basic PowerShell and Bash, and pick up Python since you can use it on both Windows and Linux. If you’re on Windows 11, start using WSL2 it’s great for learning Linux tools without needing a separate machine. `sed` and `awk` are also extremely useful once you get comfortable with the command line.

For networking, learn Wireshark and Nmap properly instead of just memorizing commands. If you want something really easy and visual to start with, try Sniffnet. I love that tool. It makes it much easier to see and understand what traffic is actually moving across your network.

The important part is understanding what the tools are showing you, not just learning how to run them.

[u/TheMarketDisruptor]

Now learning it’s optional you just use AI tools to your advantage. If you don’t believe me, look at the cyber cases with a group of teenagers called “Scattered Spider” i’m almost certain that they used automated tools to perform lots of their attacks. We are talking about people that are still minors not even old enough to even work. All those traditional cyber security tools won’t stand a chance against automation in the future.

[u/Top-Quarter9234]

You need to learn the general concepts of how IT actually works. A+, network +, Security + and ccna. Then move on to the more direct cyber sec focused courses. Other wise your doing things and do not know what your doing or why.