Hackers Learning Path

Table of Contents

Want to learn how to hack computers?

You: “Of course!”

Whether you want a job or it’s a hobby, everyone can learn to hack.

Prepare to learn a broad set of skills, core computing knowledge and problem-solving. Early warning, it’s more involved than a single degree or certification… it’s a ‘whole life’ thing. If any of that sounds interesting, carry on!

Since hacking can take years, here’s my list of courses, videos, books and games to help your journey. Have fun, fellow newbie hacker.

*Disclaimer, ongoing list, I’ll update when I can. Approx times and price tags for each resource, check to confirm. This is a guide and not a strict order, learn how you like.


Tech is a big industry and hacking falls under the Cyber Security field.

Wow, slow down there laddy! Before jumping into Cyber Sec, you need skills in basics computing 1) Virtualization 2) Operating Systems 3) Networking and 4) Programming.

Start with Hoppers Roppers Introduction to Computing Fundamentals 100hr free. This introduces you to the above four areas, and most importantly, Linux. To scaffold your Linux learning, see CISCOs Linux Unhatched 8hr free and NetworkChuck’s Linux for Hackers 3hr free video series.

Roppers will also show you programming with Python via Code Academy – Learn Python 2 25hr free/cert cost and Automate The Boring Stuff with Python free. If you can, get the Automate with Python Udemy Course 10hr low cost do it. Follow the creator, Al Sweigart as the course is given out for free a lot. Learn Python The Hard Way free is also worth going through for it’s well-written exercises.

Next, go to Hack The Box Academy and take on these three fundamental modules 1) Linux 15hr free 2) Networking 15hr free and 3) Windows 15hr free.

These double down on everything you’ve touched on from Roppers plus some.

Then start the TryHackMe – Complete Beginner Learning Path 50hr free/some costs. It does require a premium plan, if that’s not possible, tackle the free walkthroughs: Linux Fundamentals Part 1, Part 2. Part 3, Introductory Networking, Nmap, Web Fundamentals, OWASP Top 10, OWASP Juice Shop, Pickle Rick, Encryption – Crypto 101, Windows Fundamentals Part 1, Part 2, Metasploit, Blue, Linux PrivEsc.

After, take FreeCodeCamp’s Information Security courses 50hr free and lastly, take Introduction To Computer Science CS50x 100hr free/cert costs.

Wow, that’s a lot of learning! Now you’re ready to get into the Cyber Security field!

Capture The Flags

To apply your hacker skills start some Capture The Flags (CTFs).

These are gamified experiences based on real technologies and techniques. Designed to continue learning while creating a fun competitive environment.

To start, go to Roppers Networking with Capture The Flags free and Roppers Introduction To Capture The Flags free. Roppers shares OverTheWire’s – Bandit free, see Bandit 0 – 4, Bandit 5 – 10 and Bandit 11 – 15 for help.

Head back to TryHackMe and take on RootMe, see write-up for help. Then pick from their free CTF rooms available, keep working on them until the list runs dry! Jump over to PicoCTF free for their Gym CTF’s, here’s my General Skills write-up. Then back to Hack The Box, but this time their CTF platform and not their academy.

After you get comfortable with the basics of CTFs, you’re ready to check CTF Time free and find a live in-person or online event at your skill level. Some CTFs are team-based, it’s a good opportunity to meet new people and learn from the community. If that’s daunting, you can do some CTFs solo.

A great starting CTF comes from Trace Labs free. They provide crowdsourced Open Source Intelligence (OSINT) to assist law enforcement with real missing person cases. They throw virtual search parties, so you learn hacking while helping, amazing.

Build Labs

Create your own virtual lab environment to play, test and try out your hacker skills.

A lab means using virtualisation software to replicate a real network of connected computers.

This can be done on almost any modern computer.

The most popular software for this is 1) VirtualBox 2) Hyper-V and 3) VMWare. Each has their own pros and cons, do a bit of research to find which suits you, I recommend VirtualBox.

Since you’re spawning mini virtual machines on your host computer, be aware of your CPU, RAM and HDD space i.e. hardware limitations.

For a basic cyber sec lab, use Kali Linux free and VulnHub machines free. You’ll need at least a 4 core CPU, 4Gb RAM and 50Gb HDD.

VulnHub is a platform for vulnerable virtual machines, similar to walkthroughs and practice CTFs.

Start with Metasploitable free to practice penetration testing using the framework Metasploit free. This is a collection of tools likened to the Swiss army knife of pen-testing. It’s worth reading Metasploit – The Penetration Testers Guide costs for a more detailed history and looks into the tool.

Option 1, for an intermediate Cyber Sec lab using VMWare, follow CyberWox home lab (use my write up for VirtualBox) which involves pfSense free, Security Onion free eval, Ubuntu Desktop free, Kali Linux free, Windows Server free eval, Windows Desktop free eval, Splunk free dev and VulnHub machines free. At least 8 core CPU, 16Gb RAM and 500Gb HDD.

Option 2, for an intermediate Cyber Sec lab using VirtualBox, follow da667′s Building a Virtual Lab.

Ideally, you follow all three labs and have a dedicated lab machine. Maybe you have an old laptop or unused gaming PC you can convert. If you’re buying hardware, I recommend 12+ core CPU, 32Gb+ RAM and 2Tb+ HDD. If you’ve never built a computer before, this is great practice, plus it’s your sandbox to safely hack.

Some people go all out buying routers, switches, dedicated servers etc… it’s up to you how far you’d like to go given your budget and situation. I don’t think you need to spend much if anything.

If purchasing hardware, please look second hand, it helps the environment, keeps consumerism down, plus you’ll find sweet deals! One man’s trash is another man’s treasure.

Content and Community

In order to stay focused while learning, not to mention keeping up to date with the ever-changing field that is Cyber Sec, you need to find some good content.

These are the guys and gals out there, other students on the same path or experts who have been in the field for years! Learn from others, always! Plus, all those courses, capture the flags and labs get a bit exhausting, so break it up!

Share Your Journey – #100DaysOfHacking

This is optional, feel free to ignore it, but I HIGHLY recommend this. All the courses, books and resources you find and put through that beautiful brain of yours, share them!

Start a YouTube channel, write a blog, set up a podcast or sign up for a Twitter account. It doesn’t matter what or where, just share.

There are a few benefits to this:

  • Meet others in the community.
  • Better understand what you’ve learnt.
  • Help others and add to the community.
  • Increases luck surface area.
  • Nurture writing/video/audio skills.
  • Make yourself accountable.

If this sounds exciting to you, start your own #100DaysOfHacking to stay motivated while learning. Tweet me and announce to the world what you’re working on!


For much better lists, see Simply Cyber’s Free Resource and Roppers Things Worth Doing.

Here’s more I’ll add in the future:

  1. People on Twitter.
  2. Practice Exams and Certificates.
  3. Programming and Lab Projects.
  4. Output: Note-taking, write-ups and active recall (Quizlet)
  5. Hacker101
  6. PentesterLab
  7. Beginner Network Penetration Testing (2019)
  8. CTFLearn
  9. Cybrary

I agree, this is a rough list, but I’ll pad it out over time.

If you have any feedback, please send me a message @mrashleyball.

This is Day 5, 11 and 16 of #100DaysOfHacking, subscribe to my newsletter to follow the journey!

Happy Hacking.

About The Author
Ashley Ball

Ashley Ball

“Learn, create, share, repeat.” • IT teacher, former web designer, learning #cybersec • Road to #100DaysOfHacking
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