David Bombal #529: 2026 Cybersecurity roadmap: Your path to success with a Master Hacker
Jan 7, 2026
Guest OTW (Occupy The Web) is a seasoned hacker and educator dedicated to practical cybersecurity training. In this discussion, he outlines a roadmap for aspiring cybersecurity professionals by emphasizing mastery of operating systems and essential certifications. OTW dives into the importance of scripting languages like Python and Bash, and the need for hands-on practice using virtualization tools. He also highlights the necessity of continuous learning amid AI advancements, and advises building real-world experience through open source contributions and networking.
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Master Your Primary OS First
- Know the operating system you use every day and understand its inner workings before moving on to other skills.
- Use CompTIA A+ or equivalent study to prove foundational competence rather than just completing courses.
Learn Linux With A Security Focus
- Learn Linux with a cybersecurity lens and validate skills with a recognized exam like Linux+ or a security-focused cert.
- Use hands-on practice tailored to hacking/defense, not only admin tasks.
Get Strong Networking Fundamentals
- Study networking fundamentals and pursue Network+ or CCNA to demonstrate real-world competence.
- Choose CCNA if you plan to specialize in networking because it carries more industry weight.
