the hacker’s roadmap (how to get started in IT in 2023)

A practical, eight-step roadmap for breaking into IT and moving toward cybersecurity in 2023 centers on one idea: build job-ready fundamentals first, then stack security and hacking skills on top. The fastest route to employment isn’t jumping straight into “hacker” topics—it’s layering core IT knowledge (so we can troubleshoot, network, and understand systems) before attempting advanced offensive work. The payoff is employability: the path is designed to land an entry role—often help desk—where real experience accelerates everything else.

The first five steps apply to nearly any IT goal. Step one is “foundations,” starting with CompTIA A+. The rationale is twofold. A+ is positioned as a zero-to-competent starting point that fills gaps in “things you don’t even know you don’t know,” and it also functions as a resume signal for the first job, where employers typically want proven troubleshooting ability (including familiarity with concepts like virtual machines). The transcript also acknowledges the debate around A+, but argues the certification’s market value and breadth make it useful—especially for newcomers.

From there, the roadmap pushes security credentials early with CompTIA Security+. It’s framed as a foundational security requirement for many employers, including government roles tied to DoD 8570 compliance. Networking comes next because cybersecurity depends on understanding how systems communicate. Two certification tracks are offered: CompTIA Network+ (vendor-neutral) or Cisco CCNA (Cisco-focused but described as the “gold standard” for practical configuration knowledge). Linux is treated as essential “feet wet” knowledge rather than an attempt to become a Linux expert; the goal is to learn enough to operate confidently across the rest of IT work. Coding is placed later in the sequence—not because it’s unimportant, but because it’s more productive once networking, Linux, and security basics are in place. Still, the guidance is to start early enough to build familiarity, with Python recommended for beginners and Go as a faster, newer alternative.

Once fundamentals are in motion, the roadmap shifts into hands-on hacking. It recommends starting with CTFs (capture the flag) using platforms like PicoCTF, TryHackMe, and Hack The Box, emphasizing that early practice reveals whether someone actually enjoys hacking and highlights which foundational skills are missing. If hacking interest turns into a career direction, the next step is junior penetration testing certifications: CompTIA PenTest+ or the eJPT from INE. Both are described as similar in intent—preparing for entry-level penetration testing—while differing in training availability and cost. Finally, the path culminates with OSCP (Offensive Security Certified Professional), but only after PenTest+ or eJPT experience, because OSCP is portrayed as significantly harder and more “real hacker” in feel.

The roadmap ends with a career strategy: certifications matter, but on-the-job experience matters more. The ideal outcome is to start earning experience as soon as possible—often while continuing to level up with Security+, networking credentials, or Linux skills—because real-world tasks build competence faster than additional credentials alone. A short practice-exam segment reinforces the A+ foundation with sample questions on services, printers, batteries, multiplexing, and troubleshooting methodology.