the hacker’s roadmap (how to get started in IT in 2025)

About this video

Chuck lays out his 2025 roadmap for getting into IT fast, without college, aimed first at a help-desk job and then at ethical hacking. Phase 0 is counter-intuitive: polish your resume and LinkedIn and start applying immediately, because he says employers mainly want customer-service skills and experience beats study; he says he got his first IT job with no certification, reframing his Starbucks work (fixing the printer) as IT experience, and urges networking with people in the field throughout. Phase 1 (he estimates two to three months) centres on CompTIA A+ — he states the current exams cost $253 each and there are two — while starting Linux and Python a little at a time and building a home lab (VirtualBox VMs, Ubuntu, pfSense, a DNS server), treating each project as a resume line. He names free options such as Professor Messer’s YouTube courses and his own academy, priced at $12 a month. Phase 2 (another two to three months by his estimate) is CompTIA Security+ ($404 in his figures, and he notes it satisfies a DoD directive many employers require), plus security-flavoured Linux via OverTheWire’s Bandit and a Python project such as a network scanner. Phase 3 is networking: CCNA ($300, his pick and the harder, Cisco-focused option) versus Network+ ($369, vendor-neutral), more Python for network automation, and replacing your home network as a lab challenge; he estimates this phase at up to about four months for CCNA. Phase 3.5 is simply ‘get that job’ before specialising. The hacking path then stacks junior certs (eJPT at $249 including three months of INE training, or PenTest+ at $381 in his figures), Hack The Box’s CPTS ($490), and OSCP, whose Pen 200 bundle he puts at roughly $1,600 — all prices are his stated figures in the video. He adds shortcuts (skip phases you can already prove, take a job that jumps you ahead), says a degree is optional but recommends programs like WGU that embed certs, and closes with John Hammond reviewing the roadmap: Hammond endorses learning Linux and Python early, questions whether deep networking/CCNA depth is needed for hacking, calls OSCP the crown-jewel target, and agrees college is helpful but not required.

Key takeaways

• Phase 0: start applying for help-desk jobs before studying — Chuck says customer-service skills and any experience matter most, and to tailor your resume/LinkedIn to the job you want.
• Phases 1-3 build foundations in order: A+, then Security+, then networking (CCNA preferred over Network+), each phase estimated by him at roughly two to three months (longer for CCNA).
• Linux, Python and a home lab run through every phase in small weekly doses; each lab project becomes a resume line demonstrating passion to hiring managers.
• Certifications are framed as proof for HR filters rather than knowledge itself — his stated prices include A+ at $253 per exam (two exams), Security+ $404, Network+ $369 and CCNA $300.
• For the hacking specialisation he sequences eJPT or PenTest+, then Hack The Box CPTS, then OSCP as the resume-gold standard, with John Hammond broadly endorsing the plan while questioning deep-networking requirements.

Episode details: published January 28, 2025 · 33:50 long. Summary written by Self Growth Videos from the episode itself. Business results and any income figures mentioned are NetworkChuck’s own claims, shared for education — they are not typical or guaranteed.

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