Owen Holdeman

The Plan

The path from zero to red team operator — updated as I go.

  1. Stage 1

    Foundations

    TryHackMe Pre Security and Cyber Security 101 — networking, Linux, security fundamentals, and core hands-on lab skills.

    Done

  2. Stage 2

    Jr Penetration Tester

    TryHackMe's Jr Penetration Tester path — the transition from fundamentals into practical, hands-on pentesting.

    In Progress

  3. Stage 3

    PJPT + eJPT + Hack The Box (Free)

    Earning TCM Security's Practical Junior Penetration Tester (PJPT) and INE's eJPT certifications, while starting independent practice on Hack The Box's free tier — building problem-solving skills beyond guided labs.

    Planned

  4. Stage 4

    Web App Pentesting + Red Teaming (TryHackMe)

    TryHackMe's Web Application Pentesting and Web Application Red Teaming paths, continuing HTB practice alongside.

    Planned

  5. Stage 5

    PNPT

    Practical Network Penetration Tester certification — validating broader pentesting ability.

    Planned

  6. Stage 6

    Red Teaming (TryHackMe) + Hack The Box (Paid)

    Transitioning into red-team-specific training, upgrading to paid HTB for structured learning paths and independent machines.

    Planned

  7. Stage 7

    OSCP

    Offensive Security Certified Professional — the advanced pentesting baseline.

    Planned

  8. Stage 8

    Home Lab + Portfolio

    Building a realistic home lab with GOAD (Game of Active Directory) and GHOSTS for simulated user activity, documenting engagements as professional writeups, and publishing them here.

    Planned

  9. Stage 9

    BHIS Visibility

    Antisyphon training courses, active participation in the BHIS community, and building toward a guest blog pitch.

    Planned

  10. Stage 10

    First Role

    Joining Black Hills Information Security (BHIS) as a penetration tester, building real client-facing experience.

    Planned