Further Reading: Career Paths and Continuous Learning

Books

Tribe of Hackers: Cybersecurity Advice from the Best Hackers in the World Marcus J. Carey and Jennifer Jin, Wiley, 2019. Interviews with 70 cybersecurity leaders about their career paths, advice for newcomers, and perspectives on the industry. An excellent resource for understanding the diversity of careers in security.

Tribe of Hackers Red Team Marcus J. Carey and Jennifer Jin, Wiley, 2019. The red team-focused companion to the original, with interviews specifically covering offensive security careers, methodologies, and professional development.

Penetration Testing: A Hands-On Introduction to Hacking Georgia Weidman, No Starch Press, 2014. Beyond its technical content, this book provides an accessible entry point for people beginning their penetration testing journey. Weidman's own career path illustrates the transition from aspiring hacker to professional practitioner.

The Pentester BluePrint: Starting a Career as an Ethical Hacker Phillip L. Wylie and Kim Crawley, Wiley, 2020. Specifically focused on starting a career in penetration testing, covering certifications, skill development, job hunting, and professional practice.

Bug Bounty Bootcamp: The Guide to Finding and Reporting Web Vulnerabilities Vickie Li, No Starch Press, 2021. Practical guidance for building a bug bounty career, including finding programs, reporting vulnerabilities, and developing the skills needed for consistent success.

Dissecting the Hack: The F0rb1dd3n Network Jayson E. Street et al., Syngress, 2010. Security concepts taught through fiction. An unconventional approach that demonstrates how storytelling can make technical concepts accessible and memorable.

Certifications and Training Resources

OffSec PEN-200 (OSCP) Syllabus and Preparation Available at offsec.com. The official OSCP course description, syllabus, and exam information. Supplementary preparation resources include the OffSec PEN-200 course text and lab environment.

TCM Security Courses and PNPT Certification Available at tcm-sec.com. Heath Adams's (The Cyber Mentor) training courses, including Practical Ethical Hacking, which maps to the PNPT certification. Known for excellent, affordable training.

SANS Training Catalog Available at sans.org. The complete SANS course catalog, including SEC560 (Network Penetration Testing), SEC542 (Web App Penetration Testing), and SEC565 (Red Team Operations). Premium pricing but industry-leading content.

CREST Exam Preparation Resources Available at crest-approved.org. Syllabi, preparation guides, and recommended study materials for CPSA, CRT, CCT, and advanced CREST certifications.

TJ Null's OSCP-like Machine List Available on NetSecFocus and various community repositories. A curated list of Hack The Box and Proving Grounds machines that simulate OSCP exam difficulty. Essential for OSCP preparation.

Practice Platforms

Hack The Box (hackthebox.com): The leading platform for penetration testing practice, with machines, Pro Labs, and the Academy structured learning platform.

TryHackMe (tryhackme.com): Beginner-friendly platform with structured learning paths and guided rooms. Excellent starting point for newcomers.

OffSec Proving Grounds (offsec.com/labs): Practice machines similar in style and difficulty to OSCP exam machines.

PicoCTF (picoctf.org): Carnegie Mellon's beginner-friendly CTF platform. Excellent for absolute beginners and students.

PortSwigger Web Security Academy (portswigger.net/web-security): Free, structured web application security training with hands-on labs. The best free resource for learning web application testing.

CTFTime (ctftime.org): Aggregator for CTF competitions worldwide. Find upcoming competitions, team rankings, and past challenge write-ups.

VulnHub (vulnhub.com): Free downloadable vulnerable virtual machines for offline practice in your home lab.

Podcasts

Darknet Diaries (darknetdiaries.com): Jack Rhysider's podcast featuring true stories from the dark side of the internet. Compelling storytelling that covers hacking, cybercrime, and security culture. Essential listening for anyone in the field.

Risky Business (risky.biz): Patrick Gray's weekly cybersecurity news and analysis podcast. The most efficient way to stay current with industry developments.

The Cyber Mentor YouTube Channel (youtube.com/@TCMSecurityAcademy): Heath Adams's educational content covering penetration testing techniques, career advice, and certification preparation.

IPPSEC YouTube Channel (youtube.com/@ippsec): Detailed video walkthroughs of Hack The Box machines. Demonstrates methodical penetration testing approaches and teaches tools and techniques in context.

SANS Internet Storm Center Daily Podcast (isc.sans.edu): Brief daily updates on the latest security threats and developments.

Conferences

DEF CON (defcon.org): The world's largest hacker conference. Las Vegas, annually in August. Essential experience for any security professional.

Black Hat (blackhat.com): Enterprise security conference with world-class briefings and trainings. Las Vegas, annually in August (before DEF CON).

BSides (securitybsides.com): Community-organized conferences held worldwide. Find your local BSides at the BSides wiki.

Wild West Hackin' Fest (wildwesthackinfest.com): Deadwood, South Dakota. Strong focus on penetration testing and hands-on training.

ShmooCon (shmoocon.org): Washington, DC. Intimate, community-focused conference with strong technical content.

Community Resources

InfoSec Twitter/X: Follow researchers, practitioners, and thought leaders. Key accounts include @_johnhammond, @ippsec, @TJ_Null, @TCMSecurity, @staborhack, @taborhack, and @NahamSec.

Reddit Communities: r/netsec (technical security), r/AskNetsec (career and questions), r/oscp (OSCP preparation), r/cybersecurity (broad discussion).

Discord Servers: Hack The Box, TryHackMe, TCM Security, and Nahamsec communities provide active, supportive learning environments.

OWASP Local Chapters (owasp.org/chapters): Monthly meetups worldwide focused on application security. Free to attend.

2600 Meetings (2600.com): First Friday of every month, informal hacker meetups in cities worldwide.

Career Development

CyberSeek (cyberseek.org): Interactive career pathway tool showing cybersecurity roles, certifications, and job market data. Published by NICE (National Initiative for Cybersecurity Education).

LinkedIn Security Community: Follow companies, join security-focused groups, and maintain an updated profile highlighting your certifications, achievements, and contributions.

Glassdoor / levels.fyi: Salary data for cybersecurity roles. Useful for benchmarking compensation and understanding market rates by role, location, and company.