If I Had to Start Cybersecurity Over in 2026... I'd Do This

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If I had to start my cybersecurity career over in 2026, there are a few things I would do differently. In this episode of The Hacker’s Cache, I break down my full cybersecurity journey from joining the Air Force, earning Security+, Linux+, CCNA, CISSP, OSCP, and other certifications, becoming a penetration tester, building a YouTube channel, dealing with burnout, and pivoting into AI security. I share my biggest cybersecurity career regrets, what was actually worth it, what I would skip, and the advice I’d give to anyone trying to break into cybersecurity today.


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As a cybersecurity professional with over seven years of experience, I focus on strengthening digital assets against ever-changing cyber threats. I specialize in penetration testing, ethical hacking, red teaming, and offensive security. I excel at uncovering and addressing vulnerabilities in networks and web applications.

My mission is to make cyberspace better & safer for everyone by committing to lifelong learning, sharing knowledge with the community, and inspiring others to do the same.

Credentials:

• 8+ Years Cybersecurity Experience

• BS & MS in Cybersecurity Management and Policy from UMGC.

• 19 certifications including OSCP, OSWA, CISSP, CRT, PWPA, OSWP, SAL1, SecurityX, PenTest+, CEH, CPSA, SecAI+, CySA+, CCNA, Cyber Ops-A, Cloud+, Linux+, Security+, and Network+.

• Pwned 100+ HTB machines and mastered 200+ THM rooms, securing top leaderboard rankings on both platforms.

• United States Air Force Veteran

Time Stamps
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00:00 Introduction to Cybersecurity Career Journey
02:41 Early Military Experience and Certifications
05:20 Transitioning to Advanced Certifications
08:00 Overcoming Challenges and Failures
10:35 The Importance of Networking and Coding
13:16 Pursuing Higher Certifications
15:43 The Role of Internships in Career Development
18:25 Navigating Job Opportunities and Promotions
21:06 Reflections on Certification Choices
23:16 Current Status and Future Aspirations
26:01 Investing in Certifications: A Costly Journey
31:22 Navigating Life's Challenges During Certification Pursuits
36:25 The Importance of Continuous Learning and Adaptation
40:10 Balancing Education and Certifications: A Personal Reflection
45:32 Career Setbacks and Lessons Learned
50:41 Reflections on a Chaotic Career Path


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Tags
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#Cybersecurity #infosec #informationsecurity #datasecurity #cybersecurityexpert #cybersecurityexperts #cybersecuritytips #cybersecuritytraining #hacking #hacking_pro #hacker #hackers #ethicalhacking #ethicalhacker #hackerman #hacked #penetrationtesters #penetrationtesting #pentesting #pentesting #pentesting #pentester #redteam #redteaming #offensivesecurity #security #technology #tech #IT #informationtechnology #Cyber #computerscience #LearnShareInspire #KyserClark #Kyser #CybersecurityCareer #CybersecurityJobs #CareerAdvice #CareerChange #AISecurity

Disclaimer
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Attention viewers: This video is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.

The postings on this site are my own and may not represent the positions of my employer.