With 20+ years of cybersecurity work, Tom unpacks the complexities of penetration testing, discussing the roles of vendors, practitioners, and technological advancements. He also shares his perspective on what makes a good pentester, the value of mentorship, and the ethical challenges in this line of work. Explore this conversation to learn:How pentesting changed over the years and who’s shaping it [03:02]How to avoid burnout and deal with imposter syndrome [09:13]Why he seeks and values mentorship for personal and professional growth [19:44]The importance of constant learning and networking with your peers  [23:23] How compliance brings down the value of pentesting and what to do about it [30:04]How cultivating range can help you in your pentesting career [37:24]How to set healthy boundaries to protect your health [41:11]This episode with Tom is a must-listen if you want to learn how to showcase your work and elevate your thinking and tactics.Resources from this episodeTom’s personal websiteTom on LinkedInTom on TwitterThe Shared Security podcastThe People Hacker book by Jenny RadcliffeTom’s journey from offensive security to leadership at the Phillip Wylie ShowEthical hackers and the legacy of the hacker manifesto for Cyber EmpathyTib3riusJason Haddix Dave Kennedy

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