Curiosity, clear thinking, and a calm plan can beat even the smartest phishing email. We sit down with Trent, a cybersecurity analyst at Mercury IT, to map a practical path from the help desk to a rewarding security career, showing how real client problems, steady mentorship, and daily learning build the right instincts. If you’ve ever wondered whether certifications or degrees matter more than experience, or how AI is reshaping both attacks and defences, this conversation offers a grounded, human take.

Trent shares why working the help desk was an underrated superpower: it reveals how systems behave, how people really click, and where gaps hide in plain sight. We dive into internal training and phishing simulations that catch staff on those Monday mornings and Friday afternoons, not to trick them, but to build habits that last. From translating jargon for clients to designing controls that aren’t “doom and gloom,” Trent explains how trust and empathy strengthen security far more than fear ever could.

We also explore concrete steps for breaking into cyber: pick one certification aligned with your tools, pair it with hands-on practice, and seek out mentors who explain without talking down. Trent outlines how AI now powers convincing social engineering—and how defenders use automation to remove repetitive tasks and focus on higher-value analysis and incident response. For small businesses who still think they’re invisible, we walk through why size offers no safety and how preparedness beats panic every time.

If this resonates, follow the show, share it with a teammate who needs a nudge toward better habits, and leave a review with the one security tip you think every business should adopt next.