Why You Should Tinker: The Ultimate Career Power Move
As a CISO, I’ve spent years building security programs that balance technical rigor with human leadership. But in a world where AI can hallucinate a resume and a "talent shortage" often feels like a "referral-only" secret club, I wanted to dig into what it actually looks like to build a resilient career from the ground up.
Enter Rob “Bowtie Security Guy” Whetstine. He didn’t start with a degree; he started with a soldering iron and other people’s trash.
The "Tinker" Mindset: Bringing Calm to Chaos
One of the highlights of our talk was Rob’s early days "dumpster diving" behind Best Buy. While it makes for a great story, the lesson for our industry is profound. We’ve entered an era where "paper tigers" candidates with every cert but no instincts, are struggling in the real world.
My Perspective: I’ve seen this time and again. If you’re going to secure a system, you have to understand how it’s built, how it breaks, and where the layers live.
Rob shared a brutal truth: when he interviews for Fortune 500 staff roles, 10 out of 15 "entry-level" candidates can’t answer basic troubleshooting questions because they’ve never broken anything. They’re trained to pass a test, not to solve a problem.
The takeaway? Don't just stack certifications; build a home lab. Break things. Fix them. That "street-smart" logic is what carries you through a six-hour gauntlet at a place like Disney or Amazon.
Leadership with Intention: "Is Anyone Dying?"
We spent a lot of time talking about the human side of leadership. Rob and I both agree:
Success must be defined by the leader. If your team doesn't know what "winning" looks like, they’ll burn out trying to find it.
Rob uses a powerful de-escalation tactic during incidents: asking, “Is anyone dying?”
In cybersecurity, we often live in a state of artificial emergency. By grounding the team in reality, he brings a level of calm that allows for clearer thinking and faster resolution.
While many legacy leaders still manage through fear or "constant vigilance" (the stressful kind!), Rob’s approach aligns with the Polyvagal-informed leadership trends we’re seeing in 2026. It’s about nervous system regulation—helping your team feel safe so they can actually perform.
Neurodiversity as a Strategic Edge
Rob was incredibly candid about his social anxiety, ADHD, and autism. He turned a bowtie—initially a source of discomfort—into a brand that forced him to engage with the world.
As a community, we need to do better. Standard interview processes are often designed to filter for "charismatic extroverts," which means we're missing out on some of the most brilliant pattern-recognition minds in the field.
What leaders can do today:
Provide interview questions in advance.
Focus on work samples and practical demonstrations.
Normalize the phrase “I don’t know.” As Rob says, "Your response to what you don't know tells me more about your character than what you do know."
Final Thoughts from the Garden Wall
Reinvention isn't a neat pivot; it’s a grind. Whether you're a prop builder or a marathoning mother of three (like our previous guest, Saeger Fischer), the throughline of a successful career in cyber is relentless curiosity.
I’ll leave you with Rob’s favorite metric for a new hire: The courage to be the "best worst person" for the job. You don't have to know it all on Day 1, you just have to be the person who is obsessed with finding the answer by Day 2.
Stay Vigilant, Stay Human.
