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The Skills I Buried Still Work

Nobody told me my old job would show up inside my new one.

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The Skills I Buried Still Work
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30 years in creative leadership (in the ad industry as a Creative Director) taught me one core skill: dissecting complex systems and finding the flaw before someone else does. My tech roots run back to 8-bit machine code on a C64 (yeah – 80s, baby!) Today, I’m combining that legacy hacker curiosity with modern threat detection and offensive security. BATTLE-TESTED LOGIC: Decades of high-pressure problem solving and systems analysis. HACKER MINDSET: I don't just follow playbooks; I reverse-engineer how the attack path actually works. CONTINOUS SKILL-UP: CompTIA Security+ certified (among other certs), building home labs, and constantly training for L1 ops to future Pentesting.

Part 12 of an ongoing series. [Start from Part 1.]

Tuesday, two tabs open on the same screen.

Left tab: Burp Suite, intercepting requests on a login flow, hunting for the one weak step in an authentication chain. Right tab: a blank wireframe, because someone on the team needed funnel ideas and I was the guy in the room who'd built more funnels than anyone cared to count.

I closed my laptop that night and wrote a line in my journal I hadn't planned on writing: "My skills (old) sometimes are still needed — but I also lost connection to them."

I sat with that sentence longer than anything else I logged this week.


Here's what I mean by "lost connection." For thirty years I thought in funnels without noticing I was doing it. Where does the user drop off. Where does the story lose them. Where's the one step in the journey that's carrying too much weight and about to break. That wasn't a skill I studied — it was just how I saw things. Client work, pitch decks, landing pages, doesn't matter. Same question, every time: where's the gap.

Then I spent a year and a half deliberately not thinking that way. Head down in TryHackMe rooms, Sec+ material, THM's SOC path, trying to build a completely different set of instincts from scratch. And somewhere in there I started believing the old ones had gone quiet for good. Not gone — quiet. Retired. A drawer I'd shut.

Tuesday, someone opened the drawer without asking.


The pentest and the funnel work aren't as far apart as I would've told you a year ago.

A login flow is a funnel. It has a start, a set of steps, and an intended endpoint — and somewhere in that chain there's a step that's weaker than the others, doing more work than it should, trusting something it shouldn't trust. That's exactly what I used to look for in a checkout page. Where does the friction live. Where's the step nobody stress-tested because everyone assumed the step before it handled the risk.

I spent the morning in Burp Suite looking for that gap in an authentication flow. I spent the afternoon looking for the same gap in a conversion funnel. Different stakes, different vocabulary, identical question. I didn't plan that symmetry. I noticed it after the fact, the way you notice a joke lands only once you're already laughing.


Underneath that same day's entry, I wrote something else: EVERYTHING. TAKE NOTHING FOR GRANTED.

All caps. I don't usually shout at my own notebook. But that's the actual lesson underneath the funnel-and-Burp-Suite coincidence — I'd taken it for granted that the old skills were retired, that "career change" meant zeroing out and starting fresh at nothing. I built an entire narrative around being a junior again, and most of it's true. I am junior at this. But junior at pentesting isn't the same as junior at pattern recognition. I've been doing pattern recognition since before some of the SOC L1 material I'm studying existed.

Nothing gets to just sit in a drawer marked "old career, not relevant." Not if it still fires when the moment calls for it.


The other line from this week, the one that made me smile instead of think: "I am pretty good at improvising."

Thirty years of client meetings will do that to you. No brief survives first contact with the client's actual opinion. You learn to think on your feet because the alternative is going blank in front of someone who's paying you to have an answer. I didn't know that was transferable. Turns out walking into an ambiguous pentest scope, or a THM room with no walkthrough, or a "just take a look at Cloud Armor and figure it out" — that's the same room. Different lighting. Same requirement: don't freeze, work the problem in front of you with what you've got.

I used to think improvising under pressure was an advertising skill. It's not. It's a skill I happened to build in advertising. Different container. Still mine.


I don't think the answer here is "actually, my old career prepared me perfectly for this, no reskilling needed." That would be a lie, and a lazy one. I genuinely didn't know where to start on a pentest this week — I wrote that down too, plainly, no spin. The tools are new. The vocabulary is new. Cloud Armor still doesn't fully make sense to me and I'm not going to pretend otherwise.

But the instinct that tells me where to look — that's not new. It never left. It just went quiet for a while because I was too busy proving I could learn something completely foreign to notice the parts of me that weren't foreign at all.

The comeback was never going to be throwing out thirty years and starting at zero. It was always going to be this: finding out, one Tuesday with two tabs open, which of those old muscles still fire — and building the new ones next to them, not instead of them.