Why The IT Dilemma Exists
Technology failures rarely start with technology.
They start months, sometimes years, earlier — with a local admin account nobody revoked, a switch that
was “good enough,” a backup nobody’s tested restoring from, a vendor login that’s still
active two years after the vendor left.
Every one of those looks fine. Right up until it isn’t. That gap — between working and
actually protected — is The IT Dilemma. It’s the pattern I see in almost every business
I walk into:
The IT Dilemma Series
Real businesses. Mistakes that looked harmless at the time.
A running collection of real problems, real businesses, and what actually fixed them.
I Was Excited to Buy AI Glasses Until I Started Thinking Like a Security Engineer - What began as shopping for prescription AI glasses became a personal journey into the next major workplace security debate. After DEF CON, the Air Force, and Philadelphia courts restricted recording-capable smart glasses in 2026, the question is no longer if businesses need an AI wearables policy, but when.
Part 4: A Responsible Neighbor: A Civic Framework for Data Center Development - A balanced civic address for residents, public officials, utilities, workers, and technology companies seeking a fair framework for data center development.
Part 3: The 100-Gigawatt Answer Hiding Inside America’s Power Grid - Flexible-load agreements could unlock existing grid headroom while protecting ratepayers and host communities.
Part 2: The Billion-Dollar Project Nobody Trusts - Four human perspectives reveal why billion-dollar data center projects can fracture trust before construction begins.
Part 1: The Cloud Isn’t Weightless. Your Digital Life Has a Physical Address. - The cloud feels weightless, but it runs on physical infrastructure that concentrates power, water, land, and heat impacts in host communities.
AI Has Made Phishing Cheap, Fast, and Frighteningly Convincing - AI lets attackers create polished, personalized phishing campaigns at machine speed. One click can turn a generic message into a sustained, highly targeted attack.
The Grand Slam You Are Missing - Tyler clicked a link, downloaded a blank PDF, and moved on. What he did not know was that a ransomware script was now sitting on his computer waiting to run. What stopped it was a policy that had been set once and running silently in the background for two years. That is Active Directory.
The Catwalk - There is a moment in The Phoenix Project where a mentor takes a struggling IT leader above the factory floor and shows him the whole system at once. That image never left me. Because it is exactly what I do every time I walk into a business that is having problems.
The Flat Network Problem - When I connect to a customer's guest Wi-Fi as part of an assessment, I run a LAN scan to show them exactly what is visible to anyone who walks through the door. What shows up would surprise most business owners - and your guest Wi-Fi may be putting a stranger on the same road as your payroll server.