Lessons from an Engineer’s Biggest Fails

I’ve made some spectacular messes as an engineer. Once, I brought OSPF crashing down without a change ticket, staring at a dead network praying no one would notice. Spoiler: they did. Those flops weren’t résumé highlights, but they shaped me into the CTO I am today—humble, adaptable, and a little wiser. Here’s a trip through my hall of shame, and why it matters for the teams I help now.

OSPF Meets My Overconfidence

Picture this: I’m a cocky network engineer, tweaking OSPF—Open Shortest Path First, the routing protocol backbone of many a network—because I “knew” what I was doing. No change ticket, no heads-up, just me and a console. One typo later, routes vanished, traffic halted, and my inbox lit up like a Christmas tree. I fumbled for an hour, heart pounding, before rolling back my genius move. My boss didn’t fire me, but his “What were you thinking?” still echoes. Lesson one: arrogance is a lousy co-pilot. I learned to double-check, document, and—most importantly—plan your work and work your plan.

Fiber Under the Floor, Mid-Day Madness

Then there’s the time I ran multimode fiber under a data center floor during peak hours. I’d pushed for the change ticket, swore it’d be quick—splice, test, done. Instead, I’m belly-crawling under tiles, dust in my lungs, as servers hum overhead. A cable snag later, a critical link flickered, and ops scrambled. It worked out, but only after a tense hour and some choice words from the team. I’d underestimated the risk, assuming my prep was enough. It wasn’t. That day drilled in respect for timing and the chaos of “minor” changes—stuff I now flag for clients before it bites them.

ATM: Not What You Think

Ever met an engineer who rated himself a 10/10 for ATM and routing? I did. During a review, I asked what ATM stood for—expecting Asynchronous Transfer Mode, the old-school telecom tech. “Automatic Teller Machine,” he deadpanned. I blinked, laughed, then realized he wasn’t kidding. He’d aced routing, sure, but his ATM was cash withdrawals, not packets. It was a hilarious reminder: don’t assume everyone’s on your wavelength. I stopped nodding along to buzzwords and started digging deeper—a habit I carry into every client gig, ensuring we’re all speaking the same language.

The Lunchtime Backbone Betrayal

Midway through a major backbone upgrade—think routers humming, cables everywhere—one teammate just… left. The PBX went silent, pagers buzzed unanswered, and we stared at a half-finished mess. He called later: “I was hungry, needed a burger.” We laughed it off eventually, but in the moment? Panic. I had to rally the rest, patch things up, and pray the network held. It did, barely. That guy taught me team reliability isn’t a given—some flake under pressure. Now, I watch for those cracks in client teams, helping them shore up before upgrades turn into outages.

The Brick and the Top Hat: A Tale of Two Teams

We had a ritual for screw-ups: the Brick. A literal brick passed to whoever botched the last change—like me after OSPF. It was a gag, sparking debates over what “failed” meant. Was it downtime? Bad planning? We’d argue, laugh, and move on. It built camaraderie. Years later, I tried the same vibe elsewhere, swapping the brick for a KISS top hat—a cool relic from a concert. Big mistake. That team didn’t gel like the first; they saw it as mockery, not motivation. Morale tanked, and the hat hit the trash. Same trick, wrong crowd. I’d misread the room—a humbling gut punch.

What Those Flops Taught Me

Those moments stick like burrs. OSPF taught me caution—assume nothing, verify everything. The fiber fiasco showed me timing matters as much as tech. ATM Guy? Clarity over jargon. The lunch deserter highlighted team trust. And the top hat? One size doesn’t fit all. I was green, eager, and fallible—qualities I don’t hide now. They forced me to listen harder, adapt faster, and own my mistakes, not bury them. Humility isn’t just saying “I messed up”; it’s learning from it, then showing up better.

Why It Matters Today

As an independent CTO, I’ve been the guy who broke it, fixed it, and learned to spot it coming. Clients don’t need a flawless guru—they need someone who’s navigated chaos. I catch risks others miss, like a sneaky change window or a team vibe off-kilter, because I’ve lived those flops. I ask dumb questions (thanks, ATM Guy) to avoid costly assumptions. I push for plans that fit the people, not just the tech—Brick vs. Top Hat proved that. My past isn’t pristine, but it’s why I can walk into your mess and say, “I’ve got this.”