Everything breaks all of the time [2026w23]

In this episode of leadprompt.sh, I explore why accepting that "everything breaks all of the time" is actually the foundation of a resilient engineering culture. Instead of chasing the impossible goal of perfect uptime, I break down how you can build systems designed for rapid recovery using observability, auto-remediation, and AI predictive tools. Beyond the tech stack, we dive into the reality of managing a Sev-1 outage, where I share my strict "facts only" rule for communicating with business stakeholders and shielding your team while the red lights are flashing. Join me as we unpack why inevitable system failures aren't just an infrastructure problem, but the ultimate test of your leadership. Show notes are here: https://leadprompt.sh/a/745-Everything-breaks-all-of-the-time-2026w23 Keywords: Engineering Leadership, Tech Leadership, SRE, Site Reliability Engineering, DevOps, System Resilience, Incident Management, Software Engineering, LeadPrompt, John Collins, Observability, Blameless Post-mortem, Auto-remediation, Infrastructure as Code, Tech Podcast, Root Cause Analysis, Uptime, Sev-1 Outage