Billing
The Discount That Never Expired
A promotional price was granted as a temporary exception. Nothing in the system was built to end it, so it became permanent — quietly, and at scale.
Operations
Operational failure modes in modern software businesses — billing, support, vendor handoffs, the parts that aren't in the code.
Operations
The Dependency You Inherited at 2am
A production system fails outside business hours. The fix requires understanding a component integrated under pressure and never properly documented. The on-call engineer pays the cost of decisions they never made.
Operations
The Work That Became a Performance
Building in public was meant to make solo work less lonely and more honest. Somewhere along the way it tilted: the work and the broadcast became the same activity, and one started shaping the other.
Handover
The Knowledge That Walked Out the Door
A long-tenured person leaves. Standard offboarding happens. Months later, decisions take longer and feel less confident. The thing that left was never written down — because nobody knew it was there.
Change Management
The Human Side Doesn't Update Automatically
A return to social media, a domain that finally found its purpose, and one observation that will make or break a start-up: AI can build the product, but it cannot repair what breaks between the business and the client.
Operations
As the world reshapes and indie start-ups are taking over, new negative patterns arise
Billing. Support. Product trust. Marketing. Failures rarely come from code — they come from decisions. A record of recurring failures in modern software operations.