“How much sleep should I lose over this?” I’d just finished going over some areas of high risk for this customer, some projects that had been delayed, appropriately up until now, due to larger business issues.”
“None, I only lose sleep when there isn’t a plan in place.”
Look, we all live with business risk and most of us live with some technical risk. The most successful people live with the most risk and sleep just fine. They also have a plans on addressing the risk, mitigating the risk or responding to it.
You’ll always have risk, just have appropriate plans to match.