I was heading to dinner with a friend who worked in infra. Google maps said we could bike across town in 20 minutes. He suggested we leave 40 minutes ahead of time and grab a drink at the bar if we got there early. When I raised an eyebrow, he goes:

"What, do you not live your life based on 99th percentiles?"

I tend to think of work as upside-based on downside-based. Most feature work is upside. 10% lift on conversions is great, 40% adoption is winning, and you're playing for the moonshot of 10x. Infra work is downside-based. 98% secure, 98% available, 98% acceptable performance -- that'll all failure. Winning means the thing works as expected and nobody notices.

Not everything sorts cleanly into upside vs. downside, but a lot does. Allocate your risk accordingly.