To hit Ruby3x3, we must first figure out **what** we're going to measure, **how** we're going to measure it, in order to get what we actually want. I'll cover some standard definitions of benchmarking in dynamic languages, as well as the tradeoffs that must be made when benchmarking. I'll look at some of the possible benchmarks that could be considered for Ruby 3x3, and evaluate them for what they're good for measuring, and what they're less good for measuring, in order to help the Ruby community decide what the 3x goal is going to be measured against.