The OP's question is a good one: Work up to what?
Working up to pressure signs is ineffective. Flattened primers are not a reliable indicator, measuring case head expansion is deeply flawed, and the other signs kick in around 70 KPSI. Primers fall out at about 80 KPSI.
So what do you work up to?
You do need a chronograph.
Some powder/cartridge combinations reach a point where more powder does not produce more average velocity, but does produce more variation. Working up a load involves making sure you are not in that condition.
As long as increments of powder are producing regular increments of velocity, you are not in that condition.
Given that, find the load you like below the "book" maximum velocity for that powder and bullet. Chamber geometry, bullet mass, cartridge length, etc all drive pressure and pressure drives velocity. Velocity is very highly correlated with peak pressure, and is the best indicator most of us have.