Depends on the cartridge, what I want it to do, and how hard you have to push it to get it to do that.
For instance, my .35 Whelen. I would like it to shoot a tad flatter, so I take it to max. It also has a super-long throat and can be seated long. MAP for .35W is 62,000psi, so going to max in it isn't really "going to max" per se. It has siblings like the .270 Winchester that go to 65kpsi, same casehead, same action. So pressure-wise, going to max in the .35W is like taking it easy with the .270.
Other rounds I regularly take way over max like .45 Colt in a Ruger or .45-70 in a Marlin. Sometimes max data is a historical relic, sometimes it is somewhat arbitrary like the -06 family, sometimes it is a line you are smart not to cross. I take it case by case.
I sometimes will also run up to max or a tad over max with a very small batch to make sure I have some room on the top end of a "production load" that I plan to make by the hundreds or by the thousands since I will not be weighing every charge.