You relube it the moment it squeaks or once you get home. Squeaking means minute vibration at that interface, and that means accelerated wear. Expensive machines have instrumentation or service measuring devices that listen for that squeak or vibration, to service a bearing before it becomes critical.

If your chain is lubed with oil, some feel that a wipedown and relube is enough. I like to clean in solvent to remove the metal dust, was a pain, but buying an "on-bike" chain cleaner made that *really easy*. Park had them first, but there are much cheaper copies on amazon now. I use tiki-torch fuel (cheap open bottles at end of season at goodwill store) as solvent, it's 99% mineral oil. Clean, dry, lube.

Melted wax is a better lube, but needs chain removal to lube. However, WAY cleaner to handle, and doesn't require cleaning, as metal dust is just shed as it forms. Just put in the melted wax, any metal dust will settle to bottom of pan. Pull chain out (easier if you've short-laced it onto a spoke or wire), let it drip over the pan or wipe down (without burning yourself), put back on bike, done.

Whether wax or oil, I typically need to lube my chain about every 600-700 miles. With wax, it's when I hear a squeak. With oil, it's when the oil turns to the consistency of peanut butter (paste), due to the emulsion of the metal particles; It may not squeak, but those metal particles in solution will accelerate wear inside the chain links, rollers, and pins. The more standing-climbing I do, the greater load on the chain, and the faster the wear.

After a clean and lube, it's very satisfying how noticeably quiet the drivetrain is.