Unless the caulking is stripping away from your cheapass shower/tub enmasse and you've peeled off as much as you can and need a quick fix and don't have several hours to spend with a razor and a bottle of rubbing alcohol and all of your nails have bent backwards at least once and you're cranky and sick and have no idea how you or your housemate is going to cope with not having a shower in the morning but it needs 24 hours to cure and there's little that can be done about it and if you don't caulk it now, it'll just be that much longer 'til you can use the shower anyway so get over it already, ldy.
I promise, I'll be in a better mood tomorrow. On a Friday (which is always a long day at work). After missing work on Thursday (which will increase craziness exponentially). And after not having taken a shower in the morning.