You're thinking about it wrong.
If you don't have a powder check die, it might be time to consider adding one.
But, in my opinion, the best way to do it isn't to load until you run out of powder, it's pick a number of rounds you want to load and make sure you have MORE than enough powder in the measure to load that many rounds.
When you hit that number (20, 50, 100, whatever), Take the powder measure off and dump it out.
Then change your powder.
The method you're asking about is a good way of either getting rounds with no powder, getting rounds with inconsistent amounts of powder, or getting one or more rounds with very light powder charges.
I would NOT attempt to go the route you've described.