> When I find that the only tube of toothpaste left is that special, sentinel toothpaste, then I know it is time to buy more toothpaste. And then I have ample time to do so.<p>I might suggest phrasing this a little differently. Obviously, when you find that <i>any</i> tube is the only tube left, you know it’s time to buy more toothpaste. The problem is that you realize this early in the morning or right before bed, and so you’re likely to forget. The advantage of the “sentinel toothpaste” is that it continues to remind you after that moment, so that you’ll actually remember when you have time to do something about it.<p>And I think that captures the key thing about a sentinel value: it captures state in a place where you’re already storing state, without requiring you to wrap the state in some external structure, e.g. putting a sticky note on your mirror or storing a string’s length in a separate field.