Who is supposed to "Cry It Out," me or my toddler?

My youngest child -- he's 2 -- has never been big on sleep. As newborn, he'd doze only if he was being held; as a toddler, he refuses to nap, even when he's falling down with fatigue. He sleeps through the night just fine, but putting him to bed can take ages. When bedtime runs into deadline and I have work waiting for me downstairs, the battle of wills becomes really hard to bear.

When my son was even younger, we tried "cry it out" with absolutely no positive results. The child can outlast me; this is one battle of wills that he wins hands down, and I have to admit I'm a little upset by how I can't handle the screeching.

But right now, he's upstairs, upset at having to go to bed at all, and I'm downstairs, guiltily unable to turn off the monitor, trying to get my work done.

This sucks.

Now, his wail changes: "Mama, Mama, Mama, Maaaammmmaaaaaaaaa...."

This sucks even more.

The big kids are at their mom and step dad's house, so I don't have to worry about him waking them up. (Why do I worry about it? Because a sleep-deprived teenager or two is not something I particularly want to add to my work-life juggle right now.) My 4-year-old is fast asleep, enveloped in a cloud of the rose-scented perfume that I spray around her room to ward off monsters and bad dreams (she believes in it, so it works, even though it's cloying and permeates everything in her closet).

My 2-year-old isn't old enough to be swayed by cheap perfume. He's never been into his stuffed animals or a blanket or a pacifier, instead preferring to hold one little paw to my cheek at all times, even as an infant. It's sweet and adorable and frustrating when bills are due and work is waiting to be done in order to pay them. I feel guilty for being frustrated by this simple need of his -- the need to be close to his Mama, the inability to find comfort elsewhere -- especially when I know, from our older kids, that 10 years from now I'll wish I could comfort him so easily.

Tonight, though, I grit my teeth and count to 10, again and again, willing myself to wait five more minutes before capitulating. I know he is safe and warm and full and dry. I know that he is tired, and needs to sleep. I force myself to work, wondering where that line is between cuddling and coddling, between soothing and spoiling, and whether I'm anywhere near it.

Fifteen minutes pass -- only 15? -- and I hear silence in the monitor. I wait a few more minutes before going upstairs to check on him. I pull the sheets up around his fleece-clad little self and kiss his completely dry, surprisingly not-at-all tear-stained cheek. Battle of wills. But, this time, I've won.

I think. Maybe.

What do you do when you have to work, your child has to sleep, and you can't seem to make either thing happen? Single Working Moms, please weigh in -- how do you do it?