The lovely blog "Letters of Note" published one of his letters to his half- or step-brother (I find wikipedia, nndb.com and other sources muddle those distinctions and I'm too lazy to go to the library and figure this out, also it's SUPER hot outside so I'm not going across the street to the library for nothin' today).
Anywho, this half/step-brother was asking for money. Lincoln noted that given this dude's constant pleadings for $$, this was just not going to happen. I've been down this road with people twice. It's tough to tell them no, but it has to be done.
Here's the link to the letter:
Here are a couple of my favorite bits.
Your request for eighty dollars I do not think it best to comply with now. At the various times when I have helped you a little you have said to me, "We can get along very well now"; but in a very short time I find you in the same difficulty again. Now, this can only happen by some defect in your conduct. What that defect is, I think I know. You are not lazy, and still you are an idler. I doubt whether, since I saw you, you have done a good whole day's work in any one day.
The common sense approach:
You are now in need of some money; and what I propose is, that you shall go to work, "tooth and nail," for somebody who will give you money for it.
And the incentive:
I now promise you, that for every dollar you will, between this and the first of May, get for your own labor, either in money or as your own indebtedness, I will then give you one other dollar.
And the best possible outcome:
Now, if you will do this, you will be soon out of debt, and, what is better, you will have a habit that will keep you from getting in debt again. But, if I should now clear you out of debt, next year you would be just as deep in as ever.
Nice. And true.