Thinking about supporting writers

[This started as a status update on my personal facebook page, but I realized I was interested in getting as many opinions as possible and that it might help to post it here. Please do comment if you have anything to share, and hopefully there will be more interesting content up here in the next day or two.]

Question: How many people donate to favorite internet writers through “tip jars” or voluntary “subscriptions”? Do you do it regularly, or only when particularly inspired? When you’re inspired, is it because you’re feeling rich/generous, or because the author is struggling financially, or both? Are you ever insulted by the presence of a tip jar/donate button on a blog/website? What about direct requests for cash?

Personally, I think I would have to produce a lot more content and post more regularly before I could feel comfortable doing this sort of thing, so that’s not the main reason I ask. I ask mostly because I have donated to more bloggers than usual lately. Not much, because I really need to be pinching pennies at least until my employment situation is more stable, but a few dollars here or there.

And I’m kind of wondering what inspires me to do this. If I were being rational about this, I would make a budget for this sort of thing and portion it out on a regular basis (monthly?) based on some objective criteria–posts I really liked, bloggers in particular need, SOMETHING. But really I tend to do it spontaneously, when I’m feeling relatively secure about money (looking good on my budget for the month, getting positive feedback in the jobs arena, been really good about discretionary spending like eating out/coffee lately) when a blogger happens to make a request or write a really fabulous post.

This process kinds of rubs the rationalist in me the wrong way, and feels a little capricious. I mean, why should these people’s income from their work be more determined by my whims (and current psychological state re: money) than by some kind of objective criteria? But that seems to be holding myself to a rather absurd standard. “Tips” are USUALLY made somewhat irrationally, and very small expenses. And anyhow, if I can impulsively buy an itunes game or a fancy cup of coffee every once and awhile just because I feel like it, isn’t it just as reasonable to toss $3 or $5 at a writer whose work I really appreciate and who could use the cash, just because it makes me feel good?

It feels a little weird to give ‘donations’ sometimes when frankly I could use them myself… but frankly I think that’s part of why I do it. Because I want to live in a world where people can make a living by producing awesome content ‘for free’, and because I hope that if I write stuff as meaningful and valuable to others as some bloggers’ stuff has been for me, that they’d be willing to toss some change in the tip jar too. Which is probably why I’m donating more lately (as in, I think I’ve spent $10 this way in the last month, woohoo Ms. Moneybags!). I know how much of myself I put into my posts, and I want to show my appreciation for other people who do the same.

Anyhow, I started this as a question, and I really do want answers. Thoughts?