[editor: this post is unfinished, but the statute of limitations has passed, so i’m making it available anyways. show your work. :-]

Strangely, I’ve noticed that the software I pay for legally, out of respect for the developers and the value it brings to me, not to mention the desire not to be arrested, ends up being the software I find myself using the LEAST after I buy it. I’ve been thinking about why that is.

My theory is it has something to do with what I call the Ink Problem — I rarely print anything, even though I have a high-quality printer, because I don’t like the idea of wasting the ink and the paper on anything less than perfect. Since nothing is ever perfect, I tend to not print. Ever.
Somehow, my expensive, languishing software feels related to my dusty, unused printer — it’s as if, because I paid money for them, these vaunted, paid-for programs feel different, loftier, as if I must approach them with exalted purpose and singular resolve to create excellent work. Anything less makes me feel like I’m perverting the reasons I bought them in the first place.

So maybe the result is just, don’t buy software. :-/

Except that I enjoy paying for good software. I like supporting smart hackers and great designers who make things which make my work interesting and my brain inspired. But it’s a rare program that I pay for and then continue to use regularly. I could graph the cost of software I’ve paid for on a chart and draw a black line above which I almost never use the program after I buy it — that line appears to hover around USD 99.

OmniOutliner, SnapzPro, ToggleMouse, iWork : I use.

TinderBox, MaxMSP, ReBirth, and Delicious Library*: I don’t.

* (JM3: technically the software is only 39 but i bought the wireless reader which adds $175)
(I also paid for and don’t use Skype, but that one fails the $99 test so I omitted it)

Does this sound familiar to you? I should be clear about something — I’m refering here to software that’s not strictly required to do my job. All of these programs are “fun” programs that I can use for work, but are not strictly necessary. In my case, another two-fold factor also applies:

1. I love new things.
2. I want things I don’t have.

Once I buy it, the “not having it” goes away, meaning my lust for it fades. And once it’s no longer new, the deck is stacked against me using any paid-for program that doesn’t weave itself into my life; the psychological pressure to “get my money’s worth” out of the software, combined with the lack of new-ness, the (possible) hassle of ham-handed corporate serial numbers and updates, all conspire to let these programs gather proverbial dust in my Applications folder.