There are two main classes of license you should consider when you can
set the licenseing for a piece of software:  GPL[1] or BSD[2]. (the
debian-legal list frequently suggests zlib and mit licenses as
other alternatives for permissive licenses if you don't like BSD for
some reason)

GPL vs BSD is a flamewar on par with vi vs emacs--or put another way,
it's a personal decision like preference for text editor is.  For your
own code it comes down to your own preferences for what happens to the
code when others create derivative works: GPL is written to preserve
everyone's right to get the source for derivatives, while BSD is written
to preserve the most rights for those who receive the source (including
the right to withhold their own derivatives from others).

(when it comes to contributing to an established project, of course,
your only choice is to contribute in compliance with the terms of the
established license; this isn't the case at hand)

IMO, the single worst thing you can do is try to draft your own license.
debian-legal frequently finds that this or that well- intentioned phrase
is hard to reconcile with their "free software guidelines"[3].  Software
that is heavily dependent on a windows-only commercial program won't
become a part of debian anytime soon, but the guidelines do a good job
of capturing what is important to me about Free software while
encompassing many distinct licenses.

Jeff
[1] http://www.gnu.org/copyleft/gpl.html
[2] http://www.debian.org/misc/bsd.license
[3] http://www.debian.org/social_contract#guidelines

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