Wikipedians speculate about the future all the time. And yet I say we rarely engage serious discussion of priorities, dreams, timelines, goals, and opportunity costs. Why is this? In part, it is because we don't have detailed comparisons with other similar organizations and situations; only hearsay and vague rules of thumb.
Threads and policy subpages about what should or should not happen, with hypotheses about the results of community or policy or organizational change, often go on for months and hinge on unknowns. But people are far more willing to speculate absently about human nature than they are to research what has happened to similar efforts in the past.
Reading and learning about how other projects and international volunteer efforts work, and how similarly bold historical efforts have grown and transformed, can help turn these discussions from circular arguments to analytical collaborations. This can also help avoid "reinventing the flat tire".
These comparisons *should* be made. Fundraising; volunteer attraction, empowerment, and retention; administration; handling of software and article bounties; multilingualism; logo and trademark licensing; partnership and promotion; selection of advisors -- these are all general problems. Wikipedia is different in details, but shares a great deal with the thousands of thoughtful institutions that have dealt with these issues in countless contexts, since before the first Wikipedia logo was a twinkle in the Cunctator's eye.
Unfortunately, these discussions tend to peter out and get lost. Mailing list threads are dropped and never wikified -- as happened with the "Wikimedia in five years" thread from last August, and with the interesting Apache Foundation thread. Wiki pages are abandoned and forgotten.
Help keep these discussions alive, and give them shared context. Here is a page for gathering links to these discussions, and for encouraging investigations into groups (such as the Red Cross) that have been suggested many times for comparison:
http://meta.wikimedia.org/wiki/Parallels
Do you know someone who works at a multinational volunteer collective? At a major political campaign, grassroots news foundation, or a branch of the UN? At a global NGO? Find out what they think the parallels are between their organizations or projects and ours. Ask them for documents and essays, or even for their take on the greatest obstacles our projects will face in the near future. As with the NetBSD essay, you may be amazed to discover how much of existing discussions apply to our communities.
++SJ
ps - Reading over the discussions about Wikipedia's future that have inspired or provoked me over the past few years, I noticed that Anthere and Erik Zachte have been involved in, if not the initiators of, a majority of them. Rock on.
pps - this is thread 3 in a 3-thread microseries. see also http://mail.wikimedia.org/pipermail/foundation-l/2006-September/010247.html
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