This seems to be predicated on 3- to 5-year planning.
Long-range planning 
Mainly non-technical issues. These have less actionable deliverables, but have mission- and vision-related implications. It can help frame today's actions and find long-term supporters.
- What will funding models look like?
- What does ecosystem and related projects look like?
- We have a big goal now -- are other big goals related? How to break it down / build it up?
- Compare growth of WM as an idea with that of the Red Cross, the university system, the Peace Corps.
- How do we develop the support for Free Culture needed to make parallels to WP last?
- Consider what foundations (C, MA, Kn) and individuals (C, F, R) have done. How does the change of publishing and news impact this?
- How do we build identity and commitment to values through the use of the site? From visual id to slogans to other bits around it?
How can we reflect on the past 3-5 years to extract relevant steps in the above? What sorts of thoughts about 2025 make sense?
Discussions underway 
- Private v public postings : what are the risks of posting all rough drafts publicly? Can we remove the 'threat' of overhead of having to explain oneself by tutoring new people re: how to be a good reader?
- current article is a fork of strategy, proper history of Strategic planning 2009 to be found partly in history of strategy. Dedalus 14:33, 22 May 2009 (UTC)
For clarification, I put the link to the Public Outreach pages next to Participation. Currently, the Public Outreach department at the Wikimedia Foundation focuses primarily on developing more participants in the projects. Reach is primarily concerned with who has access to and uses the services.Jennifer Riggs 01:06, 4 June 2009 (UTC)
notes on planning dimensions 
from the main page:
Levels of planning 
- How do we plan for next year, or a few-year financial crisis?
- How do we prepare for the next magnitude of contribution (1M active contributors)?
- How do we prepare for the next magnitude of content (a major people or books/citations project might involve tens of millions)?
- What is impact? How do we compare?
- Who is the audience for impact : current readers/editors v. future ones? all humans v. weighting in one direction?
Areas of focus 
- How do we combine Planet Wikimedia, Twitter and similar updates, and non-minor edit summaries from central pages into a central exchange of wm updates and project highlights?
- How do we communicate new announcements across projects? unified randomized sitemessages. js banners with info.
- What does it mean to be an archive of knowledge? Of revision histories and metadata? How central/essential is this? How many copies are needed to keep stuff safe?
Scope and project creation 
- What areas of knowledge are worth covering? Why are some not - or is this only a matter of time? How do we decide, expand, modify?
Org structure 
- What structure should the overall org take?
- Should there be structure to support non-wiki-editors to submit carefully written work or reviews (without giving the edits special privilege, but giving the editors a way to view their original contributions)?
- How do we sustain funding? What new groups of funders aren't being engaged? How can reliance on funding be lightened?
- How do we sustain contribution? What new groups of contributors or readers aren't being engaged? How can reliance on direct contributors be lightened?
Video Reading 
LETTER FROM JIMMY WALES http://www.youtube.com/watch?v=lftF7VUHUdk
Mdupont 19:16, 23 September 2009 (UTC)
Old project 
Compare: NEH grant/Five year development plan for NEH grant, a big project and an empty page for it... --Nemo 16:20, 27 July 2010 (UTC)