First of all, it's obvious that the part of our movement already suffers from the "old grey man" illusion, although the most of us are not old nor grey.
That's typical modernist paradigm, which brought many achievements to our civilization, but also removed decision-making power from the majority of population: women + minorities consist definitely more than 50% of population.
We have to move from that point. Yes, it's hard as our main product is of modernist nature, but I think we are clever enough to overcome it.
Participation in Wikimedia movement requires a lot of time. That's the reason why we have to have fun while working on it. Otherwise, anyone not willing not to have fun during significant portion of their everyday life wouldn't be excited to be with us. And there are many reasons why we need them.
And not just that. I am sure I am not the only Wikimedian significantly demotivated to work on important things for our movement just because we are boring. It's exhausting to work on various issues if the only set of benefits is consisted of "Thanks! This is important!" and similar more or less elaborate variants. I want to be eager to do those things, to expect fun after spending time on doing "important things". Although my beard is partially grey, I definitely don't strive to be an "old grey man", emotionally fulfilled exclusively by the fact that I did something important.
Think about what we are offering to any of us, as well as to newcomers: * You are working on an epochal project. * You have to have all "serious" qualities to do that. * If you are suffering from OCD, you'll find that it's extremely fun to correct typos and categorize pages. * You could become a member of your own local organization and spend a lot of time arguing with other people suffering from OCD. You know, it's a kind of fulfilling. * We are more and more important and you'll find it's fun to participate in official ceremonies and cocktails with important people. * <put your own idea here>
Basically, we tell us and newcomers that we have to work an unpaid and boring part time job because we'll be more successful in doing other boring things. It is important, but it works for just a small part of population. And, of course, it's not fun.
* * *
But let's go to the brighter side... From your responses, including a couple of them sent to me privately, I'd conclude the next and call for action.
* There is one thing I missed while writing this. Obviously, some Wikimedians do have fun anyway. It could be because of different cultural expectations, but also because some of you know and practicing something the rest of us don't. So, please, share with us how you have fun during Wikimedia meetings and conferences! Let's start here, then we could create a Meta page for sharing ideas.
* There are a number of fixable things and they are related to what Chris said: event management and meeting skills. I think we are mature enough to find a way how to get and share the knowledge on those topics.
If WMF requires from chapters and other affiliate groups to develop strong formal procedures, it could also at least offer help in making our events and meetings more interesting.
If contemporary progressive companies all over the world are able to make things a bit more shiny with all of those "team buildings" and similar bullshits, I am sure it would be much easier to achieve that inside of our, mostly volunteering environment. Mostly, we are not here to do boring things; we are here to have a kind of fun, no matter how weird it could look like. So, it shouldn't be hard to get positive outcome if we implement some of the contemporary straight-forward HR and organizational methods.
* Software. How hard is to implement XMPP-based web chat? I see a number of contemporary free software web platforms offering it. Yes, we are a decade late, but it's better sooner than later anyway. Other social features? Any *really* *interesting* and educational game around? And, of course, opt-in only because we have "old grey men" which would be offended by the idea that serious work could be also fun and social.
* The level of our culture is the most complex one. Bad news is the fact that there are no howtos for making a culture more fun. Good news is that it's not hard to have fun and to spread it around yourselves. And that should help. And, yes, everything above counts in changing the culture from being boring to being fun.