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Windward Version 4.0

Moving into the next phase of our organizational life


Andrew, 2015: A few notes before we begin. This article was originally posted in 2005 by Walt, Windward's senior most steward and the only remaining founder living within the community.

In the article, Walt elaborates both on why Windward is in pursuit of young people of good character to take the baton of community into the future, as well as some of the fundamental aspects of Windward that have kept it going through the years.

As of 2015 Windward has several new members of the community, including myself, but we are still looking for more courageous hearts to join us on this journey.



A glimpse at the shifting mosaic of community members and participants. From top-left going clockwise photos are from 2010, 2011, 2012 and 2015. While the people may change, the underlying "operating system" does not. It goes on evolving as people continue to contribute to it.

Windward is like a Social Computer

It's not too much of a stretch to suggest that Windward is a sort of social computer with its own operating system, and actually an analogy to the Windows operating system works on a number of levels.

As a social computer, Windward's operating system functions in the background so that our members can operate their own programs within that larger community context. Just as very few people power up their personal computers in order to stare at the nifty icons that populate Window's blue screen desktop, so too few people come to Windward with the intention of focusing on our organization's operating systems. Which is a shame since it's what makes all the rest of Windward possible.

Rather, their initial concern is focused on how Windward can work for them; it's only later that they become interested in understanding how Windward functions at a systems level. That's understandable since if Windward doesn't work for them, then it doesn't matter much (at least to them) how well it works for others.

Once someone has made a successful transition from the consumer world to the cooperative world -- once Windward is up and working for them -- that's when people start to turn their thoughts to questions along the line of how can we enable Windward to work better?

Another "feature" that intentional communities share with the Window's operating system is periodic system crashes. Perhaps the most challenging stage in the development of any intentional community comes when their initial social structure proves unable to cope and crashes. Some communities will be able to find the internal resources needed to reboot, but most will just call it a day and dissolve.

For example, it's fair to say that Windward'itself came about because of a massive, non-recoverable systems crash in a previous community that was forming in the Caribbean. We took what we learned there, rewrote the operating system and booted up Windward Version 1.0.

Bob, Cindy and Walt. What would be considered the original members of Windward 1.0

Any life-support system crash is a major stressor, but there's a lot of truth to the adage that those things which do not kill us, make us stronger. Recoverable system crashes can be blessings in disguise in that they're often the only way to find out what works when the usual options don't. It's almost impossible to see a system crash coming, and often all one can hope is that sufficient safeguards are in place to insure the survival of the organization, and forge on ahead.

Windward's operating system has been running for 27 years now, and over that time we've had three full system crashes -- hence the title of this article since this is our fourth time we've tinkered with our system software and rebooted. After each crash, we've made changes calculated to either prevent the problem from reoccurring further down the road, or if the flaw is inherent in the situation, to enable us to deal with it better in the future.

Not So Simple Problems

Some of the problems that have traditionally plagued intentional communities can be taken out of the dynamic all together, but there are others that can't be "solved." To understand the distinction, consider the difference between someone who's addicted to nicotine and someone who has an eating disorder.

It's entirely possible (albeit not at all easy) for a person to cut nicotine out of their life for good, at which point the host of problems that arise from an addiction to nicotine -- physiological, financial, social, etc. -- go away so long as the addict stops using tobacco.

It's not that "simple" for the person who has an eating disorder. Eliminating food from one's life isn't an option; rather, the only viable course involves undertaking a series of steps designed to manage food intake in ways that enhance life rather than limit it. So too, there are problems that a community can not hope to eliminate; the only option is to be aware, prepared, and truth be told, a bit lucky.

Windward is real -- which means that it has flaws and shortcoming. Moreover, all of the people here have flaws and short comings as well. The goal of our operating system is to create ways that (1) we can cover for each other's shortcomings, and (2) pull forward in unison towards our common goals. Given the challenges involved, a study of the history of intentional communities quickly leads to a sense of amazement that it can be done at all.


Windward is real, and we make mistake. Jewel, the goat in the above picture died in childbirth, in large part due to our lack the members skills in mid-wifing at the time of birth. Here's and article about it

So far, our operating system has crashed three times in 27 years, and each time we've been able to pick up the pieces and proceed. Each crash cost us dearly; we lost good people and a lot of organizational momentum, but we learned from each debacle, formulated new guidelines, changed our by-laws if necessary, and moved on towards our goal.

Windward's organizational ability to do that is perhaps our most important feature. Any person or group can keep their cool when things are going their way; it's when things aren't working that character counts the most. It's how we deal with adversity that most truly shows who we are.

The problem which has nailed us three times so far actually doesn't have much to do with Windward, so there's not that much we can do to prevent it other than to be aware and insure that it doesn't blind-side us yet again.

A Core of Strong Women

Windwards circle of strong women in 2012

For more than 20 years, women have made up the majority of Windward's Board of Directors. As a long-timer, I have no doubt that this is one of the core reasons our community has survived so long and accomplished so much of what we set out to do. On the other hand, it's also what exposes us to a problem which isn't intuitively obvious.

Our experience is that many of the women who seek out community do so in major part because they do not have a positive relationship with their mother. Lacking a supportive bio-family context, they undertake to create an intentional family that can meet their needs. There's nothing wrong with that; indeed, there's a lot of things right with it.

It's fair to say that the a person's most important role model is their same-sex parent, and if a daughter's mother is caught up in a dysfunctional relationship, her response will often be to build an identity founded on the premise that "I am NOT my mother."

That's an identity foundation that can work for many years, but life is a timed event and no one gets out alive. It's hard enough for anyone to deal with the death of a parent since that triggers a host of feelings centered around loss and a newly impressed sense of one's own mortality, but it can be especially devastating for the person who's primary self-identity is based being different than the lost parent. Having lost their polaris, they find themselves adrift.

Cindy (right) and Joyce (left) we're both critical members of the Windward for many many years.

Windward has a core of strong women -- that's not going to change. Windward works because those women are entrusted with significant levels of power, and that too is not going to change. All we can do is to be aware of the problems that arise by virtue of those traditions within our structure.

Our most recent systems crash took place in May of 2003. Over that summer we all took a long look at what each of us as individuals wanted to do; some wanted to go forward, and some wanted to go in other directions. By that fall, the ones who wanted to move on had, and the rest of us started the process of healing and reflection that needs to happen before opening our doors and hearts to new relationships.

Just as it's important for someone coming out of a divorce to not immediately rush into a new relationship, it's also important for a group to take the time necessary to distance themselves from previous relationships that didn't work out before undertaking new relationships. Otherwise, there's too high a probability that the old dynamics will reassert themselves.

Since then we've done a lot of organizational soul-searching, made a few notable changes to our by-laws based on what we've learned, and are slowly starting to rebuild the membership. On the one hand, it's hard, but on the other, it's exciting to be entering a new, more focused phase in our organizational life. All in all, we're excited about where we are, and looking forward eagerly towards the development we see coming in the years ahead.