How do you handle your annual planning?

This may be as easy as a spreadsheet but we are an all volunteer organization with a set series of milestones that repeat every two years. This is in addition to any additional projects. We are constantly being "surprised" by how little time we have to prepare for events. We enter a float in the local July 4th parade and every year it is a huge shock that we have only a couple of weeks to prepare. We need to document the milestones in our two year cycle. How does your organization do this?

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