(Updated: April 17, 2022)
Needs for the homestead change rapidly as we figure out what we want. Even with planning, as time goes by we find that the things we once wanted are no longer the priority. We, like the homestead, are constantly evolving and so is our planning for the season.

When and How to Plan for the Season
So how do you plan for a season when things keep changing? Well, generally we sit down once a year (usually in December or January) and go over the previous year: what worked, what didn’t, and what we want to try in the future. Then we compare them to our list of goals that we revisit every year. (See our goals template here, which includes examples from our previous smaller two-person homestead in South Texas, USA.)
Because the goals are broken down into categories, and we have 1, 2, 3, 5, 7, 10, 15 and 30-year goals, it allows us to prioritize and make small achievable steps for the short term. In essence, these are small simpler plans for each season. Not only does this prevent taking on too much at once, but it also means we can break big things down into little steps done in efficient order that the big project takes less overall work. No sense in planting seeds before you dig the garden bed!

The Importance of Records
By keeping records of these goals, it also serves another purpose: motivation. Sometimes you get so caught up in the day to day that you lose sight of what you have already done. Looking back can show you the progress you’ve made when you feel like you haven’t done anything.
I have another set of records I keep for tracking our groceries and feed expenses. There are many ways you can track this and I find that how I track it changes every year. (Especially when I discovered my food intolerances!) But my main goal in tracking groceries is the weight in pounds and categories of the produce and meat we purchase. This allows me to cross-reference how much of what we ate the previous year. That figure lets me calculate how much food I need to grow/raise.
Why We Plan for the Season Like This
If all this seems like a lot of work, it is. But that is why we do our long-term planning during the winter. A real benefit of doing all this paperwork is that the rest of the day to day tends to run much more smoothly. This prevents us from wasting time doing non-priority projects or a step that inhibits a larger goal later on.
Now we are part of a much larger homesteading community. So planning proves to be even more helpful in making sure that everyone is on the same page. Whenever the usual person who performs a task may take ill or be needed elsewhere on the property, there is an established and simple routine for the other person stepping in to follow. This keeps them from possibly messing up a trial garden or feeding animals the wrong thing or the wrong amount. Clear communication is key for a healthy homestead, and group planning plus documentation certainly helps!

Overall, planning for a season can seem tedious but since this is our life and not a hobby it is critical that we are efficient. Besides, it’s really fun to plan the gardens together every year and dream about what to grow! Doing it on paper first just keeps us all informed and working towards the same shared goals.