Doing What Matters Most: Personal Project Management for the Burgeoning Homesteader

06 Sep, 2023

This article is part of a new series titled "Doing What Matters Most," which looks at how simple, flexible, personal, project management systems can help people make sense of their lives.

For the past year, my fiancée and I have been rehabbing a large piece of land in New York's Hudson Valley. The project is massive¹ with many moving parts, dates, deadlines, craftspeople, heavy machinery, purchases, deliveries, mechanical breakdowns, forestry plans, builds, teardowns, and mud. Lots and lots of mud. Instead of hiring general contractors to oversee the work, we've chosen to manage the never-ending list of projects on our own. We can now say that after living for a year in tiny, 200sf trailer, heated with firewood, plumbed with water we cart in from a local spring, and with just enough internet, our system works.

These are the six steps we take when beginning any new project:², ³

1. Define project
2. Brainstorm tasks
3. Gather resources
4. Do only today's tasks
5. Record progress and correspondence in a log

Here's how we do it.

1. Define project(s)

A project is not something to do. It's a goal you want to achieve, an outcome you want to see manifest. In our system, we don't do projects. We do tasks that, when completed, result in the completion of the project.⁴

Whenever we're ready to start something new, we first decide what it is we want to accomplish. Then, we convert the desired outcome into the project's title. If our goal is to have a new fence around the yard, then the project is called, "Install new fence around yard." If the goal is to turn a monoculture plot of weeds into a vibrant and diverse meadow, then our project is called, "Sow wildflowers in the meadow." Goals are translated into projects by condensing the language and phrasing it as an action (ie "Take down barn" not "Barn Takedown"). Naming our projects in this way allows us to look at a project's title and know exactly what it is we're trying to accomplish.

For the purposes of this article, I've set up two projects to work on:

1. "Build a tool shed" (due 10/1/23)
2. "Create a path to tool shed" (due 11/5/23)

Like all projects, these have due dates.⁵

2. Brainstorm tasks

Next, we immediately list all the tasks we can think of that will lead to the completion of the projects:

Brainstorming tasks gives both a broad sense of the scope of the project, as well as tasks to get started on. Obviously, these lists are incomplete, and the tasks are in no particular order. But, things will change.

For example, the list of tasks associated with the project "Create path to tool shed" assumes we're making a gravel path. But, what if we change our mind? What if we're undecided as to whether we want the path to be laid with gravel, pavers, or wood? And, what if a determining factor in this decision is cost? In this case, we add new decision-making tasks to the list (shown below in bold):

By keeping things flexible, allowing tasks to come and go, the scope of our projects grows organically. This has the added benefit of helping us keep track of where we're at in the process. A newly added task is a newly added indicator of where we're at.

3. Give "do" dates to any tasks you can

In the productivity world, a distinction is made between a "do" date and a "due" date. I define each as follows:

Once we've brainstormed our task list, we give do dates to any tasks we can. We start with the ones most likely to occur at the beginning and end of the project, since the timing of these is easier to predict:

We arrive at these dates by looking at the completion date of the project alongside our calendar. We take into consideration weekends when businesses are often closed, as well as our own schedules. Initial calls for quotes can usually happen right away, while finishing touches can happen on the days leading up to the due date. We try to schedule deliveries a week or two in advance of the date we need the materials.

We never worry about being locked into do dates, since many will change. Unlike due dates, we find do dates to be quite flexible.

4. Gather resources

Throughout the ideating process (even before the project is fully defined), we start collecting bits of information needed to check tasks off the list.⁶ For the projects above, we'll need phone numbers to get quotes; names, address, and websites to buy materials; more than a few YouTube videos on how to square foundations; and a design to work off of so we can physically lay out the path. Anything we can think of that might help us take action goes on our resources list, which we pull from to populate tasks in our task-management system:

5. Do only today's tasks

Unless there's a specific reason to press forward, we typically resist the urge to "get ahead" and, as often as possible, only do today's tasks.⁷

Our reasoning is simple: mental and physical health are fundamental to any sustainable project management system. Burnout is very real and very debilitating. We take our free time seriously, inspired by the work of radical homesteaders, Helen and Scott Nearing, who divided their days into two four-hour sessions:

"Suppose that the morning was assigned for bread-labor. We then agreed upon the tasks that each member of the group should take on … in the garden, in the woods, on construction, in the shop, at sugarmaking or packing. If one’s bread-labor was performed in the morning, the afternoon automatically became personally directed. One might read, write, sit in the sun, walk in the woods, play music, go to town. We earned our four hours of leisure by our four hours of labor."⁸

Limiting ourselves to working only on the current day's tasks regularly has us wondering at the end of the day, "Is that it? Is that all we have to do today?" Even though the answer is almost always "yes," the internal voice that says, "Do more. Get ahead. Keep working." is never far behind. However, so long as we've dated our tasks, know our project's timeline, and have successfully navigated delays and hiccups, we rarely feel the need to push forward.

Task-Focused vs Project-Focused Systems

The beauty of this approach does not stop at an increase in leisure time.⁹ Not only does sticking to today's tasks feel less burdensome, but the time we spend laboring turns out to be time better spent. The trick is staying task-focused.

Project-focused workflows convey a false sense of time, especially in regards to when projects should take place. Looking back at the projects I chose for this article, it would seem that building the shed should come before creating the path that leads to it. After all, it might be difficult to create a path to a non-existent shed. When we bring our attention down to the level of tasks, however, we see that the projects are actually progressing side-by-side.

Below is a task list containing tasks for both of our projects (A and B represent "Build a tool shed" and "Create a path to shed" respectively). September 5 shows how task-focused project management allows multiple projects to be worked on concurrently:

Task-focused systems enhance our output by initiating action plans on projects that would otherwise linger in waiting. This also makes for a more diversified and dynamic workday. Looking back at the tasks to be done on 9/5/23, we can see how different is each task:

Checking to see how much lumber and tin roofing we have means going to the barn, climbing up into the lofts, and rooting around to see what we have on-hand. These are physical activities. On the other hand, I can call suppliers anywhere there's cell service: at home, at the café, dog-sitting our friends' pup, or while making dinner (I've done it). By contrast, reviewing the shed design is, for me, a relaxed, creative activity, usually done while sitting on the couch or in bed. Six tasks, all of which should take at most two hours to complete, each moving its respective project one step closer to completion, each subsequent task a palate cleanser that clears the mind and gets the body moving in new ways.

6. Record progress and correspondence in a log

The final step in our system is, in many ways, the most important. Whenever we call a supplier, speak with a tradesperson, schedule an appointment, or happen upon some new information, we record it in log¹⁰ putting the most recent entry at the top:

We always put the day of the week next to the date, since it's common to reference the day when talking about recent events (ie "Did you get the email I sent last Monday?").

Keeping a log has been an absolute game changer for dealing with dozens of people and vendors. On any given day, we might speak with three to five people each with different information, some in conflict with each other (ie different quotes and timelines for the same service). Keeping track of these variables and having this information in a central location, is essential.

How It Looks In a Digital Project Management Platform

For collaborative projects like those above, we primarily use ClickUp,¹¹ which we organize according to this hierarchical folder setup:

• Areas
• Aspects
• Projects
• Tasks
• Resources
• Logs

In ClickUp the hierarchy looks like this:

Areas are folders representing overarching elements of our life that will never end.¹² Health, Finances, etc. are examples.

Aspects are the components of those areas with which we can actually engage.¹³ Aspects of our "Health" area might be "physical," "mental," "dietary," etc. Aspects of our of "Finances" area might be "credit cards," "auto," "home," etc.¹⁴

And that's it.

DM me with any questions.

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