How to make progress on a daunting project

“Just keep going until it’s done” is okay advice sometimes, but it’s not always a sustainable strategy. (Roswell, Georgia, December 2019)

A lot of us have the same problem: There’s something we want to accomplish, and we don’t know how to make it happen.

We undertake the journey with excitement and cheering crowds, like Dorothy on the yellow brick road, and then fizzle out when everyone else has gone home and we realize how hard it’s going to be.

Or we work diligently, day by day, and then realize that we don’t seem to be getting any closer to our desired outcome.

Or we might agonize over how to even get started, pondering endlessly but never launching.

Or (my personal favorite), we’re in motion, it’s total chaos, and we’re always coming across something we should have thought of and hoping it’s not too late to fix it.

Whether we’re going in circles, stalled out, or moving forward in spite of ourselves, we have the same problem: a faulty plan. If we improve the plan, we can ensure the appropriate support, anticipate problems before they happen, reduce overwhelm, and proceed with confidence.

So how do we figure out what to do? How do we come up with a better plan?

If you’re like me, you have a rich history of skipping the planning stage and launching straight into the project. This only works when it works, and it often doesn’t. So first, we need to make space for planning and acknowledge that this step is a legitimate part of the work. Measuring is just as much a part of carpentry as the fun part where you use the table saw.

As for the actual planning, I’ve always found it a challenge to think past the immediate steps I see and grasp the project as a whole. Often, this is a recipe for stuckness. The first step I can think of might not actually be the first step. I don’t know what comes after that and I get discouraged. I discover midway through that I need a tool that I don’t have.

To push through the overwhelm, I start with writing down whatever I can think of. As I go, I start building a sequence. Of course, the order in which I think of tasks isn’t necessarily the order in which they are to be done. Sometimes, I’ll write each item on a little slip of paper or an index card so that I can move them around in relation to each other, or I might use a Kanban-style application like Trello to help me.

Inevitably, the tasks and ideas that I come up with make me think of more tasks and ideas. I will see prerequisites that I hadn’t identified and actions that will come as a response to other actions. These incoming additions to the project overwhelm me and stress me out if I don’t have a solid plan, but they are a welcome gift otherwise. This is exactly how things are supposed to go. This is a sign of progress. The project may seem like it’s getting bigger and more complicated when every task makes me think of more tasks, but it’s not; it’s just getting more visible, as though each task is a candle that I’m using to light more candles. I’m beginning to see the true outlines and dimensions of the project, visualizing what is to be done, determining what resources will be required, and estimating how long each part will take.

As the work ahead becomes more clear, I face key decisions. Now that I can see how big the project really is, I might actually not want to do it. Or, I might not want to do it alone. Again, this is progress. I’m getting the answers I needed, even if they’re not the answers I wanted. I’m much more likely to be successful if I know what I’m getting into. I can renegotiate deadlines, bring on additional support, or rework the project into something smaller and more manageable. There’s no shame in any of these options.

Moments of panic may come up during the planning. You might realize that you don’t know how to do part of it. Well, then learning how to do it is an important part of the project, isn’t it? Or maybe finding someone else to do it. It’s funny how often I discover that underlying my dread and procrastination is something very basic, like, “I’m unfamiliar with this tool,” or “I’m afraid I’ll look stupid.” Once these dark little hiding places are exposed to the sunlight, they aren’t such a big deal.

Even once you’ve done the planning, committed to the project, and launched, you’ll continue to rearrange the order of tasks and think of new ones as you go along. For me, knowing that the whole thing is changeable and adaptable makes it easier to do the work itself. I don’t have to keep tinkering with the plan until it’s perfect, and I don’t have to do the work perfectly, either. I can put in a bit of effort in any given moment and be certain that it’s in the direction I want to go, even as I make tiny adjustments along the way. Instead of barreling along and burning out on the work in one go, I can pick it up and put it down as needed, referring back to the plan to keep me on track.

Life is still messy, and I still have too many projects to keep up with. But when I know how to plan, I can be more intentional about the time that I spend, the effort and energy I am willing to devote, and the outcome I am hoping to enjoy as a result. The process isn’t polished, but most of the time, I don’t need it to be.

If you are struggling to get a project going, you might find that there are gaps in your planning process or in the plan itself. You can resolve those by building on whatever you know as a means to explore and identify what you don’t. Day by day, little by little, you’ll figure it out, discovering the pieces of the puzzle, putting them in place, and building toward your vision.