What Works

10Planning Projects

I once had a therapist tell me that flexibility without structure isn't flexibility at all; it's just chaos.

— Amanda Montell, Cultish: The Language of Fanaticism⁸⁹

MY HUSBAND OFTEN tells me about the projects he's “planning.” He plans to grow hops off our side porch, so it can wind its way up to the Juliette balcony above. He's plans to line our backyard fence with mosquito-repellent plants. He has plans to rearrange the living room and make radiator covers from scratch. But when my husband says he's planning, he means he's daydreaming. It took me forever to understand this. Probably because I'm extremely literal. Planning, to me, means research, timeframes, and budgets. For him, though, daydreaming is how he processes what he really wants out of life. It's how he creates his own personal vision.

For others, planning means making a linear list of tasks, putting dates on calendars, and doing their darnedest to see it through. Instead of visionary or strategic, it's super task-oriented. Creating a vision is important. Following through on the work is important (I cover that soon). But these two different ways of approaching “planning” belie a key issue with how the vast majority of us approach projects—both personal and professional. Planning a project is neither creating a vision (or a daydream) nor is it a checklist. A project falls somewhere in the middle. It's a discrete unit of your strategy—the trail you've chosen to travel on. Further, you can plan ...