For Big Projects, Try a Cone-Shaped Schedule

Procrastination is one of the most discussed topics in freelance circles. Tips on combating dread, getting started, and powering through abound. Some of the advice out there has value, but the very focus on procrastination is often misplaced. I’ve found that, in terms of productivity, there’s more to be gained from shaping your project’s trajectory than from shaping your anticipation of the work. That holds true whether you’re working for yourself or for someone else.

The single biggest motivator in getting a project done — and done well — is a sense of progress. Sure, there’s an art to getting started (as I’ve discussed previously), but once you’ve begun, awareness of your forward movement is what carries you through. One way to achieve that is to spend less time on each step than you did on the previous one so that your schedule looks like a cone turned on its side — with the broad base on the left and the pointy end on the right. That doesn’t mean scheduling work sessions to artificially force earlier and earlier quit times; that approach just leads to a marathon “final push” right before the deadline. The cone-shaped method, in contrast, means observing these five, more organic principles:

1. Survey the entire geometry. To identify where the base of the cone is, you first need to look at your project in all its initially shapeless complexity. That allows you to see what you have, what you don’t, and how everything might fit together. You can’t possibly create an efficient plan without knowing which end is up — or, in this case, which end should be on the left and which on the right.

2. Respect the inherent properties of the work. Every project has its own deep structure that may not match how the people who ultimately see the work will experience it. In short, the beginning is not always the beginning. Sometimes, working backward from the intended endpoint for your user allows the earlier pieces to fall into place more easily as you develop them. Other times, the most substantive part (the part where you should start) is in the middle. Bottom line: your process and the end user’s experience are often two entirely different objects. Your audience need never see that you’re really just a conehead.

3. Make gross movements before fine-tuning. As soon as you’ve identified the heart of your project, start doing the heavy lifting. The first full-fledged work session should be your longest and most difficult. At that point, the project is likely to feel relatively new and fresh, and fatigue won’t be as much of a limiting factor. Besides, you’ll feel freer to move things around and take risks with the basic structure when you haven’t invested yourself in minutiae and aesthetics, important as those things are in the end.

4. Gradually narrow the window between sessions. As the cone narrows, so should the time between the periods when you sit down (or stand up) to do the work. A key to creating momentum on a project is having session duration decrease as the gap between sessions also decreases. That creates the illusion of speed — like you’re walking downhill rather than uphill. And, actually, it’s not entirely an illusion. You are, after all, moving toward the end at a faster pace. It’s just that you’ve deliberately structured your schedule to achieve that effect.

5. Take pleasure in the polishing. With the toughest parts behind you, enjoy the little pleasures of the tip of the cone — the niceties, the trim, the tassels. Imagine yourself sitting in the audience at your own play and appreciating the small things. Doing that can make a deadline feel like the celebratory debut it should be rather than the exhausting finale it often is. A cone tip is most pleasing when it’s sharp and shiny. Take your finger to it (gently) and see just how good it feels.


About Steven DeMaio
Steven DeMaio teaches English and math at the Community Learning Center in Cambridge, Massachusetts, and the Somerville Center for Adult Learning Experiences in Somerville, Massachusetts. He also works as a freelance editor and writer. This is a continuation of his blog that ran for 10 months in 2009 on

One Response to For Big Projects, Try a Cone-Shaped Schedule

  1. Scott says:

    Good post, Steve. The only item I feel belongs in the above (and I think is personal preference) is that the project should look like an oval, not a cone, though many of the principles listed above remain very relevant. With an oval shape, the first few tasks are short providing quick wins that help with the motivation factor. Starting a large project with a significant chunk of work can be very daunting for some.

    Of course, using effort-based planning, not duration-based planning is essential to ensuring a smooth project run. It really helps to identify any gaps before they become too large and cause significant budget and scope issues.

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