The Secret Of People Who Always Meet Their Deadlines

The unexpected isn’t really unexpected. People who meet their deadlines know how to keep moving forward.

The Secret Of People Who Always Meet Their Deadlines
[Photo: mavo via Shutterstock]

Life was going well for Chris Bailey. A longtime student of productivity techniques, he’d launched a blog to chronicle his experiments with different strategies. The blog became popular enough that he got a contract to write a book called The Productivity Project. He was about halfway through writing when he decided to go to Ireland last February “to brainstorm a little bit, to celebrate that I was ahead of schedule, to give myself a rest, to be kind to myself,” he says.


But, “at the beginning of the trip everything went to hell.”

He was walking home from a friend’s place after midnight when he slipped on a steep cobblestone sidewalk. He fell and couldn’t get up. His cell phone had died, and since he was out in the country, no one heard him shouting. He lay there in excruciating pain, crumpled and shivering for three hours until people found him. In the hospital he learned he’d shattered his ankle and leg bone. He endured reconstructive surgery, therapy, and he needed a cane for months. “I’m still in recovery about a year after the injury,” he says.

Yet he turned in his manuscript on schedule. In fact, the book actually shipped six weeks early.

No Excuses

Talk to book editors, and they’ll complain about how many of their authors miss their deadlines. Most of these people can’t blame major medical trauma. But Bailey, who could, said, “I think moving the deadline would have been kind of the lazy way out.”

His study of productivity had helped him hone the techniques that allowed him to meet his deadline, even as he battled pain, lethargy, and the dark mental state an injury can induce. “Productivity is often a process about understanding your constraints,” he says.


Some of these constraints are pretty common, as they’re part of the human condition. People are shockingly optimistic. We have a tendency to believe that our future selves will be far more energetic and productive than our current selves, so we don’t mind assigning them stuff we don’t want to do now. “The longer-term a project it is, the easier it is to put it off until tomorrow for your future self to do,” says Bailey. We also believe that life will be smooth sailing. Today is the day there won’t be traffic during rush hour, and this is the winter no one in our families will be sick with the flu. But this is silly; “The unexpected will happen,” says Bailey. “It always does.”

If you know these foibles of the human mind, you can do a few things in order to meet your deadlines. The first is build in a buffer. “The more critical a project is for my work or my life, the farther in advance I try to do it,” says Bailey. In order to plan for the unexpected, set a pre-deadline ahead of the real deadline, and aim toward that. That’s how Bailey was operating a month ahead of schedule when he embarked on the ill-fated Ireland trip.

Then break the required work down into chunks that you plan for certain segments of time ahead of the pre-deadline. “If you look at someone who doesn’t achieve what they intend to, they don’t step back frequently to plan what they’re actually going to work on,” says Bailey. “They work more in response to whatever comes their way, as opposed to stepping back and planning how they’ll spend their time.”

Part of this steady progress involves anticipating obstacles. A book writer might assign herself a chapter every two weeks, but if she plans to take a vacation in there, maybe that chapter needs three weeks. “Obstacles are so much easier to deal with in advance than they are to deal with at the moment they come up,” says Bailey. People who meet their deadlines are constantly looking forward.

Slow progress Is Still Progress

Of course, even if you look forward, sometimes the obstacles are truly unexpected. Still, progress is possible. When Bailey was in the early days of recovery, he started setting small daily intentions that he would be able to meet. At first it was simply taking a post-operative stroll around the hospital hall with his walker. “Each morning I checked in with myself. I observed how much I would be able to bring to the project, to writing the book. Over time, I saw that increase. I took it easy on myself.”


Setting three daily intentions doesn’t sound like much, but three per day is 15 per workweek. That’s 60 per month, and 180 in three months. If each of those intentions was “write 200 words” in three months, you could write 36,000 words, which is half of a full-length book. Bailey also figured out ways to accommodate his limitations. Lacking the energy to type, he discovered dictation.

As a result of these strategies, he turned in his manuscript on time. Presumably, if he’d asked for an extension, people would have understood. But reliable people know this secret: “I think there are always ways to achieve what you intend to, especially if the time frame is long,” says Bailey.

Even if life isn’t easy, you can still keep your word.


About the author

Laura Vanderkam is the author of several time management and productivity books, including I Know How She Does It: How Successful Women Make the Most of Their Time (Portfolio, June 9, 2015), What the Most Successful People Do Before Breakfast (Portfolio, 2013), and 168 Hours: You Have More Time Than You Think (Portfolio, 2010). She blogs at