Deadlines and Project Management in ADHD

In me projects move at two speeds: not at all and all at once.

While the deadline is far away, the project is a calm box in the calendar. As the date approaches the box grows, and then one night it fills my whole life. The next morning the job has been delivered, and I spend a week trying to pull myself together.

I described the emotional and motivational side of this cycle in the article on panic productivity. Here I look more at the mechanics of the job: why a deadline does not feel real in an ADHD mind, and how I try to run a project toward that date.

The date in the calendar, the date in the body

Knowing a deadline and feeling it are different things. I know the date. It is written in the calendar, my phone reminds me. But that date does not settle anywhere in my body.

In Barkley's model, the difficulty with inhibition in ADHD also affects the executive functions that carry the future into today's behavior: holding time in mind, linking a future outcome to a present action (Barkley, 1997). Working toward a deadline requires exactly this.

A meta-analysis that brought together time-perception studies also shows that children and adolescents with ADHD perceive duration both less accurately and less consistently (Zheng et al., 2022). These studies were done with children and adolescents, in a laboratory and with short durations; they are not the same as a project lasting weeks. Even so, they helped me understand why the knowledge "there are three weeks" produces no urgency in me. In the glossary this is called time blindness.

The date is written in the calendar, it is not written in my body.

Why I always underestimate

The second problem is estimation. I say "this job will take two days" and the job takes four. Every time.

This is not a problem belonging to ADHD alone. In the classic studies on the planning fallacy, when people estimated how long their own jobs would take, they hardly looked at how long similar jobs had actually taken in the past; they focused on an optimistic plan of how the job would go. They also explained past delays by conditions specific to that job and did not include them in the new estimate. When estimating other people's jobs, however, they did not show the same optimism (Buehler et al., 1994).

The most useful part of this finding is the last one. What I cannot see when estimating my own job, someone else can see when they look at my job.

I dealt with the day-scale form of the estimation problem in the article on pomodoro and time blocking. At project scale the problem grows, because small deviations pile up over weeks.

Why project tools are so often abandoned

There were periods when I tried a new tool for every new project. Colorful boards, cards, labels. The first week goes very well, because setting up the tool is new and interesting. In the second week the tool is not updated. In the third week looking at the board produces guilt, and I do not look.

The problem is not in the tool, it is that the tool is not tied to a habit. The board does not update itself, and the intention "I'll look once a week" does not happen until it becomes a calendar appointment. So for me what matters more than the tool is a fixed moment when it is looked at: the weekly review.

Planning by starting from the end

The project plan I find worth trying is one page and starts from the end.

1. Write the real deadline, then subtract a buffer. The last two or three days before delivery are not part of the plan. Unexpected things always come up on those days.

2. Define "done." What will be delivered, in what state? "A report" is a vague goal. "A ten-page, three-section report with the visuals placed" is a visible goal.

3. Divide into stages, backwards from the end. Delivery, final read, writing, draft, research. Give each stage a date. In the glossary: staged delivery.

4. Plan the last ten percent as a separate job. Checking, editing, putting the file into its format, sending. Jobs often get stuck at ninety percent, and because that last part was never planned it is left to the last night.

5. Show the estimate to someone else. Show the stage durations to someone you trust and ask "is this realistic?" The cheapest medicine for the planning fallacy is another pair of eyes.

6. Put in checkpoints from outside. Promise to show someone something at least at one of the stages. A midpoint date you give yourself is an intention; a midpoint date you give someone else is an appointment.

Write the first movement together with the date. Next to each stage add the first physical movement of that stage: something like "open the file and write the headings." When the date comes you do not have to decide what to start with.

More than one project at the same time

Planning a single project is one thing, running four at the same time is another. Most of the time the second is where I struggle most.

When there are several projects, two tendencies of ADHD magnify each other. The first is to dive into the project that attracts me most and forget the others. The second is to leave all of them in the "not now" zone until the nearest deadline. The result is that while I am in hyperfocus on one project, the other three quietly fall behind.

There are a few principles I find worth trying:

All dates on one page. Each project may have its own plan, but all deadlines and midpoint dates should stand on one page, in calendar view. Looked at separately, each project seems reasonable; seen side by side, three deliveries falling in the same week appear.

Not putting two big deliveries in the same week. When a new date is being discussed I look at this page first. If possible I spread the big deliveries across different weeks. This requires being more of a negotiator in the conversation about dates, but it prevents the collapse of the last week.

An upper limit on the number of active projects. Keeping the number of projects I am really working on at the same time limited. If a new project is going to start, first waiting for one stage of one project to close.

Rotating touch. So as not to drop the others entirely when I am locked onto a hyperfocus project, touching each of the other projects for at least ten minutes every day. An e-mail, a note, writing down the next step. This small touch keeps the project alive in the mind and makes returning easier.

A weekly sweep. Once a week, looking at the one page of all the projects and writing the next step of each. This is the most reliable way to see which project has fallen behind before the deadline does.

Three questions I ask at the start of a project

When a new job comes and the deadline is being discussed, I ask myself three questions:

• Have I done something like this job before, and how long did it actually take?
• What other dates do I have in the same period?
• If I miss this date, what happens, and whom do I need to tell and when?

The first question is against the planning fallacy, the second against imagining my future self as too free, and the third against leaving the problem invisible until late.

If the date is going to be missed

Sometimes, despite all the plans, the date will be missed. The most expensive mistake is to pass that moment in silence. As the date approaches the shame grows, as the shame grows telling becomes harder, and in the end the news arrives together with the date itself.

A short message sent before the date arrives protects most relationships:

"The project is going more slowly than I planned. I can deliver this part on Friday and the rest next Wednesday. If this creates a problem for you, let's set the priority together."

A situation, concrete dates and a question about the other side's need. There is no need for a long paragraph of apology.

These skills can be learned

For a long time I took my difficulty with deadlines to be a character problem. Today I see it as a matter of skill, and there is evidence that skills can be taught.

In a randomized controlled study with 86 adults whose symptoms continued despite medication, cognitive behavioral therapy was compared with relaxation with educational support. The program included skills in organization and planning, prioritizing and problem solving, coping with distractions and responding to stressful situations with adaptive thinking; setting up a calendar and a task list and dividing big jobs into manageable steps were part of it. In the therapy group ADHD symptoms improved more, and this gain continued twelve months later (Safren et al., 2010).

This does not mean the same result will be obtained in everyone; decisions about treatment should always be made with a specialist. But it told me this: my relationship with deadlines is something that can be worked on.