Is planning two weeks ahead possible or just a productivity myth? Here is a practicalmethod to stay ahead — even with unexpected tasks pile up.

“I’m behind the power curve.”

“There is too much on my desk, I can’t do it all.”

“How shall I do all the unplanned tasks that come on top of my daily tasks?”

Sounds familiar? You’re not alone. Most entrepreneurs have a ton of things on their desks, and I have myself felt close to drowning many times. Irrespective of the planning method and the productivity tools you use, the number of things on your desk will not decrease.

When we reorganized our team at Yonder and didn’t replace some of our leaving colleagues, some additional tasks landed on my already full desk. I then decided to organize my work differently to keep the upper hand. I have experimented with time-blocking and personal sprint boards in the past, but I felt I needed something else to react on any short-notice tasks, and also to have enough time to keep ahead of the curve.

My personal solution is to create two weeks of headstart in everything I do. You read correctly. I want to be ahead of the curve by two weeks, which means I want to complete tasks due in two weeks today.

Establishing a 2-week headstart cannot be achieved in one big step. Here are the steps I took over three months to achieve my 2-week headstart.

Step 1: Expand Your Planning Horizon

For many years, I have used Asana for personal work organization. I have built a personal sprint board that holds all the upcoming tasks I need to complete. I use the following columns for my tasks:

  • Backlog: All the tasks that I haven’t done anything with yet, and for which I need to prepare.
  • Ready: All the tasks that aren’t done yet, but I did all the required preparation work.
  • Clear: Every evening, I shift all the tasks that need to be done the following day into the “clear” column. In this way, I have an accurate feeling if I’m going to have time to work on larger tasks the following day, or if I need to run a tight and efficient schedule.
  • In Progress: Some tasks cannot be done in one go, especially the larger tasks. Just like in development work, once I start working on such a task, it goes into the “in progress” column. I am paying great attention not to have too many “in progress” tasks in order not to lose focus.
  • Waiting: Many things that I work on depend on other people. Whenever I cannot continue before somebody else has done their part or replied, the tasks go into the “waiting” column. Every evening, I check the “waiting” column to see whom I need to chase the next day to finish these tasks on time. Those who have worked with me know that I can be an absolute pain in chasing people — now you know the methodology behind it.

I have been using this system for several years. What I changed recently is the planning horizon: At the end of every week, I put all the tasks of the upcoming four weeks into the backlog column of my personal sprint board.

Step 2: Prepare As Much as You Can

When stuffing tasks for the next four weeks into the backlog column of my personal sprint board, it can look overwhelming at first sight. And that’s exactly the point. The more of the tasks in your backlog column you prepare and move to the ready column straight away, the more headstart you gain. It takes some discipline to plan meetings three weeks away on a sunny Friday afternoon, but it’s worth it. When unplanned tasks come in at a later stage, you can focus your thoughts and time on them, and you’re still prepared for the regular meetings you planned what feels like a long time ago.

Step 3: Define Leading-Edge Tasks

For every quarter, I define 10–12 leading-edge tasks. These are larger tasks, almost projects, that I want to work on in the upcoming three months. They also go into my personal sprint board, to make sure I don’t lose them in the sea of daily tasks.

To have enough time to work on the leading-edge tasks, I block myself 2–4 days a month to work undisturbed on the leading-edge tasks. And because things are dynamic, I plan and replan those blocker days every Friday when I plan the following weeks.

Step 4: Keep it below 100

Now that’s a lot of tasks. I love Asana’s ticket counter in the “My Tasks” view, and I always make sure that not more than 100 tasks are on the list for the next 4 weeks. In this way, I manage to keep some kind of prioritization even when lots of things are going on at the same time.

Conclusion

Planning two weeks ahead isn’t an illusion, it’s a matter of discipline. However, never let go. The headstart is gone much quicker than it was created.