Plan to Be Surprised

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I've had a love/hate relationship with planning, and I've finally figured out why. Although I love the clarity I get from planning, and I see that planning helps me in the long run, I had always been distressed when a project didn't go as planned.

This is crazy. Most plans fail. Even excellent plans. I have a new approach to planning, which eliminates this distress and ensures that I make the best use of my planning time. I think of it as planning to be surprised. It has three elements:

1. Give the plan your best shot

The whole purpose of planning is to take advantage of your knowledge and experience to identify the best path forward to your goals. If things go wrong, you should be surprised.

On the other hand, if things go wrong, and you're not surprised, why not?

Suppose your plan is interrupted by a last-minute request, and you are not surprised because "someone always interrupts me." That's something to address in your next plan. Maybe you need to plan an hour in the afternoon to handle issues that come up during the day. Or if these interruptions happen only once a week, maybe you need to schedule a weekly time block to cover them. Or maybe you need to plan how to protect yourself from interruptions.

"Planning for surprises" means that you plan in flexibility to deal with known unknowns. For example, it takes me 2-4 hours to write one of these articles. I don't know how difficult a particular article will be until I am about an hour into it. So if possible, I work for an hour on the article the day before it's due, so that I can better predict how long it will take me to finish it.

When you plan such that you are surprised by anything that goes wrong, you know you are taking advantage of your knowledge and experience as effectively as possible.

2. Summarize your reasons for the plan so that you can recover gracefully when it falls apart

When you plan, don't just make a list of tasks to do. Capture the thinking that went into the "to do" list. Summarize your reasons in terms of the time budget, the dependencies, and the high-level priorities.

a) A plan isn't complete unless it includes a time budget for each task, and a reason for that time budget. A time budget is critical for figuring out if you are on schedule, and for regrouping if you are not.

I mentioned that I budget 2-4 hours for my newsletters. At the end of 1 hour, I generally know whether it will take me 1, 2, or 3 more hours to write. If after one hour, I am still unclear on the topic, I know I'm in trouble and I need to adjust the plan. If there is a hard deadline, I may drop the topic and repurpose an article from 10 years ago so that I can get the task done on time.

b) A plan isn't complete unless you have a summary of the dependencies within the plan. You need to know how one task depends on another, and how tasks connect to hard deadlines in the world.

For example, after I draft my article, I send it off to someone to proofread and choose a picture for it. This needs to be done with enough time for a back and forth, before we finalize the newsletter content on the Tuesday before it goes out. Because I know all the key dependencies, I know where there is flexibility in the schedule, and where there isn't. It's easy for me to re-plan if something comes up and I get behind by a day or two.

Many times, these dependencies are left implicit. You know them. They influence the order of items in your "to do" list. But if you don't write them down anywhere, it's easy to forget them when the plan goes awry. If task #1 runs long, should you go through tasks 2-5 in order? Or is it more important to go on to #3 and reschedule #2 for tomorrow?

If you summarize the dependencies with a few bullet points when you make the plan, you can easily refresh your recollection and adjust the plan as needed, without redoing the planning process.

c) A plan isn't complete if you haven't related it to your high-level priorities.

My top priority is my book. Many tasks are planned for Tuesdays and Thursdays to ensure that I am free to work on the book on Mondays, Wednesdays and Fridays. I need to be able to wake up on those days without time- sensitive tasks on my mind. That leaves my mind free to dive into creative work. In order to keep my mind free on those mornings, it may be critical to pay the bills and make some phone calls on a Tuesday, even if technically the task is not that time sensitive.

If you see each day's plan as supporting your most meaningful work, you will find it easier to stick to your plan, and you will be better able to adjust your plan without affecting your top priorities.

You don't want to overplan. Planning should take at most 5% of the total time for your work. If you work a 40-hour week, this is about half an hour a day, plus an extra half an hour a week.

If you document your reasons for your plan when you make it, it will be much faster to re-plan when something takes you by surprise. So as part of your plan, make a short bulleted list explaining the time budgets, the dependencies, and how the plan supports your top priorities.

3. If the plan falls apart, turn to re-planning, not self-recrimination

Your plan will likely fall apart sooner or later. Don't fall into a self-recrimination loop when that happens. It's not logical.

You might think, "I should have known better." But could you have? If you gave the plan your best shot, there is no justification for believing that you should have known better. You are not a fortune teller. You do not have a crystal ball. There is always uncertainty in predicting the future. Your surprise is evidence that you didn't have certain information before. In such a case, self-recrimination is illogical.

It's illogical even if you did slip up. For example, suppose you planned to get up early to exercise, but when the alarm went off, you didn't feel like it. You hit the snooze button. Should you engage in self-recriminations? Chastise yourself for your lack of self-discipline? Obsess about your lack of integrity? No. Punishing yourself with self-recrimination just makes the situation worse. It sends you into a negative spiral, which makes it harder to regroup and focus on your goals.

When you slip up, what matters most is that you factor that information into your plans immediately. Perhaps you can adjust the plan to create another opportunity for the workout.

Suppose you get up 15 minutes late. If you recover quickly, perhaps you could get in a short workout.

Or suppose you get up 45 minutes late, so you couldn't even do a short workout. Perhaps if you recover quickly, you could get to work 15 minutes early, take some extra time at lunch, and exercise then.

If you made a good plan, and don't fall into a funk, you can quickly find the best way forward from here.

The best time to take charge of your mind would have been a little while ago, to avoid the mistake. The second best time is right now. Respond to a lack of willpower with an act of willpower. Use self-discipline to recover from a slip in discipline. Draw on your integrity to move forward to your goals.

When you plan to be surprised, you can quickly regroup and move forward, no matter what unexpected obstacle you encounter.

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