Getting better at planning

The more people you’ve got involved in your expeditionary forces, the more detailed your plans need to be. (University of Victoria Libraries)

I’ve observed that many high-achieving creatives, leaders, and business owners have a dirty little secret: They struggle with planning.

They rely on a clear vision, external accountability, or both in order to successfully navigate professional life.

And sometimes they pull all-nighters or all-weekenders in order to make up for the missing plan.

In reaction to this frustration, they (um, we) try to fix the problem by treating the solution like another project on our to-do list: “I’m going to fix this once and for all!”

With the focus and intensity we bring to our best work, we then create a detailed plan that incorporates several new habits and routines we’ve been trying to establish, carefully scheduled to the minute.

Then, when our plan inevitably doesn’t match reality, we give up.

Thus, a lot of us have two modes that we vacillate between: “I’m really going to get my s**t together this time” and “total chaos.” We set the bar too high on the former, and then give up and yield to the latter.

It’s understandable that we haven’t found it motivating to prioritize planning. When we finally have the time, space, and focus to make a plan and the plan goes awry on step one, we wonder: what was the point of making the plan?

But planning is not a “one and done” project. It’s a skill that we can practice and improve at. The fact that our plans didn’t match what happened speaks to how difficult planning is, not the pointlessness of it.

Every plan is an experiment. An experiment doesn’t fail when the result is different from what we expected. No — we’ve gained data.

We might know this intellectually and still beat ourselves up when we can’t make ourselves do what we said we were going to do in a given day. However, it’s important to respect and honor our daily rhythms. Just because we find ourselves with the wherewithal to make a plan doesn’t mean that we should make the plan something that requires us to be more disciplined and virtuous than we were before we had the plan. That would be a failure of the plan , not us.

Thus, the plan needs to take into account our existing limitations, preferences, and quirks instead of trying to change them or squash them. It can leave room for spontaneity if that’s what we favor. It can be tightly structured if that’s what allows us to do our best work.

One of my clients, new to planning, found himself frustrated with his inability to follow through with his plan on Fridays. He always got less done than he intended because he had a habit of using Fridays as a catch-up day to finish tasks from earlier in the week. Plus, his energy was low on Fridays.

He came to realize that this wasn’t evidence of personal weakness or the futility of planning, which had been where his mind went first. In fact, it was just the opposite: His planning process allowed him to see that he was underestimating the time needed for certain tasks (thus, the necessity of Friday catch-up). He was also able to see clearly his pattern of lower energy on Fridays and take that into consideration in planning future weeks by giving himself less to do on Fridays.

Every time we make a plan and examine where it deviated from reality, we learn. Then, we can tweak our plan for next time. We know more about what works, and we know more about what works for us. Over time, our plans will become more useful and we’ll become more confident in making them. We’ll even improve at adapting our plans on the fly.

Just like any skill, we might need to tolerate a period of being inept as we learn. But through practice and repetition, the process will get easier and we will see better results. That will motivate us to keep going — and when it comes to planning, we’ll see a cascade of positive impacts on our life and work as a result.