What to do on which day

Obviously, my workspace looks just like this and stays just this pristine from day to day. (Image by Pexels)

On the one hand, a hand-written to-do list is simple and elegant.

You write down what you’re going to do, and then do the things, one by one.

It has its limitations, though. One weakness of the written to-do list is that today is the only day that you can plan for.

My days got a lot more productive when I could assign tasks to specific days in the future and track them accordingly.

Then, I was free to do today only the things that I needed (or wanted) to do that day.

In fact, I dislike doing the things today that must be done today. I prefer to do tasks that aren’t urgent whenever possible. That minimizes resistance and increases my effectiveness across a week or a month. However, this approach requires more careful planning. If I were to do make a handwritten to-do list, it would already be too late by the time I jotted down my tasks for the day.

Therefore, I use systems like Sunsama and ClickUp that allow me to plan out my entire workflow for a project in advance and distribute tasks across days, weeks, and months. Plus, of course, an old-fashioned calendar to keep track of meetings.

This way, my to-do list for each day is a prepared menu. If I don’t like what’s on the menu or the total time required for my work and my meetings exceeds the time available, I can rearrange things and bump tasks to different days until I find something pleasing.

It’s important to note that there are a few levels of planning involved, and they all count as work tasks (or even projects) in and of themselves.

I used to only think about one day at a time — sometimes a few days ahead if I had a deadline. Consequently, I was driven by my meetings and my email, that was enough to take up a day.

I wondered why, day after day, I wasn’t accomplishing the things I cared about or building anything bigger. Well, that’s because I wasn’t investing any time today for the future. I wasn’t planning any projects or setting any goals.

To change this, I had to begin to consider longer-term projects in my planning, not just the day’s work. Based on what I wanted to have accomplished six months from now, what did I have to start doing now?

The answers to such questions radically changed my work routines. Working backward from the desired result, I added a lot of short and seemingly insignificant actions that combined to create a profound change.

For example, I’m headed to Mexico City in April, and I’d like to improve my Spanish before then. It’s one of the only places I’ve been that my global privilege as an English speaker is not useful. That gives me three months to practice, and I can tell you right now that this practice will not happen unless I take the time to work out what I’m going to commit to, put it in my system, and receive a reminder of my commitment each day.

Of course, whether I actually improve my Spanish will depend on whether I follow through with the necessary actions each day. But that’s where this type of system has another layer of usefulness. When the tasks come up on today’s to-do list, it’s like a directive from my boss. The fact that the “boss” is my past self is not important. I function best when I follow the list without questioning it, doing it all until it’s done.

I’m not always so compliant, but the more effective my planning cycles get, the more I’m able to anticipate what my future self is going to want to do, creating more harmony between the plan and the eventual reality. Over the weeks and months, that saves time and energy, meaning I can accomplish more of the things that matter to me.

What is your relationship to planning? Are you getting the results you want? What habits and practices work for you? What would you like to change? I’d love to hear your perspective.