Without a checklist I wonder aimlessly. I do what’s necessary to move along. I tend to feel anxious and at loss.

With a checklist, I feel like I have a purpose and I know the exact steps that I need to do everyday in order to fulfill it.

Whenever someone becomes privy to my checklist system, their immediate reaction is to say that it’s too mechanical and controlling. I started to feel the same way about it because I’ve heard it so many times, but now that I’m thinking more about it, I’ve come to realize that it’s actually my way to be at my best.

When I sit down to think about what, why and how I want to accomplish something, that’s when I’m projecting myself into a future with new possibilities. The checklist is what’s required of me to do in order to materialize that future.

Over the years, I’ve changed my checklist system many times. I can think of a few things that make it endure as I myself change:

It must take less than a minute to spawn a checklist from a template that has 80% of all items filled in1. Then another 10 to 15 minutes to fill in custom items. This is for the whole week. Planning shouldn’t happen more than once a week2.

Every six weeks3, I take a week off from the checklist in order to distance myself from the work I’m doing and to have a wider perspective on things. I’m free to work on other stuff or the same stuff in different ways or even just binge on movies for a week. Everything is on the table including abandoning the whole thing. This does a couple of things for me, one, it makes me appreciate my system and how it had been helping me out. And second, it gives me a break from the system because it does start to feel tiring after several weeks.

There’s a conversation going on between the world and the checklist. It shapes my world, but the world also shapes it. As I sprint through the weeks, the routine starts to become too rigid. Unplanned events feel like a major annoyance. I try to be more realistic and improvisational and rewrite the checklist to match what’s inevitably going to happen. This flips annoyance into enjoyment. For example, my mom decided to come and spend a week with me in Argentina. My first reaction was: fuck, I’m going to lose 30 hours of work, how can I fit her in. My second reaction was: let me make that week’s checklist all about her. Show her the best time and spend as much time with her as possible. Work only if time allows4.

The ability to take a goal or a quest and break it down into baby steps makes me feel as if everything is possible. This system has helped me build and sell a few companies, learn to speak Spanish, learn to dance Tango, get my Toastmasters certificate, move to new countries, and it continues to support me with my current quests.

The biggest drawback to adhering meticulously to this system is it lessens serendipity. And sometimes, good luck is all you need to fulfill your purpose. Be wise. Know when to let the world take precedence over the system.

  1. Mostly routine items like exercise, meditate and journal. Goal/Quest related items are what require some time to think about. ↩

  2. Though modifying the plan is natural and happens throughout the week. The plan is the ideal, I don’t expect to hit the ideal every day. ↩

  3. I arbitrarily picked six weeks. I might change this one day. ↩

  4. I used to keep my plan the same and figure out how squeeze unplanned events within it knowing that it was impossible. Then as the days unfolded, I would feel annoyed at not being able to finish what I had planned. Magical thinking. ↩