#51 - Should you kill your to do list?
Revisiting the place of one of the most ubiquitous task management tools we have, and recommending a modified task management approach to test out... I call it the Three Layers of Offense
This letter is more of a true public journaling. It’s written more as a review of how I’m approaching task management these days, while re-appreciating tactics that have worked.
I took last week off of work to reset a bit, do some writing, and enjoy the wonders of being at home (#staycation). I envisioned an ultra relaxing week, where I would spend most of my days writing, reading, taking long walks in the park. This is not what happened.
What actually happened was a list of To Do’s came up, and I ended up spending (probably) most of last week just working through life chores.
This has come at a time when I’m generally re-evaluating how to balance rest with productivity when the work schedule keeps me busy. To help in this evaluation, I spent a bit of time re-reading up on how very “busy” people manage their schedules.
Some of the busiest people I’ve ever met are startup founders. They’re all balancing personal lives with a weekly schedule that can easily range from 70 to 110 hours (check out this great article on startup founder time management from the CEO of Levels published via first round capital). This is where I spent some time trying to learn. One of the most powerful takeaways from this article was the idea of killing your to do list.
Wait, what?
The idea here is that you should be using your calendar as your To Do list, something I’ve done on and off over the years.
How can you actually make this work?
I’ve personally found it difficult to fully adopt this system, BUT what has worked is allocating a consistent portion of each day to general task management. This is my whole idea of GSD, GNT, GTD — get shit done, get nothing done, get thinking done.
One of the biggest mistakes a person can make is to be in meetings all day, every day. Trust me: I’ve been here a lot, and this is almost never the state when my best work is being done.
The implication for Managers is to structure work in a way that deliberately gives extra space or “slack”
We’ve historically tried to model out 70% of a person’s time actually be on their core responsibilities, with the remaining 30% being for things like time away, admin, compliance, learning, and other special projects
If you’re in an organization and role where you have some control over your schedule, you can take advantage of this whole “calendar as your to do list” way of thinking
But what if you work in a job where you have zero calendar control?
Then you should probably keep a To Do list. But not just any ol’ list… You should keep a prioritized list, so that you know what to get to first when that inevitable free space opens up.
My approach — Just like companies, your own personal management system probably needs to change over time…I have the Three Layers of Offense
I’ve changed my own task management approach probably once every six months for the last 15 years. Some specific tactics have earned their way to surviving each of these changes. They include:
Rebuilding your To Do list on a regular basis
Finding great joy in removing things from the list (…which can mean NOT doing a thing)
Always keeping a “backlog” of things you’ll do at some point
Having separate categories for Personal Life and Work Life, and always filling out and looking at the Personal Life category first
Here’s a screenshot of what my Notion categories look like
The most critical items across these lists get pulled over to my calendar to make sure I’m building in space to get them done. And if they don’t get done, then they get moved into another day on the calendar.
This sort of triple redundancy is how I personally stay on top of all the different threads of life
Layer 1 = identifying the need and internalizing it in my brain
Layer 2 = writing it down on my to do list
Layer 3 = calendar-ing the most critical and time-sensitive things
These three layers of offense can take a bit more time to setup, but I’ve found it to be effective
Tactically, I don’t recommend having multiple calendars or multiple lists. Strive to have things in one or two places max. My setup is:
Notion for To Do lists and general Life Operating System
Outlook for calendar
And if I do schedule something from another calendar, I add it to my Outlook/work. Yes, this means that my “work” calendar also has personal stuff on it. I use the “personal” marker to preserve some privacy, but I know that by doing this I am giving up some degree of data privacy. This is something I’m comfortable with, as the stress of checking multiple calendars just did not work for me. Maybe it’ll work for you.
So, should you do it?
My personal answer is No, killing the To Do list in its classical, list-based form is probably not the move for most people. I think if you work in a job with a moderate-to-high degree of uncertainty day-to-day, it can be super challenging to make this work. I have seen CXOs who have admins make it work as well as some very super organized people, but for most of us mere mortals it’s just probably not totally reasonable.
However, I do think it’s wise to take inspiration from this idea, as it can help you make sure you’re allocating time to tackle the things that are most important. For example, I have a 2.5-hour block later this week to just think through and write about my org’s corporate strategy. That is a super duper important exercise that, if done well, can materially impact the trajectory of our business. But I’m not calendar-ing everything I have to do.
If you want to use your calendar as a productivity tool, you actually do have to adhere to it. What value is putting something on the calendar if you’re never going to do it? I think it’s important to be realistic about this, lest your calendar artificially starts to look like a Tetris board and will stress you out even more. I re-learned that lesson recently when an Life item (…part of our taxes) sat as a recurring reminder for two months before it got touched.
Which leads us to the end, and back to this idea the sparked this letter — balancing rest with productivity. There’s no universally golden ratio for everyone, but I’ve generally found that it’s a healthy and productive thing to prioritize recovery…But that as your life complexities grow, you have to really work at carving time for rest and relaxation.
I’ve found the mix of To Do List, Calendar, and strict rules around hours worked and keeping at least ONE weekend day totally open for fun+relaxation to be helpful.
If you have any thoughts, please share them either as a reply or a comment. Always looking to learn what others are finding helpful / not helpful.