Sisyphus and the Focus Boulder

Here's a story for you…

Try to work.

There's too much to remember.

Make a list.

The list is overwhelming.

Throw away the list. You don't need it.

Try to work.

Too much to remember again.

Make a new list.

The new list is overwhelming.

Prioritize the list.

Try to work.

Your highest priorities are hard.

You realize out that you are ignoring hard priorities, and only finishing easy work.

The highest priorities build up until they become overwhelming.

Throw away the list.

Try to work.

There's too much to remember…


Sound familiar?

Finding rest in the work

I've been pushing this boulder back up the hill for over ten years, and in the last year or so, I think I'm getting pretty close to finally defeating the frustration boulder. I believe there are three levels to productivity Hades, and three correlating skills to help you escape:

Universal capture so you don’t forget anything. Contextual prioritization so you focus on what's important. Time stewardship so you invest in what is important.

You have to build a system to remember things for you, and you have to be able to trust it.

Universal Capture


The first principle is universal capture. If you can't remember everything, build a system that can remember everything for you.

Our poor Sisyphus was faced with too much to remember, so let's build a system that remembers for him.

I do mean everything

Everything you own in the box to your left.
– Beyoncé

In my first job, I had an email inbox. Work came into that inbox, I finished the work, and I deleted the email.

It wasn't a bad pattern.

As my career grew, so did the sources of work and noise. Google Chat. Basecamp. Trello. Slack. Client meetings. Jira. Paper folders. In my current role, I think I counted at least seven different ways work arrives at my desk… and all those channels expect the work to return the way it came. Mostly.

While I look back with fondness at the simplicity of the Inbox Zero world I used to live in, it still wasn't perfect… email is a todo list where anyone can re-adjust your priorities and add work.

The first step to beating the boulder is to bring all your work into one place. That way you can have a full view of your tasks, establish priorities, evaluate tradeoffs, and choose to say no to what's not important. Whether it is a list on the back of an envelope or software costing hundreds of dollars, it needs to all be in one place.

I've used paper lists on the backs of giant sticky notes, trello, bullet journals, Apple Reminders, and I'm presently using Things. Whatever works for you.


Make it so easy you can't say no.
– Leo Babauta

You must have rituals for placing the things that you capture.

You have to make it easy to put things on your list. You can leave your bullet journal open on your desk. You can use Siri to quickly add things to your inbox. You can email things to yourself. I don't care. Just find a ritual that fits your system that you can do subconsciously as work enters your world.

My system heavily uses Things's Quick Entry with Autofill to bring work from other applications and websites into my system.

Contextual Prioritization


You'll find it just where you left it.

Once you have designed a system to remember for you, you have to be able to trust it to bring the right information to you at the right time. If you can not trust your system to remind you, you will end up anxiously re-reading your list for the umpteenth time, desperately trying to remember that task you feel is missing… instead of doing your best work in peace.

After you've captured everything that is coming through your life, you have to put it in a place that makes sense.

A skilled craftsman places his tools where he can easily reach them while he is working… he knows that after he finishes cutting the dovetail joints for a drawer he's going to need to sand and file the angles until they are perfect. Therefore, he will learn to put that saw and that file near each other.

David Allen calls these "contexts"… saying it is "what you need to be able to carry out an action." This could be a place, good morale, access to a computer, time left undisturbed to focus… the longer you think about designing your system the more possible kinds of context you will find.

Some interesting contexts I've used or encountered:

  • In college, I kept the todo list for each class on a giant sticky note attached to the textbook. I always had it in the class so it was easy to add to, and when I opened the textbook to study, that's when I was greeted with the terms I needed to research or tests I needed to prepare for. Context here is a book as a proxy for a place or time to study.
  • For a while, I used separate emails for home and work. This naturally created two contexts depending on which one I opened up. Email addresses as a proxy for which sphere of life I was operating in.
  • While planning our wedding, my now-wife and I made a giant list of all the decisions that need to be made. We tagged ones that only she could do (I can't try on the wedding dress, it turns out!) and I started tackling all the rest. Here, we separated contexts based on who could perform this action to make a giant list more manageable.
  • I currently am playing with a tag in my task manager for how much focus the work defines, aligning it roughly along the lines described in Deep Work. Based on how much time I have in front of me, I can filter my tasks to either Low or High focus tasks.

It is tempting to over-engineer your contexts, to figure out every possible way to categorize and separate your tasks. Please don't.

When your system gets overwhelming and you find yourself reading the list over and over, then think carefully and discover contexts to make the list more manageable. The key to contexts is less about "where does this item belong?" and more about "what is important to me here and now?"

I don't need to see my house cleaning tasks while I'm at work. I don't need to see my evening tasks in the morning. I don't need to see the tasks for any other project while I'm deeply focused on the most important.

You don't need many contexts… but you probably need a few.


You have to build into your system some kind of ritual or reminder to bring things automatically into your attention when you are in that context. In the story from my college years, that ritual was looking at the sticky notes attached to my textbooks. For a while, I was using Apple's Reminders lists as contexts, making use of the alerts by location to prompt me when I got to work or got home. Today, that is switching Areas in, and using searches on the labels that I have. (I'll make a post about that eventually.)

Probably the most basic alert is based on time… if I am going to travel this weekend, I need to pack my bags by Friday. That's usually enough for a lot of productive life, but as you start to learn and listen to yourself, you might find others. I have an "Errands" tag in Things for stuff that I do when I'm out and about, and it automatically triggers every time I leave my home. I have searches for people and needs for when I'm in a meeting with that person... if that person asks me "do you have anything for me?" I can ask my system if I have anything for them.

Grooming and Priority

To work, you must know the right thing to do. You must do that thing, and nothing else.

Once your system has given you the right list of tasks for your current context, you still need to start working on the right thing. You need to identify which thing is most important right now.

You need to maintain your lists and contexts periodically. I recommend scheduling time with yourself on a daily basis to evaluate what is most important for tomorrow, and monthly to review everything in your system to see if some things are no longer important. Do not be afraid to delete or archive things that keep getting de-prioritized or skipped… maybe it is not that important.

If this seems overwhelming… simply take 5 minutes each evening to identify the one most important thing for tomorrow, and commit to doing that thing. (H/T to the amazing Shawn Blanc for his writing on The Note)

Time Stewardship

"Dost thou love life? Then do not squander time, for that is the stuff life is made of." – Benjamin Franklin

The last step is follow through. You have remembered all the things, you have focused on the most important thing, now you have to commit and execute.

Because you have remembered everything, and separated out that which you don't need to see by contexts and prioritization, at this point you know what you have to do.

Now you have to do it.

This is much harder than it seems… you are going to encounter a lot of the "Resistance" that Steven Pressfield preaches against in The War of Art. I've been wrestling with this for a couple of years though, and the strongest victories I've achieved have to do with making time for that which I've decided is most important.

This investing of time is deeply personal and dependent on your personality and gifting. For me, I've seen a lot of success using some kind of time-blocking technique like pomodoro or hyper scheduling. I schedule time for all kinds of meetings and things that aren't really important to me and somehow they get done… I've found more success achieving my highest priorities within a context if I've made time for them. Sometimes I just make a block of a couple of hours named "Focus: Highest Priorities," and spend it on the task at the top of my list.

Whatever works for you is fine with me. Some people strategically pressure themselves out with deadlines so that they feel compelled to work against their goals. Some people when faced with a deadline freeze and procrastinate endlessly. Know thyself, and improve thyself.

Boulder begone


There are endless books and conferences and seminars about all this stuff. I'm just parroting things I have learned. I think the only insight to be gained here is the idea of three progressive skills to master... it's changed the way I counsel myself and others when I realize they may not need everything that works for me, just whatever tool or technique to help them get to the next rung on the ladder. There may be more levels of "enlightenment" to achieve that I haven't even perceived yet, but hopefully following along on my battle with focus and productivity will help you in your fight with your personal boulder.


  • 2022-06-08 11:31:29 -0500
    Rename articles

  • 2020-06-18 14:26:02 -0500
    Move everything to CST

    Don't know why I didn't do that before. It caused _no_ end of

  • 2019-10-09 10:46:33 -0500
    Add podcast references, The Note by Shawn Blanc

  • 2019-10-09 10:25:02 -0500
    Fix typo

    Thank you @philtr!

  • 2019-10-09 10:03:43 -0500
    Posted at correct date