Hi John,

Those are my basic root folders. Sometimes I’ve had variations where I’d put 
some of that in a personal folder, or if there’s a big thing going on like 
building renovations I might make a temporary folder for that, but that’s the 
gist. BS is by far the biggest folder. My Finance folder is sparse enough to be 
merged with Reminders, but I like having it top level to be 150% sure all my 
bills are paid and I’ve been paid everything I’m owed.

The main point of anything you put in MLO, or any other app for that matter 
regarding productivity, is either to:

1) Give you a list of options to select what you would like to do immediately
2) Act as a reference when you are prompted to need it by the world around you

I go through all the stages of workflow outlined in GTD, though like everyone a 
lot of that will happen all at once and back and forth. It seems like an issue 
you’re running into is that you’re trying to use MLO to manually manage every 
stage of that process in a linear fashion, which isn’t really the point of 
Allen’s model there, nor is it really what MLO is intended to do.

If I’m planning or thinking about something complex, I might make a mindmap, or 
an outline, or any number of things, all with that intention of thinking all of 
that through. Once you organize your thinking in that way, then you don’t 
usually need much if any of that material as anything but a reference, from 
there making lists of specific projects and actions you want to do, and 
deciding when and where you’d like to be reminded of them. For Allen, he uses 
context lists as those reminders. It sounds like what you’re trying to do, 
however, is use a great number of contexts to guide anything that pops into 
your head through MLO. That’s actually a much greater effort than being looser 
with things and using MLO to hold the results of your thinking, and one you’re 
unlikely to get anything out of. I also recommend not writing everything down, 
in MLO or otherwise. It’s fine to let plenty of your thoughts go, which I say 
as someone that has hundreds and hundreds and hundreds of megabytes of 
plaintext with ideas and similar things in them.

The main point of any context list, or productivity system, is to help you 
decide what would be the best use of your time right now in the moment you are 
engaging with the system. For me, Starred tasks are what I’m committed to do 
that day, at times at that particular time if I get that granular, which I try 
not to be. Because of that, plenty of tasks that show up don’t make it out of 
the inbox if they’re that urgent, they’re simply made and starred. If they’re 
small tasks, I often do them as I’m processing my inbox anyway, like “email 
john about ABC.” I primarily use MLO on iOS between my iPad Pro and iPhone X, 
but it’s pretty much the same on all platforms now as far as how this workflow 
would apply. If I’m making a task I know would need to be in a specific folder, 
I can parse things there directly when writing it in the inbox popup, drag it 
to that folder from elsewhere—which is easy when you have so few—or simply 
click on the folder and add a new task under it. All of those things are 
basically a click. Sometimes if I’m in starred views, adding a new task makes 
it directly under the one selected in the main outline, so I’ll click it after 
and move it to have the proper parent after, though plenty of times I’ll just 
leave it. The Career folder is one of the only ones I focus in on, at times the 
relationships one too.

When Allen says engage/execute, he means doing your tasks, though he also wants 
you to regularly ‘engage’ with your systems to help that. Capturing is writing 
anything down. Reflecting and reviewing your systems is more where that other 
meaning of the word engagement comes in. The ideal point of all of this is to 
keep as much out of your head as you’d benefit from, and take you from thought 
to action in as frictionless a way as you can.

Whatever contexts you use, they should likely be selected on the basis of how 
well they facilitate that, not guiding anything that came into your head 
through a linear model. Context lists and other elements of the GTD system were 
not meant to house or facilitate any of that. Allen was actually adamant that 
you probably shouldn’t because it’s a monumental overhead that’s very 
crazy-making without any real benefit, and hierarchy has a cost, the latter of 
which you’ve noticed. 

I think everyone that gets into GTD or productivity and apps goes through an 
OCD phase with it—myself included. I’ve done the infinite context thing, 
infinite hierarchy, all manner of things. But my current setup is the result of 
getting over and around all that over the years, and over my feelings on it, to 
the point that if something isn’t in the right folder, I’ll sometimes just 
leave it there if it has a star on it anyway because it’s going to get checked 
off at the end of the day.

Might also help to change how you’re viewing your tasks that you write down and 
organize. I know now that most of the things I write down will never get done. 
My continued use of MLO has proven that without a doubt. New work comes in, the 
nature of what I’m doing changes, and on and on. The point of an app like MLO 
is to help decide what I should be tackling at the moment, and not get behind 
on anything because I forgot about it, with the understanding that I’m not 
going to be able to get everything on there done. My BS folder tends to house 
of lot of that stuff that just didn’t make the cut compared to all else I had 
going on and what’s in my system. 

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