That is in fact the core of the idea. I suck at low-level planning. All the wishful annual life goals have to trickle down as concrete daily activity to get anywhere. My mind is excellent at building castle projects in the air and even good at high-level analysis of them using flowery language. What it sucks at is converting all that into concrete steps. That's why I have to explicitly break them down into monthly, weekly, daily, and even hourly chunks.
TLDR some aspects were a progression, but the planning part was something I had to try out over a year to convince myself that I finally have something that works.
I'd say I have always done the daily todo all my professional life. Started it as my daily work plan when I was a salaried employee. Only tracked work-related tasks with it, but it was necessary because I had multiple project responsibilities and deadlines then. I actually thought of myself back then as a very disciplined person.
Even the life goals thing is something I have been doing from my salaried years. An annual document where I wrote details about my career wishes and personal improvements for the coming year. There were plans in those docs, but they were rather nebulous and not tracked.
That system worked ok for my salaried life. But when I became a consultant, things fell apart. When I had client projects to work on, my work-life balance became terrible, I missed project deadlines constantly, missed out on hobbies, and felt stressed and demotivated.
When I did not have client projects, I went the other extreme - making lots of plans but terribly distracted and not finishing anything.
Until then, I had not realized just how much of my earlier discipline was not because of me alone, but actually because of the structured and supervised environment inside a company. When I went alone, much of my discipline disappeared, and along with it, my self-confidence. I had actually refused lucrative client projects because I wasn't confident of meeting any deadlines.
I tried many planning systems over those years. GTD, Trello, Mind mapping tools. It's taken me a lot of self-analysis, experimentation and tweaks to understand why I had planning problems, and what I should do to overcome them. The main evolution between the system I have now versus the system I had back then is that all life goals now trickle down into concrete hourly tasks. While 2015 was a terrible year professionally, this system helped me improve my situation in 2016, and more so in 2017-2018. It's working out for me, thankfully.
Do you have a routine to (re)visit your plans and see if you're on the right track? Do you even have a concept of the wrong track under this system?
How does your work time, according to the `todo`, fare against leisure time? Is it similarly scheduled, or does it come whenever the work hours have been accomplished?
Do you ever miss your goals during the hours of work? What do you do if that happens?
Revisiting: Yes, all the time. The yearly plan would be framed at the start of the year, but new opportunities and personal ideas arise quite often and unexpectedly. If something can help me achieve my life goals better, the entire planning cascade gets reprioritized from that point on. I have done things like defer personal projects, drop ideas that turned out to be impractical after prototyping (an example of a wrong track), and renegotiate scope of client projects. It's a dynamic thing - the idea of the system is to force life goals to convert into concrete daily activities, but the goals themselves can and have changed.
Leisure time: Leisure time is very much part of the daily plan. I put tasks like jogging, workout, reading, going out in all my plans. Even have things like fitness annual goals and explicitly write them in my weekly schedule and daily plans. Anything that I should allocate time for goes into these files.
Missed goals: Yes, that happens. I'm quite bad at time estimation, and some ideas involve a lot of exploratory prototyping that may take much more time than anticipated. I mark incomplete tasks as [PARTIAL] or [SKIPPED], analyze at the end of the D/W/M what made me skip them, adjust scope if required, and modify my plans to correct the problem by next D/W/M.
You can be as meticulous or as high-level as you want, depending on your disposition.
Because my default state is one of procrastination and laziness, I have to explicitly plan such things. If I don't, the other work or distractions will just expand to fill my time, and I'll just keep perpetually delaying them only to find at the EOM that I didn't indulge in my favorite hobby for even 1 hour the entire month, and that feels really bad. My system has evolved to overcome my own mental handicaps.
But I personally know 5x times more productive people - with spouses and multiple kids and time sinks like house constructions - who don't do anything like what I do and still manage to fulfil all their professional and personal plans much better than I do.
I have only one daily, one weekly, one monthly and one yearly file. Each file covers all categories of life goals. Organizing categories into multiple files seems natural at first and I had tried it in the past with mind mapping tools, but quickly realized that tracking and updating them is inconvenient and didn't really help me with planning my day.
Here's an excerpt[1] from my daily todo to show what 2 days daily plan looked like - maybe it gives a better idea of what I'm describing.
I feel, with a certain definitiveness, that I need a schedule. Rather than working on a strict task-to-task basis, I feel like what I need is an obligation: "Do project X at 10, for at least an hour, then take your time until project Y at 2" etc.
I can't speak for OP, but I've been addressing "leisure planning" primarily with logging and reminders instead of planners: I received a Fitbit over the holidays which has done a great job of encouraging me to block out 10 minute activity breaks and to stick to a certain wake-up time. I just used break time to do some cleaning and often start chores like laundry and dishes on breaks too. When the "activity day" ends, it's functionally like "work is over, real leisure can begin," although since I am working independently I tend to spread everything across the day, just now I bias towards household chores and physical work early in the day, and mental work later. It works for me since I no longer have to feel disciplined about physical activity - it's simply built into the schedule that I will get up and do something, so something will get done at random, and when the break is over I can just put it down and come back to it.
For gym time I use the FitNotes Android app to track progress and set session goals. I have done this for about two years successfully. Since this has gotten me on a roll, most recently I installed ActivityWatch to correlate the sleep/activity/health metrics against my screen time. What I find most important for myself is closing the loop of goals/plans/feedback: if some part of it is missing then progress stops. Usually it's lack of feedback that causes the biggest problems.
I've been thinking about specified breaks. My idea was: a 5- or 10-minute break every hour, away from the laptop, doing anything at all. I've noticed that, once AFK, I have my mind back: it springs back, outputs ideas, regains its perspective...
I've also been thinking about implementing pre- and post-workday breaks, for 1 and 2 hours, respectively.
The former is about starting the day right: instead of diving into whatever web the Internet has for me (a web of my own making, don't get me wrong), I could take a walk, or do a little cleaning, or cook, or read, or...
The latter, preceded by an hour of review, is to wind down, in order to maintain a proper sleep pattern (which I have serious problems with at the moment: waking up at 1 PM is not good for me).
Let's see how it works for me.
Best wishes to you and your own scheduling. I hope it works out to an excellent result for you.
Do you consult upper-tier lists when making lower-tier assignments?