How do you visualize your work, week by week, from a 10,000 foot perspective?

[beck]

Maybe it was because my life was simpler then, but years ago, I had a yellow notepad and I would budget projects in pomodoros. Every line on the left would have the sort of high level goal (e.g. design logo) and the right side of the page I’d draw however many boxes (pomodoros sessions) it should take to do that task (e.g. four boxes).

I’d count up pomoodoros, divide by two, multiply that number by my hourly rate, and pitch that to a client. If I got the job, I’d begin work on any given line, crank the timer, and try to finish it in fewer pomodoros than I budgeted for a better rate.

All my projects were contained in this notebook and everything was already budgeted out time-wise, so adding new projects was a fairly simple review/calculation. It worked really well, but it just doesn’t seem possible now. There are some apps that allow you to budget pomodoros for each task, but they fall short in other ways.

[anon41602260]

Do you still think of your day in pomodoros?

[leo]

Pomodoro blocks never worked for me. Once I have momentum on a task it is really hard for me to let go when the timer gets off. And if there is momentum I might work for 4h or more straight and I’ll be surprised that time did fly by so quickly. The 25 min. timer kicks me out of that “flow”. Even if I decide to not take the 5 min. break and restart the timer for the next block to have a lightly longer pause block at the end. It just seemingly makes the system less rigid and still doesn’t help to improve my estimations.

I really struggle to put a somewhat precise time estimation on longer projects with steps that by nature are not entirely clear and might also require some serendipity. As an example, which is accessible for most might be “writing your first book” (no plans, just a good example). I think everybody has a rough idea what steps would be necessary, but it is hard to put a time cap on each of them. Especially when the task involves iterations and a constant back and forth between research and creation.
Are there any tricks that work for you?

Another interesting tidbit: I listened to a podcast with one of the guys from Basecamp and he said that they strictly subdivide their large scale projects into features, which are individually developed in chunks of max. 6 weeks by teams of max. 3 people. If it takes longer or requires more people it has to be stripped down to meet the criteria. During this time the small team’s only responsibility is this feature and they can stay away from all other things going on in the company.
It’s an interesting approach to break down tasks, but I fail to apply that logic to my own projects, where I mostly work as a solo freelancer. Especially since you very rarely have just one project going on.

[beck]

I don’t think I ever thought of my days in pomodoros, but I do still think of a good many of my tasks in that framing. For example, here’s a recent-ish attempt to estimate work required for some interviews.

When I started doing pomodoros (I think it was around 2007, but hard to remember for sure), I read this 40-page PDF (I still have it!) that Francesco Cirillo made freely available at the time. He suggested spending your first few pomodoros reading through it to learn the method. It seems like the technique has become mostly about focus/deep work, but his framing in that eBook was that it’s a way to gain awareness of internal/external distractions and get better at estimating.

To bring it back to the OP, and @anon41602260, an earlier contribution you made to this discussion… I guess I’m saying that, in my experience, good estimates are a way to get better at having perspective on one’s work, and PT is a way I’ve used to get better at estimating.

[beck]

@leo

the guys from Basecamp

In my experience, those two say a lot that sounds good (and with such conviction!), but never works for me. Like a really awesome cookbook with crappy recipes.

[Doty]

Over the weekend, I purchased QuickPlan Pro. It’s ok, but not exactly what I’m looking for. But just now, I realized that Trello released a new timeline view that looks interesting. I might give it a spin as we are already using Trello.

[anon41602260]

The thing about Trello timeline view, or SheetPlanner, or similar, is that it doesn’t meet the requirement that I think underlies this thread: knowing not only when work is planned but also how much effort does it take? Does my task take two 12 hours days or two fifteen minute sprints on two consecutive days? Big difference between those two scenarios.

[Bill_Aus]

Hey @beck thanks for the tip on the PDF, had a bit of a hunt and found it. Looking forward to digging into the details from the founder.

While I have never used the technique itself, I do allocate time to tasks and then try and beat that time. Part fun, part productivity hack. Always useful.

[MartinPacker]

I don’t think I saw it in the thread so far but I have to ask “what is the purpose of visualising your work, week by week, from a 10,000 foot perspective/”

Not “is there any point?” But what? The answer to that might well govern how.

[anon41602260]

The OP hasn’t returned to the thread since the first post, but, speculating, I think “from a 10,000 foot perspective” is similar to "I want to get a broad – i.e., ‘high-level’ – understanding of my calendar and commitments and find a better approach to deciding whether to accept new projects and when to start that commitment.

[snelly]

The frustrating thing about this question is that there isn’t really a good automated way to do this outside of Excel.

I use Cushion to manage my business, and it works well and gets me halfway to this goal. You can plan out roughly where you think your workloads are going to go and see how much time you’ll have left in your week against whatever availability you set up. But it isn’t automated.

What I’d love is for a system where I can do the following:

• Punch in my weekly working hours
• Add projects with expected due dates, start dates, and total amount of hours expected to work
• See if I’m over or under-booked, based on the amount of work I have to do and when I need to do it by
• Track my time and see if my expectations line up with reality. If not, how off am I? How much does it cost me every time I underestimate a project’s timeline?

There are bits of software that will do one or two of these things, but nothing I’m aware of that will let you do all of this without significant manual effort. The best solutions typically involve multiple apps and significant manual tallying at the end.

This is also very different from task management. While I love OF and Things, it doesn’t really do any of this for you. It’s not the 10,000 foot view that I think the author is looking for (and certainly not the similar thing I would love).

[MacSparky]

I have an OmniFocus perspective (and Obsidian page) showing active projects … but that doesn’t make its way to my calendar in total. The stuff on my calendar is the stuff where I think, "Today is

[leo]

@MartinPacker

what is the purpose of visualising your work, week by week, from a 10,000 foot perspective

The issue is that we all face an ever-increasing level of action autonomy in our “knowledge work life”. Especially so if self-employment or freelance client work is involved for which we never got prepared. The majority of our education (school, university, training on the job etc.) imposes a rigid external time framework (semester exams, quarterly results, yearly release schedules etc.) onto us for decades of our upbringing.
Also life in general seems to get more complex. Over 1/3 of the US labor force is working in the so called “gig economy” and are multiple job holders.

All this paired with this quote, which carries a lot of truth (especially the first part), is a dangerous combination:

“Most people overestimate what they can achieve in a year and underestimate what they can achieve in ten years.”

I’d go so far to assume that the stress of making false judgements in this planning state is directly related to the increase of burn-out, depression and other problems. All this makes our work-life balance unhealthy.

The 10.000 foot view’s promise is to provide clarity. It should help to abstract your work, review your work to gather lesson’s learned from previous projects, see the larger picture, budget time, resources and even energy.—Basically your life’s project portfolio management, but across all areas of your life with the goal to get to a healthy work-life balance.

The problem is indeed this “what”. The data required to see the full picture is often scattered across multiple buckets. Be it your personal and work to-do list, notebooks, personal/work calendars, shared calendars and schedules of your family members, which influence your personal schedule and much more.

The promise is attractive, but the execution is still hard, hence this discussion.

[cornchip]

Raise your rates! If you’re able to accept so much work as a solo practitioner that it’s difficult to predict schedule collisions, you should be able to charge more. That will help keep your schedule legible.

[bradgibson]

I’m a little late to this party but here’s my way of looking at this type of 10,000 foot stuff. (Plus, it also adds a bit of a look “up” into the higher elevations if you set up your projects with the right info.)

I too am an OmniFocus user, so my approach is 100% OmniFocus-based. I am assuming that you are running a solo or small shop operation. Gantt charts may look great but they are almost always wrong and introduce an overhead for micro-businesses like ours that offers no value.

The solution I believe, is a Perspective! Two Perspectives actually. They are very similar in construction, with subtle changes in the way they are sorted.

I call the first Perspective the “Quarterly and Annual Planning Review”. This Perspective groups all of my current and upcoming projects with Due Dates by Project, then by Due Date. The second Perspective is very similar and is called “Significant Milestones”. The grouping by Project gets dropped and only tasks with Due Dates appear in the Perspective.

All of the sample data is tagged “sample” so that I could put some fake, but relevant tasks together to provide an example of how I look at these two Perspectives to make a decision. So if you make these Perspectives, you do not need the “Tagged with Sample” condition. Each of the tasks are broad — they are at the 10,000 foot level on purpose. You may actually want to tag 10,000 foot tasks as such for inclusion in these or any other type of Perspective you come up with.

Let’s say I’m currently working on “Project 1” and “Second Big Project”. Later in the year I know I will have “Something to do in Quarter 2”, “Project for Mr. Burns” and “The Biggie Later Project”. Now, along comes a client request to get something done in the next couple of weeks (let’s say it came in on Feb. 23…). I think I can do it and I enter the project into OmniFocus as “Should I do this Project?”. There are 2 key tasks to do for the project and they will total about 150 hours. The project is due on Mar. 15.

With the proposed project and its framework (ie: 10,000 foot level) tasks entered, I can now take a look at my two key Perspectives to see how things will land. I should likely also have my calendar open too, in order to check on upcoming holidays and family commitments. (You actually could put that stuff in OmniFocus too I guess, but that’s not how I do it…)

Let’s look at the “Quarterly and Annual Planning Review” Perspective first. What I like about this Perspective is that, because it is grouped by Project, the task that has to be done first pulls the whole Project ‘up’ toward the top of the Perspective. So, even though “Project 1” is not due until Apr. 2, it shows up as needing attention ‘In the next month’ because there are 2 tasks to be done by Mar. 21. In fact - wow! - there are 3 overlapping projects to work on over the next month. Now of course, one of those is the “Should I do this Project?”. Well, should you?

Let’s go to the “Significant Milestones” Perspective now. Take a look at the cleaner task listing in the Perspective. Now consider the underlying message in the data. It tells me that the answer is “No” to taking on the “Should I do this Project?” project. 150 hours of new work to be done by Mar. 9 (remember, it’s Feb.23 when we are looking at this data) when I already have 240 hours of committed work to do by Mar. 21 isn’t possible in my world. Of course it depends on what kind of work you are doing and if you have some other trusted people you could call in to help.

I use these two Perspectives a lot to assess what I will be doing in a “big picture” sense. They also help me in determining when I should say “Yes” or “No” in the months ahead.

[DrJJWMac]

@bradgibson

I use these two Perspectives a lot to assess what I will be doing in a “big picture” sense.

Wow! Nice.

In the analogy of flying, I’ve immediately taken to the Quarterly Review as my new “Inbound” perspective.

Thanks!

–
JJW

[joshgibson]

Very interesting… I’m pretty tied to OmniFocus honestly, but maybe not for good reasons. I’ll definitely take a closer look at Asana!

[joshgibson]

Honestly, I love a lot about Notion’s timeline view, and I love a lot about their calendar view as well. A few minor things that were annoying hurdles to overcome:

• In my work, like most other people, I’m usually juggling several projects simultaneously. Some are large, more long-term projects, and some come and go in a couple days or so. A lot of my projects (as a video editor and producer specifically) start and stop multiple times throughout a several month period. With Notion, you can set up a view to see a timeline of a certain card’s start and end date, but you can’t add multiple dates to one card and have all those dates shown at the same time, if that makes sense. Plus, after fiddling with Notion trying to get the square to fit in the round hole, I realized it wasn’t worth all the effort because really all I wanted to see was a calendar grid that I can glance at and see what projects are coming up, and see when I’d be most busy (shouldn’t accept more work/clients,) and when I’d be available to take on more work.
• A small thing, but Notion doesn’t support deep linking or URL schemes so linking back to an OmniFocus project and keeping those two in sync was kind of a pain. You basically just have to copy and paste the Project or Task deep link text into Notion manually, and when you want to go back to OF from Notion, you need to manually select the link’s text, and paste it into Alfred to get it to activate. Small nitpick, but it adds friction that I don’t want to deal with.

I guess the reason I stuck with something like the Calendar app or Fantastical was I could really easily drag and drop Projects or Tasks from OF anywhere on the calendar view (either time-blocking a specific day, or creating all-day tasks to span a couple weeks or whatever,) and the event would be created with a handy (and clickable) link back to the OF Project/Task. Now, if only there were a script/automation that would detect when I dragged an OF Project/Task to the calendar, and added a note or something to that item in OF (or even a link) to the calendar event – having them back linked to each other like that would be awesome.

Anyway, sorry for the long-winded answer. Feel free to let me know if I’m missing something though or am not using a feature correctly!

[joshgibson]

I’d love to hear more about your workflow. Keeping everything in one (the Omni app) ecosystem sounds very appealing to me. I guess I always saw OmniPlan as a project management app that only was beneficial if you were managing other people, etc. – not for solo use.

[joshgibson]

Yeah, I think that’s why I came and posted here, is I realized I was trying to make Notion do a thing that it doesn’t do well (at least with regard to my workflow and other tools/systems I use.) I understand the fundamentals of time-blocking, high-level planning, and time estimates pretty well (I’ve been learning the hard way for over 10 years now ) but I guess I was getting tired of reading a wall of text every time I wanted to see how busy my next few weeks were looking.

No project is the same for me, so they’re very often different every time I work on them. I also have ADHD so crafting an experience and making it as beautiful and enjoyable to use as possible is something that can help keep my mind on target.

Anyway, I’m sort of rambling on now, but the reason I was curious what everyone else did (and if there were any obvious tools I wasn’t noticing,) is I wanted a way to visualize what I’d be working on, in a beautiful and interactive way, to keep the important stuff top of mind.

Thanks for your advice!