Daybook Journaling: Calendar-Centric Work Management

I am finding Daybook Journaling the most natural work management I’ve used, and I have tried every possible approach under the sun.

0. TL;DR

This post is overly long. Apologies.

The first section, Revisiting Work Processing, is a recap of points I’ve made in earlier posts about ‘work processing’ (see Work Processing: Coming soon to a ‘Doc’ near you, and ‘Work Processing’ and the decline of the (Wordish) Document). If you’ve read all those posts already, you can jump ahead to the second section, Introduction to Sunsama, below. If you want to jump to the description of Daybook Journaling, that’s in section 3. If you’d like a demo of Daybook Journaling with Sunsama, sign up to be notified when I schedule such an event, here.

1. Revisiting Work Processing

Over the past few months, I’ve been exploring the possibilities of using new coediting tools — like Dropbox Paper,, Quip, and Nuclino — as a medium for content-centric work management. I explored the idea in several posts, and introduced the term ‘work processing’ to denote this flavor of work management.

I described ‘work processing’ this way:

Using something like Dropbox Paper as a way to share work-related information is quite different than using a conventional work management tool. Instead of putting lists of tasks at the center of the stage, relatively unstructured content — written text, images, tables, videos, audio, and other forms of content — takes the central role in information sharing, while tasks are indicated by checklists.

Metaphorically, work management is based on the human tendency toward making lists, while work processing relies on our natural urge to tell stories. Or, less romantically, work processing is more like writing in a journal, where occasionally you might add a list of things to do, but where the prose is where the most important information is found.

I worked at work processing pretty diligently for a few months, but I had started to drift toward a model based on three sorts of documents:

  1. Planning docs — For each project or on-going initiative, I would create a corresponding doc, in which I would keep tabs on critical information — like goals, deadlines, contacts, links to supporting docs, and checklists.

I found that I spend the greatest amount of time in journaling. Creating a plan of attack at the start of every day (as a standalone doc or a section of a weekly journal doc) became a daily ritual, and I updated that doc numerous times throughout the day. This is all discussed at some length in Work Processing: Coming soon to a ‘Doc’ near you, and I liked a lot of what the approach afforded, although I missed the model of richly-defined tasks. As I wrote,

Dropbox Paper would be way more effective as a work processing solution if checklists were more task-like, and not just one of various sorts of lists, like bulleted or numbered lists. While checklist items can be used to indicate a task, and the checkbox can be checked to indicate being completed, if checklist items only had a bit more of a task model — with due dates, assignment, and so on — I would be more likely to promote Paper as a foundation for work processing.

I also countered that with this:

Other aspects of the experiment worked surprisingly well for me. I thought I’d miss a rich task model — due dates, notifications, etc. — more than I did. What I learned is that I relied on propinquity: the week journal doc was basically open all day, and as I was adding more information to the various sections I would reacquaint myself with things I need to be working on for Friday, or next week, as I entered new content. And I felt like I had a better big picture sense of what I was working on each day and for the week, than when I just relied on a work management list of tasks.


Journaling and task management aren’t organized around semantic nesting of docs in folders or the semantic structuring of content within docs, which is the organizing principal of Dropbox Paper (and other tools like it). Journaling and task management should naturally be based on time — hours, days, weeks, and months — not semantic nesting. Yes, I created a form of doc based on a weekly journal, but it’s not native to Paper, just a poor approximation.

So what if we started with a calendar, and added the richness of work processing and task management to the mix? That’s exactly what the folks at Sunsama have done. And I am a total convert.

Introduction to Sunsama

Imagine a team calendar that supports sharing of events, coediting of events, and comments/chat on every event. Imagine also if that team calendar supported a rich task management capability, with start/due dates, assignment, and notes. That is Sunsama in a nutshell.

The Calendar

Sunsama is, at its core, a calendar, based on a week- or agenda-style calendar layout. I selected the M-F option in this display:

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Sunsama Event

In the left margin is a calendar picker, a list of teammates (I’ve been adding teammates on an event by event basis, so the list here is short), and a list of projects. Clicking on a teammate or project is a way to filter events and tasks.

In the center is the calendar pane, with a familiar look and feel. Note that I filtered all actual events — many came from syncing with Google Calendar — in this display, with the exception of the one I am editing in the right side margin.

Note that event is titled using the day’s date, and I have gone so far as to assign some of the attributes — location and project — as well as to indicate it is an all-day project, and to add a few agenda items. You can see that there are notes below the agenda items. (In my use pattern of a Sunsama event as a journal item, I don’t use the time feature — which is organized for actual meetings, and could denote that the agenda item will take so many minutes, for example.) I have not assigned the agenda items to a teammate, although I could do so, and that would give access to that event.

Note: The edit option at the top left of the event allows me to modify information that gets synced to the Google Calendar entry that corresponds to this. So if I want some info there, like the location or other notes, I have to click edit, and a new UI opens. Sunsama automatically includes a link to the Sunsama event in the Google Calendar event. (I’d like a feature to copy all the agenda items and notes, as well.)

Further down are ‘action items’ which are full-featured tasks. Here I am assigning getting a hotel to myself, and setting the due date to ‘today’.

Below the action items is a chat input box, which I could use to communicate with teammates — if any — or to append notes to myself, as well.

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Expanded Action Item

I can expand the action item to gain access to other attributes such as project, and a start date — here the start and due dates are the same — and the task notes field. Note that it is when adding notes to tasks and events that I most find myself missing the ability to @mention and notify another teammate about something explicitly, a feature not yet implemented. Yes, I can do that in part with the chat capability, but it’s not as fine grained — all teammates on the event are notified.

Sharing An Event

Here’s what a user sees of an event when they’ve been invited to an event, and accepted, but are not a user of Sunsama: a web page is created and shared. I added a task and assigned it to the other stoweboyd, and he’s indicated it’s been done.

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Shared webpage

Another way to share is to send out 1/ the agenda of an event for review, 2/ the finished summary (theoretically after a meeting is over), and a sharable link (on clicking leads to a webpage representation of the event for non-users, and opens the event for Sunsama users).

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Sharing event with invitees

Sending the finished summary leads to an email with this HTML:

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Event summary email

I find that I have been sharing the notes and actions items after meetings with others, none of whom are Sunsama users; at least not yet. In this case, I am the only attendee shown — I didn’t share this with anyone else.


In the first screenshot above (see Sunsama Event) in the center panel there was a second option to Calendar: Tasks. Below, I’ve filtered so that only the tasks associated with the ‘workify’ project are shown, and you can see the layout of the task panel. You see I’ve selected incomplete tasks, which are broken into three major groups:

  1. working on today
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Tasks panel for a single project

And here’s a display of the tasks for selected projects in the unexpanded view, in the right side next to an agenda view of calendar events:

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Agenda view with selected project tasks

In the ‘working on today’ section you can see the various selected projects’ tasks are arrayed in the right hand side.


Search works as you might imagine, although the search approach yields inexact matches as well. Here you see ‘scanning’ when I searched for ‘planning’. In this case, no big deal, but it can be a headache if you have a lot of false positives.

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Search results

3. Daybook Journaling

After a few weeks of using Sunsama, I can’t imagine moving away from journaling as my primary mechanism for my work management. And I am gradually introducing this for coordinating, communicating, and cooperating with my immediate network, which is made up of people from dozens if not hundreds of different companies.

My basic pattern of use is this:

  • Each morning, I create a daily journal entry — a Sunsama full day event named after the day in ‘yyyy-mm-dd’ format.

My growth into journaling, in general, and with Sunsama, in particular, has been very much a day-by-day, bottom-up experience. While I started out with the perception that time was a critical dimension — if not the critical dimension — of my work management needs, I was uncertain exactly how the levers and knobs on the tools — Dropbox Paper and Sunsama — would work to help me (or hinder me) in figuring out a workable way to keep track over everything.

Through daily use the system has revealed itself at the interface between the affordances of the tools — which have been changing over at Sunsama, as I have been barraging them with feature requests and bugs — and my own growing understanding of how to work this way.

I am therefore calling this Daybook Journaling, partly because daybook is a synonym for a diary or a journal, and I’ve always maintained that creatives need to capture and develop ideas for new work, and that professionals need to track and manage the myriad details of their work to be productive. The answer in both cases, is a daybook (or daybooks).

Here’s a newly extended table that contrasts calendar-centric work management with other sorts. Calendar-centric tools like Sunsama that support sharing, I characterize as Journaling in this chart, and that is quite different to the Work Processing supported by Dropbox Paper and others.

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Various flavors of work management

There is a broad range of alternatives for work management, and they are extremely different in what they accentuate and what they filter out.

I am finding Daybook Journaling the most natural work management I’ve used, and I have tried every possible approach under the sun. I hope in the near-term to use it in larger groups and to explore how others feel about the approach.

In the near term, I plan a few additional activities that might be of interest to those who have managed to read this far.

  1. I’ll likely write a comparison of this journaling technique with others, like Getting Things Done, and Bullet Journal technique.

Written by

Founder, Work Futures. Editor, GigaOm. My obsession is the ecology of work, and the anthropology of the future.

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