Ideas on a Napkin: Integrating Email, Todos and Calendar

Brad Feld just wrote a post on why email clients suck. Go read Brad’s post if you’ve not read it yet.

Brad makes a point that we keep doing the same repetitive tasks, like adding someone to email chain, or moving someone to bcc, and the tools just don’t get it.

The collective of these small inefficiencies is a giant waste of our time.

Both individual and collective time is being massively wasted.

Those of you who read my blog regularly know that I am productivity-obsessed. I’ve written a bunch about managing email, calendar, and getting things done, particularly for startups.

I’ve been thinking about this problem for sometime, and it is time we solved this problem by having smart, single flow between email, calendar and todo lists.

Here is what I am picturing:

1. My calendar each week is organized into different BLOCKS

2. There are BLOCKS of different kinds of times:

a) Weekly recurring meetings
b) Weekly time spots for calls
c) Daily Email
d) Daily Exercise
e) Daily Todos
f) Weekly Email
g) Weekly Todos

Each block is “smart” and specific. The email block “understands” that it is for email and what email means, just like Todos block “understands” that it is for tasks.

3. My Todo list allows me to add tasks, just like regular todo list. But more importantly, it allows me to schedule a task to a particular block in the calendar. This is a crucial point and a big disconnect between what is out there today and what would work a lot better.

Any task you do takes time, and need to be scheduled.

Unless it is scheduled, unless it is on the calendar, you have to keep in your head. You have to remember that you need to do it. And that causes stress.

Separation of tasks, calendar and email is the biggest source of stress for modern workers. Particularly email because it keeps arriving while we are working, and there is just a ton of it.

4. Each email can be either answered immediately or can become a task. Typically, some emails are less important or take longer to answer and people tend to process those emails less frequently.

Imagine when the email arrives and you mark it for later, it prompts you to either create a task and/or place it into specific block.

Now you are no longer stressed. You don’t have to star emails or keep read emails in your inbox. The fact that you scheduled that email, created the task, means that you took care of it, and out of your head at the moment.

And that’s it. That’s the whole system:

Emails are either processed quickly, or become tasks, and are scheduled. Tasks are always scheduled into time blocks, and calendar is divided into typed, smart blocks ranging from exercise to daily emails and tasks.


You might say that Gmail or Google Inbox kind of has that. Or that others are trying to do that already.

The closest product doing what I am describing that I’ve seen is called Plan. But even that product isn’t quite there yet. There is no mobile app that does this well either.

Back to what Brad was talking about – context.

Calendar, Email, Task list, each of them should get smarter and learn about what we are doing. Most organized people organize calendar into blocks, people routinely mark emails for later, add people to threads, move to bcc, reply with the same text, schedule to work on todos, etc.

All of these things are just little bits of contextual smarts that we expect from current tools. Slack has done a great job adding these little smarts into chat and group communication.

Now we need Slack for personal productivity.

If you are working on this problem would love to hear from you, and would love to learn more about your product.

I think this is a very much needed product.

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1 Comment Leave a comment

  1. Nice idea Alex. I think one of the challenges with productivity software is deciding where disciplined methodology intersects with the feature set (and maybe that’s where software becomes an art). If you go after a large market ideally you want the tool to just work, or you risk only catering for a small niche (which is obviously fine if that’s the objective and the pricing model is appropriate).

    On the other hand if you find a way to build this sort of methodology into the software in a way that people don’t even realise it, things become interesting. Will give some more thought to this, really like the thinking…

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