Is This Helpful?

If you’ve received an email from me since 2008, you’ve likely seen those 3 words concluding my message.

I initially added them to my email as a soft way to confirm my message was, well, helpful. I envisioned them as a tiny step towards measuring the value of email in a new, qualitative, way. I didn’t envision how they’d change my writing.

With “Is this helpful?” as part of my default email signature, they are the first 3 words I see when I start a reply to you. Over the past 6 years these 3 words have challenged me to: re-read your original message, think through your question a little bit more, book the meeting on my calendar, double check my work, and be more constructive. They have continually challenged me to level up.

“Is this helpful?” is now a question I ask myself throughout the day. Not just in email, but in all my interactions with the world. It has become a touchstone for how I spend my time and where I direct my attention online and off.

“Is this helpful?” implies a goal and measurable forward progress towards achieving it. As a nemonic for larger goals these 3 words have a powerful ability to keep me from getting tangled up in The Daily Outrage. They also continually remind me that I don’t know everything – and measurable progress is the best way to uncover the unknown unknowns.

In short, these 3 words have become the qualitative value metric I originally envisioned.

How to Empty Your Email Inbox

TL;DR: The calendar is the vessel, not the inbox.

According to my email service, I receive approximately 1 non-spam message for every 4 spam messages. Everyday 400 obviously unwanted messages are destroyed for every 100 allowed through. Many of those 100 are easy enough to delete as well. Over the course of any given day, it’ll take me around 2 minutes to process 98% of those messages. That leaves 2. Two messages that for whatever reason – I can’t just immediately delete. Two messages I actually need to think about.

What do I need to do? How do I respond?

I have a daily goal of clearing out my email inbox. Just as I have a daily goal of cleaning out my physical mail box daily. Most days, both are easily achievable. In all honestly, the hardest messages, the ones I’m really truly avoiding aren’t sitting unread in my email. The ones I’m avoiding are partially written drafts – or worse – not yet started (except they have been – a thousand times in my mind) drafts. But that’s a different conversation – this conversation is about processing the email inbox.

Notice, we don’t really have 400 – or even 100 – messages to deal with. We really only have 2. Two messages that require our response. You might be thinking, “oh, Garrick – 2 messages is so cute. I’m a very serious high powered executive – and I have hundreds of messages daily requiring my response.” Two, I say. Two. Any more on a regular basis and you may be using your unread count as a status symbol. So, for the next 1500 words we’ll agree there are only 2. Cool? Cool.

Great, let’s take a look at those 2 messages.

One of them is sneaky. By all appearances, it looks like it shifts huge obligation onto your back and that you need to respond immediately to accept this obligation. But re-read it. Do you see it now? That’s right, the whole reason you weren’t able to process this message in the first round is that you’re scanning brain didn’t notice that a key bit of information was missing. In my client work, the things frequently missing from these sorts of emails are: attachments, targeted dollar amounts, dates and locations. Once you’ve figured out what was missing – hit reply and ask for it as apologetically as possible. For missing attachments, I like to use something like, “I’m sorry, the attachment didn’t come through on my end. Please re-send. Thanks.”

Some people enjoy using various auto-responders and snippet extenders to even more quickly reply in these recurring scenarios. If that works for you – excellent. This is more about realizing you haven’t received the information you need to confidently move forward and are replying appropriately. Of the two – this is actually the easiest to deal with. So reply and get it out of your inbox. Don’t fret, when the original sender replies with the requested information – the new message will be unread. Beauty.

When this message returns, it will be that lone message sitting in your inbox keeping you from the clarity of doneness inbox zero brings. So, what do we do with this sole, haunting message. First off – stop. Yes, stop, and ask yourself this one questions: “Are you in a state of mind to actually approach this email in a clear meaningful way?”

Yes, I’m serious.

Up to this point, you’ve been making ruthless, kneejerk decisions to hundreds of messages – rightfully so. None of those messages deserved your full attention. This one does. Stop and breathe. You need to be in the right frame of mind to meaningfully address this message. Clear your mind of any stress, bias, or intonation. This will prevent your kneejerk self from interfering with the thoughtful, calm, deliberate planning stage you’re about to enter. Always start from a place of clarity. If you need a quick, easy way to get there – step away from your devices and take a short 10 minute walk outside. It’s February in Minnesota as I write this – do not doubt my seriousness.

Now that you’ve the energy and clarity to look at this message, what’s likely the very next action you need to perform? Is it; review the proposal and provide a recommendation? schedule an interview with the candidate? prepare monthly progress report for the board?

It’s likely something similar, which means it belongs in your calendar as a commitment – just as a doctors appointment, team meeting, or the board meeting itself. Look at your calendar and schedule when you’ll actually do this thing. Yes, weigh all the constraints, deadlines, and other commitments, move things around if you must. But this first step isn’t really answering ‘what’. It’s answering ‘when’. If you look at your calendar and can’t find a 90 minute block within normal business hours over the next 5 business days where you can dedicate the mental energy to this one task – you’re the wrong person for this one task.

The goal is to move the message from your inbox to a scheduled time on your calendar with all the appropriate information moved into the calendar appointment. The calendar is vessel, not the inbox. The calendar knows your limits and your capacity. The inbox knows nothing of either – it only knows how to receive. To achieve inbox zero reliably and consistently – you must trust your calendar.

If you are the right person, and are unable to find 90 minutes for this task, case, look at all the commitments across your calendar and this new one – and as quickly and ruthlessly as you deleted those 98 emails earlier – identify the commitment you’re going to break. Now draft the appropriate message to the person whose commitment you’re breaking – the key thing here is to gracefully hand over the reins to someone more appropriately skilled.

Even after multi-week stretches of inbox zero, the right message will sit ‘read’ (though marked ‘unread’ repeatedly) while I contemplate the next action. Sometimes, it takes hours to figure out what the missing piece of information was that I still needed (like I said, these #2 messages can be very sneaky). For these messages, I quickly scan my calendar make the appointment and reply something to the effect of: “From your message, I assume X, Y, and you’re ready for me to get started.” More than once the reply has been – “Oh, no. We’re not ready for you yet.” Great. Suddenly I have 90 minutes available on Tuesday.

Either way, I can now focus on my calendar and not on my inbox.

Notice, we still haven’t reached that message where you are actually obliged to work on something. About that lone message that you’ve scheduled time to do. Immediately after scheduling a 90 minute block on your calendar – start a draft reply. Now you won’t need to be search for the original message to initiate a reply – it’s already started in your Drafts folder.

It’s always amazing what can be accomplished in 90 minutes of deliberate effort. In most evenings it’s the time I have for my discretionary activity – watch a movie, read a book, fix a bug, add a feature, write 1000 words. All these things take about an hour and half. Ninety minutes of deliberate effort is more than enough time to do something of significance. Commit to it. During this 90 minute block you’ve dedicated to start working on this task, fully focus on the task. This is the only time you have committed to it and you need to move the project forward. Get to work.

After you complete this first 90 minute session of work, it’s likely that the task is done and the drafted message can be completed or an additional 90 minute session should be scheduled. Do what’s appropriate. Then, instead of reviewing your inbox – do the next thing on your calendar.

Your work is in your calendar – not your inbox. Schedule your days as if every obligation is a it-takes-months-to-get-reservations-at-this-place appointment. It is. Nature abhors a vacuum. Especially when that vacuum is your iCal. If you don’t block off time to do your work – it will be quickly eaten up by pointless meetings, inane conversations, and trolling Facebook. Mapping your day on your calendar – especially a week or two in advance will give you greater confidence, more control over interruptions, and a stronger sense of what is important.

Fine, I’ll admit that email is scheumorphic.

  • ‘Forward’
  • ‘CC’
  • ‘BCC’
  • ‘Signature’

All of these elements are carry-overs from, not only an archaic communication model, but an extremely bureaucratic one. One where high value is placed on traceability and formality. I suspect those two concepts by themselves result in higher communicatations costs, reduced message volume, and higher default priority.

Do we have a communication interface that reflects our current world? One where communication is casual, informal, cheap, and 99.9% of it is unwanted, unactionable, and otherwise unnecessary?

Email’s IMAP protocol could still support this, it’s the interface on the client side that requires the most significant updating.

And I don’t mean echoing the interoffice envelope.

$0 is No Longer an Innovation

“I wish there were a for-pay service I could switch to which would be easy and fast and nothing would break. I think the free email has killed off all the good for-pay email.” – Dave Winer

From Opt Out’s ‘Free as in Lunch’ chapter:

“An email client that can handle today’s daily onslaught of email hasn’t been released. The $0 price tag has effectively killed any re-thinking of the email and the email application as a whole. This means our understanding and experience with one of the most mature, open, and decentralized communications technology is frozen in a time before any of my, and perhaps your, children were born.” – Garrick van Buren, Opt Out