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The Breakout Email Management System

The Breakout Email Management System

An email management system for overwhelmed creatives who want to get back to work.

This is a collection of my thoughts over the last year of trying to solve my email overload problem. I’ve certainly not fixed my email problem – you might be reading this while you wait for a reply from me 😂. The key here is that my stress from email has significantly dropped after implementing these techniques.

The Breakout system is about going deep to the root of email overload and fixing communication problems at their source. It’s about putting in place the processes and forming the habits that will fix your email overload and free up your time to focus on your work and flourish creatively.

While tools are an important part of Breakout, they aren’t the focus. No tool, email client or iPhone app is going to save you if you can’t first break through to the underlying issues at hand – why do you get so much email in the first place, and why are you so bad at dealing with it?

Decide

The core of breakout is that you likely don’t have an email problem, but a decision problem. It’s human nature to avoid having to make decisions or to defer to a better time – a time when you think you can make a better choice, a time when you are less busy, any time but now.

You have hundreds of emails sitting in your inbox that need a decision from you. You open them, read it, and close it down. "I’ll deal with that later".

Soon this piles up and becomes a back and forth of "Sorry for the late reply…" emails.

When you open an email, you need to decide immediately how to deal with it and get it out of your inbox. The rest of these steps are going to provide a few different ways to deal with your emails so that you can get it off your plate and get back to work.

Kill it at the Source

Whenever an email comes into your inbox, ask yourself "Can I stop getting this type of email? Why am I receiving it? How can I not get this email in the future?".

Do customers keep requesting amendments to their receipt? Build something so they can do it themselves!

Are you receiving questions about a product or service that you provide? You are probably doing a poor job communicating on your website. That is an opportunity to fix and clarify your website’s copy. If you get the same email more than three times, stop and fix it at the source because something is broken and your email is just the dumping ground for the broken glass.

Your inbox isn’t the world’s todo list

Your inbox is not a todo application and you should not treat it as one. If an email contains a task that you must do, transfer it out of your inbox into a proper todo application or project management tool.

This follows David Allen’s Getting Things Done fairly closely. The mantra is get it out of your head and into the system. The same goes for tasks in your inbox – if you get them out of your inbox and properly categorized into your todo application, you both lighten your cognitive load and ensure that you will not forget about this task.

I personally keep a todo application with "areas of focus" – each area could be a specific project, a list of things to do around the house, little tweaks I need to make on a site, or links I should tweet. Then at the beginning of every day or so, I’ll review these areas and pull a few tasks into my "today" — these are the things and the order in which I will complete them.

My GTD workflow goes a little beyond the scope of email, but this is exactly how I deal with tasks that show up in my inbox. I’ll try and deal with tasks right away, but if I am unable, I’ll stick both that task and any relevant information, including the link to the original email into an area of focus.

Clear inbox, clear mind. Get back to making things.

Filter

Newsletters and transactional email add visual clutter to your inbox. Trim down notifications from applications by turning them off or creating a filter where you can cleanly sweep them all from your inbox.

Here is an example of a filter and tag I use so I can delete everything at once.

Matches: from:([email protected] OR [email protected] OR [email protected] OR [email protected] OR [email protected] OR [email protected] OR [email protected] OR *@asana.com OR [email protected] OR [email protected] OR [email protected] OR [email protected])

Another one to filter out of office replies from long chains or email blasts in every single language. This is pretty specific to my own use case, but you get the idea. Figure out what works for you and implement it.

Matches: ("Automatische Antwort" OR "Automatic reply" OR "AutoReply" OR "Out of Office" OR "Xesc Duran" OR "Abwesend" OR "Absence" OR "Absence du bureau" OR "À l’extérieur du bureau" OR "Réponse automatique" OR "Abwesenheitsnotiz" OR "Resposta automática" OR "Automaattinen vastaus" OR "Automatisch antwoord" OR "Afwezig" OR "Afwezigheid" OR "Niet aanwezig" OR "Poza zasięgiem" OR "Na wakacjach" OR "Poza biurem" OR "Automatyczna odpowiedź" OR "Z dala od komputera" OR "Αυτόματη απάντηση" OR "Εκτός γραφείου" OR "na dovolenké" OR "mimo kancelárie" OR "automatická odpověď" OR "Autosvar" OR "Fora do escritório" OR "na dovolené" OR "mimo kancelář")

co-workers, clients and newsletters

co-workers and clients who email with problems and questions can be trained. Email likely isn’t the best spot – tickets can be created in bug trackers, responses and file uploads can be logged in project management software.

Aggressively unsubscribe from newsletters that mean very little to you. These are just adding noise to your inbox. If something worthwhile is happening, you’ll hear about. Gmail tabs does a great job at filtering things into their own tabs.

Automate & Expand

Tech support should be directed to our slack channel. Obscure programming questions get sent to stack overflow. Questions about my text editor, theme or what type of toilet paper I use get sent to wesbos.com/uses. Advice and "please motivate me" requests get sent to my AMA.

All of these redirects can seem brash and cold – I don’t like that part of it. So – I’ll use Text Expander for common emails – it helps me seem more human.

One reason we abandon emails in our inbox is that we simply don’t have the time it takes to write a meaningful or empathetic email back to someone. A short, terse response may come off worse than no response at all.

So, how does a busy person instill empathy into our emails? How do we give people the time of day when we really don’t have it for ourselves? For me, many of my emails start off with a nice text expander base.

Text Expander will auto populate common things like the sender’s name, a random greeting and the base for the email. From there I can take 30 seconds to personalize the email a little more and answer any questions that the snippet didn’t cover.

For me it’s not so much that Text Expander cuts down on typing, it’s the fact that it cuts down on thinking how to reply to an email.

Keep Commonly used info at your fingertips

I’ll also keep things like phone numbers, airline mile numbers, house addresses, postal codes and any other commonly asked for info in snippets. It’s a quick way to bring up info you forget, or hate to type over and over.

For sensitive information like banking details, I keep them just a password away in LastPass so I can quickly copy/paste.

Dictate it!

I’m at the spot where I can think and speak much faster than I can type. Recently voice dictation, or speech-to-text, has gotten really good and we are now able to just speak our thoughts and have the computer type them up for us.

For an email that is an easy response but requires 3 or 4 paragraphs — "What do you think of ____" – I’ll usually turn on dictation and speak my response. Every few sentences I’ll pause and fix any errors and keep going. An added benefit to this is that your emails come off more casual and conversational.

The biggest barrier to this is that it’s uncomfortable or weird to do when people around. I don’t have a solution for you other than that you should get over that, because if you were talking into a phone it would be totally normal for you.

Use Video Responses

The breakout email system is not just about the email that you receive, it’s also about the email that you send out. How do we send out quality replies while not burning up our day?

While rare, sometimes an email contains a list of questions that text isn’t a good medium for. Rather than try and respond to each one at a time, I’ll just flip on my camera and talk through them to the camera. This allows me to both respond faster, and more importantly to deliver my free thoughts along with the tone that I intended.

This is also really helpful when trying to resolve a problem or provide feedback on a visual design, flip on a screen recorder and show the problem in 20 seconds rather than 5 minutes of email no one will bother to read.
I use Cloudapp in my OSX menu bar as it’s really fast and there is no exporting step – it’s like screenshots for video .

Should you Defer?

Deferring email should be a last resort. If you need to reply to an email but you are waiting on another party, defer it. This means you clear it out of your inbox and have it come back at another time. Boomerang and inbox for Gmail do this.

I’m not crazy about getting to inbox zero, but I do find if I defer things too long, they get lost in my inbox.

Batch Process

Many people recommend closing their email and only opening it up a few times. While this is ideal, many of us aren’t able to have that level of absenteeism.

For me, I have my email open all day long, but I only batch process it once or twice per day. This allows me to quickly jump on important and time sensitive emails quickly, but leave everything else for a couple times a day.

I use the Gmail labs extension send and archive so emails are out of my inbox as soon as I reply. Then I use auto advance so it puts another email on my plate as soon as that last one is sent – there isn’t a chance to escape when it drops another email on your lap!

Remember that your job is likely not to reply to email — focus on doing your job and don’t worry about those emails building up in your inbox.

Stop Emailing Yourself

I often see people emailing themselves things because they don’t want to forget it. They often congregate with tab monsters who have 10,000 articles they want to read open in idle tabs.

Stop emailing things to yourself. There are unlimited number of solutions to fix whatever it is that you are trying to move or remember.

  • TODO items go in your todo app
  • Phone numbers and emails go in your address book
  • Reminders go in your calendar with an alert
  • Bookmarks go in your browser, Evernote or Pinterest.
  • Files go in Dropbox, Google Drive or Air drop.

That’s it

Try and implement this stuff – you’ll have to work at it but I bet it will help you out.

Comment below if you have thoughts or ideas on your own workflow.

If you found a spelling mistake you can correct it here.

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2 Responses to The Breakout Email Management System

  1. Evan Read says:

    I think the thing everyone wants to know is what email client do you use and does it have a Cobalt2 theme?

    We need to Cobalt2 all the things. 🙂

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