Escape Your Email

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Escape Your Email by Mind Map: Escape Your Email

1. Lack of a (or bad) System

1.1. Missing infrastructure to manage multiple accounts

1.1.1. Solution: Advice on technology solutions (i.e. HelpScout

1.2. Uncertain about what to do with processing and deciding

1.2.1. Solution: Teach AE email system

1.3. Downloads folder fills up

1.3.1. Solution: File Management (SaneAttachments, Hazel)

1.4. Worried about not being able to take next action on emails once she’s moved them

1.4.1. Solution: Teach system for filing and attaching reminders

1.5. Overwhelming amount of information saved for access “someday”

1.5.1. Solution: Have appropriate filing containers (task manager, reference file)

1.6. Exhausting clearing email everyday

1.6.1. Solution: Streamline the system so it’s easier and doesn’t take as long

1.7. Using email as a “holding tank”

1.7.1. Solution: Touch it Once, know where to put things

1.8. “Clip” a lot of things, but they end up just becoming someday/maybe stuff

1.8.1. Solution: Have a process/system for dealing with attachments/saved files

1.9. Using email as a task management system

1.9.1. Solution: Use a task manager and clip/send emails to that instead

1.10. All in with Apple Mail (Mail Act-On, Spam Sieve, etc.) on Mac, but can’t send directly to task management system on iOS

1.10.1. Solution: Use Dispatch or Airmail on iOS that can send straight to OF (or other task manager) and don’t use mailto: feature

1.11. Get lazy and neglect the system that is set up

1.11.1. Solution: Streamline the system so there’s less friction

1.12. Leaving things in your inbox because there’s a higher chance you’ll get to it later than sending it somewhere else (don’t trust the system)

1.12.1. Solution: Develop an air-tight system you can trust

1.13. Using folder for organization of file attachments instead of saving them to correct folder locally

1.13.1. Solution: Find a good way to handle attachments (i.e. Sanebox, Dropbox/Drive, etc.) - possibly Hazel to manage them once you save them to your hard drive

1.14. Struggle separating personal and work email

1.14.1. Solution: Separate apps for each inbox?

1.15. Don't trust email system because it lies on top of untrusted task management system

1.15.1. Solution: Solve one problem at a time and don't add complexity you don't need

1.16. Leaves things in their inbox that don't need a due date (unsure about how to use defer dates, so just leave those in their inbox)

1.16.1. Solution: Having a place for everything that comes into your inbox

1.17. Leaving messages in your inbox as "reminders"

1.17.1. Solution: Know how to use a task manager and email together

1.18. Feel like they've got it all under control when they don't ("Superhero Syndrome")

1.18.1. Solution: Be real and make adjustments when necessary

1.19. Inbox gets unruly after taking a trip

1.19.1. Solution: Have a system that doesn't require as much maintenance so it's easier to recover

1.20. Sending actionable emails to a "Reply" or "Action" folder, then forgetting to do anything with them

1.20.1. Solution: Don't use email for task management! (no reminders, contexts, due dates, etc.)

1.21. Know what to do, but give up on the system (lack of willpower to keep up with it)

1.21.1. Solution: Eliminate the friction in the system

1.22. Working for governments/financial institution and not being allowed to use  cloud-based tools like Evernote/Dropbox because of security concerns

1.22.1. Solution: Manage everything (files/attachments) locally using tools like Hazel

1.23. "Polluted inbox" leading to the "nuclear option"

1.23.1. Solution: Eliminate the cruft

1.24. Sanebox creates more inboxes

1.24.1. Solution: Use a blended approach (Inbox every day, SaneLater 1x week)?

1.25. Uncertain where to put things from your inbox

1.25.1. Solution: Reduce the number of tools that are in your system (condense & simplify) - make sure every tool solves a specific need/problem and don't duplicate functionality

1.26. Not sure how to send emails from different accounts within their email applciation

1.26.1. Solution: show them how to do this, bonus: Postbox domain fencing

1.27. Having a bunch of email accounts you need to monitor

1.27.1. Solution: Unified inbox


2.1. Feeling like I should be achieving Inbox Zero every day when I’m not

2.1.1. Solution: Understanding the value and urgency of certain emails

2.2. Checking too many times throughout the day

2.2.1. Solution: Trust your system

2.3. Has all the tools, but is worried about missing things

2.3.1. Solution: Fix the holes in the system so it can be trusted (message URLs in Dispatch/Apple Mail)

2.4. Worried about missing important information from checking so many accounts

2.4.1. Solution: Tighten up system, get rid of account for junk, make it simpler

2.5. Uncertain whether things are important

2.5.1. Solution: Show him how to determine whether something is important or not

2.6. Keeps checking email when she knows she shouldn’t

2.6.1. Solution: Assemble the tools she already has into an air-tight system she can trust

2.7. Like receiving email (finding “goodies” I can apply)

2.7.1. Solution: Be more selective about things you subscribe to

2.8. Scanning the inbox looking for things that are “urgent”

2.8.1. Solution: Accept that you will not get to some things immediately and that’s ok

2.9. Can't resist looking at new emails that are coming in

2.9.1. Solution: Turn off notifications, "Compose-Only" view (email on iPad?), type them in a separate app (i.e. Evernote)

2.10. Feeling resistance with archiving emails

2.10.1. Solution: Have a system you can actually trust so that you do't feel hesitation putting into your system

2.11. Worried about missing out on online flash deals

2.11.1. Solution: Be ok with not spending money :)

2.12. Scared to hit delete

2.12.1. Solution: Provide a checklist people can use to evaluate whether they really need to keep this email or if it's ok to get rid of

3. Too much email

3.1. Having trouble unsubscribing

3.1.1. Solution: Inbox training, mark as spam, filtering (, SaneBlackHole)

3.2. Being distracted by other messages in the inbox

3.2.1. Solution: Move messages out of the inbox ASAP and into the appropriate containers

3.3. Too many emails from social media (Facebook)

3.3.1. Solution: Customize notifications for social media accounts (

3.4. Wishes there was a better system for sorting Facebook group and Google group notifications

3.4.1. Solution: Customize notifications for social media accounts (

3.5. Having trouble even starting to check email because it’s overwhelming

3.5.1. Solution: Just start, use a timer, solar flaring

3.6. Dealing with too many newsletters, doesn’t want to read them in the email app

3.6.1. Solution: Forward to a Read-it-Later service (Instapaper, Pocket)

3.7. Getting lots of email during specific busy times (April) because of academic schedule

3.7.1. Solution: Pedal before the hill (Clear to Neutral) so you can handle the influx

3.8. Multiple sources (i.e. Team communication and Customer Support) funneling to the same inbox, resulting in a huge amount of email

3.8.1. Solution: Have specific buckets for each of these, recommend other tools more efficient for that purpose (i.e. Help Scout & HipChat)

3.9. Number of emails I get daily is increasing over time

3.9.1. Solution: do an email “checkup” and evaluate what you want to stay subscribed to

3.10. Receiving a lot of emails every day that are unactionable (information flow)

3.10.1. Solution: Convince your team to use more effective tools for information archival and project management

3.11. Having to deal with customer support tickets via email

3.11.1. Solution: Use a different system like HelpScout

4. Dealing with other people

4.1. Not getting enough information leads to a lot of back and forth

4.1.1. Solution: Training people how to write effective emails

4.2. People outside of his organization are very slow to respond

4.2.1. Solution: Setting clear expectations (& consequences) when writing emails outside his team

4.2.2. Solution: Find the right communication medium for those people he works with

4.3. CC’d on every calendar invite

4.3.1. Solution: Teach people to use a scheduler instead of email

4.4. Immediate response expectations in the organization (feeling “on call”)

4.4.1. Solution: Setting realistic expectations

4.5. Notification interruptions from having to constantly monitor

4.5.1. Solution: Communicating the lost value to the organization by having to constantly monitor

4.6. Having trouble saying no to requests

4.6.1. Solution: Realize you can’t please everyone and use scripts/templates to say no nicely

4.7. Getting spam from others/clients

4.7.1. Solution: Spam filtering (Sanebox)

4.8. Getting emails at multiple addresses without any clear instructions/next steps

4.8.1. Solution: Communicate frustrations and propose solution

4.9. Feeling like you have to say “yes” when people ask you to do something via email

4.9.1. Solution: Learn to say “no”, wait a set time period before responding

4.10. Having to send the same responses over and over

4.10.1. Solution: TextExpander, Canned Responses (Gmail)

4.11. Having to respond to VIPs quickly

4.11.1. Solution: Set up VIP filters (Apple Mail, Airmail)

4.12. Scared of the response when telling people you’re unavailable for certain periods via email

4.12.1. Solution: Decide who you’d rather let down - other people, or your future self - and be ok with your decision re: boundaries

4.13. Dealing with emails people send that don’t have next steps defined

4.13.1. Solution: Explain a better way (show them the right way to do email) and explain how that will help you help them faster

4.14. Having to monitor at multiple times because of dealing with people in different time zones

4.14.1. Solution: Embrace every day approach and pick a time where it overlaps time zones

4.15. Being interrupted by employees sending email to thing that they should be able to deal with

4.15.1. Solution: Implementing effective training systems, FAQs in email (TE)

4.16. Working with people outside your organization who break your system

4.16.1. Solution: Hold the line with people/clients who won’t work the way you work

4.17. Having higher-ups who expect immediate responses and not having time to do important work

4.17.1. Solution: Coming to an agreement with higher-ups on what biggest value to the organization is and carving out time to do that

4.18. Knowing email isn't the best tool for the job but being required to use at a corporate level (i.e. Outlook for tasks/calendars)

4.18.1. Solution: Work with the tools you have and develop the most airtight system you can

4.19. Team-based ineffective communication ("Big 3: Face-to-face, phone calls, email")

4.19.1. Solution: Recognize that there are communications that need to take place outside of "The Big 3" and find tools that facilitate friction-free- communication

4.20. Others not following "email etiquette" (creating a new message instead of replying so it's not part of the thread)

4.20.1. Solution: Person-based communication view? (MailMate has thread arcs, other apps have person-based views, BusyContacts pulls in email from Mac Mail database)

4.21. Can't schedule interruptions

4.21.1. Solution: Yes you can! (turn off notifications)

4.22. Miscommunication re: email expectations (i.e. wanting a response by a date but not putting the date in the email)

4.22.1. Solution: Write better emails with clear instructions and expectations when asking for something

5. Lack of Focus

5.1. Getting lost down email rabbit trail

5.1.1. Solution: Set a timer

5.2. Hard to transition back into important work after checking notifications (dings)

5.2.1. Solution: Tame your notifications (VIP-type filters)

5.3. Feeling like I have to respond to notifications (not enough willpower to ignore them)

5.3.1. Solution: Turn off notifications! (Pull, not Push)

5.4. Dealing with a lot of emails causes them to make bad decisions

5.4.1. Solution: Obtain distance and minimize number of emails

5.5. Not sure what to do when email is part of the deep work you need to do

5.5.1. Solution: Draft emails in other apps (i.e. Evernote, Drafts)

6. Common Pitfalls

6.1. Missing a day and feeling a “phobia” of looking at your email again because of how bad it will be

6.1.1. Solution: Day of pain and suffering (how to recover)

6.2. People outside your regular contacts breaking your email system

6.2.1. Solution: Be willing to tell them how you are going to work

6.3. Leavening things in your inbox so you don’t forget to do something with it (anxiety from feeling like I need to “just check”)

6.3.1. Solution: Have a good system (point to the system inside the course)

6.4. Deal with attachments all the time and need to find them easily

6.4.1. Solution: SaneAttachments (save to Dropbox) + OCR + Hazel to auto-file them where they belong

6.5. Inefficient implementation of email system on different platforms (going mobile)

6.5.1. Solution: Knowing the roles of the different devices (i.e. using mobile for triage)

6.6. Using email as a to-do list

6.6.1. Solution: Get things you need to do out of email as quickly as possible because email has a negative mindset (inefficient way to do things)

6.7. Receiving a lot of unactionable emails (information flow) that add up to several hundred messages a day

6.7.1. Solution: Get your team to use other tools for information flow and project management

6.8. Overcoming a corporate email culture

6.8.1. Solution: quantify the problem, "motivate the elephant" (idea from "Switch")

6.9. Being required to use a PC at work / managing email from multiple platforms

6.9.1. Solution: Develop a system that incorporates cloud-based tools so you can keep tabs from anywhere (Asana, ToDoist, Evernote, etc.)

6.10. Can't manage information flow well so it takes awhile to respond to emails

6.10.1. Solution: Have an air-tight reference system so you can instantly find whatever you need

6.11. People lacking "email etiquette" because there's no standard (people don't "learn" how to do email in a class)

6.11.1. Solution: "Email 101" class like tripwire?

6.12. Having to use Outlook against your will

6.12.1. Solution: "Maximizing Outlook" type master class (give best practices assuming this IS their system)

6.13. Not having enough self-discipline to turn off notifications

6.13.1. Solution: "Motivate the elephant" to turn off notifications

6.14. Being stuck in a Windows environment

6.14.1. Solution: Show how to implement Touch it Once, GTD, etc. using all Windows-based tools

6.15. Resigned to the fact that Inbox Zero is not possible for them

6.15.1. Solution: Show them that it is and they can reclaim their sanity

6.16. End up deleting a ton of messages (but these add to the feeling of overwhelm)

6.16.1. Solution: Make sure these emails you don't want to see don't get there in the first place