Blog Post

Why are bad email habits so hard to break?

I love the idea of making email suck less.

As a reporter, email is one of the most important tools of my job: for communicating with sources, my editors and colleagues, companies I cover, receiving news tips, and more. Admittedly, my current email work flow is pretty awful. And I know I should get better about managing my email, especially on my phone, where I check it roughly 500 times a day. Still, I can’t get myself to let go of my bad habits.

It’s weird too: when it comes to mobile mail, today is one of the best times in recent memory to find a better solution. My Twitter feed has been filled with glowing reviews from many people who’ve tried Mailbox. And I love Taskbox’s motto: “make [email] something people don’t dread and people feel in control of.” So I gave Mailbox a go. The experiment lasted less than a week (it still tells me I have 22,200 unread emails). I also gave Taskbox a try for at least two weeks for my work email only (current unread email count a slightly less intimidating 722). Both seem like great products, but I realized I don’t have the patience to get into either of them. I don’t think it’s anything to do with those apps themselves — which plenty of people seem to love — but about the idea of change to a routine that is so critical to modern work — and life.
Mailbox email

My inability to stomach change is even more ridiculous because of how awful my current email work flow is both on my desktop and my iPhone. I use Gmail’s color-coded labels, which is plenty useful. But if I get an important email that I know requires my response but not immediately, I “star” it and mark it as unread.

It was Andrew Eye, CEO of Taskbox, who jokingly pointed out to me how broken email is: if “the only way to stay organized in email is to lie to yourself” that you haven’t read something when you actually have.

He’s right! But still — the idea of learning a new system of email, whether it’s by prioritizing items or “snoozing” them kind of freaks me out. I can’t miss an important email or misplace one even temporarily put it in a folder where I’m not immediately sure how to find it.

And, no, I’m not completely averse to change when it comes to my digital life. I don’t participate in the massive freakout when Facebook (s fb) makes one of its inevitable design changes. I was plenty adventurous about trying out several new calendaring apps; getting deadlines right is also critical to my job, but I was able to successfully switch over to Sunrise from my iPhone’s basic calendar app.

But totally altering my mobile email routine seems like rebuilding the plane in mid-flight: there is never a good time for change.

I don’t think I’m alone either. Email is something people are super sensitive to altering. Even Google had a rough time rolling out too many changes at once: at one point even the labels feature was too much for non-power users to adopt.

Labels are standard now for a lot of email users, including me. And that gives me hope that some day I’ll find a service that’s able to drag me along to better email habits. But for the foreseeable future, I’ll be at inbox 22,000.

12 Responses to “Why are bad email habits so hard to break?”

  1. Alan Ralph

    For me, the biggest inbox-killers are social media notifications, followed by over-eager newsletters. (Looking at you, GigaOM, by the way – yours only has a few stories from today plus all the ones from yesterday).

    I now have most email notifications turned off for Facebook, Twitter, LinkedIn, etc. except for direct messages. And the majority of the newsletters I receive are now weekly rather than daily. Then I filter social media messages and newsletters into two folders, and drop receipts into a third.

    The big problem I have with current email systems is that they aren’t that much more intelligent than the one we had 20+ years ago. Yes, you can create rules to filter particular emails, and spam detection is pretty good now, but they stiil require training and feeding of information to do their job effectively. I recall when came out there was talk about improved organising abilities, but I’ve not heard any more about that – it’s something that I think should be developed a lot more. It shouldn’t be that hard for your inbox to see what’s a receipt, what’s a newsletter, what’s a mailing list, etc. and file them accordingly, as well as spot physical addresses, RSVP dates and similar useful information.

  2. Michael

    I remember a phrase from my grandfather…”a poor workman always blames his tools”…todays email clients are all excellent it is the user that needs to be updated ;)

    I routinely receive 100+ emails a day 6 days a week, some requiring immediate response some not. At the end of every day though I will have less than 10 emails in my Inbox. How do I do this without spending all day on email? Try these straightforward steps that I have borrowed from others over the years:
    1. UNSUBSCRIBE to any emails you can’t read in 30 seconds or don’t read daily
    2. DO NOT RESPOND to emails unless the sender is directly looking for a response from you (don’t even say THANK YOU)
    If you choose to look at an email, you MUST action it, so either DO IT, by replying with required information, DELEGATE IT by forwarding it to someone who can reply with proper information and then let the SENDER know you have delegated the responsibility, finally DELETE IT immediately so it does not clog up your Inbox.

    Remember to think of your Inbox like a highway, it works best when there is a flow of traffic. Parking an email in your Inbox as a reminder to do something, is like pulling over on the highway and stopping…even if you are on the soft shoulder, the traffic will begin to slow and back up and the traffic jam is imminent, along with some frayed nerves.

    Good luck


    • Alan Ralph

      Hi Greg,

      Your 3 rules definitely make sense to me. I know many instances where people have sent emails to me with incomplete or blank subject lines or haven’t trimmed their message if it a response to one I sent them. I have to admit, I’ve fallen into that trap myself a few times. The only probably I see if your 3rd suggestion is that in-line replies seem to have gone out of fashion – most email clients expect you to respond at the top of the message, and make it difficult or impossible to reply in-line. Of course, I’ve been around long enough to remember when email software wasn’t nearly as fussy, and in-line replies were the norm…

  3. Martin Focazio

    My work and personal email are so completely different.

    My personal email is 97% email from machines – reminders, receipts, offers and announcements. Very few human beings send me a message requiring a response, and so it’s really easy to ignore most of the mail – select all, mark as read, done.

    My work email is 40% machines telling me about things to do, places to go and stuff like that, 40% people covering their ass with FYI messages, 10% “news I can Use” and 10% stuff that needs to get my attention.

    I think what I’m getting at is that the bulk of my human-to-human messaging has moved to Skype instant messaging, text messaging and Facebook – by ignoring email long enough, it’s gone away. My kids don’t use email at all, except to communicate with teachers.

  4. Bart Jellema | [email protected] | LION

    Hi Erica,

    From doing research into this for the last 2.5 years, I’d say it’s not so much an unwillingness to change habits, but that many of the new tools are just not better enough. Email habits are strong and new products that make email 10% – 20% better will find it hard to retain users. A new email solution needs to have a ‘can’t live without’ feature to make it stick.

    Anyway, we can help you deal with those 22,000 easily at ZeroMail ( Ping me for a trial account.

    [email protected]

    • Alan Ralph

      I tried out SaneBox, and it is certainly good at organising your mail for you, but I ended up cancelling the trial run because I couldn’t justify the financial cost of using it full-time.

      One thing that I noticed with SaneBox – and it’s the same with GMail’s filters system and similar systems for other email providers – is that you can end up with a bajillion rules or filters depending on the number of networks, newsletters, blogs and sites you sign up to. Trying to amend or prune down that list is quite a task in itself? We need such filter- and rule-based systems to be more intelligent – for instance, able to determine purchase receipts or social network messages from personal messages and news letters, or able to prune out redundant rules in response to an unsubscribe message.

  5. My main complaints about email are 1) some people seem to think it requires an immediate reply, 2) some people reply to a group when the email would be better as a personal reply, 3) others use an email that has been about a particular topic to inject something off-topic, and 4) important email from someone already in my contacts is put in my trash (thank you, Yahoo, although the Russian and Romanian spam is put in its place most of the time).

  6. matthew holt

    If youu se gmait priority inbox. You can keep 30-50 emails on one page that have a to do attached. Then use the getting things done rule. Reply in 2 mins using “send & schive” or leave it for a time you can deal with it. I have year old emails at the bottom of my list I will get to eventually, and 2 week old non urgent tasks half way down.

    All my emails and 98% of todos are on my list whenever I login, and I manage it and get most of my work done.

    If you get more emails than you can hand AFTER using this system, you need to hire someone!

  7. Johnson

    Systems like InboxZero and Getting Things Done are worth looking at if you’re stuck as to how to manage your email and you find general task/reminder management is getting out of hand.