It’s a blessing on your best days and a curse on your worst, but it’s impossible to argue with the fact that email has revolutionized the way we work. Used equally for improving sales, coordinating teams, and maintaining networks of contacts, it’s hard to imagine where we’d be without it.

But at the same time, it drives us bonkers.

Personally, I think email is by far the most efficient communication medium we have available to us, and I prefer it to phone calls for work communication. But even I have some days where I want to punch a hole through my computer monitor.

So what is it, exactly, that drives us nuts about email? In this article, I seek to explore some of our most shared—and most agonizing—annoyances with the platform, and hopefully, provide a few remedies. At best, you’ll find a brand-new strategy you can use to mitigate your daily grievances, and at worst, you’ll have someone to commiserate with.

1. Trying to find that one email you swear you saw when you didn’t need it.

I’m just going to spitball a few potential examples here. A client sent you formal approval to go ahead with a project last week, but now you can’t find record of it. You got a PDF of concert tickets for a show that’s coming up tomorrow, but you aren’t sure which account it was connected to, or when it came in. Your boss gave you three pieces of feedback a few months ago via email, but now you can only remember two of them, and you’re paranoid you’re screwing up that third one.

It’s a problem because if you’re thinking about it, you’re in need of it. And if you don’t know how or where to find it, you’re probably missing out on something important. It’s especially frustrating when you can picture the email in your head—a tantalizing reminder that you could find what you’re looking for, if only you could remember one key detail, like when it was sent or what the subject line was.

Are We Doomed?

Okay, so there are a couple of approaches that can bail you out of this one—a proactive approach and a reactive approach.

Proactively, you can avoid this kind of scenario by employing a detailed, thorough, and consistent system of organization. Gmail makes this easy with its system of stars, labels, and categories, but you need to acquaint yourself with this system before you start using it. In the Settings menu, you can turn on the option to have different colored stars and labels, which you can use to mark up certain types of emails (such as those with attachments or important information) with intent. Later, it will make sorting for those emails much faster.

Gmail Star Markers

But let’s face it. If you’re already stuck between a rock and a hard place, those stars and labels aren’t going to save you. But before you give up hope, you should realize how robust Gmail’s search feature really is; click the arrow on the right side of the search bar to open up the advanced search box, and you can filter emails based on variables like the sender, the recipient, the subject, the size, the date range, and even specific words that are or aren’t present in the email. Even if your memory is fuzzy, it should narrow the list down to a few dozen candidates.

2. Waiting for a reply to that risky email.

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Nothing makes you sweat at a keyboard quite like sending a risky email and anticipating a potentially devastating reply. There are several potential conditions here. For example, you might be making a bold request, such as asking for an extra week off of work during an especially busy period. Or you might have written something at a peak emotional state, only to question the wisdom of that decision moments after you hit send, such as telling off a coworker or disclosing romantic feelings you probably should have kept to yourself.

It’s nail-biting, to be sure. There’s no telling if or when a recipient has gotten your email, and what’s going through their mind once they’ve seen it. Are they contemplating a way to fire you? Are they laughing at you with their peers? You can click refresh all you want; it’s not going to make that email come any faster.

Are We Doomed?

A good first step here is to keep your emotions in check. If you’re feeling angry or frustrated, give yourself a few hours (at least) before you draft a reply. If you have a heavy conversation to bring up, try to do it in person, or at the very least over the phone or in a context where you can guarantee a fast reply.

You can also use a third-party app like Boomerang to employ read receipts, so you can know when your email goes through (and if and when it was read by your recipient). The advantage here is that you can quell your anxiety if the email hasn’t yet been opened. The disadvantage is that once it’s read, your anxiety will spike until you get that reply. You may also be able to use EmailAnalytics to gauge your recipient’s response patterns, and predict when they might send a reply.

Part of this problem stems from our habituation to watching our email constantly for updates. We expect a fast reply, and know it will come through the instant it’s sent, so we can’t help but keep watching for that reply. Conditioning yourself to check email only during certain windows of time can mitigate this effect.

Otherwise, your options are limited. You can pick up the phone and call your email recipient to get a slightly-faster response, or you can find something to do to distract yourself until that email finally comes through.

3. Reading through paragraphs of unnecessary text.


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We all have that one coworker who somehow finds a way to write, in five paragraphs of text, what could have been said in the span of a single sentence. You’re no master of eloquence, but you know when a message could be truncated easily without sacrificing its meaning.

This is problematic because it takes far more time to parse the meaning of the message—both because there are more sentences to read through and because the baseline message can be obfuscated. On top of that, these unnecessarily lengthy messages often lead to misunderstandings, which can compromise the quality of your work. It gets even more complicated when you realize this message was sent to multiple people, as each new recipient multiplies the problems involved.

Ugh.

Are We Doomed?

If you’re an employer or a supervisor, you have some control over the long-term direction of the situation. You can use an analytics platform like EmailAnalytics to measure exactly how long each of your employees’ emails are, and use that data to start a conversation about the appropriateness of email lengths. A quick exchange here will likely be enough to guide the employee in question toward more concise emails.

If the power dynamic is reversed, you may have trouble broaching the subject—but you still have a few options. One helpful method is to reduce the email yourself, wading through the text and producing your own, concise summary, presenting it as a request for confirmation that your understanding is correct. If the email is sent to multiple people, it should reduce the cumulative reading time necessary to understand the email. And if you repeat this process enough, eventually your long-winded recipient will start to see the ways they can communicate more concisely.

As a short-term fix, your options are limited. You could adopt speed reading methods to cut the time necessary to get through the text, or use a text-to-speech app to read it out loud for you. No matter what, you’ll need some way to extract the meaning from the message.

4. Not understanding what this email is about at all.

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Have you ever had an email so devoid of semantic normalcy that you had to verify whether or not you’d just experienced a stroke? I’ve had one or two I could have sworn were written in hieroglyphics. There might be a one-word subject line like “Status?” or no subject line at all, and the body of the text makes you wonder what project this was intended to reference.

Now, we all make typos from time to time, or get in a rush and write an email that doesn’t make sense. Typically, these problems are quickly resolved with a follow-up email that contains a sensible correction or a simple request for elaboration from the recipient (you).

The bigger problem is when someone has a tendency to send these zero-value emails on a regular basis. What are you supposed to do with this?

Are We Doomed?

The straightforward, non-confrontational route is to simply ask for clarification whenever a senseless email like this comes up. Most people are pretty accommodating, even if they’re temporarily annoyed at having to spend more time thinking through their sentences in a follow-up. You can make this process even smoother by simplifying things with your correspondent; instead of asking for a general elaboration, you can ask pointed questions, like, “Is this about the pizza I left in the break room overnight?” or “By ‘conquistador,’ are you referring to our latest client?”

If you continue to get nonsensical email responses, it’s a sign there’s something wrong with the other party. If English is their second language, or if they’re sleep deprived to the point of delirium, chances are all their emails are being met with a similar level of confusion. At this point, it’s in both your best interests for you to express your concerns. You may not be able to solve the problem, but hopefully, you’ll draw their attention to it.

5. Playing Russian Roulette with a no-subject email.

If you’re like me, you experience a small wave of terror whenever you get an email with no subject line. Is someone inviting you to lunch casually, thinking there’s no need for a subject line for something so trivial? Or is someone in full-blown panic mode, with no time to think up a subject line, let alone type one?

The “no subject line” problem is a doozy because it’s bad form on every level. It’s unprofessional, it fills you with uncertainty, it demands your immediate attention (since you don’t know whether it’s an emergency or not), and it makes it much harder to find and/or sort through in the future, since you won’t have ready access to a quick summary of the email’s contents.

Are We Doomed?

Nope! You may not be able to immediately cancel out the stress or frustration you experience when a new email with no subject line wanders into your inbox, but you can make some changes to improve your position.

First, if the no-subject email line has started a conversation, you can edit the subject line for your own convenience. When you open a reply window, click on the dropdown menu in the upper-left corner of the window and click “Edit subject” to change the subject line.

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Second, you can enable the Preview Pane, giving you the chance to glimpse much of the body of the message from the high-level inbox view. To turn this feature on, head to Settings, then click on the Advanced tab. There, you can click Enable on Preview Pane, and start using the feature.

Of course, I also recommend being upfront and honest with your coworkers about your subject line preferences. Leaving a subject line blank is considered a breach of etiquette in most work places, so you might be doing them a favor by bringing their attention to the habit.

6. Deciding to delete that annoying newsletter rather than go through the hassle of unsubscribing.

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Are we masochists? Every time we get a new email from that online store we haven’t visited in years or that newsletter that never has any useful information, we immediately click delete as a conditioned response. It takes us a few seconds, and deep down, we know we’ll be spending another few seconds in a day or two when the next useless email comes in.

Thanks to the CAN-SPAM Act, you can pretty much guarantee the possibility to unsubscribe from any of these email newsletters and promotions. Most of the time, it only takes a click or two. So why is it so hard for us to make the commitment to spend a few extra seconds getting rid of the incoming email for good?

Are We Doomed?

There are a few root causes of this problem. First, status quo bias makes us underestimate the potential value of cleaning up our email subscriptions. Second, our tendency to seek instant gratification makes us prefer the shorter method of cleanup—i.e., an immediate, singular deletion rather than a full-on un-subscription (even if it’s only shorter by a few seconds). Third, and more rarely, we hesitate to unsubscribe because we think someday, maybe, we might want to get this type of email in the future.

I can’t help you with number three, but there are a couple of things you can do to stop this time loop from continuing. First, try to stop subscribing to stuff you don’t need. This is sometimes unavoidable if you buy something from a new online store or if you want to download a whitepaper, but try to avoid it where you can. You can also use Unroll.me, a free service that helps you clear out all your cluttering subscriptions in one fell swoop.

For most of us, it’s easier to take a few minutes and clear out all those subscriptions at once than it is to do it a minute at a time as we receive new emails. Finally, if you want to see how you’re doing, use EmailAnalytics to gauge how much time you’re spending on unnecessary emails—and pinpoint your most problematic sources.

7. Getting CC’d on things you shouldn’t be CC’d on.

Why did they include you on this? I wish I had an answer. All it takes is one ill-timed or poorly thought-out inclusion on an email chain to suck you into an inescapable whirlpool of messages that have no relevance to you or your position. There are many dimensions to this problem; you’ll get new notifications every time someone replies-all to the thread (and they’re almost always replies-all), you’ll need to look over the new messages just in case something’s relevant to you, and you don’t have much recourse to exclude yourself from the conversation.

This is typically a problem because thanks to easily expandable email addresses in the CC field, it only takes a button click to add a new recipient to the email chain. It takes a second for the email sender, but takes minutes to hours of time for the unlucky irrelevant recipients.

Are We Doomed?

If you feel confident you have no reason to be on an email thread, or continue getting notifications from it, you can always use the Mute option. Click the vertical ellipses on the conversation of your choice, and click Mute. From that point on, you won’t get any notifications from emails on this chain.

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If you find yourself constantly CC’d on threads where you don’t belong, it’s likely due to one of two scenarios: either there’s role confusion about what your responsibilities are, or there’s a culture in your workplace that involves CCing as many people as possible, for the sake of transparency or openly available information.

If the situation is the former, ask your supervisor to clarify any confusion about your role and responsibilities. It’s okay to cite these unnecessary points of inclusion as the impetus for your question; in most cases, you’ll either resolve the confusion or the needless CC inclusions will stop. If the situation is the latter, you’ll have your work cut out for you. Changing a workplace-wide habit is nearly impossible unless people at both the highest and lowest levels work together to accomplish the transition. In other words, get other people on your side before you start fighting for a culture change.

8. Navigating an epic thread you never wanted.

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It’s hard to tell what, exactly, will turn into an epic thread. Sometimes, you send off a few paragraphs of instructions only to get back a “Got it, thanks.” Other times, you send a simple yes-or-no question, and before you know it, you’re swimming in a dozen back-and-forth emails, possibly all on topic but more likely meandering between a handful of tangentially related subjects.

This is problematic because it’s distracting, and hard to sort through. When new emails are added to the chain, you may have to read through all the old responses to get enough context to make sense of it. And later, if you’re looking for important information in the thread, it’s a pain to sift through each individual email to find what you’re looking for.

Why does this happen? In most cases, it’s due to people not realizing the importance of keeping email threads light and on-topic. They get an email from you, are reminded of something else they need to ask you, and instead of opening a new thread, decide to ask you here and now. Repeat that a few times, and suddenly the thread has grown out of control. This can also happen when you have too many recipients in the CC line and they keep using Reply All.

Are We Doomed?

There’s no catch-all solution to this problem, but there are some strategies to help you with the individual consequences. For example, if your main beef is not being able to easily find the information you’re looking for, take advantage of Gmail’s robust search feature. Remember, Google made this—as you should rightly expect, the search tool is amazing.

If you get the sense that the email chain is going to continue indefinitely, you need to make the first move. Take it upon yourself to start a new thread, with a new subject line. And, if necessary, include all the background information from the previous thread so it’s easier for you both to find. You can even explain it as a move to keep things organized. Of course, if you want to take care of the problem immediately and resolve the conversation, you can always pick up the phone and call your correspondent.

If you want to get a clear picture of how email threads are affecting your work habits, the best tool to use is EmailAnalytics. With it, you can see who’s starting threads, how long your threads usually last, and even how much time they’re taking you. It can’t fix the problem directly, but it can give you all the information you need to fix it yourself.

9. Dealing with an ambiguous “see below.”

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At the risk of stereotyping, people in upper management and those in positions with non-email-centric responsibilities tend to think email is beneath them. They don’t put much time or effort into their messages, instead letting the conversation play out on the shoulders of other people.

For example, instead of posing a question or problem to you, they might copy and paste what they received from a client, or from another member of your team, with the phrase “see below,” or if they’re feeling particularly obliged in giving you direction, “Thoughts?” Sometimes, you might even get the utterly ambiguous “FYI.”

The Atlantic once delved into the psychology of this phenomenon, and it’s worth a full read if you’re particularly aggravated by it. They refer to this as the “corporate email forward,” and describe the core psychology behind its motives. I love it, so I’ll include it rather than putting my own spin on it: “Why? Ultimately, the power of the corporate email forward comes from the fact that its contents go unprocessed. Rather than make direct requests, we obfuscate. We prevaricate. As with driving, the best way to work today is defensively: Insure you can never be put in a position where your words, deeds, or ideas can be traced back and used against you.”

In other words, the onus is on you to not only read the message that was sent to you, but figure out what your forwarder meant when they included that short, ambiguous message.

Are We Doomed?

Occasionally, you may find an email like this with crystal clear intent. For example, you might have engaged in a discussion with your boss about how you wanted to learn more about SEO, and they forwarded you an invitation to an SEO webinar with “FYI.” Clearly, they wanted you to be aware of the opportunity if your motives still stood.

But in the vast majority of cases, this is an unhealthy and counterproductive way to email. There are two potential resolution points, one of which is squarely in your control. You can always attempt to resolve the ambiguity of the phrase by calling for more explanation. If your boss emails you “see below,” email back, “how would you like me to handle this?” or “what is my action item here?” It’s entirely reasonable to ask for clear direction.

Of course, that doesn’t resolve the problem of reading unnecessary email forwards and spending time trying to hash out their meaning, which can take up too much of your time. Resolving this would require a behavioral pattern change (i.e., convincing your correspondent to start including more descriptive text or, ideally, stop ambiguously forwarding emails in the first place). As this person is often your boss, you may not have much power over this—but you’d be completely justified in a request for “more direction” in the emails you receive.

10. Getting roped into a meeting invite.

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Today’s meeting invites are almost exclusively done via email, which has been both a blessing and a curse for anyone trying to save time. No matter what email system you use, there’s probably a built-in calendar and meeting tool. That means you can create a new meeting event with the click of a button (and possibly even see your attendees’ schedules so you can find the right time slot). It also means you can add other attendees with the click of a button, and you might even get a list of recommendations to add to the party. Oh no.

Meetings aren’t inherently bad, but in general, they tend to be a waste of time. And the more people attend them, the more that waste grows; for example, a 1-hour meeting with 3 people would cost 3 hours, but a 1-hour meeting with 10 people would cost 10 hours. Not only that, but the more people you add, the more complex the conversation will become and the more likely it will be that the meeting will waste time. Getting a new meeting invite pulls you away from work for some duration of time, and, if you don’t belong in the meeting, is a sign that the meeting planner doesn’t really know what they’re doing.

I’m exhausted just writing about it.

Are We Doomed?

On a small scale, this isn’t a big deal. It takes one click to verify your attendance, and then you just have to suck it up and get through the meeting, right? But on a chronic level, this can get tiresome and chip away at your productivity.

You can start fighting back by hosting better meetings. If and when you create new meetings, only include the people that truly need to be there, and consider whether the meeting could be substituted with an email update.

For meetings outside your control, send an email to the meeting organizer and ask to see a copy of the meeting agenda. If the meeting agenda doesn’t seem relevant to you, explain yourself, and attempt to excuse yourself from the meeting. If there is no meeting agenda, it’s a sign that the meeting isn’t being adeptly organized. Depending on your rank in the power hierarchy, you may be able to excuse yourself from the meeting based on this lack of organization.

The best long-term fix is to address the problem of meeting culture with your boss—and/or someone as far up the ladder as you can find. Explain why and how meetings waste time, and recommend alternatives, such as shorter meetings with fewer people, and email-centric updates for all matters that don’t require active conversations or contributions.

11. Trying to manage an ongoing conversation.

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I’ll admit that email is a flexible medium, but there are some forms of communication for which it’s ill-suited. It’s primarily intended as a form of thoughtful, written exchange, so people can relay instructions, confirm details, or send and receive attachments.

When that exchange becomes lighter, faster, and less thoughtful, problems begin to emerge. Your coworker might ask you rapid-fire questions about a project, or jump from topic to topic, all within a short span of time. Your email chain has become a full-on conversation, and it’s a total misuse of the medium.

Are We Doomed?

Conversations aren’t bad; they’re necessary, and oftentimes productive. The problem is trying to maintain a conversation in an email format, which requires more time and is an easy system to clutter with unimportant lines of exchange.

Thankfully, you have several options to resolve this. The first and most obvious is to shift the conversation to an appropriate medium. Depending on your work culture and the resources available to you, that might mean starting up an instant message session (which, if you’re using Gmail, is a built-in option) or picking up the phone for a quick call.

You could also use a more passive approach; if the conversation has been a rapid exchange between you and your correspondent, you could avoid responding immediately, and let their last question simmer until after 5 pm, or otherwise outside the hours in which they’d normally respond. This break in momentum may be enough to bring the conversation to a halt, and restore law and order to the email medium.

12. Finding a way to organize your inbox–and sticking to it.

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Do you have those friends who, every January 1st, claim that this will be the year they get fit? They get a gym membership, they buy all-new workout clothes, they brag about cutting junk food out of their diet, but by March, they’re calling the gym to cancel. And to their credit, it’s incredibly hard to change a habit when that habit is easy to maintain. It’s way easier to eat junk food and never exercise than it is to track what you’re eating and work out every day.

But just because it’s easy doesn’t mean it’s good for you. With email, the easiest thing to do is let your emails roll in, one after another, and take care of them if and when you see fit, with no method of organization. But if you want to find your emails easily, keep tabs on what you have and haven’t addressed, and operate more productively overall, you’ll need some way to organize your inbox—and then muster the will to stick to it.

Are We Doomed?

There are two mini-problems to deal with here. The first is finding a system of organization that works for you. Fortunately, Gmail offers tons of features and options you can use to stay organized, so there’s no real excuse for not finding something that works for you on an individual level. You can start by toggling on different tabs, which automatically filter out emails like promotions and social notifications into their own respective categories. From there, you can use labels to systematically categorize all your incoming emails. Or you can use Gmail’s custom stars and markers to designate emails however you want—for example, maybe urgent emails are red, while low-priority incomplete ones are green. With Gmail, you can create a system all your own, customized for all your needs, preferences, and habits.

The second is creating a new habit for organization, and making that habit stick. It doesn’t matter if your system is perfect when you aren’t using your system on a consistent basis—and it’s easy to get pulled away from your system after you start getting used to it. A single flood of emails might disrupt your momentum, or you might find it not working for a specific chain of emails, so you abandon it altogether. Unfortunately, I don’t have a quick fix for this one. You’ll need significant willpower and discipline to make any habit stick for the long haul.

The best piece of advice I can offer is to implement your new system immediately and consistently; in your first week of execution, don’t let a single email get by unmarked or unsorted. After a few weeks, you’ll be so used to doing it, you won’t have to think about it anymore. From there, you can use EmailAnalytics to gauge your email habits, and determine whether your new strategies and tactics are improving your productivity overall.

13. Getting an URGENT email that’s (spoiler alert) not urgent.

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Yet another reason I’m glad to be a Gmail user is the fact that there’s no easy way to mark a message as “high priority” as a sender. In Outlook, senders have the ability to mark emails with a blue arrow, indicating it as low-priority, or a red exclamation point, indicating it as high-priority or urgent. But let’s face it, most people abuse this system. They send normal emails when the message is low-priority, and urgent emails for anything normal priority or above. The blue arrow is almost never used.

Of course, Gmail users committed to marking their emails as more important than everyone else’s still have a few techniques they can use, such as incorporating attention-grabbing symbols (*****) or using URGENT as the first word of the subject line.

This seems innocent enough, but it comes with a few major problems. The first is the spike in blood pressure you probably get whenever you see a red exclamation point or URGENT email subject come through. While there may be some situations that truly warrant this emergency-level reaction, for the most part, it’s just bad for you.

The second problem is the “cry wolf” scenario. You get so many “urgent” emails from people that don’t have any immediate relevance, so you start to filter them out as white noise. They stop mattering, and eventually, you ignore them or at least treat them as a normal-priority email. Then, when truly urgent emails do come through, you won’t treat them with the urgency they demand.

Are We Doomed?

The first thing to do is start using Gmail if you’re using Outlook. If you’re used to all the folders and features of Outlook, there are analogous features you can use in Gmail—it just takes a few days to get used to everything. I’ve written a guide on how to switch from Outlook to Gmail here. This will prevent you from getting those red exclamation points.

As for the emails with a manually typed URGENT subject line, there isn’t much you can do. You can use a third-party extension to edit the subject lines in your inbox, but that only works after the initial email comes in. Thankfully, these are rarer (and tend to be more accurately urgent) than the red-exclamation-point emails in Outlook. You can also have a conversation with your worst offenders about how unwarranted urgent markings can diminish the power of truly urgent emails.

14. The late-night or vacation email.

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It’s 10:30 pm on a Friday and your phone buzzes. You have a new email. If you’re like most of us, you get a feeling in the pit of your stomach. Is this just some dumb newsletter you got on the mailing list for? Or is this your boss chewing you out for something you forgot to do before you left today? Your curiosity gets the better of you, so you take time out of your personal life to check your email, and possibly tumble into a rabbit hole of work-related communications.

This tends to happen on vacation, too, even if you feel protected by the blanket statement you wrote in your automated vacation response. And you know what? It sucks. It allows work to creep into the pores of your personal life, making your hours of freedom far more stressful without even boosting your productivity.

Are We Doomed?

Your fix to this problem may depend on the culture in which you work. If you’re working for a hyper-aggressive company that puts competitive pressure on its employees, or if you’re in a field that demands fast response times, you really might be doomed on this one.

But chances are, your coworkers and bosses will understand when you don’t respond to a Saturday email, or an email that hits on your second day of paid vacation. If you want to resist the urge to check your email, start by turning off notifications. On all your devices. In fact, if you’re going on vacation, I’d recommend unlinking your accounts for a few days so you aren’t even tempted to check your email. If it truly can’t wait until the next morning, or until you’re back from your trip, they can call you or find someone else to take care of the problem.

Everyone deserves time away from work—and that means time away from email, too.

15. That annoying notification when you’re trying to work.

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You’re heads-down, working on a project that demands your concentration when you notice it. There’s a bleep from your computer, notifying you of a new email that’s just come in, or a new number on your email tab, indicating an unread message. And sure, you could ignore it—but what if it’s important?

Even if you don’t check it right away, the mere fact that a new email has come in can be distracting, and it doesn’t take much to distract us. On average, it takes us 23 minutes to fully recover our focus after getting distracted. Extrapolate that information, and you might draw the conclusion that throughout the day, your constant email notifications are preventing you from ever achieving maximum focus.

Are We Doomed?

Again, my advice here is to turn off notifications. Instead, manually check your email at set intervals, such as every hour or even every 30 minutes. You’ll still get annoyed when your alarm goes off to check your email, but it’s much better when it’s predictable and finite; unpredictable cascades of emails can throw you for a loop. You can even use a third-party app (like BatchedInbox) to “batch” your emails, withholding incoming emails until a time period you specify, then releasing them all at once.

Alternatively, you could schedule specific hours during the day, during which you’ll be available for open email, and opposing hours, during which you’ll be unavailable for communication. For example, you might work on heads-down projects from 1-3 pm, then be available for email from 3-5 pm.

16. Knowing you’ll never be fully organized.

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Inbox Zero is a white whale for professionals everywhere. Some of us have a system of folders or labels we use to categorize some of our most important emails. Some of us have a priority system attached to stars and marks, which would hypothetically help us stay on top of every email as it enters our inbox.

But for the most part, a fully organized email inbox is just wishful thinking. For some of us, the problem lies in the gap between theory and execution; we might have a foolproof way to keep our inbox organized on paper, but when it comes to following those rules and restrictions, we’re practically helpless. For others, the problem lies in the sheer volume of incoming emails. Applying the right labels and markings to an email may only take a few seconds, but when you’re dealing with hundreds of incoming emails per day (and real-world distractions on top of them), some emails are going to get left behind.

Email organization is truly a Sisyphean labor. Or is it?

Are We Doomed?

I’m going to tackle this problem in three steps, because only with all three will you be able to curtail this problem once and for all.

To start, you need a solid system of organization. Gmail, thankfully, gives you plenty of options to accomplish this. You can enable as many different colored stars, marks, and symbols as you’d like to mark your emails, and create as many labels and sublabels as you’d like to keep those emails in their proper categories. There’s practically no limitation here, so you can devise any system you’d like to stay organized.

Next, you’ll need some way to hold yourself accountable to this system. Having a good idea for how to label your emails doesn’t matter if you never actually label them. This is also a problem because it typically demands that you go through your current inbox, and label all your existing emails appropriately. For some professionals, that means wading through thousands of emails, some of which haven’t been relevant in months. Thankfully, Google makes this step a little easier with automatic rules; in the Settings menu, you can head to Filters and Blocked Addresses to set up filters designed to keep your emails organized as they come in. That should take a significant amount of pressure off you.

Finally, you’ll need to stay consistent over time. It’s very easy to lose momentum on your organizational system, hitting Inbox Zero only to climb back to hundreds, if not thousands of emails. This one all comes down to your willpower, and your commitment to keep that inbox clean.

17. Feeling pressure to check your email constantly.

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Do you ever get nervous when you realize you haven’t checked your email in a while? Or do you always work with one tab open on your email account, so you always have an eye on your incoming messages? You’re not alone.

As you might imagine as a chronic email junkie, there’s a clear correlation between the number of times you check your email over the course of a day and your stress levels. Put simply, the more you check your email, the more stressed you are, independent of other variables, such as how many emails you actually receive.

I wrote in an earlier section about the work environments that demand constant email attention, and those that might crack down on you for not checking your email often enough, but these are few and far between. Most work environments aren’t going to nail you for only checking your email a few times a day—you just put undue pressure on yourself to do it.

Are We Doomed?

Check out my tips in section 14 (“The late-night or vacation email”) if you want some tips on turning off notifications. This can help you eliminate distractions while you’re working, but the bigger problem here is your internal urge to check your email. After all, it doesn’t matter if your notifications are on or off if and when you check your email manually throughout the day.

Instead, I recommend you find a substitute activity to fill in for this habit. For example, whenever you feel the urge to check your email, take a moment to write down the five things stressing you most today, or your five highest work priorities. This will bring your attention to something work-related, but something more constructive than refreshing your inbox. If you want to be an overachiever, you could use this time to practice a few minutes of mindfulness meditation. In any case, repeating this habit instead of merely checking your email can help you resist those urges to stay informed and on top of your inbox at all times.

18. Emailing a different generation.

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I’m not here to get in the middle of a fight between baby boomers and millennials about which one is ruining or has ruined the country. But no matter how old you are, you know, intrinsically, these generations use email very differently.

To the average baby boomer, email is a secondary medium. They developed their professional skills in a world that ran on in-person meetings and, occasionally, phone conversations. Less experienced baby boomers may struggle with email altogether, and even technologically competent ones tend to avoid using email, or rush through their written content.

To the average millennial, email is a primary medium. They grew up in an age where email not only existed, but was the fastest and most efficient way to communicate. Millennials are extremely comfortable with email, to the point where they’ve grown to hate phone calls. Accordingly, their emails tend to be concise and thought-through, and they may cover topics that would be better suited with a real-time conversation.

Disclaimer: these are general trends, and certainly don’t apply to all individuals within these groups.

When one of these groups emails the other, there’s usually a disconnect. Baby boomers might not use specific enough language, or reply fast enough. Millennials might write long-winded emails, or expect boomers to be familiar with features they’ve never used before.

Are We Doomed?

As with most forms of communication, the real secret here isn’t communicating in the best way for you, but rather communicating in the best way for your correspondent. You don’t talk to your 5-year-old niece the same way you’d talk to a middle-aged man at a bar, so why would you send all your emails the same way to all your business contacts?

If you’re emailing someone you don’t know, you can play it safe with a general formula. Otherwise, cater your email to meet the skills and expectations of your recipient. A baby boomer might want a shorter message, with gaps filled in by real conversation. A millennial might prefer more specificity and elaboration.

Of course, there’s no guarantee your correspondent will return in kind. All you can do is compromise where you can and hope it’s enough to bridge the communication gap.

19. Finding the appropriate greeting and closing.

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This is a minor problem, but it’s an inconvenience I’ve struggled with on occasion. Greetings and closings should be low-tier priorities in the grand scheme of things, but they can form lasting impressions.

For example, “Dear ____,” is personal, but may sound too formal, and “To whom it may concern,” when addressed to a group of people sounds super cold. Even basic differences between “Hello,” “Hi,” and “Hey” could make a difference in how your email is perceived.

In closings, “Sincerely,” “Cheers,” and “Thanks” all have different tones and rhetoric surrounding them.

Are We Doomed?

This is a problem exclusively with new contacts, since presumably, you’ll have enough rapport with existing contacts to know what’s appropriate and what isn’t (and easily recover from a bad move). It mostly lies with the lack of visibility into the crux of the problem; you can’t ask the contact directly which greeting or closing they’d prefer, or you’ll lose face.

I don’t have a sophisticated resolution or life hack for you here. My best recommendation is to go with a neutral greeting that demonstrates your personality best; unless you do something truly bold or norm-breaking, it’s not going to affect your relationships one way or another.

20. Never knowing for sure that you haven’t embarrassed yourself.

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We’ve all sent embarrassing emails before, accidentally sending an email to the wrong recipient, then quickly following up with an admission of our screw-up. But things are way tenser when you aren’t sure about whether you’ve embarrassed yourself or not.

For example, let’s say you’ve written a long email detailing the progress your team has made on a project, but after you send it out, you realize you called a coworker by the wrong name. Did anyone notice? Or did it just get lost in the void of the body of your email?

Or what if there’s a typo in the report you just sent your boss? You could send a follow-up email explaining the typo, but if it went unnoticed, you’d be doing more harm than good.

When you send an obviously embarrassing email, you can admit to it, apologize, and start facing the consequences of your mistake. The dilemma enters when you aren’t sure whether you should speak up or not. You’re faced with the ugly anticipation of being called out for your mistake, and the agonizing indecisiveness of whether to draw attention to the embarrassing detail, or let it go, gambling that no one will ever notice it.

Are We Doomed?

Your acknowledgment of the error or embarrassment depends on its severity and influence. If it’s a mistake that has the potential to cause further damage if unnoticed (such as if there’s a typo in artwork that’s gone to print), I’d argue that it’s your ethical duty to say something. If the mistake won’t harm anyone by going unnoticed, I don’t see an ethical issue in staying silent.

You can prevent some of these incidents with the Undo Send feature in Gmail, but it won’t save you from mistakes you don’t realize immediately. For those, you could potentially ask a coworker you trust to tell if you if the mistake was noticed by anyone else. Short of that, your best option is a Mission: Impossible-style operation that permits you access to your recipient’s email account, so you can delete it from within—and for obvious reasons, I can’t formally recommend that strategy.

21. The devastation of tonal ambiguity.

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I sometimes wonder how many people lost their jobs, or thought they were losing their jobs due to a misinterpretation of tone.

As much as I love email and the written word, there’s one glaring disadvantage of this medium that’s impossible to ignore; it’s incredibly easy to inaccurately convey or misconstrue someone else’s tone. In spoken conversations or in-person interactions, you can quickly gauge a person’s body language and inflection; a casual smirk or an upward inflection at the end of their sentence might clue you into the fact that they’re being sarcastic. But in email, tonal conveyance and interpretation is entirely dependent on your word choices and sentence structures.

Scientific studies confirm that we’re highly sensitive to tone in written communication, especially in our modern age; even the inclusion of a period on a text message is enough to trigger a concern that you’re angry or distant. In the body of an email, tonal ambiguity can put you in quite the pickle.

Imagine this scenario: you ask your boss for a few days off work during a period of especially high stress in the office. They reply: “Sure. Go right ahead.” The shortness of these sentences seems to suggest hostility, and the “go right ahead” sounds sarcastic. But imagine someone in person saying this with a sincere, friendly tone.

Now you’re left with a dilemma. You can ask for clarification, but you’ll make yourself vulnerable in the process. Asking “are you being sarcastic?” could be met with, “No. Why would I joke about something like that?” or “Seriously? Now’s not a good time to take off” in equal measure. As much as we hate trying to decipher an ambiguous message with no clear solution, we probably hate looking like a fool even more, especially if we’re communicating with someone in a position of higher authority.

Are We Doomed?

I don’t have a perfect solution for you, but I do have some tips on how to navigate this destructively abstruse domain. First, you can reduce the prevalence of your interactions by making your own tone crystal clear. Before sending any email off, read each of your sentences aloud, and play around with the most sincere and most sarcastic tones you can muster, along with the angriest and most neutral tones. If your sentences sound equally plausible in each scenario, it’s a sign you should try different phrases.

And as much as linguistic purists would argue otherwise, sometimes emojis and slang can help you convey an accurate tone. Tacking on a “lol” to the end of your sentence isn’t the most formal option, but it will instantly make your email seem friendlier and less hostile.

You can also preempt tonally ambiguous emails by asking clearer, more directed questions. For example, instead of asking, “How would you feel if I took the next few days off?”, ask “May I have your permission to take off Thursday and Friday this week?” This structure practically forces a yes-or-no response.

But for the matter of parsing out the meaning from your boss’s seemingly cold, semi-sarcastic email? If asking directly for clarification is out of the question, you could dig into emails you’ve gotten from them in the past. Do they joke around a lot in email, or is their tone fairly consistent and sincere? Are there any signature words and phrases that only appear when they’re in a certain mood, like playful or irritated? If you can’t get past this stage on your own, consider calling in a squad of your coworkers to help you figure out this tonal mystery.

Conclusion

Is email a perfect medium? No. But it’s still a hell of a lot better than conference calls, at least.

Is it going away anytime soon? No. So there’s no use wallowing about these annoying email problems.

The fixes for many of these problems have the potential to positively impact not only you and your work, but your entire team of coworkers, so put them to good use. Correct whatever you can, and try not to sweat the stuff you can’t.

In the meantime, EmailAnalytics is here to help you better understand how and when you’re using email. It’s the perfect tool for an imperfect communication channel, and you can sign up for a free trial today!

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