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The feeling is always the same. First, you’re calm, you’re approaching the task at hand diligently without fear. You check it, you double-check it, you send it to someone else to triple-check it, then another person to quadruple-check it. You check your list, your subject line, your links. You basically do as much as possible to procrastinate before the moment that always causes panic to rise in your chest – when you hit send on that newsletter. 

As a generation, we should be used to communicating with potentially massive amounts of people at once. Social media has given us platforms – some larger than others – to quickly disseminate fleeting thoughts and feelings to thousands, so why is it that sending emails specifically to large groups of people can give us the fear?

E-mail is one of the most common triggers for social anxiety and productivity-related anxiety. In this article on Psychology Today, Dr Alice Boyes, author of The Anxiety Toolkit puts this down to the fact that emails are asynchronous – there’s a delay between sending and receiving a response – and also because context clues are missing from it as an interaction: “You don’t know if the person replying to you is sick or just got yelled at by their boss. These factors mean that email can feel very emotionally confusing and anxiety-provoking,” she says. 

Chris Lochery is an avid reader and writer of newsletters, managing lists for various clients some of which number in the hundreds of thousands. “The major newsletters that I’ve been responsible for (i.e. the ones that actually earn my living, rather than any I’ve done as part of fun projects) have all been sent under the name of the company – and I do feel a greater sense of pressure sending those out,” he tells me (over email). “With something under my own name I know that it’s quite easy to send a follow-up with a personal response, churn out some self-deprecating line and correct whatever mistake I made. When it’s done under the guise of the company though, I feel that’s a little harder to walk back without the company taking a dent to its reputation.” 

The concern Chris mentions is backed up by Dr. Boyes. “Email can be especially stressful the less power you have in an organisation,” she tells me. “In an evolutionary sense, we’re wired to care what others think and to want to make a good impression. That won’t change.”

Ironically, part of the fear of how we communicate in this relatively new medium may be down to old-fashioned ideas. Namely, etiquette, or digital etiquette. Etiquette is defined as a kind of formalised politeness, a set of rules to follow that will mark you out as being of good standing. While it can be identified in things like holding the door open for someone, or knowing which fork to use for which course at dinner, it is rooted in an upper-class understanding of values, and so often feels like it’s in place to catch people out, or to make people who aren’t of that class feel uneasy. 

One marketer I spoke to, Aditi, tells me she’s “a bit more nervous sending emails which are targeted towards older people rather than a younger audience because they tend to be more fastidious.” She added: “I think a lot of people my age (early 20s), often don’t really know what’s the right tone to strike in emails, as it’s not really something you cover until you start working.”

Have we unwittingly put in place a similar code for email that may be making us feel nervous before we’ve even begun? A quick search throws up a whole host of rules for sending an email. We should be sparing with exclamation marks. Our salutations should be professional. We should be brief. We should know our audience. We shouldn’t be overly funny. We shouldn’t use emojis. 

When a lot of other digital communication is grounded in informality, then maybe this feeling of strictness around email jars, and could be down to how old a function it is in comparison to things like social media, blogging, or other ways in which people communicate digitally. 

For Sian Meades, creator of the hugely popular Domestic Sluttery and Freelance Writing Jobs newsletters, email etiquette is as simple as “being respectful of people’s time,” but still the anxiety remains. “I think it’s a similar feeling to when you send an editor a pitch you’re really, really excited about, or when you send a text to someone you fancy. The reaction to the content of your message is something you can’t do anything about.” She also saves a certain amount of ire for spam filters, telling me “if I’m sending a newsletter with an advert in, the last thing I want is for it to get stuck in spam folders. There’s just nothing you can do about it once you’ve hit send,” and also Mailchimp’s attempts at cutesy animation: “MailChimp has this really annoying thing where there’s a little animation of a sweating finger over a big red button. I’d feel a lot happier about hitting send if they did away with that.” Reader: I’m pretty sure the sweating finger is, in fact, a monkey’s paw, as the Mailchimp mascot is a monkey, and I hate it too. 

That’s the thing: everyone agrees. From people in junior roles in communications departments to freelancers to folk who’ve just set up a tinyletter or substack account for their pet project. From concern over typos to fear over worrisome responses, to plain anxiety that you might be ruining someone’s day by dropping into their inbox uninvited like a U2 album, sending mass e-mails is like digital stage fright. Maybe then the key to addressing the anxiety is to lean into its universality and make it a team job rather than an individual one – get your links checked, your copy proofed, your design tested. Then take a deep breath, close your eyes, and hit send. 

Also, for the love of God, if you’re going to put “Dear [name]” make sure your data is formatted correctly. 

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