Consider the genre informally known as the Annual Holiday Letter. Sent to friends and family in late December, it’s a rundown of what has and has not changed in the lives of a household’s residents since the last edition. A certain amount of performance is involved; this is not the place to confess a drug habit or wallow in the year’s setbacks. The whole thing is usually and transparently mass-produced. Paper letters are photocopied and later printed out, with aesthetic signifiers of intimacy — personally addressed, maybe hand signed — to help overcome the reality that is a unidirectional, one-to-many undertaking, a form of broadcasting.

Personal newsletters that serve a similar function have existed as long as email, and while the introduction of platforms like Facebook might have made them seem quaint, services like MailChimp (launched in 2001, offered on a “freemium” basis since 2009) and Tinyletter (launched in 2010 and acquired by MailChimp in 2011) helped build them into a genre, a featured form of publishing as opposed to a supplement. This has changed the dynamic between sender and recipient, expanding the range of potential content. For the writer, a numbered but closed audience provides the impetus for a thoughtful letter; for the media company, it provides the feel of one.

Some newsletters have created forums or programs for community members, but the daily newsletter’s sales pitch is an argument against collective experience: This is for you

The walled-off confine of the inbox has become a launchpad for new ways of speaking online. What the Fuck Just Happened Today, which delivers daily Trump news in digest form, began as a personal project, and became a viable media product. Lenny Letter, launched by Lena Dunham and Jenni Konner in 2015, concretized the among-friends editorial tone of blogs like Jezebel and the Hairpin by delivering it “one-to-one.” (It is now a full-fledged website.) There’s The Hustle, a self-described “friend” that covers the day’s startup news; and the Skimm, which summarizes the day’s major news stories for young, female professionals in what presumes to be the knowing voice of a peer. The Skimm has drawn ire for its glibness — a recent item likened the collapse of Spain and Catalonia’s power sharing to friends fighting over the controller when playing Mario Kart — but the offness goes deeper than the content. The “in-jokes” are an awkward hybrid of friendly and institutional writing, presuming shared understanding of an audience of millions; if the tone were less conspicuous, it might be more cause for alarm.

The Skimm, and newsletters like it, publish in a voice that feels like an uncanny amalgam of ideas about their readership. The form of their delivery blurs the distinction between personal correspondence and broadcasting, making it harder for the recipient to tell who is addressing them. A daily news roundup, or magazine published by direct delivery to one’s inbox may be harmless enough, but its hybrid tone feels insidious, and demands caution: It blurs the line between institutions and friends.


Email has been around long enough that only technologists of a certain age can truly remember its launch, and its ambient quality has obscured the extent to which it is a distinct medium. In its 20 years of mainstream usage, email has been the internet’s foundational access interface, as well as a meaningful link between friends, a cesspool of unwanted advertising, a clearinghouse for all professional correspondence, a byword for scammers. Many of those roles have been taken over by other services. Group chains, long a source of reply-all nightmares, were displaced by other platforms: texting or chat for personal plans, Slack and its ilk for work. Family updates migrated to Facebook. Email remains nearly as technologically limited as it ever was; its main weaknesses have not been fixed so much as they’ve been largely obviated.

But its social role has changed. Email, individually among other popular platforms, is good for messages without character limits, that needn’t be written in a single sitting or tethered to a single second in time. It’s also good for eliding the difference between one-to-one and one-to-many communication. The length of messages, the fact that they don’t refresh at the speed of a social timeline, the experience of reading one message at a time, all create a sense of privacy. Compared to the cavernous spaces of Facebook or Twitter, where sound bounces off every surface until the user is overwhelmed, the architecture of email is at something approaching a human scale. Even the language of email — newsletters are “sent,” which is softer than “published” — works to reify that sense.

As email was ceding ground to other social media, its users were also broadening their definitions of friendship. In earlier generations, personal email correspondence served primarily to connect individuals who knew one another offline. The lack of a built-in discovery mechanism meant that email largely confirmed existing connections. Internet-first relationships were built in chat rooms, forums, Tumblr, Facebook, and then Twitter — new ways of socializing that forged new forms of acquaintanceship, many of which consolidated in the inbox. You may be closer to and more interested in dispatches from people you know ambiently than those you know firsthand. Newsletters like the Skimm capitalize on this idea: a tonal composite of various people readers may recognize from Facebook or Instagram, performing for a different platform.

While verbal eye-rolls from friends can reflect true understanding, the same gesture from a mass newsletter reads as a probabilistic bet on your ignorance

While a newsletter does not belong to a single recipient, its existence is still largely limited to private spaces. It is received individually, without the space of a comment section (for better or for worse), or necessarily the option to share; you can forward it, but not engage immediately in public. Some newsletters have created forums or programs for community members, but the daily newsletter’s sales pitch — that it seamlessly integrates into your life — is in one way an argument against collective experience: This is for you. The other recipients remain a largely theoretical proposition; the experience of subscribing is meant to feel like a relationship, or at least like one of the many kinds of relationship one might form, distantly but directly, with individuals on other platforms. The familiar voice — its distinctive tics, the references it falls back on, its threshold for humor — is the ambient noise of any relationship. It does not always matter that the person regularly addressing you is not necessarily someone you know.


Brands will flee towards intimacy. As your news feed becomes crowded and impersonal — a clearinghouse for offers eerily reminiscent of earlier versions of email — they’ll search for other ways to reach you. No brand wants to end up in a graveyard solely populated by content marketers and growth hackers.

The Skimm is less abrupt than many other newsletters, but the basic bargain being struck here remains relatively stable: In return for access to more intimate parts of your presence — goodbye generalized feeds; hello DMs — they’ll make an effort to fit in. This, like the Annual Holiday Letter, is broadcasting with a certain sensitivity for context.

Slate’s Christina Cauterucci wrote of the Skimm, “Its patronizing tone assumes that female news consumers tune out anything of import if it’s not processed through verbal eye-rolls.” But the use of a performative voice is not only what grates — much of personality is performance — so much as the question of who is performing. Verbal eye-rolls from friends reflect true understanding of your interests. When a mass newsletter does it, the gesture reads as a probabilistic bet on your ignorance. These discordant notes are the hallmark of mass newsletters not quite written by an individual and not quite by an organization. Their content may be benign, but the subtle psychological shift they effect is more insidious: We risk losing sight of the relationship we bear to the voice addressing us.