desk with desktop computer pens flowers

Hear me read this post below:


Before I say anything about email, I want to make a public declaration. Because public declarations make things true.

The relaunch of, brought to you by The Darling Tree & Sprout New Media, is happening on March 1, 2014.

This event isn’t just a complete visual overhaul, but a whole ‘nuther experience. I think of this site, right now, as a cozy living room to shimmy into; the new site is a rustic house on the water for small gatherings and stories around the fireplace. New services: primarily editing and copyediting for big-thinking creative entrepreneurs, but branding services as well. And I’m getting rid of Disqus, because it’s hideous and often impossible to log into.

March 1. Be here. Or follow me on Twitter, if you haven’t yet, because I’ll probably be jumping out of my skin with delight. And maybe giving out housewarming gifts.

& now… about email.


I want to warn you, first off, that I’m not going to have a solution for your quest to reach Inbox Zero. I’m not going to be able to tell you whether or not you should have a mailing list, if you’re an entrepreneur (my advice is, and is always: heed your intuition). There’s not a PayPal button with which you can purchase a Get Rid of Inbox Guilt pill at the bottom of this piece for the low, low price of $99. But I do have stories.

I’m also here to defend email.


The gifted Amanda Farough — owner and smarty-pants behind Violetminded Media, recently kicked her mailing list to the curb.

She says:

“Inboxes are slammed with emails from our favourite people, our not-so-favourite-people, brands that we love, and lists that we felt obligated to join because we love our friends and family. Everyone is clamouring for Inbox Zero. It’s a mark of honour to have an empty inbox. We’re valourous in our attempts to thwart the internet monster and its great hoard of email.”

Her thesis: we do not like getting email. Established business practice states that we ought to build our mailing lists. These two don’t compute.

In conclusion? “Email marketing sucks for digital creatives.”


When I last peeked at Chris’s phone, his Mail icon’s little red circle — a circle that strikes fear into my heart, by the way — was alerting him to the presence of 11,126 unattended emails.

Let me say that again: 11,126 unattended emails.

Chris is not Kanye West or Jeff Bezos. He works at a high school, plays the banjo in our living room, and occasionally socializes at a bar for expat New Orleanians. However, when he inadvertently gets subscribed to the Ben Sherman mailing list because of a Ben Sherman purchase, he will never take the action to unsubscribe.

A few hours after I sent out my last With Love & Squalor email — mainly, a wrap-up of 2013, a list of the 10 most-clicked pieces that year, & a preview as to what 2014 would be bringing, along with some brand-new film photography — I asked him if he’d seen it.

“No,” he said. “I haven’t been getting your emails for a while. But it might have something to do with the fact that ever since Gmail started that whole Promotions filter tab, I never look at anything in there.”

I immediately thought about the mad rush of discussion I saw, both from business owners and in my own inbox from businesses, about the importance of letting customers know to drag desired “promo” emails into their Inboxes. I’d refrained from saying anything like that in my own messages — I’d seen plenty of angry tweets from folks who were tired of being told what to do with their inboxes.

I said as much to Chris, and he said, regarding the ability to drag emails from Promotions to Inbox, “That’s stupid. People shouldn’t assume that everyone knows the technical side of how to manage their inboxes.”

journal oracle cards


Email overwhelm isn’t new, but the fervent discussion about email — especially in entrepreneurial circles, where there’s an enormous drive to list-build as the key to success — is getting louder. Alex Franzen’s particularly on this tip; a few months ago, she launched an (email)-driven mini-course called I (Heart) Email, created for those who’d “like to write better emails, get fewer emails, and feel differently about emails” — another iteration of which is starting tomorrow, January 10th — and focuses on writing emails that are helpful, kind, and, above all, short. Haiku-like.

Gala Darling — and I can’t imagine how many emails that lady gets every day — tweeted recently:

I wish someone awesome (like @jendziura, @Alex_Franzen or @DanielleLaPorte) would write a piece on “inbox guilt”. It’s REAL.


Here are two major reasons that inbox guilt happens:

  • Creative entrepreneurs, and especially those who work in soul-related fields, get really touching emails. I know I do. Often, these touching emails are incredibly long, and incredibly long emails, while made of stardust, and are one of the reasons I do this whole writing thing to begin with, are tough to reply to. Who wants to reply with something short and pithy when someone’s just shared with you their heart’s depths? For me, those emails end up sitting in a folder I’ve labeled On Hold. You can guess how often I dive into the On Hold folder — I do, but it’s a process that involves tea and a rose quartz.
  • That red number, or whatever marker you have in whatever app you use for email (I use Airmail & Boxer), can act as a giant bullhorn hollering at you about your inadequacy as a human being. Or, at the very least, it’s like having dirty dishes in the sink. The dirty dishes are annoying to look at every time you pass the sink; often, you entertain the idea of hiring someone to come and wash your dishes. Or you think about throwing away all of your dishes and eating off of paper plates. (Analogous activities: hiring a VA and actually deleting/archiving your entire inbox.)


Entrepreneurs are told to use mailing lists as a major marketing channel.

Non-entrepreneurs get a lot of email, much of it mailing lists, but often don’t know what to do about it. I’ve told Chris plenty of times to use, a batch unsubscribe/roll-up service that I’ve found to be a godsend; he’s not interested.

Entrepreneurs get a lot of email, and sometimes know what to do about it (see:, but also don’t know what to do about it, giving people like Alex the chance to espouse the virtues of helpful, brief emails via classes and blog posts.

Inbox guilt happens because we not only want to be compassionate human beings who write back to other human beings who’ve taken the time to write to us, but also because we don’t like the pileup of dirty dishes.

lace dress in the sun


I love long letters that come in the mail, written on vellum and that enclose feathers and crystals.

And you know? I also love long emails.

I love long emails because they remind me of the long letters that I used to get — and still do get, but to a much lesser degree — in the late 90s and the early 00s. They’re not quite as good as the paper sort, but I print them out. I put them in my Filofax.

I love long emails because they’re usually heartfelt, and often from friends that live far away. They tell me what’s going on in their lives.

I love emails that are little cards from friends that tell me that I’m going to be okay.

I don’t want people to forget that in the hubbub of hating email, of striving for Inbox Zero, and wanting to write the shortest, more concise emails possible, that there is a beauty in receiving email.

It’s not that email is bad. It’s that certain kinds of email are annoying, and that we get a lot of it.

When I read Amanda’s piece, I thought for a moment about abandoning With Love & Squalor. But I didn’t, and I won’t be for the foreseeable future. With Love & Squalor is my way of sending a lovely, long email to my audience. Whether they unsubscribe, roll it up, or delete my communiques is totally up to them — because everyone has a different relationship to their inboxes, and to email.

Email is a way for me to connect to my family.

Email is a way for me to hear from my friends about what’s in their hearts.

Email is a way for me to meet with strangers, and to become friends.

There’s lots of junk; I won’t dispute that. But let’s not forget that email can be deeply intimate.

Chris has, somewhere, copies of all of the emails I sent to him during the beginning of our relationship. That’s something like hundreds — or thousands — of emails from 2001-2003. And yes, there are also scraps of paper kept, and mix tapes rediscovered. But there are those emails.

And that is a kind of magic.

With love,