My Experiement with Letter.ly; or, My Letters from Europe Are Now Online and Free

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In early September I decided to start a private, paid email newsletter called “Letters from Europe,” documenting the 10 months my wife and I are now spending based in Berlin. (She received a fellowship to do dissertation research; I tagged along.) I was intrigued by Sam Lessin’s launch of Letter.ly, and his own post about moving from open and unpaid blogging to private and paid newsletters. I’d been reading his own “Modest Proposals,” which is very sharp and mind-opening about technology and business. While it seems to suit his communications needs — and likely those of other users — it just wasn’t what I ended up needing. This weekend, after almost three months of using Letter.ly, I’ve dropped it for a free, public website on Posterous (shown above). Here’s why:

  • I want more control over how readers are reading what I’m producing. With Letter.ly, account holders send their dispatches to a unique @letter.ly email address, which then sends the dispatches to all subscribers. In the five letters I sent out (averaging about 1,000 words), there were three formatting snafus, which I couldn’t be aware of until the letter was already out in people’s inboxes. The most frustrating of these was a process that changed apostrophes and quotes in one very long letter into “â"s and line breaks into "Â"s. (It’s possible this came from me using a particular program I shouldn’t have, but I couldn’t have known that.) The other two snafus were more minor — the titles of the posts themselves had been altered to include strings like ”=?iso=8859=1?Q?“ at the actual Letter.ly/schenkenberg website, where potential subscribers would sign up. There was nothing to be done about fixing the first problem; the emailed essay was already in readers’ inboxes; as for the title problem, because Letter.ly has no back-end that account holders can log in to, I couldn’t simply go in and fix it myself. (Here’s what the title of #5 looked like.) I emailed support about the first title weirdness, and Sam got back in touch almost immediately, then fixed it. Awesome service. It’s been about a week since I asked Letter.ly to fix the second title problem, but I haven’t heard back.
  • I overestimated the number of people who would subscribe. There are people selling Letter.ly newsletters with serious name recognition, and to say that I’m not one of them would be an understatement. Still, I thought more people would subscribe to mine. I know that some people tried to subscribe but couldn’t, because they don’t have an Amazon account, which is the payment gateway Letter.ly uses. I was happy to add them — and a handful of close friends and family — to the ‘free’ list, as I simply wanted them as readers. As for others who had expressed interest in following along with our travels but who didn’t sign up, I’d be surprised if the actual two dollars was an issue. Some of them may never have known where or how to subscribe (my heart was never in selling a paid service to acquaintances — not a good marketing strategy, I know…). For others who were aware of it, I imagine the whole thing felt like an oddity. No matter the reason, the fact is that there were people who I’d like to be sharing our photos and stories with who weren’t seeking access to them on their own.

  • I mentioned photos earlier. Once I got here to Berlin, I realized that a lot of what I wanted to share with people was photography: photographs of our apartment, our favorite neighborhood restaurants, sights we were seeing. In the first few letters, I used basic hyperlinks to send readers away to a special Flickr slideshow (on a Guest Pass, to keep everything still private) to see photographs related to what I was writing about. This was an extra step for me, and for the reader. About a month in, I decided to start a Posterous website that would serve as a web version of the Letter.ly project; if readers wanted to read each letter that way, they had the password and could do so. Up to them. I soon realized two things: The blog-posting format was the ideal one for my purpose (Posterous’ ability to have a gallery of photos embedded into a post is an especially good feature for me); and creating two versions of each letter was not how I wanted to be spending my time.

  • As soon as my Posterous website was up, I started feeling less enthusiasm for the old email version. I love posting to the web — I’ve had a blog for years and run a few other websites — and I was digging getting to know the Posterous system. I emailed a few subscribers and asked their thoughts about LFE becoming just a website (still password-protected, still $2); both remarked that it would likely lose that old-school epistolary nature of the emails — something from me showing up in the mailbox of people waiting for it, rather than yet another website to check or feed to subscribe to. I agreed. I spent another week debating it in my head. Ultimately, the benefits of moving to a blog system for me outweighed the downsides. What about cost and access? Yes, I could have moved to Posterous and still kept it private, charging $2/month using Google Checkout or PayPal, but all that effort didn’t feel worth it. 

  • At the end of the day, the $2/month I was charging was so small as to be more of a weird issue than something that truly affected my monthly balance sheet. I had 28 subscribers total, about half of those freebies. Though I appreciate the money I made these first few months — I delivered several thousand words that should have made it worth subscribers’ while — I feel fine now eliminating the financial aspect from the project. 

  • When I mentioned the hope that this change would bring more readers, I was mainly referring to friends and relatives who weren’t finding or reading it. But since I’m a full-time freelance writer, editor, and communications consultant, it’s certainly occurred to me that opening it up to more visitors could also mean a client lead or two. If I were to get a single project assignment from a connection made through this, it would provide much more money than a year’s worth of $2/month subscriptions from such a small number of people.

Though it feels good to have made this transition, I will say that there was something special about seeing an Internet pal whose work I respect, or a family friend who heard about it through the grapevine, show up in my inbox as a new subscriber. They’d taken the unusual step these days of saying, 'Okay, I’ll invest a couple bucks in this content; seems like it might be worth it.’ I’ve told them that I appreciate their initial investment, and I hope they maintain interest in this publishing experiment — I’ve called it an experiment from the start — even as it changes form.