I have spent at least four hours today (and yes, it IS/WAS Christmas, so this was ostensibly fun/vacation time) wrangling with my email contacts in my address book(s) and searching for a cost effective (read “hopefully free”) option to send out several hundred Christmas cards by email. This has been a rather tedious process, but I the “end” is in sight as I write this. I’m curious to learn if others know about better or more effective ways to deal with this situation.

spam gmail
Creative Commons License photo credit: notoriousxl

I have been dealing with two related but different challenges:

  1. “Cleaning up” my personal address book, which has accumulated lots of duplicates as well as “orphaned” email addresses (without identifying names) over the years. (This is in-part due to bad contact sync experiences I’ve had with Plaxo.)
  2. Sending out our family Christmas card as a PDF attachment to several hundred email recipients. (A harder challenge than it was years ago, thanks to anti-spamming features of most email services.)

Challenge number one is something that really just took a lot of time. I’ve used a variety of third-party email clients and web-based email options over the years. These have included:

  1. PINE (oh yes, those were the days weren’t they…)
  2. Eudora
  3. MS Outlook for Windows (still using this at work, actually/unfortunately)
  4. MS Outlook Express for Macintosh
  5. Outlook for Mac OS 9
  6. Entourage 2001 and 2004 (I have 2008 but don’t use it now)
  7. Yahoo Mail
  8. Google Mail

In addition to dealing with my own email needs and issues, I’ve helped different family members, friends, and university faculty/staff members with email over the years. No one has “seen it all,” and I certainly won’t pretend to have when it comes to email issues, but I certainly have dealt with a fair number of email clients. Currently, I use GMail for all my personal email (where I haven’t seen “inbox zero” for many months, unfortunately) and Microsoft Exchange, which I access via its webmail interface on my Mac, via a WinXP desktop in my office, and via Microsoft Remote Desktop Client for Mac (free) on our LAN when I’m in the office and via a VPN connection when I’m not. Usually I find it faster and easier on my Mac to just use the webmail interface for Exchange, unless I need access to my PST folders. I have been a .Mac user for years, and have used Mobile Me since it was announced.

The advent of cloud computing and web-based email options has been great and offers important advantages over strictly client-based POP email clients, but it also poses new challenges. Handheld smartphones, like my iPhone, also offer wonderful new functionalities and communication potentials, but again with added complexities. One of the biggest complexities I have not yet handled satisfactorily is synchronizing my address book contacts across multiple platforms: My Mac OS X address book, my WinXP work desktop/MS Exchange account, my iPhone contacts, and my Google Mail contacts. Mac OS X does now sync to Google contacts, but until this evening I wasn’t actually syncing my Mac address book to Mobile Me. Now I am, and it appears that FOR THE FIRST TIME my address book changes are syncing across 3 of my 4 platforms:

  • My Mac OS X Address Book
  • My Mobile Me Contacts (and therefore my iPhone)
  • My Google Mail Contacts

I am delighted to see it appears this address book sync across platforms is working well AT LAST. The bulk of my time this evening working on these issues was spent culling down over 1600 address book contacts to less than 800. Since I’ve tried to do this previously with Plaxo and failed, I really am pleased that perhaps my address book woes are over. I COULD attempt to get my Exchange contacts at work to sync up as well after the holiday, but I may not press my luck there. Having my contacts synced as they are now is a HUGE step forward for me, and I may bask in the joy of this victory for awhile before attempting any further “tweaks.”

Cleaning up an electronic address book can be time consuming, but I think it is one of those necessary evils we must face if we want to live a large portion of our communication lives in digital spaces today. My second challenge of the day may not be as common as the first, but it was still important to overcome. Stated simply, the challenge was this:

How can I send an email message with a PDF attachment to hundreds of recipients, WITHOUT having my email account suspended or shut down as a suspicious email spammer?

In “the old days” of email before spam accounted for more than 90% of all the messages sent worldwide (as it does today, sadly) it was relatively easy to send out mass emails. For several years I maintained a mailing list I called “Tools for the TEKS,” and eventually managed manually a list of just under 1000 teachers.

At some point I switched from using a Eudora email distribution list to Filemaker Pro and the CNS SMTPit Plug-in, but I still had to manually remove subscribers who asked to be removed from my mailing list. I had considered setting up a Yahoo Group, but the main way (at the time) that I obtained new email list subscribers was by obtaining the email addresses of teachers who attended my educational technology-related workshops around West Texas. Email was in the early 2000s and still is today for most K-12 teachers a “common denominator” for communication. Anyone could provide their email address on paper during a workshop to subscribe to a mailing list, but not every teacher was going to take the time (practically) to create a new Yahoo account and subscribe to a Yahoo mailing list. I wanted a solution that was as barrier-free as possible to send out educational technology updates, and so I used what I had learned could work.

I had learned to use Filemaker and SMTPit while working as the webmaster and director of distance learning and faculty support at the Texas Tech College of Education. Our main implementation of these combined solutions was to send customized email messages to entering student teachers prior to their student teaching semester. In the summer of 2005, the light bulb really went on for me that blogs were the way of the future when it came to “one to many” communications like my edtech updates. Rather than messing with teacher emails and subscription/unsubscription requests, I could simply publish updates to my blog and educators could “pull” those updates via a variety of options, which DID still include email. My days of managing email lists were OVER, or so I thought.

Now let’s add the prospect of electronic Christmas cards into this discussion.

holiday cards
Creative Commons License photo credit: tifotter

I DO like paper-based, snail-mailed Christmas cards. We receive a bunch of these every year, and now every two to three years we actually mail out printed photo Christmas cards. The best thing about printed Christmas cards is that the photos can be put on the refrigerator, and all of them can be kept (if desired) for years in a shoebox. The biggest problem with atomic/analog Christmas cards is they are EXPENSIVE to make and send, if you want to send out a bunch. In comparison, electronic Christmas cards are almost free– at least their additional marginal cost to create is almost nothing since we already have computers, Internet connections, digital cameras, editing software, etc.

In addition to periodically sending out educational technology updates via email, I also maintained a “friends and family” email list which I used at least once a month to send out links to new photo galleries and web-posted iMovies of our kids and family. That list moved from Eudora into Entourage, but eventually (just a few years ago) that mailing list also died. The biggest reason for this was the same difficulty I faced today in trying to send out our Christmas card to several hundred recipients: SMTP servers which relay email are now (in many cases) restricted to NOT permit an unlimited number of recipients in either the To, CC, or BCC lines of an email. This varies by ISP, but I do know that GMail as well as Yahoo Mail limit how many folks to whom you can send the same message. (GMail’s current limit is 100 recipients.) I did setup and try using a Google Group for our “friends and family” updates, but the same problem I’d anticipated for a Yahoo Group for my “Tools for the TEKS” updates cropped up: The process of creating a Google account and subscribing to the list was too complex or too much of a hassle for LOTS of people who were on my earlier email distribution list. I still hear from people who say things like, “You used to send out updates all the time with photos and movies of your kids. What happened?”

What happened was I got tired of manually managing an email distribution list and jumping through hoops to send our mass emails. Now I publish photos regularly to Flickr and restrict most of the pics of our kids to family/friends only. Unfortunately, from a photo sharing and communication standpoint, I would estimate less than 10% of the people to whom I’d previously sent these updates now are registered/recognized friends or family on Flickr.

Isn’t it amazing how in many contexts, we’ll default back to a tool or procedure we know, we’ve used in the past, and with which we are familiar rather than blazing a new trail into the unknown? Today was no exception. Since I own a licensed copy of Filemaker Pro 7, I researched different plug-in options for sending email from Filemaker since I’ve done this successfully in the past. I found the “360Works Email plugin” and MondoMail, but I couldn’t get either one to readily work. With a little more research, I learned that CNS has released a new version of SMTPit for newer versions of Filemaker, called SMTPit Pro. I ended up using it with my version of Filemaker to email out our Christmas card as a PDF attachment. (Yes, I could have posted this online and emailed out a link, but the multiple recipient issue would still have been a challenge. In addition, I find it better now that more people are accessing email with smartphones to send the actual attachment in cases like this. I could be wrong, but I think that’s more user-friendly.)

The last challenge I faced was getting my email addresses out of the Mac OS X address book (or GMail contacts) and into Filemaker. Some commercial plug-ins are available to do this, but I didn’t want to spend additional money. The exported CSV files from GMail contacts would not import neatly into Filemaker or Excel, and the Mac Address Book wouldn’t export in a format Filemaker could readily open either. I ended up:
- creating a new distribution list in the Mac Address book
- opening the Mail application
- addressing a new email to the distribution list
- moving all those email addresses into the message body so their full addresses were displayed
- copying that text block into TextWrangler
- Using Textwrangler’s GREP search and replace features to replace all commas in the list with line breaks
- Importing that saved text file into Filemaker

The work required to figure all this out today was on the order of ridiculously arduous. Was there an easier way?

I guess I could have sent several emails with GMail and BCCed less than 100 people per time. If those emails resulted in too many bounces, however, that could have risked suspending my GMail account temporarily. As it was, I used the open/unauthenticated SMTP server address for my high-speed Internet provider (via Filemaker/SMTPit Pro) and didn’t use my GMail account at all.

Any suggestions for making this process easier next year? I think we’re due to send printed Christmas cards in 2009, so I probably won’t face this same set of challenges again till December 2010. Maybe we will have stopped using email by then in lieu of something better? I doubt it, but we can always hope…

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