Shutterfly: Cloud Christmas Cards



2003 holiday card

I sent my first holiday cards out in 2002. I selected the least dorky cards I could find so late in the season. Based on what I saw, I was hoping that all of the fun cards had sold out. I hoped prepackaged cards really were better than what remained on the shelf that year oh so close to Christmas.

I bought my first digital camera a few months later that next year. I loved the instant feedback from the camera, and a surprisingly capable manual mode that came with the Canon Powershot S50. That year, my mother gave me a set of candle holders, which became the three wise men in the following year’s holiday card. Since then, I’ve always sent out a holiday greeting each year. In a highly digital world, I always appreciate exchanging physical mail!

My traditional process

Over the past decade, I’ve worked with various vendors to print cards. While each vendor has its strengths and drawbacks, they all required me to address, stamp, and mail the envelope. Once my mailing list got larger than about 20, I needed to invest in mail merge. I’m blessed that my list has grown longer over the years. I’ve also added international mailing addresses in various formats.

Additionally, each year Microsoft makes mail merge “better,” and my printer manufacturer slightly tweaks their drivers. Each year is a lot of troubleshooting to create the mail merge and tweaking output to correctly align the printer to the mailing labels.

After the dark art of printing the mailing labels, what follows is a relatively straightforward process. I place two mailing labels (addressee and return address) on the envelope, stamp it, and lick it shut. Some vendors over the years have added return addresses on the envelopes, which is certainly appreciated.

I’ve always been intrigued by a wax seal on an envelope. I obviously can’t wax seal cards in this day and age. A few years ago, I added a monogram stamp that included my return address, which I felt added creative touch.

What brought about changes?

However, my process has proven error-prone over the years. What inevitably crept in?

  • I forgot to add a stamp to the envelope.
  • I put a domestic stamp on an international destination.
  • I had an old address for someone who had moved.
  • I did the mail merge incorrectly which dropped someone I cared about.
  • I didn’t order enough cards for everyone I wanted to reach.
  • I ran out of time physically labeling the envelopes sending them on Christmas Eve.

In my industry (software), we have the default assumption that “cloud” is always better, so I wanted to see what the cloud could offer this holiday card mailer.

Shutterfly vs Postable

I only considered vendors that had a Windows or Mac web experience. I send too many cards to be constrained by a mobile app. That narrowed the field considerably to Shutterfly and Postable. I chose Shutterfly as they had designs that fit my look more closely. Postable was cheaper, but hey, we only live once, right?

Overall I was thrilled with Shutterfly. I can highly recommend them to anyone looking to do the same thing next year.


  • Shutterfly (and TinyPrints) have the best platform with the most options to customize your card: designs, paper type, envelope interior, and exterior fonts.
  • Flexible web-based editing and mailing experience
  • Address book and mailing experience that supports international addresses easily.
  • The address book upload was manageable from a Microsoft Excel export.
  • Shutterfly’s address book provides a stable home to store addresses for future years.
  • Simple mail merge function. Just select all of the addresses in your address book (or select all) and add them to the cart.
  • I didn’t have to include shipping time to me and my own processing time in my timeline. Shutterfly consolidated those two steps into one.
  • Easy to send cards in bulk or one-offs if I missed someone.

Watch: Pricing is highly variable throughout the Christmas season. Once time had passed to deliver cards by Christmas, pricing dropped significantly. In other words, New Year’s cards are considerably cheaper than Christmas cards, lol.


  • Definitely more expensive than do-it-yourself by about $0.60 per card (but saves me from a time-intensive, error-prone process best done by machines).
  • The address book needs a search function. I’m often scrolling through the address book trying to find a recipient to make sure I have their current address.
  • The address book doesn’t have an export function. Apparently, from this Facebook post, Shutterfly will do it on a one-off basis. This leaves me without a central address book that works across the Apple ecosystem like I had to do it by hand.
  • There’s no way to add a personalized note to specific recipients. I’m hopeful they will add that in future years. Still, I did miss dropping a small handwritten note highlighting a special memory from the year to that recipient.
  • The default fonts on the envelope looked flat to me. I’ll make a note to adjust next year.

The 2020 card story

About five years ago, I came to a place where I struggled to find the meaning of the holidays in my own context as a Californian. Christmas was very much a holiday “back east” for me. I stumbled upon a Facebook ad saying, “LGBT and struggling to find your Christmas?” Lo and behold, it was a link to that tree at

I laughed when I saw it in being the host for my motorcycle club’s Christmas party. I thought it was the perfect addition to my burgeoning holiday tradition here in California. Almost everyone who sees that the tree always has a gasp, a laugh, and a smile. It’s definitely become a welcome part of my home. I’m glad to share it with each of you this holiday season who have not seen it in person. I’ve also equally fallen in love with the doormat calling the golden state – “home”.

My partner and I have been separated since February due to the pandemic. We didn’t have any pictures in 2020 of us together, so we settled on two excellent pictures of us individually nodding towards the reality of a closed border. We were able to see each other this Christmas and are thankful for that time together. Due to a change in Canada’s border policy, I’m hopeful I will see him more during 2021!

In closing, Shutterfly was an excellent vendor to work with that allowed me to focus on my contacts and design in a crazy, time-strapped year.


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