Since Erin and I are adults with a child, we sent out holiday cards this year. Rather than hand-addressing them like Erin has done in prior years, I wanted to create and print address labels. Since the source of all this data is stored in the Contacts app on my computer, I figured this would be easy.

It can be, but it wasn’t for me.

The Easy Way

If you’re willing to make precisely zero edits to the address labels that are created from the Contacts app, it’s actually quite easy to print labels.

1. Select all the addresses you want to print by ⌘-Clicking on the ones you want
2. File → Print
3. Select Contacts in the centered drop down, and then set the type of labels you have. In our case, we had bought Avery 8160.
4. Print

The Hard Way

For me, I wanted to address couples as, say, “Stephen and Merri Hackett”, even if my contact card had only Stephen’s name in it. This got very complex very quickly, but I was able to figure it out.

1. Select all the addresses you want to print by ⌘-Clicking on the ones you want
2. Open Numbers (presumably this would work in Excel too) and create a new blank document
3. Drag the addresses from Contacts into Numbers
4. Remove any fields you don’t care about. This is, most likely, nearly all of them, such as phone numbers, emails, etc.
5. Make any edits to the data here in Numbers. This is where, for example, I changed:
   Stephen Hackett → Stephen & Merri Hackett
6. File → Export to → CSV to export the list as a series of comma separated values
7. Go to Avery’s web site and select the YouPrint option
8. Enter your product number (in our case, 8160)
9. Select a Design
10. On the left hand side, choose Import Data
11. Upload your CSV you created in step #6
12. Walk through each address and make sure that none run off the edge of the label
13. Print

Quite obviously, this was considerably more involved. However, it also had the side benefit of me being able to use a slightly more festive label thanks to Avery’s selection of clip art designs.