How to Organize Your Holiday Card Mailing Early to Avoid Stress

Organize holiday card mailing

You may think the best time to start working on your holiday cards is December. But what if I told you there’s a better way... A way to avoid adding to infamous holiday stress? A way to find actual joy in addressing and sending holiday cards?

The trick is to create (or choose) your holiday cards in the fall and mail them out either right before or right after Thanksgiving. You could follow the new trend of sending a Thanksgiving card or just hold your cards until later in December.

You could also hold them and mail them at the end of December as a New Year’s card. 

No matter when you decide to mail them, starting on them early and using the right tools is key.  When is a good time to start?  As early as possible. I like to start mine in early November since November tends to be a slow month around my house.

The first step is to make sure you have the right tools on hand. You don’t need anything fancy.. I sit down with a big stack of cards and envelopes, my address book (printed out from Google Docs), stamps and a cup of tea (or wine). I store the cards and envelopes and stamps in this simple organizer

Why You Should Send Holiday Cards

Sending out a big batch of holiday cards may seem like a time-consuming chore, especially when your goal is to declutter your life and become more organized. Why add in an additional task that involves time and money, showcases your terrible handwriting, and in some circles is no longer considered a holiday must?

Despite all of that, you should send holiday cards—a bog old batch of them!  I've found that the annual ritual of choosing, creating and sending holiday cards has several benefits.

1. A Holiday Card Can Act as A Gift.

Not to be cheap, but sometimes you just don't feel like buying someone a gift. Guess what?

I would much rather receive a handwritten card with a nice note than another tchotchke. If you're just going to send a photo card with no note, this won't work, but if you're actually going to take the time to write a thoughtful note, a card can swap in as a gift for neighbors, distance family members, and colleagues. Another bonus? A card is a gift that won't clutter up someone's home

2. Keep in Touch.

A holiday card may be the only contact you have each year with your extended family and family friends. If you have someone who means a lot to you - a teacher, rabbi, former boss, family friend, or a favorite aunt, whom you don't get to see often, writing them a short note each year keeps you connected.

3. Get Organized.

If you've moved, it's an easy way to let everyone know your new address. If your own address book is a mish-mash, this is a great excuse to update it and organize your book. You may even consider going digital.

Here are some ideas for storing your address books:

  • On index cards
  • In a traditional address book
  • In an excel spreadsheet in Google Docs
  • In a plain old excel spreadsheet in Excel

Worried about clutter? Check out some pretty paper clutter solutions.

4. Network.

Again, this may be the only time this year that many people hear from you. What happens if in June you actually need to ask someone a favor or need some assistant in networking?  If you’ve sent a car, your call or Facebook message won’t sound so random. 

A few examples:

  • If you'd like to get back in touch with a former colleague who is now in a position to assist you in a career change or move, a holiday card is a great way to reach out (you can follow-up in January with an email asking for their assistance).
  • Are you looking for a new house? A puppy? A date? Mention it in your holiday card. Ok, maybe you’re not going to say “I’m super lonely can you hook me up with someone?” but you might say “I am newly single.”

5. Say Thank You.

This happens to me all the time—I have every intention of sending a thank you note after a party or a get-together, but I forgot. If you forgot to thank someone this year for a gift or a favor, send them a card and include a "P.S. Thank you for the blender, I've gotten a lot of use out of it!" or, "P.S. Thank you so much for putting me in touch with your neighbor Hank, he was very helpful in finding the right snow blower." Just make sure you don't cross the line into bragging in your card.

6. It's a Nice Ritual.

Picking out my annual holiday card is one of my favorite traditions. I usually but them early and then spend a few hours a week writing out my notes and addressing the envelopes. it really gets me into the holiday spirit.  And I love receiving cards and then displaying them in this pretty letter holder

How to Organize Your Holiday Card Mailing

Sending out a beautiful batch of holiday cards each year seems like a daunting, time-consuming task. I've broken this yearly ritual down into four easy steps for you to follow, and now that you can order your cards online, it's even easier than you think.

1. Commit to this task.

In the age of email and Facebook, this may seem like an unnecessary chore, but I have 5 good reasons why you should commit to participating in this custom each year. 

2. Organize your address list.

You will most likely have the addresses of everyone you're going to send a card too, but they may be scattered between your home and office, possibly half in an address book and half stored in your work contact list. Now is the time to consolidate your contacts and their addresses in a consistent format. Depending on your computer skills or affinity for a paper and pencil, here are some suggestions for organizing your contacts:

  • Excel spreadsheet
  • Online card store
  • Address book

If you're missing some addresses, a quick email should suffice. Tell your family and friends you're updating your contacts and would like their latest information. You can also find most people's addresses by searching websites like switchboard.com and pipl.com are fairly reliable.

TIP: While you're collecting addresses, it's helpful to gather emails, dates of birth and phone numbers at the same time.

3. Choose your card.

Three things to consider here: cost, tone and time.

  1. Set your budget and remember that in addition to the cost of the cards, you will also need to pay for postage.
  2. Decide whether your card should have a religious theme or a more secular one.
  3. Consider the time you will put into creating, writing out and addressing your cards.

For DIY types, working on a handmade card is a great creative outlet during the holidays. If, like me, you can barely draw a straight line creating your own will add to your stress. Consider purchasing a card or creating one online at one of the following:

  • Drugstores and grocery stores have the best prices.
  • Target has a great variety of cards.
  • Specialty card shops like Papyrus have both beautiful pre-printed cards, or will custom print according to your taste and budget.
  • Online card stores like Staples offer the option to create your own card, and they will do the hard work of addressing your cards for you. You can then choose to either have them ship your cards directly, or ship them to you so you can personalize and sign yourself.
  • Many Etsy sellers offer PDF files in an array of styles and colors that you can print for yourself on card stock.

For the DIY-minded many Etsy sellers also stock beautiful card stock and pens. Got kids? They may enjoy creating a few cards themselves, just be prepared for them to lose interest after the first two or three!

TIP: Worried about offending someone on your list with a religious card? Miss Manners recommends sending a New Years card instead. Another great option is a Thanksgiving card.

4. Address and stuff envelopes.

Many people find this to be the most burdensome part of the holiday card process. Once again, how much time do you have to spend on your cards? How is your handwriting? A handwritten address is the most personal, but a printed address is better than no card at all.

Here are your options in order from least to most time-consuming:

  • Print them on labels or directly onto the envelopes using your home printer.
  • Use a professional printer (think beautiful black letterpress on a pale envelope).
  • Hand address your envelopes.
  • Use a typewriter. Dust off the old Underwood and type out your envelopes on-by- one.

TIP: If you decide to hand write or type out the envelopes, I recommend breaking this task down into smaller, more manageable pieces by committing yourself to 5-10 cards per day.

If you prefer to set aside a few hours to tackle your cards in one sitting, these tips will make time go by more quickly and may even get some Grinches into the holiday spirit:

  • Create an appropriate setting with good light and sit in your most comfortable chair.
  • Make yourself a nice cup of hot chocolate or mulled cider.
  • Light a fire in the fireplace.
  • Play your favorite holiday music.
  • Recruit some help. Your family can help you by stuffing and sealing the envelopes.
  • Consider inviting friends over to address their cards at the same time.

5. Send your cards.

You're almost there! Now it's time to send your good wishes, but use this checklist before they hit the mailbox:

  • Double-check that your return address is present and correct on the envelopes.
  • Keep a few extra cards and blank envelopes in case you receive a greeting from someone whom you left off your list.
  • Update the address of anyone whose card is returned non-deliverable.

TIP: Send your cards earlier to ensure your contacts receive them on time, and you have a chance to correct any address mistakes.