I received a press release today that discussed the finer points of whether you should send your boss a holiday card or not. And it got me to thinking about how entrepreneurs, small business owners, and side hustlers can use holiday cards to foster goodwill about their business, nurture relationships and keep their business and services top of mind.

First, which holidays do you decide to send cards for? The obvious answer is Christmas and other winter/December holidays. But that’s not your only option. For many years, I sent out Thanksgiving cards to all clients who paid me money in the previous year. It got a very good response and sometimes even led to further business. I stopped when my business tanked and I didn’t even have enough money to buy food, let alone cards and stamps. Now that I’m back on my feet, I haven’t started that up again because I’ve been so busy with my life — healing from the car accident, getting married, and rebuilding my business from scratch as a side hustle. But I do plan to re-institute it when it makes sense.

I got the idea for Thanksgiving cards from Dan Kennedy. The thought process was that everyone sends December holiday cards. By sending cards at a different time, you stand out. I’m sure you could get even more creative and send out cards for other popular or obscure observations, as well. Find observances that relate to your business or represent the message you are sending. For example:

• January is Get Organized Month — if you are an organizer, this might be the perfect time to send a card with a few organization tips.
• September 21 is World Gratitude Day — A great day to send out a Thank You card to your clients, subscribers and colleagues.
• November is Sweet Potato Awareness Month — If you’re a food blogger, why not send out a fun ode to the Sweet Potato, along with a recipe?

You get the idea.

According to the press release, surveys have shown that holiday cards “are widely appreciated in the business world as a whole; recipients are more likely to do business with a company or individual that sends holiday greeting cards.”

Traditional greeting cards that the recipient can hold — whether store bought or handmade — are a good idea for a variety of reasons:

1. As I hinted at above, a handwritten note on a card helps you connect with those you want to stay in touch with. Sending these to your clients and connections will help keep you top-of-mind, which can translate to a wide variety of business opportunities.
2. Paper cards sent through the mail demonstrates a personal touch and makes you stand out from those who don’t put in the extra effort to do this.
3. Holiday cards are an effective and efficient way to network. It is subtle, but highly effective. Think of it: Instead of spending money on lunch, the transportation costs to get to where the lunch is served, and the time to small talk, eat, etc., you spend a few minutes to write a note and send it off for less than half a buck.

Guidelines Holiday Cards

There is etiquette to be observed when sending holiday cards. Here are pointers that AllisonTaylor, a reference-checking firm, suggests:

1. Choose a high-quality holiday card that allows no possibility of offending its recipient. Remember that not everyone celebrates Christmas – be mindful of religious and cultural nuances, particularly with your international recipients.
2. Choose a design that is appropriate for your business associates.
3. Keep your contact list accurate and up-to-date. Make sure you’re not sending a card to someone who has left the department or the company.
4. Check the spelling of your contacts and their company name. Any good points you’ll score with a holiday card will be lost if you misspell your contact’s name or business information.
5. Include one of your business cards inside the greeting card. This small insertion ensures that your recipients have your most current contact information and will reinforce your name with the card’s recipient.
6. Be sure that your inscriptions on the outside of the card are both legible and attractive. Consider using a form of calligraphy to make your recipient’s name and address visibly pleasing. Also, be sure to include your return address on the mailing envelope.
7. Sign each card personally. It only takes a moment to sign your name and write a short greeting, and your business associates will notice and appreciate this more personal gesture.
8. Don’t be late. In life and in business, timing is everything. Remember that many companies close during the holidays and people take vacation to be with family, so send your cards early. Also note the possibility that a recipient of your card may want (out of consideration or guilt) to respond with a card back to you prior to the holidays. Aim to have all your business holiday cards in the mail no later than December 15 if you’re sending them within the U.S., or earlier if you’re sending them via international mail.

A Note About E-Cards: These may be fun to send to your friends who know you well, but going old school with a paper card is a much better idea in your business. They are less personal and, since they are often sent en masse, they can come off as indifferent or too casual.