Get a Head Start in September

 By “National Santa” Tim Connaghan

Starting in September

Based on Santa and Mrs. Claus starting their Holiday work after Thanksgiving, this checklist, starting in September, can help you pre-plan for the Christmas season.  With a little advanced planning, spread out between July and Christmas, you too can reduce stress and have more time to enjoy the holiday season.

  1. The first thing you need to do is make a list of every task or activity you feel you need to do, or want to accomplish, during the holiday season.
  2. Secondly, using a calendar and a pencil, block out all the mandatory daily and weekly activities, and add the holiday tasks, family events and Santa bookings that are on your list.

This will take a little work and may require some adjustments or changes. From the schedule below, you can add or subtract to start building your own schedule. The schedule is a simple tool you can adjust to your needs. 

You may want to move some things around. If you think of something else, slip it into the schedule.  If something doesn’t apply to your situation, delete it.  When possible, I suggest you get other family members involved in the tasks and planning. 


  • Go through your holiday decorations and lights.  Decide what you want to keep and what you want to get rid of those that have grown out of style.  But don’t go overboard, Remember, most pre-1950 decorations and toys are now valuable collectables.   Have a garage or yard sale to get rid of what you don’t want. (It’s ‘Merge and Purge’ time!)
  • Make a list of those decorations that you would like to add this year. Then in late September and October, when you are out and about, you will know what you need to purchase.  Many shops have pre-season sales on decorations, candles, lights, etc.  And the most popular decorations disappear quickly.
  • If you include an annual letter with your Christmas cards, start writing it now while things that have happened this year are still fresh in your mind. Simply add to or edit the letter each month until it’s time to mail them.
  • Update your holiday card mailing list. Decide what kind of and how many cards you’ll want this year.  Creating this list now, makes it easier to update each month, instead of trying to pull everything together later.
  • Decide what kind of and how many cards you’ll want this year.
  • Setup a Christmas gift idea file. Use a separate page or folder for each person on your list and start clipping catalog pages, pictures from magazines, and Sunday newspaper inserts.
  • Make out a list of the things you would like to do this Holiday Season, i.e.: attend a holiday concert; see a live performance of the ‘Nutcracker,’ visit a theme park or Holiday Village.
  • If you are planning to travel, you should be searching now for travel bargains on airfare, hotels, etc. The longer you wait, the higher the prices will be as the holidays approach.  If you are driving to an unknown location or place that is new to you, check the internet or the auto club for maps and directions.
  • Order your holiday cards if you have them professionally printed.  Get your holiday picture taken if you include a family photo with your cards.  Note: Many local photo studios have special packages for holiday family Portraits.  (Some even have photos with Santa!)
  • Start shopping for new holiday decorations.  Some shops, and especially catalogues, have pre-season sales on decorations, candles, lights, etc.
  • September is also a great month for everyone to start working on their Holiday Diets. (Santa’s are exempt from this!)


  • Update your calendar. Include all personal and family activities, school & religious events, business trips, family trips, concerts, socials, annual parties, etc.
  • Decide where you will be spending the holidays and make the necessary arrangements. If it’s at home, set up your menu and decoration plans. If it’s away, double-check school, work and social schedules that may conflict with your travel plans.  Now is also a good time to slip in a few scheduled breaks, especially if your calendar is getting full.
  • Scheduled a day or days, in December, to bake cookies, make fudge, wrap presents, deliver gifts, etc.
  • Start ordering gifts, especially ones that require special touches or that may be going overseas. Complete any catalog or online holiday ordering now before the November rush. 
  • Purchase Christmas stamps for the cards, labels for the computer, and holiday pocket cards for cash gifts
  • You might want to start buying a few gift cards ($$$) each month.  Chose popular department and specialty stores, your friends and family shop at.  Gift cards are now a very popular form of giving, as they eliminate awkward situation of giving the wrong gift.  Check and make sure the gift cards have no expiration dates.  Note: Those receiving gift cards will get a bonus when taking advantage of after Christmas Sales!
  • Hallmark often creates a special Holiday Planning Calendar that they give away to customers. Check to see if you can get one.
  • Purchase Christmas stamps for the cards, labels for the computer, holiday pocket cards for cash gifts.  (The U.S. Postal Service always has new holiday stamps.  They also have Hanukkah and Kwanzaa postage stamps available.)

The U.S. Postal Service will issue two holiday stamp sets for 2017 on consecutive days in the New York City area. A set of four stamps showing illustrations from the 1962 children’s picture book The Snowy Day will be issued Oct. 4 in Brooklyn.A different set of four, illustrating familiar Christmas carols will be issued Oct. 5 in New York City, where the American Stamp Dealers Association is holding its New York Fall Postage Stamp Show. Oct. 5-7.

In December, the Postal Service will also be releasing special stamps with Christian, Hanukkah and Kwanzaa themes.

If you need holiday-type stamps before October, the Postal Service sometimes has “Love” stamps or other lightly themed stamps that might work.  In past year’s stamps had Teddy Bears and Toy Trucks.

  • Either make your holiday labels now, or start addressing envelopes.  If you do a dozen or two a week, you’ll be done before you know it. 
  • Complete any catalog or online holiday ordering now before the November rush.
  • Start looking or rolls of gift wrap, gift boxes and bags, etc. Also ribbon, tags, tape, etc.
  • Decide now, what gifts you would like to receive.  Tired of getting something you really didn’t want or need?  Afraid you won’t have an answer when someone asks you what you want?  Why not be bold this year.  Make a list you can have close at hand. It can be a quick reminder to yourself, or you can give it to those you exchanged gifts with.  Have a variety of gifts in different price ranges to fit everyone’s wallet.  Then when someone asks that dreaded question, you can either suggest a gift, or present them with your wish list.
  • Review your schedule. Add a few appointments in December with yourself.  These are buffer times when you can relax, get a massage, go to the movies, and reduce the stress.   Plan for some quality family time, too!
  • Re-check school, church or other calendars for events that may conflict with your plans.
  • Get a Flu Shot. If you’re a senior or someone who is very active, a flu shot can help you keep your immune system in shape.  For Santa, this is especially true as he will see thousands of children during the season, thus increasing his chance of catching a cold or virus.
  • Double-check the calendar for changes in school, social or business events that may conflict with your travel plans.
  • Pre-schedule December days for yourself, and days to be with the family. Don’t assume you can just squeeze them in.
  • Make December appointments for beauty salon, barber, spa, golf, etc., before their appointment calendars fill up.


  • Address the rest of your holiday cards before Thanksgiving.
  • Proofread your holiday letter one last time, print and insert into cards or envelopes ready to mail.
  • Order any special gift certificates or purchase additional gift cards you may want to give. (Note: It is always good to have a few extra gift cards or gifts on hand for those surprise guest that show up, or for anyone you may have forgotten.
  • Start pre-wrapping those gifts you already have. Starting early on this is one of the most important ways of reducing holiday stress.  Make sure you have them well identified.  I suggest a little I.D in ink somewhere on the bottom of the gift.  In this way, you won’t forget what is inside and who you were planning on giving it to.
  • Send all your overseas gifts before Thanksgiving.
  • Start sending all your U.S. gifts immediately after Thanksgiving.  
  • Review your calendar for parties and events & any changes. You may also want to look for conflicts.  And remember that the day after a party or event, you may be a bit tired.  So, try not to book too many events that are back to back
  • Shop for any food staples or kitchen supplies you need before November 15 (Christmas is a tasty time, filled with all kinds of great food. Instead of trying to make it all, get out your recipes now and decide on your favorites. Do an inventory of the ingredients in your cupboards and stock up on what you need, when you catch a good sale.)
  • Time to get your holiday decorations ready. Decide what you are going to use and where you will be putting these and the new items you bought in September.
  • Double check all your appointments for haircuts, beauty salon, etc., now through mid-December. Don’t forget your pets grooming too! If you want to do something special, schedule a house cleaning company or maid service to clean you home before Thanksgiving and maybe one day in December.
  • Clean the House. Make this a family day with everyone pitching in.
  • Decorate the house. You decide whether to do this before Thanksgiving or after.


  • Final check of your calendar for parties and events & changes.
  • Mail your letters and cards on December 1st.
  • Enjoy a day of baking or cooking your favorite treats and dishes. Make gift plates or boxes to deliver as gifts, with greetings for friends, relatives and shut-ins.
  • Double check your gift lists and finish wrapping all presents before Dec 15th.
  • Then, schedule a pre-Christmas massage, a day at the spa or a round of golf, or something special to de-stress, and finally . . . . pat yourself on the back for getting ahead this year!

I hope these ideas will help you to reach your holiday goals and give you more time to enjoy your family, friends and the true meanings of the Holidays.

May the Joys of the Season be with you every day.

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This article is © Copyright 2017 and The Kringle Group, LLC.  No copying, reproduction or use of the above material is allowed without the written permission of the author