The Definitive Guide to Strategic Holiday Shopping


There’s no question that at StrategyBlocks, we live and breathe strategy. So we feel pretty confident in saying we’re experts when it comes to building a strategy for all kinds of events and activities, even outside of the work place.

Tomorrow marks Black Friday, the biggest worldwide shopping day of the year, and the official start of the holiday buying season. To that end, we’ve designed a handy, strategic list for making the most of your holiday buying and gift giving this season.


  1. Plan ahead. No activity goes well without a plan, and holiday shopping is no different. Before you even start, it’s best to determine how much you can spend, who you need to buy for, which gifts you will store under the tree and which you must ship, etc. Also, take time to find out what your recipients really want, research where you can find the best gifts and how to get the most favorable deals. While it may not be the most exciting part of holiday gifting, a strategic plan will definitely get your holidays off on the right foot.
  1. Make a list, check it twice. Every good plan needs organization. List building helps you keep everything straight, and few things match the satisfaction of crossing off a completed task. Also, creating a list helps ensure you haven’t forgotten anything or anyone. Take a moment to mentally walk through your day-to-day life to be sure you remember far away family members, teachers and co-workers, service providers, neighbors and friends.
  1. Create a system. Successful strategy requires a system. It doesn’t have to be complicated or formal, but it should be appropriate to the situation. When it comes to holiday gift buying, it makes sense to plan a strategy around what to purchase, when, and from where. For example, should you wait until Black Friday to get the best deal, or are you worried the item might sell out before then? Can you buy last minute, or do you need to plan for shipping time? When is the best time of day to hit up the crowded mall? Taking the time to map your plan to a system will help make your holidays much more merry and bright.
  1. Fuel for the long haul. Holiday shopping is an endurance race, not a sprint. To ward off the crankies, it’s best to be smart about sustenance. Never leave the house without a bottle of water, and keep a protein bar, a bag of nuts, or some bite sized fruit in your bag. Trust us, when you’re standing in your sixteenth checkout line of the day, you’ll be glad you have some nibbles.
  1. Make those purchases count. Good strategists know that nothing exists in a vacuum. Gift buying should be strategic, helping your money go even further. For example, can you buy the same item to give to multiple people on your list? This not only saves time, but often saves money by capitalizing on bulk discounts or retail coupons. What about finding gifts that also benefit charities? You allow the gift recipient and yourself to feel doubly good about the present. And don’t forget about after Christmas sales – a perfect time to stock up for next year’s holiday giving.
  1. Wrap and ready. Don’t just stick all those gifts in a closet or under your bed. After you’ve made your purchases or your gifts have shipped to your door, take a few moments to wrap, tag or package them up. Tackling these jobs a little at a time helps keep them enjoyable, and helps you avoid the last minute, late night rush to get everything ready.
  1. Reward yourself. If you’ve completed your shopping list then trust us, you’ve worked hard! Every successful strategic execution deserves a reward, and looking forward to a special treat helps you get through some of the more unpleasant tasks. Whether it’s your favorite dessert, a hot bath or a special holiday gift, be sure and take a moment to recognize your efforts and reward yourself accordingly.


From all of us to all of you,

Happy Holiday Strategizing!