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How To Re-Gift Yourself Less Stress This Holiday Season (And Every Year To Come)

How to use Trello to reduce holiday stress

Does this ring a (jingle) bell from your experience?

Whenever August turns to September, you revel in the changing of the seasons for about a minute, and then you freak out, thinking of that next big milestone now that summer’s over: Thanksgiving, Christmas, Hanukkah, Kwanzaa, or just the whole dang Holiday Season that looms ahead with all its required planning for gifts, parties, decorations, travel, and the list goes on! 

Retailers don’t call the weekend before Christmas “Panic Saturday” for nothing.

So how can you ensure you make your list and check it twice (maybe thrice) every year? It starts with a dash of planning and of course, a Trello board full of cheer that you can re-gift to yourself again and again! 

My Trello Holiday Planning Board

A couple years back, I made a holiday planning Trello board to keep everything organized ahead of welcoming my entire extended family to our house for a two-week Christmas vacation. It included:

  • Things to buy
  • Tasks like cleaning and decorating
  • Activities that would be happening during their stay
  • Recipes that would please cheese lovers and vegans alike (just drag the URLs onto the list to make a card)
  • A gift tracker (with budgets included)
  • Addresses for friends and family not attending so I could mail them a card

Christmas 2019 Trello Planner Board
You can copy and customize this Christmas planner using my free template.

Planning stress abated, it was a very merry holiday—most of the gifts were a hit, and not once did we run out of chips or toilet paper. 

Santa’s Back In Town

Fast forward to 2018. Somehow another 9 months flew by and I was back where I started, faced with another large Christmas to plan. 

Here’s where my holiday planning Trello board really began to shine bright like Rudolph’s nose.

I re-used it. 

I made a copy, changed the year from 2017 to 2018. If you're using the Trello mobile app, you can copy the board from the menu on the right:

Copy Board from Trello app

Next, I began customizing it for the new holiday season:

  • I moved all the relevant "Done/Purchased" cards back to "To Buy" and "To Do."

  • I took a look at the recipes, sorted the hits from the losers, and archived the ones that weren’t crowd-pleasers.

  • I researched the events to see if they were on again this year and updated the dates.

  • I had a record of each and every gift I bought, so I could re-buy all the chocolate letters people loved in their stockings, and avoid that itchy sweater for Dad. Seeing my old ideas, gave me new ideas. In Trello, this was as easy as “unchecking” the items in the checklist I wanted to re-buy and adding a few more. I had a new shopping list in just a few minutes! 

Husband Christmas Gift List in Trello
I add gift items to the checklist when I plan them, then check them off once they're purchased. This is what I'm getting my husband this year (don't tell him!)

I had also learned some lessons from the previous Christmas, so I knew to double the napkins order, and skip making the wreaths from scratch. (The walk in the woods was lovely, the cuts on my hands from floral wire? Not so much.)

I was even less stressed prepping for the holidays this time around, and for a second year in a row, my Christmas Trello board transformed into a satisfying list of “Done” tasks and a fun calendar of holiday events.

the grinch at christmas
So, shocker, another 9 months have flown by and we are in the thick of Christmas planning for 2019. It's been an especially busy and challenging year, so I have been less than enthused to get into the holiday spirit. 

Thankfully, just like a trusty team of elves, that Trello board was there for me. I made a copy, changing the title’s year from 2018 to 2019… and you get where I’m going with this. 

I had already experienced the ease of picking up where I left off last Christmas, so I immediately felt more productive this time around. Case in point: I finished my holiday shopping before December even arrived thanks to a backlog of two year’s worth of gift ideas (some of which I had brainstormed, but never bought).

Pro Tip: You can even look back on all your archived cards from years past and send the relevant ones back to the board for another round of planning!

View archived Trello cards on mobile appAn archived card reminded me that I had done the research to find a wallet for my brother-in-law but hadn't bought one, so I could use that idea this year.

So instead of rushing to the stores or spending hours online, I’m enjoying my time indulging in seasonal activities (read: watching sappy holiday movies with my dog) with a hot cocoa in hand. 

The Gift That Keeps On Giving 

A Trello board in and of itself can be a gift when you’re faced with a daunting project or task list, but if you find yourself needing to repeat those efforts on a regular basis, making a template and copying all your brilliant ideas over time after time can really make your efforts go twice as far!

Get the Christmas planner template here (it’s free) and make it your own!

Christmas 2019 Trello Planner Board


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Next: The Ultimate Trello Holiday Planning Roundup