The Secret to my STRESS-FREE Holiday Season

This is a guest post by my dear friend Jessica on an exciting co-venture we're launching!

When it comes to parenting, I get quite a bit wrong. My kid eats mostly sugary food for breakfast. He asks for dessert after EVERY meal. Last year, I handmade pretty awesome “Camp Ryan” birthday invitations (complete with old maps cut and folded into envelopes) and then forgot to mail them. And recently, I tried teaching him that if you’re smart, you should probably find other ways to express yourself other than using adult words (i.e. profanity); so now whenever he hears a four letter word, he blurts out, “Mom! That person isn’t smart.” 

Oh geez.

I realize these aren’t exactly end-of-the-world parenting failures, but they’re not necessarily things I’m proud of or like to publicly acknowledge. 

Luckily, there are a handful of things I seem to get right. Planning for a memorable and less stressful holiday season is one of those things. My type-A personality combined with a history of infertility fuels my passion for ensuring we wring every drop of magic and excitement out of Christmas.

While there wasn’t anything specific that happened, I just remember being very frustrated that the joy of the holidays continually lost out to the rush and stress of this busy season. My initial plan was to cut back. For two years, my husband and I didn’t exchange gifts. Then, I didn’t host any holiday meals or get togethers. Maybe we saved some money and a little bit of frustration, but ultimately, cutting out items moved me even further away from any Christmas joy.

A few years into cutting back, nothing seemed familiar. 

Then, several years ago, I started planning ahead. On the 25th of every month starting in August, I sit down for a few hours and plan out our holiday season. The first year or two were time-consuming; figuring out what needed to be done and how I wanted to spend our time wasn’t easy. I also worried that focusing on Christmas so early in the year might actually ruin things. After all, part of what makes Christmas special is that it only happens once a year for a short period of time. 

Truth be told, this organization is what brought the joy back into Christmas. 

The main reason is obvious: planning ahead spreads out the tasks and expenses. So, many of the essential tasks necessary to pull off a memorable holiday can be done well in advance. There’s no reason why I can’t update mailing addresses, purchase stamps and print labels for our Christmas cards in early November. These annual snail-mail gifts of friendship were likely the next task on the chopping block if I couldn’t find a way to tackle the holidays so I started with them. 

What began with organizing the Christmas card process quickly turned into managing other tasks: toys are purged in October; menus, recipes, and decor for holiday gatherings are finalized by early November; and gifts are purchased and recorded on a list all throughout the year.

An unexpected benefit has been that our family actually adds events to the calendar now. While we’re still establishing a few annual traditions, the planning enables us to more easily accommodate last minute invitations or visit exhibitions that may only be available this year.

Last year alone, we hosted an Elf Party, attended the Garden Glow at the Missouri Botanical Gardens, and I gifted my husband with 12 days of craft beer. Each of these experiences were only possible because I planned ahead and ensured the routine and repetitive tasks were done well before December. 

I focus on tasks now and enjoy experiences later.

My worry about ruining Christmas by focusing on it too early was unfounded and the reality has been that I very much relish the anticipation of December because there are so many events and memories to be enjoyed. 

Last year, several friends asked me to help them develop their own holiday planning process. Knowing how I was able to turn around our own holiday experience, I was confident I could help others do the same. Seeing the nearly 50 other individuals post about their planning successes was incredibly rewarding. Their organization throughout the fall months paid off in spades come December and seeing their “sitting by the fire, sipping hot cocoa and watching The Christmas Story with my family” posts solidify that this process works.

Their monthly to-do lists varied drastically, but the end result was the same: a more peaceful and enjoyable holiday season.