The Working Parent’s Guide To Thriving Through the Holidays

A complete process—with prioritization worksheets—to plan a season of true joy with your family

Donita Brown
Oct 8, 2019 · 14 min read
Photo by JillWellington via Pixabay.

Work-life balance does not exist. It never has, and it never will. This is especially true during the holidays and — believe it or not — that time will be upon us soon.

I believed in this farce and chased the work-life balance life lie, and I lived a cranky and exhausted life—especially during the holidays—until I made a change.

The memories you are making with your family are meaningful each day of the year, but often during the holidays, they feel more urgent. Wanting to have a picture-perfect holiday, though, causes stress and steals your joy.

Every day, we have to decide which item will take our focus, and those can cause either positive or negative stress. But ultimately, it’s up to you to decide which responsibility will have your attention on that day or at that moment. You are choosing the stress of the day.

As parents, there’s even more to choose from, and as the holidays approach, it’s easy to feel overwhelmed. There’s no option but to choose the stress of the day. With preparation, you can define what’s important and what you can say “no” to in order to have a more satisfying holiday season for you and your family.

I developed this system of preparing for the holidays for myself and my own family; now I use it to help others improve their own holidays. It is a special application of the radical prioritization I teach clients in my coaching practice.

Prioritize for Joy

“The world as we have created it is a process of our thinking. It cannot be changed without changing our thinking.” — Albert Einstein

Photo by Austin Distel on Unsplash

Vilfredo Pareto developed the Pareto Principle as a theory of wealth distribution: that twenty percent of the population held eighty percent of the wealth. Since then, the Pareto principle has been a useful way to generalize that, often, most of our actual results are outcomes of a small portion of our efforts.

We can apply this to our efforts during the holiday season, too. Twenty percent of what we do during the holiday season provides about eighty percent of our happiness. Many of us make an enormous effort—that 80% to pull off feats of hospitality, gift-giving, or tradition-keeping — only to feel let down by the results. Then, we’re surprised when something seemingly minor gives us that elusive feeling of joy and happiness.

There’s a lot of holiday noise that we can remove if we have the courage and the intention to do the work to make it better — and the work we need to do is prioritization. The best way to start is to assess exactly where you are now, along with what’s worked in the past—and what hasn’t.

Let’s inspect your last holiday and see what was good about it and what you want to change.

You Are Here Exercise, Part 1

This exercise will set a baseline for your holiday season. Think about the Pareto principle and how it could apply to your last holiday season.

The “You Are Here” flag is where you finished last year’s holiday season. In this section, you will find an example to use in the next paragraph, or you may do this exercise with a blank sheet of paper. The choice is yours.

Don’t let time dull your memories. You may look back and think it was good (and it may have been). I encourage you to dig deep and think about each holiday individually. You can look through old emails from that time last year, or any journals or expense tracking you might have done to help trigger memories of specifics.

Write out on a piece of paper what was great about each of the last holidays in the season, and what you wish had gone better.

Here’s an Evernote template you can copy and use for this exercise (or create one based on the illustration below.) Use the first two columns to list what was good and not so good about previous holidays. (You will use the “Rating” column in part two of this exercise.)

Illustration by the author. You can also copy the Evernote template here:

Your next step is to rate your previous holiday season on a scale from 1 to 4. Put the rating in the last column.

I did not pick the range 1–4 randomly. When we use a scale of 1–3 or of 1–5, you give yourself the ability to stick the holiday in the middle of the scale, robbing yourself of deciding if the holiday was good or bad. By using a range of 1–4, it forces you to decide if your overall holiday experience was good or not.

Here’s how to rank each holiday:

1 — Terrible. Never want another holiday season like this again.

2 — Not terrible, not great. Need to make an improvement.

3 — Pretty good. Could have been better, but it was good.

4 — Best holiday season yet. There was not much which could have gone better.

After you’ve determined the rating of each of your last holidays from the previous year, look at it as a whole and then decide what your entire holiday season was on a scale from 1 to 4. Start by averaging the numbers you gave each of the holidays, and then do a gut check to see if that was appropriate for your season.

In the example below, my average for the six holidays was 2.8, rounded up to a 3. On the scale of 1–4, this is “3 — Pretty good. Could have been better, but it was good.”

Your Best Holiday Season Exercise

After you’ve given your most recent holiday season a rating, your next step is to think about what you think of as your best holiday season.

Think about a year that you would have rated a 3 or a 4 as a whole. Why would you give it that rating? If it was last year, then that’s great. If not, then compare your best holiday season to the previous year and determine what was different.

One of the best holiday seasons I can remember started with a very low-key Thanksgiving spent at a beautiful Tennessee state park with my husband, daughters, and in-laws. No one had to cook, and there was no pressure of cleaning before the dinner or cleaning up afterward. What was most important to my family was being together with no pressure to cook. The entire holiday season seemed to have something for everyone, which was by accident.

I can capitalize on knowing what made that season great and compare it to last year’s holidays. Then, I’m able to ensure that the activities we chose are selected on purpose.

Your best holiday season may be different from mine, and that’s okay. What’s important is that you know what your best holiday was, and use that to purposefully work towards making this holiday season a great one for you and your family.

Family Input

In this next step, you will want to determine what makes your holiday season great — and to ask your family what they would like to do during the holidays.

Often, we may think we know what is essential to our families — and we might be right. However, by asking them, we include them in the decision-making process. Give them a blank book or a sheet of paper and ask them to write what they liked about the last holiday and previous ones.

Here are a few questions to ask:

  • What makes you happy during the holiday season?
  • What was your favorite holiday memory?
  • Why was that your best holiday memory?
  • What have we done in the past that you would like to do again during the holidays?

Once you have the answers to the above questions, you will use it in the next section to help plan your best holiday season yet.

Some of my favorite Christmas memories are the simpler ones, such as holiday drives. Thinking back to my childhood and one specific memory is of our yearly holiday light drive. These drives typically started with an argument of who would sit in the front seat of my Dad’s cream-colored five-speed Jeep Cherokee. With an odd number of kids and one parent, there was always a discussion — really, what could have been a terrible argument — over who sat in the front seat. The person who sat in the front seat got to see the lights the best and got to have a conversation with Dad.

I’m sure those moments of arguments were a nuisance. But what I remember are those moments of awe and wonder at the houses lit up so brightly that we asked, often aloud, at how long it must have taken them to have put their lights on their home! Each year our tradition grew, and the drive got a little longer. Sometimes the houses changed, as all things do, but the tradition was one that built foundational memories. This was a part of our holiday tradition that any of us kids would be sorry if we missed — but that might not have been obvious to my Dad.

This exercise seems like it might be not only informative but also fun (with a little re-wording) to give to non-family. For example, your kid’s teachers, your neighbors, etc. — and if you are giving gifts, this is a great way to get an idea of what gifts would be especially meaningful.

Setting the Priorities: Creating a List

The list you made of you and your family’s must-do holiday activities is the starting place for a plan that includes everyone’s feelings. Take the list from your family in the earlier section and add your own must-do holiday activities for each holiday you choose to celebrate. This list could include elements such as those listed below:

  • Go to a corn maze
  • Go to a pumpkin patch and pick our own pumpkin
  • Go see a big drive-through light display or a holiday light drive
  • Make a holiday decoration or ornament
  • See a holiday play
  • Make a Christmas stocking
  • Stay home and watch a holiday movie
  • Go caroling
  • Make holiday cookies and deliver them

Once you have a list of good possibilities, decide as a family which event or activity is a must-do, nice to do, or “not this year” activity.

Here is an Evernote template you can use for this exercise, or you can use this illustration to create your own:

Also available at

Here’s how to think about the categorization:

  • Must do — the entire family commits to doing these. There should be only as many of these as you know you can safely decide to do together and not miss. A good practice when scheduling activities are to just commit to events which you and your family can attend without feeling stressed. For me, that means there is one must-do item per month or holiday. These are also the events that the whole family will do together.
  • Nice to do — We may do these or may not. Maybe the entire family does not attend.
  • Not this year — we have decided that we will not commit to this activity this year.

Create this list for each holiday your family celebrates. This decision-making activity is one you will want to do each year. If you notice during your holiday season that you missed an activity you would like to do, make sure you put it on a list for the following year. Your holiday list is a work on progress and will change each year based on your past year.

To use a personal example, two of my life goals are to be a seed planter and encourager of others. A seed planter is one who is OK with sharing an idea or doing an activity, they can patiently wait for the outcome to appear, the way a farmer plants seeds for a later harvest.

The holidays are an excellent time for both goals to flourish. Each year, the church I attend hosts a day for the young children of the church to make baskets for our older members. It’s a time when we can plant some seeds and encourage others, as well as be kind to one another. After we make the baskets, we deliver these baskets and visit with the older members. These visits are often heartwarming for all involved. The recipient gets a gift, and time is spent visiting with one another. Those who prepare the basket get more than they bargain, as the opportunity to do something for someone else always nets more than you expect.

Last year, this activity fell on the same day as my company’s holiday party. Logistically we could do both. But doing both would have worn us entirely out. Before I took control of my holiday season, I would have tried to do it all. I would have been exhausted. The result of this would have caused me to be angry with everyone around me, and then I would have been remorseful for being upset.

However, I decided we would not try to do it all. We would do one activity. I don’t have to tell you how difficult this decision was to make. The holiday party for my work seemed essential to my career, yet the baskets and delivering them were the most important to me personally.

Ultimately, I decided the baskets were the most important because they not only helped others, they also helped me feel better and filled my emotional tank.

After we finished delivering the baskets, we were tired but happy and satisfied. And I was glad we had decided not to do both. We went home after delivering the baskets and could relax and relish the day instead of rushing to another event with the pressure to show up. We choose family time over a commitment that was not as important to us.

During the holidays, it is essential to remember your purpose and keep it close to your heart and mind. Also remember what fills each of your family member’s emotional tanks, as it needs to stay filled for each person to have the best holiday season they can!

Your Secret Weapon — The Calendar

Preparing your calendar is a working parent’s most significant opportunity for preemptively reducing stress. In the following section, I’ll give you a few tips to make this season easier by using two types of calendars: an electronic one and a paper one.

I’ve learned that it’s essential to use both to keep yourself and the family on track. The electronic calendar is where you can easily add items from your phone or computer. The paper calendar can be placed strategically where the family can all see it, such as on the refrigerator, in the laundry room, or in the family entryway.

You will want to add the activities your family agreed to do to the calendars.

Electronic calendar

You’re probably already using some sort of electronic calendar—perhaps one that you already share with some family members. Simply add the planned activities to the electronic calendar.

Since you’re probably keeping all of your non-holiday activities in your electronic calendar as well, you’ll be able to use that overall context to resolve conflicts or note situations that require extra lead time for preparation.

Physical calendar

For the physical calendar, I use a dry erase calendar (from Amazon) that hangs in our laundry room. I can quickly see the next 90 days. There are many others that you can buy which are fancier, but this one was inexpensive and easy to use. (Etsy is an excellent place if you want to search for a more beautiful version than mine.)

Whichever calendar you choose, I suggest that it includes at least 90 days. That way you can start with October as the first month, then add in November and December. If you are using the same calendar as I’ve shown below, then you can also add the upcoming January dates to the bottom.

Image via Amazon.

Use a different colored marker to note if the activity on the calendar is a must-do or a nice to do action, as agreed upon by the previous exercise. (You can also use the same font color in your electronic calendar to keep everyone’s mind on the color-coding.)

Why two calendars?

You may ask yourself if two calendars are worth the duplication. I like to “go slow to go fast”, and find that it’s worth doing a little extra work on the front end of a task so you have less work to do later.

I once heard a story about my Dad, from a previous co-worker of his, who said my Dad called himself lazy. I assure you, he is not lazy—but he puts everything back in its place and leaves nothing out of place. My Dad said he was “lazy” because he didn’t like to do the extra work to search for something that was out of place.

If everyone in your family uses an electronic calendar, then I’ll give you permission to skip this step. However, if they cannot, then no, it’s not overkill, and I’d suggest you try it.

My daughters are young and do not have electronic devices with calendar access, but they know how to watch for and add items to the dryer erase calendar I keep in our laundry room. It works very well.

Every so often, I survey the calendar and add the new items to the electronic one. Yes, it’s double entry, but it keeps everyone on the same schedule, and during the holidays this is paramount.

Holiday Planning Guide

Here’s the final tool you have been waiting for. This is how you will prepare for your holiday season. With this guide, you’ll plan out the tasks that need to happen for each holiday, and how much lead time they require.

You will find the template here as an Evernote template. You can use this template as-is, or customize it make it your own. This is what the template looks like, with suggestions for items to include:

You will notice that each holiday has a prompt the day after to reflect on how the day went. This is key to setting up your next year for an even better holiday season. You can use a journal like this, or use any journal of your choice. The point is to capture those reflections right away, so you’ll have them for next year’s planning.

Once you’ve completed your plan, you’ll have several items to note on both your calendars to help you stay on track.

Thrive in Your Holidays

All of these exercises can help you think of the holidays the way a winning marathon runner thinks of a race.

Great marathoners have a detailed training plan. They set expectations for races. They visualize what they want out of the race and how they want to perform. They train before the competition. They map out the course and study the track where they’ll be running. The runner stretches before and after the race. When the race is over, they reflect on the results and adjust their training plan for the next one.

Now is the time for you to consider your own “training plan” for the holidays. Remember to prioritize for the activities that bring you and your family true joy, and give yourself permission to let go of all the rest, relax, and enjoy!

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Donita Brown

Written by

Professor, Working Mom Encourager, and Author:

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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