How to Plan for the Holiday Season

How to Plan for the Holiday Season

It’s easy to go on autopilot during the holiday season, whether that's because we have pain or we're just trying to get through the busyness. How can we be deliberate so that we can enjoy the season? Today we're going to talk about three main points. Number one, we're going to talk about being intentional about time and traditions. Number two, we're going to set ourselves up financially.  Number three, we're going to prepare for the emotions that come with the season.

How can we be intentional about time and traditions?

It depends on how old your kids are and what your custody situation is. If you have older kids, sit down and plan some things out or make a list of everything you want to do, take into account everyone’s schedules. For your list, ask things like, “What are the things that we love most about Christmas? What do we love doing together? What do we want to do with our friends? What do we want to do with other people and how can we make the most of it?” Make a long list then ask, “What are the five things we definitely want to do?” Once you have a list of your favorite things, then you can prioritize those based on the time you have together and get a solid list.

What's so important about what you're saying is that our kids change yet we hold onto the same traditions for years. Getting up early to at a certain point they're like, wake me up at nine or 10. The needs and the thoughts and what people love change as they get older. And so starting the holiday season by having a family gathering or a family meeting and determining what you and your kids actually want to do is a great first step.

Giving your kids a place of input shows them how much of a priority they are. You want to know what they love to do or what they don't care about anymore. They might surprise you, by the way. Your kids may still want to bake Christmas cookies at 18 and 21. But they no longer want to look at Christmas lights. The beauty of having a meeting and being intentional helps you manage their expectations and your own. This can be a way to avoid disappointment, avoid missing out on something that they love or that you love because you can plan ahead according to what you want to do.

Time management is so hard during the holidays regardless of your custody situation. There's Christmas parties, your kids' Christmas parties and there's all kinds of things going on. So, paying attention to time is really important in addition to traditions.

If you do have 50/50 custody, you can create your own tradition that doesn’t involve the kids. And still there are some things you can compromise on too. For example, “I know you don't really enjoy going to see Christmas lights with me, but I really enjoy it. Would you be willing to go with me for 30 minutes?”

The other practical side of looking at time is if you're meeting upfront, not just getting their opinion, but you're actually looking at your schedule and if you're so far out, you can plot out what you'd like to accomplish. You can have conversations early with your ex, which is really important. You can ask, “Is there any way we can do XYZ ahead of time instead of waiting until the last minute when everything gets compressed.” Think about Christmas at the same time you’re thinking about Thanksgiving. Trying to navigate what's on the calendar and what you’ve got to do, is more stressful in the holiday season. Try to think ahead about the childcare you need if you really want to go to a Christmas party. Have some deliberate planning way ahead of time.

It can get a little sticky and emotional, but having conversations with your co-parent about planning is so important too. Ask your co-parent, “How can we best support what's good for our kids during the holidays by having proactive conversations?” You can't control your co-parent, but you can control how you approach it. It's difficult to have these conversations, but you might come to an understanding if you're not in the heat of it.

And don't forget while you're looking at your time and traditions to carve out time for yourself. It's really important to put multiple things on the calendar that you can do for yourself to recharge. It's not just about honoring the family and the traditions. Know that if you're not refilling your tank, especially right now because you're already dealing with everything you deal with on a day-to-day basis, which is overwhelming and there's no margin. Don't neglect yourself because you and your own self-care could be the first thing to go drop off the list, but don't do that.

How can we be more intentional about our money walking into the season?

Planning ahead also includes making a budget for the holiday season. I would get a general ballpark idea of what you think Christmas costs ahead of time. Write down extra expenses like decorations, teachers' gifts, food if you're planning to host a party, all the people on your gift list, if there's anyone at work that you need to buy presents for your kids' friends, etc. Making a list and getting an idea ahead of time can help you set realistic expectations for yourself and for your loved ones. A specific list could go a long way toward reducing stress especially if you love giving gifts and tend to spiral with spending money on gifts.

There's enough time to actually observe your lifestyle as you're living right now and maybe cut out some discretionary spending instead of January or February when you're forced to after overspending. For example, instead of going to Chick-fil-A three times a week, you can eat at home and save the money for Christmas spending. If you’re intentional about what you want to spend, then start stockpiling a little bit on the side so that you walk into it. You're not overwhelmed by either guilt or overspending.

There are also creative ways to increase income. Maybe you have a kitchen table from grandma that you're now ready to let go of on marketplace or you know have clothes that have tags that don't even fit. Those can be sold at a consignment store. Can you get creative and find a way to make a little bit extra that will help Christmas be less stressful?

You could also do homemade gifts. You could go to a craft store and make earrings. Being able to find cheap ways to show someone you care, and show someone you've thought of them goes a long way. And that can obviously also be true with your kids if they want to give their friends a gift, encourage them to make something.

Sometimes you just have to have a hard conversation with your family that normally gets gifts from you. Just let them know this year is tight so you can’t be as generous as you’d like to be. You might only be able to give a $5 gift card to Starbucks. If you have a big family, you could draw names and set a dollar amount. You can make this idea fun by doing a White Elephant theme or saying you can only buy something from a thrift store.

Whatever you decide to do, involve your kids in the whole process. They can bake cookies with you or you can take them to one of those paint-your-own pottery places. You can buy a mug and paint them together. We say more is caught than taught sometimes. The principle is basically not just telling kids what to do, but actually doing it with them because they will catch on, they will emulate, and they'll carry with them.

Teacher gifts can be a big thing. Your kids may go to a school where you feel you get nickeled and dimed to death throughout the school year. One of the things that we've done over the past couple of years that’s helpful for parents on a budget, is we ask all the parents to chip in $10. We pool the money and work together to get a great gift for the teacher. It’s so much better to be able to give a teacher a $250 gift card that we’ve just all collected $10 a piece because it takes a lot of pressure off of trying to figure out what to get the teacher.

It’s also appropriate when we're talking about budget, allowing the holidays to still be a time when you can plan ahead to think about a way to show your kids how to give back to the community by serving in some way. One example is Operation Christmas. It can become something you look forward to. You can't always, but when you can, find ways to incorporate serving others into your holiday conversations.

The bottom line is the holiday is expensive, there's just no way around it. You can be intentional and reduce your stress by budgeting ahead of time, having conversations that are important and saving money.

We all know that Christmas can be one of the loneliest times, but it's supposed to be the most joyful time. It's really both/and because it highlights that we’re not an intact family like we were before, and our kids are missing their other parents because their parents are no longer with us.

How can we be deliberate and set ourselves up emotionally going into this volatile season?

So many people fall into the trap of avoiding your feelings. You're going to be tempted to check out. You're going to be tempted to numb out, push it all down, power through it. But don't do it because it’s going to pop up again at some point. It's never going to leave you until you feel it, deal with it, name it and have people around you who can help you through it, especially in the first few years. Allow yourself to sit in it and cry and feel the grief and the sadness.

The truth is the sorrow and sadness isn’t with you the entire time. You will have joy too. When you numb out you miss the joy. But you can't have the good without going through the bad in a genuine way. We can’t emphasize that enough, especially for those who are in their early years of getting through.

So, you need to prepare yourself to be able to face this. Make a decision to face the pain. It’s an incredible act of self-care to allow yourself to feel your feelings and deal with whatever you need to. Let yourself feel your true feelings and they will begin to dissipate. You can also receive care in the midst of it. You don’t have to go it alone. If you don’t you can end up numbing out through being too busy, overspending, emotionally eating all the Christmas treats and living in regret about it all.

Definitely don't try to do this alone. Since the beginning of our groups, we have this thing that we call a plus one. We encourage people to find a plus one that they can walk this stretch of road with, especially during the holiday season. What does a plus one mean? Plus one is finding someone that is of the same gender that you can call if you need to vent or cry. Someone who can support you and come alongside you.

Support groups are especially helpful during the holidays. So, consider trying to find a plus one to walk this season with you, someone that you can call at any point.

You can reach out now to someone and say, “Hey, listen, the holidays are coming. It's only my second or third year of divorce or it's our first year of divorce. I'm really going to need someone I can reach out to. Will you be that person for me?” You will be amazed at the graciousness of people who respond, especially if you're proactive about it.

A lot of times a person asking someone else to be a plus one feels ashamed to ask or they feel like they're less than or they're defective. To be on the receiving end of someone asking for help is a place of honor. It really is. So don't second guess yourself and think that you're going to come off too needy. You're honoring someone. When you say to them, will you be a plus one? You’re saying, “I'm acknowledging that you've got a little more road underneath you, you've got a little more time. And I could really use someone stronger to lean on.”

The worst part of the holidays that everyone dreads the most is when your kids go with the other parent on Christmas Day. It’s really, really, really hard. Not only are you dealing with the emotional side of it, but you’re alone and if you don’t plan ahead you may have nothing to do. The silence may make you feel grief-stricken. Isolation can be dangerous. Go ahead and plan something that is enjoyable for yourself. There are many ways Christmas day can look like if you know you don’t have your kids. Be proactive and ask yourself, “What am I going to do? Am I going to call my plus one and see if I can come and have lunch with their family? Am I going to sit down and watch a movie and just have some quiet time and treat it like that?”
You can lean into healthy distraction and healthy detachment. Movie theaters are open on Christmas Day. But really getting a game plan so that you aren't caught off guard when your children are gone, the house is quiet, and you have nothing.

Remember to be mindful of what you need. Things are going to be different. They are different. Setting your children up for that reality, setting yourself up for that reality, and planning ahead for comfort in the form of a plus one or a friend. Things are different but they don't have to be bad. It will be hard and sad, but that's different than being bad or horrible. Don’t stay in a place of denial. The first Thanksgiving and Christmas after the divorce or death will be hard. You may cry. That’s a healthy and normal reaction. But it will go better if you’re honest, acknowledge the difference and be realistic.

We put so much pressure on ourselves to get everything right. Things are going to fall through the cracks. Things are not going to be perfect, and that doesn't mean that you're failing at anything. It just means that it's different this year.

Gratitude and serving others can be another way to counteract your sadness and depression. It’s such a powerful antidote to depression. Getting outside of yourself is a really good strategy because a lot of times you feel isolated. Getting outside of yourself is a good strategy to overcome those emotions that feel so overwhelming and lonely.

One of the best ways to do this is by showing gratitude and serving others and thinking of other people. It might be reaching out to another single parent or someone who's not a single parent and just telling them how much you appreciate them. Or focusing on doing something that serves others instead of sitting in your own emotions.


You can't do everything during the holiday season so connect with your kids and maybe even your co-parent and talk about priorities going into the holiday season.

The reality of the holidays is expensive. Budgeting now and being thoughtful of not only what you want to spend but how you can get there, whether it's selling things, a marketplace, or not eating out as much. Be mindful and intentional about your finances going into the holiday season.

Depression goes up during the holiday season, so let yourself feel the pain and the joy is better than going on autopilot, numbing out and missing the joy altogether.

Listener Question

Hi, I am Shonda a single mom. How do I get my child up in the morning when asking nicely doesn't work?

The thing that came to mind is start the night before. When your child is having difficulty getting up in the morning ask yourself, “What do they need?” Instead of asking, “Why are they being so bad or disobedient?” Maybe they’re not getting to sleep on time? Is there a consistent routine? If you really need them to wake up on time, do they have a soothing bedtime routine? Are they getting in bed at a reasonable hour? Are they eating anything too close to bedtime or drinking too much water? or whatever it is that may be interrupting their sleep or their ability to feel well-rested enough to wake up on time.

Also, consider their mental or emotional state. Is there any part of your child's experience that they're avoiding? Is their school environment stressful or is there anything they're having to face that they may want to numb out or turn away from using sleep as a coping mechanism? Get really curious. What will support them in being well-rested enough to wake up in a timely fashion?


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1 Comment

Todd Nail - November 17th, 2023 at 7:50am

I was another one that had a parent that liked to use a water bottle to wake me up in the morning!






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