How to keep expectations from ruining your fall and winter holidays

by Amy  - October 13, 2021

Do you have perfect holidays? Do your holidays always go as you dreamed?

If so this article is not for you.

It actually took me a long time to figure out how to truly enjoy my own fall and winter holidays. It was my own fault and to understand this we kind of need to go back to when I was a kid.

I had a pair of sheets on my bed as a kid. These sheets had the characters from Peanuts with different sayings in thought bubbles around them. 

One said, “happiness is wanting what you have.”

This phrase has long stuck in my head. 

This phrase actually bothered me a lot when I was a kid. I had divorced parents. I had kind of a lot of unpleasant drama in my young life.

When I read this message on these sheets what I mostly remember thinking was that I did not want much of what I had in my life. 

This was super obvious to me over the winter holidays. 

My parents were divorced before it was super common to have divorced parents. There were fewer resources and it was a little harder to look around and see people who had home experiences like mine. 

I’ve never been a person to engage in the lifelong contest of who has the most suffering. In the past I didn’t talk much about my early life. That’s not going to change much but maybe a little.

Knowing about my life doesn’t really help others.


I have had a few people recently share with me that they were more open to sharing their life story with me because they were aware that I did not grow up in a fairytale. 

Holiday Planning Guide

Nobody actually has a fairytale life.

Not even real-life princesses (which we learned from real life royal Meghan Markle and even the Princess Diana documentaries show us this).

But .. a fairytale story was definitely what I wanted when I was a kid — especially for the winter holidays. 

My parents divorced when I was young. It was a fierce, expensive, ugly divorce. To make things even more of a challenge for holiday vacation plans — they lived thousands of miles apart. 

The nice part of this story is that my parents wanted to be with me and to spend time with me.

I never actually doubted that. I know that’s a big deal. 

The downside of this is that they fought a lot about the holiday custody split. I have about a dozen stories of weird holiday arrangements including a few years where some genius (maybe me but more likely a judge or social worker) decided that the most equitable solution was that I would literally fly on Christmas day between my parents’ homes. 

I still think back to this as an adult and wonder … whose actual idea was that?

Yes … unfortunately …not so merry.

What’s more when I think back to this as an adult it meant that both my parents were setting up for a Christmas holiday that they would only get part of with the kids. It boggles my mind. 

They could have alternated and one could have had a kid Christmas and the other could have gone on vacation to Mexico. Why did they do this to themselves …and to me? Retorical question. I Dunno.

Anyway enough of the Amy story. 

When you are a young kid all you know is what you see.

That’s it. No matter what it is you assume it is normal… it is normal for you because it’s all that you know.

Then at some point you hit an age where you may realize that your family or your lived experience is a little different. This is true for everybody I’ve ever met.

I knew from an early age that my holidays were different. 

For me as a kid once I realized that I then made a decision that in hindsight caused me a lot of aggravation as an adult. I decided that thought that what I saw in the movies and on TV was the real normal and that this was what I wanted.

I made that movie / tv world my expectation. 

That sucked because nobody has a movie or tv perfect life. When I made that my expectation all that meant was that I pretty much guaranteed my own dissatisfaction. Until I made new expectations.

You can have wonderful experiences but still be unhappy if your expectation is unrealistic. 

I used coach people on this in running and triathlon too. If you haven’t run the times to expect a 3 hour marathon …that’s an unrealistic goal. Let’s work with what you actually are doing now.

This can be rough – at least it was rough for me when it came to holidays. Why? Because it took me a while before I realized how unrealistic my expectations were. 

In fact, in many cases you kind of need an outside view to point out that what you might be dreaming of is not realistic.

What’s great about this though is that if  you have realistic expectations it’s pretty easy to have a wonderful holiday. 

I’ll share what I mean. 

What is an expectation?

An expectation is something that we are waiting to happen in a certain way. It can be an expectation of the way that somebody else will behave. It can be the way an event will go. It might be the way a food will taste. It’s a current thought about how the future will go in our mind.

What’s the difference between expectations and goals?

This is a really good question and I’m going to say that the difference normally comes down to the fact that expectations rely on the actions of other people.

Goals are things we do for ourselves.

For example I’m going to write a book. That’s a goal.

An expectation is: Others will want to be my friend after I write my amazing book.

Today I’m talking about holiday expectations. This in my opinion is a source of a lot of aggravation for families all over.

How to know if your expectations are unrealistic

For me the big clue was that I was pretty much always disappointed by anything anybody else did.

No matter what — they could never get it right. 

I wanted magic and beauty and perfection. I wanted no conflict. I wanted a beautiful family with a mom and dad and aunts and uncles and I wanted a laugh track in the background and honestly probably an audience. 

What I got was the human experience which can be magical but is rarely perfect. 

I was the source of my aggravation but it took me a little while to learn that. I mention that because there is a pretty big chance that you might miss this too.

How did I figure out that my expectations were unrealistic?

I learned that my expectations were unrealistic as a part of growing up and realizing that what I was dreaming about nobody could ever make happen. 

Basically, once I became a step-parent and a parent and I had to deal with some of my own nonsense. It became super clear that I was not being realistic.

I really wanted other people to do things differently … and that’s not really how the world works which I had to discover for myself.

I want to help you avoid any of this holiday frustration. 

Sometimes when I talk to people about realistic expectations they think I’m going to crush their inner dreams and make them eat all veggies all day. 

That would only be true if you love veggies. 

Or tell them they have to get along with a relative they can’t stand.

And honestly … you might decide to do that but I’m never going to tell you to do that.

But also I’m not going to tell you that I can magically make your extended family show up on time and dress up and be nice to you and buy the gifts you want them to. I also don’t have the secret to make kids behave on demand.

What I do have to offer is some tools to reduce the drama and help you be happier with the holiday events you plan.

This is about planning and hoping for things that are likely to actually happen.

This is about designing holidays and any day that leaves room for true joy and love.

If you do it correctly making realistic expectations should make everything more joyful and less frustrating

Oh and it’s not about planning earlier or doing even more work. I recently read a whole article about how to have the picture perfect holiday but doing an insane amount of work yourself and planning ahead. This is NOT my advice. If it involves planning earlier … well it’s perhaps time for a new plan.

How do expectations set us up to be happy or unhappy?

Let me give you a very small and not holiday related story about how expectations work. 

Traffic. This is about traffic. Say you set out for a drive to work and you know it’s going to take 45 minutes. You know because it takes 45 minutes most days. 

If it takes 45 minutes. You are fine. If it takes 30 minutes you might be pretty happy. If it takes 2 hours you are probably pretty annoyed. 

There are lots of trips that you probably take that are 2 hours and they don’t annoy you IF you have that expectation to start. It’s the expectation that creates the frustrations. 

And here’s a pro tip…what if you can adjust your expectations at any point. 

How to set realistic expectations for your holidays

This is kind of a crazy question to try to answer because I honestly think that every single family and every single house is probably a little different than every other one.

I can share where I have gone off the rails and seen people step off the rails. 

Why should you listen to me about this. Well you don’t have to. But I do have a pretty big blended family and I’ve been juggling lots of family events for over 2 decades. You can read about my holiday season here.

What if you don’t need to see absolutely everybody in your family at the exact same time.

The big mistake that my parents made that caused me a childhood of holiday misery was that they insisted that they both always had to be with me on the holidays. That wasn’t reasonable because of the distance between their homes. There are a lot of other ways that this can also be true including the death or illness of a member of the family. 

How to deal with this is in my opinion is to just not emphasize the importance of that specific time.

Yes, it can be wonderful to see family members, yes it can be fantastic to get together. 

Enjoy it when it happens but allow that to be great and not critically important. Allow it to be great even if you aren’t actually together. 

In this example having an expectation that it’s still joyful if you don’t see everybody in your family at the exact same time increases your joy. 

This is especially important in blended families.

It’s also okay to not want to be with some people in your family or extended family.

What if you try to release some pressure on the importance of an exact time or day

I think it’s a really good idea to just relax about the overall importance of any given holiday date. Christmas is December 25th. But if you can’t celebrate on that day … let that be okay. If travel gets delayed or somebody is sick allow you and your family the grace to enjoy being and doing whatever on another day. 

A few years ago I realized that on Thanksgiving one of my step-kids was trying to juggle 3 different dinners. This showed up when my husband asked me if I would move the meal time at our house. We had a bunch of guests and I had already told them the time so I asked why and I learned about this plan. 

I smiled because nobody can eat 3 different Thanksgiving dinners. 

I shared with my husband that I wanted to offer the kids the gift of not needing to come to our dinner. He didn’t want to do that at all. He wanted to see them. I mean of course he did — he loves all the kids. I countered with the question that yes, you want to see them but do they actually have to eat with us for us to see them? 

He said no he didn’t actually care if we ate that meal together on that day. 

Right because the eating is not actually the big deal. Keeping our eyes on what is truly important helps us reduce drama. Sometimes.

I suggested that we do a different thing with them at some other point in the weekend … just them and us. He thought that was okay. And that they could come by at any point on Thanksgiving if it worked for them. Just no pressure about the meal time and that this was a gift from us. 

They didn’t eat with us on Thanksgiving but they stopped by and chilled with us with no pressure to eat. If my memory is correct it worked out really well because at least one of the other meals was very delayed and if they had the pressure of our meal it would have been a mess for them. They truly appreciated this gift of not feeling pressured to be with us. 

What if nobody gets you the gift you want

For a while I had this expectation that if my husband and I had a good relationship he would buy me great presents for holidays. 

It never happened. Why? Because there is a second part of this expectation of mine which is that I thought he would just “know.”

My husband is a regular guy and he cannot read my mind. He’s also not great at picking up on gift hints. Actually not any kind of hints…my husband does best with direct communication.

After a few years of ridiculous self-inflicted misery I now have a different expectation which is that I will possibly get a gift on the holidays. That’s it. I’m always happy with that. Even if it’s a silly gift that I don’t really want because he thought of me and that’s all that matters. 

I say probably because sometimes we agree to not get each other gifts on holidays and in reality sometimes my husband mixes those holidays up. So, I don’t tie my happiness to gifts. I don’t need a gift to feel loved or have fun. 

Side note … This gift plan (in my experience) does not work with young kids.

When a small child says they say they want a magic pen that they saw on tv … they want that exact magic pen. That’s it. Kids are frequently very black and white. 

What if you simply allow the holiday magic to unfold – you don’t try to force it?

If you celebrate with Santa Claus you may love the idea of the magic of the season. I know I did.

Kids wake up and magically everything they’ve ever wanted is under the tree for them.

It is wonderful and when you have very little kids it can be super fun.

It can also be a HUGE amount of pressure. One year my young daughter asked for a specific dress for a doll that was totally sold out. 


I found that dress on Ebay. But it was stressful and expensive.

Which is why I suggest that there are a lot of ways to create this magic that don’t come in the form of presents. 

What I want to offer you is that if you are feeling stressed to get all the perfect gifts of a particular special item — for every single person you may want to just let that pressure go.

When you let that go you are opening yourself up to be able to enjoy the holidays even more.

It’s very hard to resist the temptation to feel like you need to buy things for people for the winter holidays but there are lots of other options. If you want some help brainstorming them reach out and let me know.

What if you let go of your picture-perfect holiday vision?

When I was a young girl I had a dream of a TV style holiday where my kids would wake up on Christmas morning and we would all be in a great mood, wearing matching pajamas and the house would be beautiful and the breakfast perfect and the birds would sing and…we’d take a family photo and nobody would have bad breath. You get the idea. Fairytale.

So, while I was super flexible with my step-kids once I had my first kid I actually tried to create that picture-perfect morning. 

I failed…because it wasn’t really possible.

Maybe you can do it and if so Yay for you … this article is for other people.

In reality on my daughter’s first big Christmas she had a cold. 

Fever, drippy nose. The works. And she had no idea who Santa was or what to do with the stocking that I had obsessed over making for her. Also she did NOT want to wear the hat or photo item I had gotten for her. 

Then the whole family was supposed to come over and I made everybody wait to open gifts and my mom was hours late. Ugh…super unhappy step-kids. 

My expectation of a tv-style picture perfect holiday literally caused the stress. 

I worked hard to release that.

Over the years I’ve I worked hard to work with what worked in my house and kept us happy and joyous. This has created some decidedly unique traditions in my house. It turns out that these unique traditions are sometimes our family favorites. 

Releasing Expectations — wanting what you have

Remember when I talked about my sheets as a kid?

They said: happiness is wanting what you have.

My adult coaching tip for that is to focus on what you already have.

Second tip: get clear on what you really truly want.

It’s not always easy to release expectations during the holidays because we are surrounded by marketing and Hollywood images of crazy impossible stuff.

I’m definitely not perfect. 

Each time I have done the work to check in with my expectations and make sure they are realistic  — it has helped me enjoy the holidays more. 

This is why I suggest it.

When I share  my expectations with you it may seem like it’s easy to see what’s going on. 

That’s because it’s in the past. I have already figured it out. That’s why I can share it.

In the moment it’s much tougher. It can also be very tough to do this by ourself.

The story behind the story is that most often we won’t even realize what our expectations even are that are making us unhappy. 

When I was a kid my expectation was that I could wake up and have a family that wasn’t divorced. Not realistic at all but I didn’t know that.

You might have an expectations that your holiday travel will not be stressful. 

When I was a new mom I thought I could create a picture perfect morning all by myself. Not realistic at all but I didn’t realize that’s what I was even trying to do. When I did the deep work I figured out that it wasn’t about the picture at all.

You might have an expectation that everybody will get along or love the gifts you buy them. Or that you will love the gifts that they give you. Not always realistic. 

I needed a bit of help to help me get clear on what I really truly wanted and how to make it happen for myself and my family.

This is how I know other people can be helpful in this process.

You might have the expectation that the weather will be perfect for whatever you want to do (skiing, sledding, surfing … whatever). Mother nature may have a different idea.

It can be very helpful to talk this through with somebody else to help you see where your unreasonable expectations might be hiding. Once you see them the adjustment is sometimes the easy part. Sometimes just talking it out is helpful.

Next steps

You can download my holiday survive and thrive guide below AND if you want you can set up a coaching session with me. 

Training for You

Grab my Steps for Happiness as a Stepparent

What I know about Latke Season


Amy Stone (she/her/hers) is a life coach who helps adults in blended families. She is a mom, step-mom and a step-grandma. Other random fun facts include that She is a 7-time Ironman triathlon finisher and many many marathons and shorter races. She created

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