Sneaky Money-Related “Shoulds” and the Holidays
The holidays are supposed to be a time of joy—twinkling lights, family gatherings, warm drinks, and a little too much dessert. But for many people, this season also brings a flood of money-related “shoulds,” the kinds of thoughts that instantly tighten your chest and drain the excitement from holiday shopping.
You may catch yourself thinking:
“I should spend more on my family.”
“I should buy everyone the perfect gift.”
“I should be able to afford the holidays without stress.”
In the moment, these thoughts feel factual, but it’s possible that they might be inaccurate. They’re called cognitive distortions—automatic mental habits that create pressure, guilt, and the belief that our thoughts are absolute truth. Oftentimes, words like “should, never, always” can hold inaccuracies that can cause us to feel more internal pressure in some way. When we don’t follow the shoulds we have of ourselves, we feel guilt and shame. When others don’t follow the shoulds we expect of them, we can feel angry or disappointed. The holidays, with their sales, expectations, and comparison traps, are the perfect breeding ground for these shoulds.
Tradition and ritual are positive ways for us to know who we are and where we come from. They help us feel connected to family, our history, and they help us feel a sense of belonging. At the same time, they can carry a lot of unspoken (and sometimes spoken) shoulds that can be rigid to the point that we don’t consider “doing” the holidays differently.
Why We Avoid Looking at Our Bank Balances This Time of Year
Not looking at bank balances is a common money-avoidant behavior and can be exacerbated during this time of year. It’s easy to say to yourself, “I’ll just pay for it in January, when I cut back on my spending” or “I’ll pay for the holidays with my 2025 tax return.” If you’re already feeling the pressure of holiday shoulds, looking at your bank balance can increase that pressure.
Looking at the numbers can feel like an emotional threat - you may worry that checking it will confirm your fears—I can’t afford this, I’m behind, or I’m failing at the holidays.
Avoidance provides short-term relief because you don’t have to face the discomfort. But that same relief allows the shoulds to grow unchecked, making spending more reactive, emotional, and disconnected from your financial limits, values, and reality. Holiday expectations—what you should spend, do, give, host, or provide—create the perfect environment for money avoidance.
It’s easier not to look than to confront the gap between reality and these unrealistic internal rules.
Where Holiday Money Distortions Come From
Should statements are cognitive distortions. Cognitive distortions are thinking habits that give us a false or unfair view of ourselves or the world around us. They may include some truth, but they twist it in an unhelpful way. Over time, these thoughts can quietly repeat in our minds and start to feel normal, even when they are not helpful or true. Holidays are primed to be loaded with potential cognitive distortions—often from family, culture, or past experiences—about what the holidays require. Common holiday money distortions include:
All-or-nothing thinking: “If I can’t afford impressive gifts, they’re going to think negatively of me.”
Catastrophizing: “If I don’t get everything on the kids’ list, their holiday will be ruined.”
Mental filtering: Focusing only on what you can’t afford and ignoring the meaningful things you can offer.
Social comparison: Believing “everyone else is doing more,” based on curated social media snapshots with no context or price tags.
Money already carries emotional meaning. Add in nostalgia, family expectations, and the marketing-fueled idea that expensive gifts equal love, and it becomes easy for your mind to exaggerate what’s necessary – and important.
How We Overestimate the Impact of Giving “Less Expensive” Gifts
A powerful but rarely examined distortion is the belief that a gift must be impressive or high- priced to protect or maintain a relationship. You might fear that:
A smaller gift will disappoint someone
It will look like you don’t care
It will reflect poorly on you
It might change how the relationship feels
These fears often dramatically overestimate the negative impact. The truth is: most people don’t judge your love and care by the dollar amount. And if they do? That’s useful information—not a reflection of your worth. Often, the emotional meaning we attach to the cost is far greater than what the recipient is thinking.
We Underestimate How Much People Understand Financial Boundaries
Most people understand that the holidays are expensive. In fact, many people are relieved when someone else sets a spending limit or chooses meaningful simplicity. But when you’re stuck in a “should,” it’s easy to believe:
Everyone expects you to spend a lot
They’ll judge you for buying less
Others don’t struggle the way you do
These assumptions almost always underestimate the empathy, understanding, flexibility, and relief that recipients have—especially the people who love you.
How to Recognize Holiday Shoulds
A cognitive distortion often reveals itself through emotional cues. If a thought produces guilt, shame, anxiety, or a sense of being “behind,” it may not be rooted in truth—it may be rooted in pressure. Watch for absolute words like should, always, never, everyone else. These are red flags that a cognitive distortion might be at work.
How to Shift Away from the Should
A cognitive distortion is basically a habit of the mind. Changing habits takes time so please be patient with yourself. Just realizing that you didn’t think through your thoughts (even after the fact) is a sign of a positive shift. Depending on the habit and the factors involved, changing habits can take anywhere between days to almost one year. It’s important to approach thoughts with curiosity and openness; without self-judgment or blame. Most shoulds crumble under honest questioning.
When you notice a should in your thinking you can ask yourself questions like:
“Is this a rule I truly believe in, or one I inherited?”
“Would I expect someone I love to follow this rule?”
“What evidence do I have that the holiday will fall apart if I spend differently?”
“What would I tell my best friend if they were having the same difficulties?”
Replace absolutes with flexible, kinder language. Rephrasing can help shift a habit of mind. Instead of thinking “I should spend the same as everyone else in my family” try “I’d like to give meaningful gifts, and their value doesn’t depend on price.” Or “I always overspend” can be changed to “I overspent last year, but this year I’m doing better.”
Thoughts that create pressure like, “I can never say no” can be changed to “I can practice setting boundaries when I need to, and they will still appreciate me.”
Remember that while making these shifts it’s important to stay grounded in realistic steps, not perfection. Think about how long it took you to develop a habit. It will take time to create a new one. Perfectionistic expectations—“I should be done with all of my shopping by December 10th”—create unnecessary stress. Instead try, “I can try to pick up one or two gifts each week. It’s not going to be the end of the world if I have one or two last minute presents to buy.” Small steps keep you connected to your real limits. Buying less doesn’t mean you care less. It means you’re honoring your circumstances instead of forcing yourself into someone else’s standard.
This season, when a money “should” pops- up, try pausing. Write it down. Think about your thought and challenge it. Rewrite it in a kinder, more flexible way. Your holiday—and your stress level—can feel completely different. At the end of the day, holiday spending doesn’t need to be driven by guilt, pressure, or unrealistic shoulds.
When you can recognize distortions and shift toward more grounded thinking, you make space for what truly matters this season: connection, presence, and peace. Learn more about shifting this thinking in my next post: Steps to Recognize and Reframe Cognitive Distortions About Money and the Holidays.