When Expectations Set Us Up for Heartache
Expectations are tricky things. They sneak in quietly, shape our hopes, and—when unmet—can leave us feeling disappointed, discouraged, or even depressed. As we move toward Christmas and New Year’s, seasons loaded with cultural pressure and emotional weight, it’s worth asking ourselves: What are my expectations? And are they reasonable?
Whether you celebrate the holidays or not, this time of year has a way of stirring up old memories, comparisons, and longings. If we aren’t mindful, we can find ourselves crushed under the weight of hopes we never examined.
A Teenage New Year’s Eve Lesson
New Year’s Eve 1967 is etched in my memory. I was a high school senior, newly dating a boy named Steve. We’d been together about six weeks, and in my mind, that meant we were going to the community New Year’s Eve party as a couple. I could practically see the evening unfolding.
Then, about a week before the holiday, he casually mentioned that he “had” to take someone else out that night—someone he’d asked before we started dating.
I was seventeen. I was devastated. Suddenly I had no plans, no date, and no idea how to handle the disappointment. I spent the night crying in my bedroom, mourning the fantasy I had built up in my mind.
Looking back, I can see it clearly: my expectations—not the situation itself—were what broke my heart. If I had known then what I understand now, I might have prepared myself, adjusted my hopes, and found a way to salvage the evening instead of letting it swallow me whole.
Teenage heartbreak is understandable, but the truth is, this pattern doesn’t magically disappear when we grow up.
The Expectations We Don’t Realize We Carry
Advertising doesn’t help. Commercials tell us what we should want, what we should buy, and how happy we’ll be once we have it. Social media adds another layer—perfect holidays, perfect families, perfect gifts.
But life isn’t perfect. People aren’t perfect. And when we forget that our expectations become rigid, unrealistic, and emotionally dangerous.
Flexibility is what protects us. It’s what keeps disappointment from turning into despair.
The Christmas of the Green Gifts
One of my favorite reminders of this lesson comes from my first Christmas with my husband, Rich. We were dating then, and I was living on a tight budget. His family had a big, enthusiastic gift‑giving tradition, and I stretched every dollar to participate.
When it came time for me to open my gifts, I had a stack of beautifully wrapped boxes in front of me. The first one held green felt‑tip pens. The next: green ballpoint pens. Then green pens with black ink. More green items followed.
And green wasn’t even my favorite color.
Meanwhile, everyone around me seemed to be opening what I considered “real” presents. With each green package, my smile grew tighter. I had expected something personal, something romantic. Instead, I felt confused and, honestly, a little hurt.
Then I opened the final box. Inside was a delicate chain with a small heart and flower. A lovely, thoughtful gift. But I was so fixated on the green theme that I didn’t appreciate it right away.
It wasn’t until later that I understood the meaning behind it all. At the time, I owned a small business called Not Just Plants. Rich associated my work—and my passion—with the color green. His gifts were his way of supporting my dreams.
My expectations had blinded me to his intention.
Today, 44 years later, the “green gift Christmas” is something we laugh about. It’s become one of our favorite stories.
The Heart of It All
Expectations aren’t the enemy. They’re human. But when they become rigid, unspoken, or unrealistic, they set us up for unnecessary pain.
As we move through this holiday season, maybe the gentlest gift we can give ourselves is permission to loosen our grip. To stay open. To let life surprise us. To remember that joy often shows up in unexpected packaging—sometimes even in shades of green.
#yesican Coaching with Karen
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