What You’re Most Expecting Doesn’t Happen Until You’re Least Expecting It

Holiday Expectations by Jann Alexander ©2013
Holiday Expectations by Jann Alexander ©2013

I was so certain I’d have those cowgirl boots under the Christmas tree that year. After all, I’d wanted them really badly last year, I’d made that clear to Santa and my parents and whomever else might have been listening, and they hadn’t appeared. So I’d been extra special good the whole next year, and I was expecting to see those boots as soon as I got to the tree on that snowy 1960s Christmas morning.

The snow was unexpected. For that, my younger siblings and I were grateful. Waking up to snow and Christmas morning brought us shivers of excitement we couldn’t have imagined. We hesitated before sneaking down the stairs, watching a quiet pre-dawn world emerge coated in clean white drifts as it slowly caught light, well aware we were forbidden to approach the tree before daylight.

The Tree. Rarely has such expectation been bestowed upon one single symbol of Christmas abundance. What would be under the tree? How many gifts would there be, how would they be wrapped, would they be large or small, what significance would size impart? How would they sound when shaken? How long could we bear to linger over our imaginings before ripping into them wildly?

My expectation was so certain to be fulfilled. This would be the year of my cowgirl boots, and no doubt, an entire Annie Oakley cowgirl outfit would accompany them.

Expectations: a strong belief that something will happen or be the case
in the future. 
“Reality had not lived up to expectations”


Expectations get me in trouble every single time.

I think a part of my childish brain realized that when the cowgirl boots didn’t appear. But it took my adult heart to understand that expectations—especially holiday expectations—can be so disappointing.

The holidays are the time when our expectations peak—and lead us to see all things magically bathed in goodness, abundance and cheer. We imagine a picture-perfect holiday meal, as painted by Norman Rockwell and rounded out by Hallmark TV, and we’re suddenly getting along swimmingly with family members we dreaded seeing all year long. We see ourselves in aprons, baking scratch-made cookies loaded with fragrant sugary scents, with our family waiting excitedly, jockeying for the piping-hot cookies as we pull them from the oven. The gifts we’ve so carefully chosen are exclaimed over, appreciated, beloved.

Having no expectations opens the world up to
surprising goodness and unexpected treats.


And maybe some of us actually achieve these (fairly unrealistic) expectations. But for those who feel like Sylvia Plath did, when she famously wrote that “If you expect nothing from anybody, you’re never disappointed,” there’s another way I’ve found to enjoy the holidays: Having no expectations. Enjoying myself in the moment, looking neither forward or back.

Having no expectations opens the world up to surprising goodness and unexpected treats. But having unrealistic expectations, as a rule, leads to:

  • keen disappointment in outcomes
  • annoyance at the unexpected
  • feeble attempts to control situations
  • angering others with our controlling habits
  • plotting and planning
  • absolute certainty our loved ones know what we want
  • imagining (wrongly) others’ actions and responses
  • magical thinking that we’ll be recognized as heroic geniuses
  • irritation when we’re not

And having unrealistic expectations, especially at the holidays, leads to big disappointment, surely. But it also leads to an inward anger that others didn’t seem to appreciate what we were offering. Or that what we really wanted wasn’t acknowledged by anyone. So that must mean no one really cares about us. And who needs that, so bah, humbug.

It took me a few decades, after that Christmas of big expectations and even bigger disappointment, to realize that letting go of how I expected things to go would lead to some extremely cool things happening—things that I could never have dreamed up. Mostly they revolved around how I felt when I stopped worrying about what I expected to happen, and started focusing on what might be wonderful to experience if only . . . If only I stopped expecting what to experience. If only this, if only that, can’t exist without expectations, and sets up a predetermined experience with no joy arising from what’s completely unexpected.

And it took me until 2005 for those cowgirl boots to arrive. I’d given up my childish expectations long before. That’s the way it works with expectations—what you’re most expecting doesn’t happen until you’re least expecting it. A check arrived I hadn’t expected. A little bonus from my parents’ estate, though it had long ago been settled. It was just the right amount to buy myself my very first set of cowgirl boots. Santa was looking out for me after all those years. When I least expected it. 

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