Older siblings have a knack for imparting wisdom—whether you ask for it or not. For me, my big sister Tara has spent a lifetime trying to convince me to set the bar low when it comes to my expectations in life, all in an effort to avoid disappointment.

“If I wake up and imagine I’m going to have the worst day ever—a bird will shit on my head, and everything that can go wrong, will—then if it actually happens, I’m not upset or surprised. I expected it! But if something, anything, happens to go my way, well then—I’m euphoric with joy!”

I’ve always found her advice a bit morbid and depressing and therefore never fully adopted her mindset—but I have to admit, I keep getting disappointed.

Reality vs. Expectations

*Mat and I, overly confident as we head to a job fair in Bangkok, January, 2025*

The gap between reality and expectations is one of life’s most persistent frustrations. And lately, it feels like the universe is putting me through a masterclass on the subject.

Let me be real with you.

My husband, Mat, and I quit our jobs last June, thrilled to spend a year traveling together. Having just gotten married the previous April, we called this “our one-year honeymoon.” Indulgent? Absolutely—but it felt well-deserved.

We’re both international school teachers, and we believed that couples without children are highly sought after in the international teaching world. Schools usually provide housing, flights, and health insurance, so hiring a child-free couple saves them money. Add that to our combined 15+ years of experience, and I was pretty confident heading into the recruitment season.

We started the job hunt in October. I was certain we'd land something by February—March at the latest.

Well, it’s April now.
And we have no work lined up.
And yes, that freaks me the hell out.

The Universe Keeps Testing Me

It feels like life is hammering this lesson into my head—hard.

*Seeking shelter from the rain. Dinagat, Philippines, 2024*

Take our six-week trip to the Philippines, for example. We rented a motorbike, planning to road-trip down the stunning coastline of Mindanao. I pictured endless sun, crystal-clear waters, and lazy beach days.

It rained.
Every. Single. Day.
Torrentially. For three straight weeks.

Reality vs. Expectation.

Or the time we returned to my favorite surf spot—a rare paradise with small, unintimidating waves and barely any crowds. Perfect, right?
Of course, a massive swell rolled in the same week we arrived. The waves were so big and powerful that I could hardly get past the break. So I sat on the beach with a book, sulking like a child.

Reality vs. Expectation.

Truth is: I was being a brat. Complaining about what exactly? That I was funemployed? Traveling the world with my best friend? Living the literal dream?

It hit me:

When our expectations outpace reality, we stop appreciating what we already have.

We compare our present to some imaginary “better version” of how things should be—and that robs us of joy.

The Answer? Gratitude.

The antidote to unmet expectations isn’t to expect nothing. It’s to practice gratitude for what’s already in front of us.

When I notice that reality isn’t matching my expectations, I try to shift my focus. I’ll remind myself of the little things:

The shade of a tree on a scorching day.
A warm cup of coffee in my hands.
Fresh fruit to start the morning.
The fact that I have the freedom to be on this adventure in the first place.

It’s a practice—not a perfect one—but it's helping.

Why We Struggle With Expectations

Expectations are a natural part of being human. We make predictions based on past experiences, cultural norms, and societal pressures. And social media has only made it worse.

We’re constantly bombarded with carefully curated highlight reels—perfect morning routines, “flawless” relationships, and dreamy work-from-home setups. It’s easy to start expecting that our lives should look like that too. But reality is messy, unpredictable, and rarely Instagram-worthy.

Letting Go of the Script

So where does that leave me? Still jobless, still figuring it out—but working on appreciating the ride.

The one thing I know I can expect, is for life to be unpredictable. So I need to find peace in that. We all do.

What About You?

Have you ever struggled with unmet expectations? How do you handle that disconnect between reality and what you hoped for? I’d love to hear about it in the comments.

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Reality vs. Expectations: Why Life Rarely Goes as Planned & How to Handle It