I was on a plane, sitting next to a woman and making small talk about my job when she asked me where I wanted to go and what I wanted to do with my life.

“I’m not sure,” I said and mumbled something about “so much for small talk” and how it took two years of potato salad, coffee, applications, and interviews to land the job I had now and that my life’s reality hardly ever matched my expectations.

“Well, as long as you have an end goal,” she said and turned back to the manila folder of data in her lap. From our conversation, I knew she worked in healthcare. From her conversations with her coworkers seated around her, I knew she was a leader.

“What’s your end goal?” I asked.

“This is it,” she said. “I made it.”

I looked at the folder in my own lap. At that moment, I was just trying to make it through the flight, the day, the week. I rarely ever think of the next month, let alone the next year. Or ten. Or twenty.

“What do you do after you make it?” I asked.

She looked at me, and I knew that for however confident she sounded and looked, that question bothered her just as much as it bothered me.

Leave it to me to make a conversation awkward.


In (500) Days of Summer, there’s a scene called “Expectations vs. Reality,” and it has to be one of the most painfully relatable moments in cinema. The movie is described as “a story of boy meets girl,” but “not a love story.” Tom is in love with Summer, but Summer is not in love with Tom.

Tom and Summer date. She breaks up with him. She’s okay. He’s not. Time passes, and she invites him to a party she’s hosting, which he hopes will be a turning point in their relationship.

“Tom walked to her apartment, intoxicated by the promise of the evening,” Richard McGonagle narrates. “He believed that this time, his expectations would align with reality.”

They do not.

All the while, Regina Spektor’s song, “Hero,” plays:

He never, ever saw it
coming at all
He never, ever saw it
coming at all
No one’s got it all

“I’m still trying to figure that out,” the woman said. She was kind. She started talking to me shortly after takeoff, when she noticed I was rigid and white-knuckling the armrest. “Afraid of flying?” she had asked, and I had looked at her out of the corner of my eye and said, “I think it’s mostly just takeoff and landing.”

“Almost there,” she had said. “I’ll distract you.”

I think that’s my default for approaching life. Focused on the beginning and end. Setting expectations or goals and chasing them and just trying to get through all the unplanned, messy moments of the plane ride, the day, the week, the next ten or twenty years in between.

But that’s the thing about expectations and goals: They are either met or disappointed in a moment, and everything that comes before and after are moments too.

My life hardly ever goes as expected, and that’s possibility. Over the past few years, I’ve rarely been confident about who I am or where I’m going, but sometimes I make a mental list of all the people I wouldn’t have met if X and Y had happened, and Z had not, and I’m suddenly grateful for the moments of disappointment.  

I look at my expectations from a year, or two, or ten ago and realize that I never would have been able to create a reality so bittersweet, so full of wonder, and drowning in grace.

I never, ever saw it
coming at all.

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