One dripping Saturday morning, I climb aboard The Soulmate, the smallest of the boats docked at Friday Harbor, and cram into the cabin with my two friends, three tourists from Texas, and Captain Bill.

Captain Bill sits us down and turns to stare outside. Losing his gaze in the horizon where overcast sky meets choppy waves, he stands silently for a few minutes; when he finally speaks, his voice is slow and low and gravelly—just as I imagine Captain Ahab’s would be.

“Usually when I take people out,” Captain Bill says, “I know where we’re going. I know where the whales are. But I’m not gonna lie to you. I don’t know where any whales are this mornin’.”

I stare at my friend, Ashley. Erika and I had flown into Seattle the day before for Ashley’s wedding the next weekend and, knowing that Erika and I both have a vociferous love for whales and a desire to see them outside of the tanks of Sea World, Ashley took us whale watching.

Ashley returns my gaze and shrugs her shoulders. We had been friends—and then roommates—for four years during college, and we can have conversations without speaking:

You found this guy online, huh?
The reviews said he was really good.
I feel like I’m on a soap opera.

Captain Bill turns his attention away from the sea gulls and pelicans of the Pacific Northwest and back into the tiny cabin.

“Now,” he says. “I don’t wanna be out there with a root canal. So if we don’t see any whales, and you’re gonna pout about it, I prefer you get off now.”[1]

No one moves to get off. Maybe because there’s still a chance we’ll see whales. Maybe because some small part of us, whether we know it or not, is afraid of what Captain Bill might do if we actually take him up on his offer and leave our reservations behind in favor of taking more certain chances in the no-refund business of whale watching.

He stares at each one of us, waiting for us to change our minds, but when we remain, he says, “Good.” Then he takes our money.

Captain Bill starts the motor and we begin a slow journey through the harbor and out into the salty ocean water surrounding the deltas and islands of Washington. As we gain speed, The Soulmate hits waves and skips like a stone, and I grip the edge of my seat and watch the coniferous pines and steel bedrock and foggy sky. Erika and I exchange worried glances—neither one of us is sure if we should get our hopes up.

I don’t feel excitement as I did when I was a child, and I’m certain it’s a consequence of disappointed hopes and faith gone awry. As I grew taller, I learned that falling down hurt a lot more, and as I grew older, I learned that the higher my hopes climbed, the harder I hit bottom. It’s not so much that I’m unwilling to take risks; it’s much more that I approach every opportunity expecting the worst. It’s like petting a dog while constantly expecting it to bite.

As The Soulmate travels farther and farther away from its dock in Friday Harbor, the less likely it seems that our tourist crew is going to see orcas that morning. Every time Captain Bill stops to pull out his map or to radio one of the larger whale watching boats, I talk my hopes down.

I do this so often in life: when I apply for jobs, when I step into a new role, when I meet a spectacular someone.

“Life is full of disappointments,” Steve Carell’s character tells his nieces and nephews in Dan in Real Life, but I wish I didn’t let disappointment define my perspective. Because, well,  it’s true that I’ve experienced more rejection letters and emails than I can remember. It’s true that those roles I take on aren’t always what I was expecting, and I fumble around awkwardly wondering what I can offer. It’s true that sometimes the fall is hard, and I get hurt.

But it’s also true that sometimes things work out.

Sometimes Captain Bill ends a radio conversation and changes direction with a new speed and the expectation of meeting a pod of orcas kissing the sky and crashing back into the deep, blue-gray tourmaline ocean in white water splashes.

And that change of direction, that new speed, feels so good.

[1] If you think Captain Bill is good, he gets better. He also wrote a novel called Sunset Run available for purchase on Amazon. Read the description. You won’t be sorry.

Cassie Westrate

Cassie Westrate (’14) graduated with a double major in writing and international development studies. She currently lives in West Michigan, where she works as a writer, hangs out with her pet bird, and fights crime by night. Just kidding about the crime.