Welcome to Tough Love. We’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Small Game and Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsideinc.com.
After my dad died, I heard “Southern Cross” by Crosby, Stills, and Nash on the radio, which is about making a big sailing trip after a divorce. And I thought, that’s what I should do! I feel like in times of grief, it’s natural to want a big project. And so I bought books about young and inexperienced sailors making solo trips around the world.
I thought I should sail from Portland, Oregon, where I live, to New Zealand, where my dad’s from. It would be a journey to try to understand someone who’s not around for me to try to understand anymore.
When I told my friend about my idea, she said, “I really support you, but I think you’re going to die if you do that. Please don’t die alone on the ocean on a boat.” She may have had a point—I haven’t sailed since I took a sailing class in sixth grade, and I didn’t like it.
Now it’s been two years. The trip remains an idea and I still have all those books, but I’m more focused on other parts of my life, like my work and my garden. When I drive over bridges in Portland and see ships on the river, I wish I could be on one of them. Because it’s easier to think about taking a grand journey than it is to take a sailing class. How do I honor the impulse to do something big even though, when it comes down to it, I don’t actually want to do it?
It took me a long time to get pregnant, and when I finally did, it didn’t stick. I told myself: this loss is okay, because I’ll get pregnant right away after this, right? I have to. That’s how stories work. Things get hard, and they get harder—but then there’s a crack of hope, just when the protagonist needs it most.
But it didn’t happen. The journey to parenthood felt random and unfair, with brave hopes that didn’t pan out and sorrows with no resolution. With each setback, I thought: this must be the moment that things turn around. Now, I thought. Now comes the happy ending.
But it didn’t come yet.
Wait—that means it must be coming now.
Nope.
I tried stuff. Is this a story about wilderness? OK: I’ll go alone to the woods, plunge into a river, come back cleansed and ready to bring life into the world.
Nope.
Is this a story about God? I’ll pray.
Is this a story about art? I’ll throw myself into work. I’ll write another book.
But none of those stories played out. At least, not in the ways that I planned them. And that made me feel more helpless than ever.
Eventually, I did have a happy ending, or at least a happy middle. But there was no clear, straightforward story I could tell myself that explained the difficulties along the way. By the time the good news came, I was so weary of hope that I didn’t let myself trust it for a long time.
The process showed me how much I’ve leaned on storytelling in my own life, and how much that instinct can backfire. Stories are, after all, threads of meaning in a chaotic world—and if finding them gives us comfort and control, losing them does the opposite.
I tell you this because you sound like a storyteller, too. And it sounds like you’re looking for a story to tell yourself about grief. A story in which you cross the wild sea and come out the other side healed.
There’s an easy answer here, which is that you should take a sailing class, or buy a ticket for a boat ride, or rent a kayak for the day. It might be fun. You might hate it, which is OK, too. That said, I don’t think the sailing class will fix you, because I don’t think you’re actually looking for a trip across the sea. I think you’re looking for a story with an ending that finds you far from where you started.
I’m hesitant, now, to use stories to predict what’s next in my life, but there’s incredible power in identifying them in retrospect. And I think that by writing your letter, you’re already a good chunk of the way there. You’re figuring out your story, even though you’re still home in Portland. You’re moving forward with it every day. So what’s the story that feels true to you, now? What’s the story that helps you live with your grief?
I’ll try writing one for you. If it feels wrong, change it. If it feels right, take it. Use it to launch your ship.
After my dad died, I became obsessed with sailing.
I dreamed of sailing to New Zealand, where he was born.
I wanted answers in the sea.
I looked at the water every time I crossed a bridge.
But instead, I found myself planting vegetables.
Seed by seed.
In my mind, I sailed. I caught the wind.
It rained.
The seeds sprouted.
I think, in a way, I’m already on the journey.
Not to find home, but to make it.
Not to seek answers, but to grow them.
