He looks at me curiously. “Shouldn’t you be asking Win that?”

I always pull the caregiver aside for a private conversation when I see a client. Sometimes, they notice things about a loved one that I would not—like a shaking hand when reaching for water, or restlessness at night. They’ll tell me if a client isn’t sleeping, if she’s moody, if she’s seeing people who aren’t there. Sometimes a client will put on a brave face and not admit to pain or fear when they’re with me, but a caregiver always tells the truth, because they think it will help me give them the answer to the question they can’t ask their loved one: when and how will it happen?

Anticipatory grief is real and devastating. It can run the gamut from How will I survive alone in the world? to What do I do when the Internet cuts out, because she’s always been in charge of calling the cable company?

“I will ask her those questions,” I tell Felix, “but part of my job is making sure you’re okay, too.” I glance around the entryway, where—scattered among the artwork—are the trappings of illness: a walker, a pair of compression socks, a prescription packet on a side table. “Your whole life has been taken over by cancer, too.”

He is quiet for a beat. “My whole life,” Felix murmurs, “is her whole life.” He glances up at me. “You’ll see. I’ve never met anyone like her. When I think about her not being…here anymore, I can’t picture it. I can’t imagine anyone taking her place. There’s going to be this Win-shaped space when she’s gone, and I’m scared it’s going to be bottomless.” When he stops speaking, his eyes are damp, and he seems startled to find me there. “I’ll show you,” he says.

He leads me into the rabbit warren of the house, which has more twists and turns than I would have expected for a tiny duplex. Win is in the study, where floor-to-ceiling bookshelves spread behind her like the wings of a great eagle. She is moving slowly postsurgery, but still moving, shuffling her feet as she puts a book back in its place. She turns to me, and I instantly mark the effects of chemo and radiation and drug therapies: the paper-thin skin, the slightly jaundiced whites of her eyes. Her collarbones jut out from above the neckline of her shirt. Her hair is soft and downy new growth, like the fuzz of a duckling. Her abdomen is distended with fluids.

“You must be Dawn,” she says, reaching out a hand.

Even in her diminished state, there is a crackling, an energy that pulls focus, so that you cannot help but have your attention drawn right to her. Her eyes are an unholy gold, set against her dark skin. I imagine how magnetic she was before she got sick. Felix never stood a chance.

“It’s really nice to meet you, Winifred,” I say, and I mean it. One of the reasons I love my job is because of the people I meet. True, I lose every single one of them, but in a way that’s why it’s even more important that I am able to get to know them before they’re gone.

“Call me Win,” she says, and she grins. “It’s quite the misnomer, since I apparently won the Death Lottery.”

“Dying is a misnomer. You’re alive, until you’re not.” I slide a glance toward Felix. “Besides, if we’re talking about unlikely labels, his name takes the prize. Felix Morse basically means Happy Death in Latin.”

Win laughs. “I think I like you.”

That is basically the point of this initial meeting—not only to see if my potential client feels comfortable with me, but to see if I feel comfortable with her. In Win’s case, her age is a factor, too. I can’t project myself onto my work, consciously or unconsciously. I can’t serve as a death doula if I’m thinking, What would I want in this situation? Or This could be me.

When I was in Chicago as an undergrad, I volunteered at a domestic abuse shelter. There was a woman there about my age, who had lost her father when she was young, and who had a two-year-old she had to take care of, and she just got under my skin—to the point where I couldn’t sleep unless I knew she had eaten that night, that her son had eaten, and that she was not at home with her violent husband. The volunteer coordinator called me in and told me I wasn’t going to last long if that was how I approached every case. She’s not you, the coordinator said. Since then, I’ve learned to maintain my distance, but sometimes, it’s too hard to do that, and those are exactly the jobs I shouldn’t take. There are boundaries I cannot cross, even in a field that routinely collapses the space between people.

“Why don’t we sit down?” I suggest.

Win and Felix settle on a leather couch, I pull up a side chair. “So,” I start, “what would you like me to know?”

“Well, to begin with, the doctors told me I have less than a month,” Win replies.

I watch Felix’s fingers tangle with her own. “That’s why they call it ‘practicing’ medicine,” I say. “They may give you a certain amount of time to live, but they really don’t know. It might be longer, and it might be shorter. My job would be to make sure you’re prepared no matter what happens.”

“We probably should talk about cost,” Felix says.

“We will,” I reply. “But not at this visit. This is really just a first date. Let’s see if we’re compatible—and then we can start planning our future.” I won’t decide whether to take on a client (or let a client hire me) until the second visit. That first encounter needs to settle.

I turn to Win. “How are you feeling today?” I always start with the physical, and then move on to emotional well-being.

“I’m up,” Win states. “I showered.”

I understand what she is telling me: today is a good day. There are some where a client isn’t up to leaving bed, or putting on clothes.

“Is there any swelling around the surgical site?” Win shakes her head. “How about your hands and feet?”

The questions follow a pattern: Do you have any pain? Are you warm enough? Have you eaten today? How have you been sleeping? I ask Felix if hospice has provided them with a morphine kit—a comfort measure that stays in the refrigerator, along with other meds, in case they are needed immediately, before a hospice nurse can arrive.

“Do you feel like you have the support you need?” I ask.

Win looks at Felix, a whole conversation caught between them. “I do. But I wish he didn’t have to. It’s not fair to him.”

“It’s not fair, period,” Felix mutters.

“Let me tell you what my role is, as a death doula,” I say, leaning forward. “I’m here to assist you and make sure your needs are met right now. I can help you with anything that’s left undone—I can work with you to plan a funeral; I can help you organize your will or your finances; I can clean your garage if the clutter is driving you crazy. I can comb through a storage facility if there’s a picture in there of your grandmother you really want to see. I can take you to see an opera one more time, or read Fifty Shades of Grey out loud to you. I can organize your social media accounts so that your friends know you’ve died, when the time comes. I can help move you outside, so you can watch the birds.”

I deliver this the way I always do: matter of fact, no sugarcoating or pretending that death is not inevitable. “Is there anything you don’t do?” Felix asks, joking.

“Windows,” I reply, and grin. “For real, though—medication. I can’t prescribe it and I won’t administer it. That’s up to you. So are diaper changes, if and when necessary. I will help with a bedding change or a wheelchair transfer, but that’s really the job of a caregiver and it’s a liability for me if I’m alone with Win.” I turn to her. “All you have to do is tell me what will create greater peace for you, at any given moment, and I will do my best to make it happen.”

She stares at me, unblinking. “Will you be here when I die?”

“If that’s what you want,” I say, “then yes.”

The room settles around us, a cocoon, and inside it we have already begun to change. “How will you know when that will be?” Win asks softly.

“I’ll be in contact with your medical team. And there are signs and symptoms that the body is shutting down.”

Win continues looking at me, her eyes narrow, as if she is weighing her next words. “I like you,” she says finally. “You don’t bullshit me.”

“I’ll take that as a compliment.”

“You should,” Win says. “How did you get into this business, anyway?”

“My mother died in hospice, and it turned out I was good at helping people prepare for death.”

“You must see some crazy sad stuff.”

“Some of it’s crazy sad,” I admit. “Some of it is just crazy.”