Case Study 1 — Jordan: What He Was Already Grieving

The Recognition

The chapter on grief arrived at a moment when Jordan had been doing, for approximately fourteen months, the most sustained self-examination of his adult life.

He had been, through therapy with Dr. Nalini, through the sleep work, through the exercise structure, through the habit changes, through the ongoing conversation with Dev — building a different kind of self-knowledge than the intellectual self-analysis he had practiced for years. Not smarter about himself. More honest.

The grief chapter added a dimension he had not expected.

He read the section on developmental losses: the losses that come simply from growing up and moving through life. The freedom of childhood. The body of youth. The potential futures that close when other futures are chosen. Mid-life is frequently a time of this kind of grief: not for something that has gone wrong, but for what was given up in the process of building a life.

He stopped reading.

He was 34. Not mid-life by most definitions. But the chapter's description matched something he had been circling without naming: the specific quality of the children question with Dev, the occasional feeling of having moved too quickly through the early chapters of his life without fully inhabiting them, the sense that the road behind him had closed in a way he hadn't really authorized.

The Anticipated Grief

The children conversation with Dev was in its eighth month of being ongoing.

Not a stuck conversation — not an argument, not an avoidance. Both of them were genuinely working. Jordan had been in therapy working on what his fear actually was (loss of control; fear of loving something he could lose). Dev had, he suspected, been working on their own version of the question, though they hadn't said so explicitly.

But the conversation was producing, Jordan noticed, a specific kind of anticipatory grief.

If they decided not to have children — or more precisely, if Jordan decided, because he was the one who didn't know — he would grieve a version of his life that included them. A future that had been held as possible and was now foreclosed. He would grieve Dev as a parent, which he had observed in his imagination enough times to have a specific, feeling-laden picture of.

If they decided to have children — if he arrived at something that felt like genuine choice rather than concession — he would grieve the life without them. The simplicity of what they currently had. The freedom. The particular quality of his relationship with Dev unmediated by parenthood.

He had not previously had language for this. The grief chapter's concept of anticipatory grief — grief for losses that have not yet occurred — named something he had been experiencing without knowing what to call it.

He brought it to Dr. Nalini.

"I've been grieving both outcomes," he said. "Before either has happened."

"That's a very precise observation. What does the anticipatory grief tell you?"

Jordan thought. "That I care about both. That the stakes are real. That this isn't a decision I'm treating lightly."

"Anything else?"

A pause. "That I've been waiting to feel certain before I move. And the grief — the fact that both directions have grief in them — suggests certainty was always the wrong thing to be waiting for."

Dr. Nalini: "Say more."

"If there's grief on both sides, I can't wait for the option that doesn't grieve me. There isn't one. I've been waiting for a costless choice, and this is an inherently costly one."

"That's a significant shift in how you've been framing it."

"Yes."

The Sunday Morning Conversation

Three weeks later, on a Sunday morning, Jordan and Dev were in the kitchen — the kitchen that had become the place where their significant conversations tended to happen, the way that some rooms become the designated rooms for certain kinds of honesty.

Dev was making coffee. Jordan was sitting at the counter in a way that was, he was beginning to recognize, the posture of someone who had decided to say something rather than continue thinking about saying it.

"I want to tell you something about the children question."

Dev set down the coffee and turned around.

"I've been waiting for a version of the answer that doesn't have grief in it. And I've realized there isn't one. If we have children, I'm going to grieve the life we have now. If we don't, I'm going to grieve the possibility of them. The grief doesn't tell me the answer. It just tells me this matters."

Dev was quiet for a moment. Then: "I know."

"I'm not ready to say what I want. I'm ready to say I'm working on it with less fear than I was before. The fear of wanting it because wanting means being vulnerable to loss — that's real, but I'm less inside it. I can see it."

Dev sat down across from him. "Can I tell you something I've been sitting with?"

"Yes."

"I've been grieving too. For the version of us that doesn't include parenthood. Even though I think I want it." A pause. "I didn't have language for that until now. I was treating my certainty as evidence that I should be ready and you should be ready. But I've been grieving too."

Jordan looked at Dev for a long moment. "We've both been carrying the same thing in different packages."

"Yes."

"I think we need to have a different conversation than the one we've been having. Not 'do we want children' as a yes/no question. More like — what would we want our life to look like? What are we building together? And children as a question inside that."

Dev: "Yes. That conversation."

Jordan: "I don't know what I'll say when we actually have it."

"Neither do I."

"But I think I'm actually in it now."

The Grief for Edward

In June, Jordan's father Edward had a cardiac event — not a heart attack, a warning arrhythmia that was caught and treated, but that required a cardiologist, a medication adjustment, and a conversation about monitoring.

Jordan flew home for a weekend.

The visit was practical: Edward was managing fine, the medical situation was being addressed, no immediate crisis. But Jordan found himself, on the drive back from the airport, in a grief he hadn't expected.

Not anticipatory grief for Edward's death — not yet. Something more specific. The grief of seeing the version of his father who was mortal in a way that had previously been theoretical. Edward had always been, in Jordan's mental map, a fixed point — the achievement-demanding, emotionally cool, structurally reliable presence of his childhood. Not immortal. But not mortal in this immediate, particular-medical-appointment way.

He sat in his parents' living room with his father for an afternoon, which was an unusual thing for them. Edward, characteristically, wanted to discuss the financial implications of the medical situation. Jordan, more unusually, let that conversation proceed for a while and then said: "Can I ask you something that isn't about the logistics?"

Edward: "Of course."

Jordan: "What do you wish you had done more of? Not career, not achievement. More personally."

A silence that, in Jordan's childhood, would have been deflected with a subject change. This one wasn't.

Edward: "I wish I had been less afraid of things being uncertain. I spent a lot of time managing the uncertainty out of situations. It made me effective and it also made me miss some things."

Jordan thought about everything he had read, done, worked on in the past fourteen months.

"I know what you mean," he said.

Edward looked at him. A different quality of looking. "You're different than you were two years ago."

"Yes."

"Better?"

Jordan thought about the therapy, the sleep, the runs, the conversation with Dev about the grief inside both outcomes. "I think so. More — present, maybe."

"That sounds like something your mother would say."

"She'd be right."

What Jordan Understood

The grief chapter contributed a lens that unified several threads Jordan had been working on separately.

The anticipatory grief for both outcomes of the children question had been producing a frozen quality — waiting for certainty that would never arrive. Naming it as grief — as the natural response to the loss embedded in both directions — unfroze something. Not the decision, but the ability to be inside the question without trying to escape it.

The visit to Edward had produced something harder to name: the recognition that the father he had been measuring himself against for his entire career — the person whose praise he had sought and whose model he had alternately followed and resisted — was also aging. Was also carrying something he hadn't named until a direct question opened it.

He wrote in his journal:

The grief I've been most afraid of — the grief of losing things I love — turns out to be present already. Dev. Edward. The life I have now. The futures I might choose. All of it is temporary, and I've been managing that fact by not looking at it directly.

The chapter's phrase: "grief is love with nowhere to go." I think I've been withholding love as a preemptive defense against the grief that comes when what you love ends or changes. The therapy has been, among other things, learning to let love in before you know how it ends.

I don't think there's a way to avoid the grief. There's only a way to stop avoiding it.

Discussion Questions

1. Jordan recognizes "anticipatory grief" on both sides of the children question — grief for having children and grief for not having them. The chapter argues that certainty was always the wrong thing to wait for. What does this insight suggest about major life decisions that involve unavoidable loss in both directions?

2. Jordan and Dev discover they've been grieving different versions of the same question. How does naming the grief — putting language to what was previously a wordless weight — change the conversation they're able to have?

3. Edward's response to Jordan's direct question — "I wish I had been less afraid of things being uncertain" — is a significant moment of intergenerational disclosure. How does Jordan's extended work on his own anxiety and self-examination create the conditions for this kind of conversation with his father?

4. Jordan's journal entry: "I've been withholding love as a preemptive defense against the grief that comes when what you love ends or changes." How does this connect to his anxious attachment patterns (introduced in Chapter 15), and what does it suggest about the relationship between love, vulnerability, and grief?

5. The chapter notes that even welcome changes — promotions, moves, new relationships — involve grief for what is ending. Jordan has been promoted, expanded his role, and moved through significant psychological transitions over 14 months. What losses has he been carrying through all of these changes, and how does acknowledging them change the picture?