Open enrollment for many private disability and life insurance plans typically closes in the spring, and with April deadlines approaching for several major group plan windows, the question of coverage — or the lack of it — is landing harder on families who have put it off. Grace Nakamura, 38, has been putting it off for three years.
When I met Grace at a coffee shop in Portland’s Alberta Arts District in mid-March, she arrived in the kind of unhurried way that suggested someone genuinely at peace with slowing down. She ordered a matcha latte, settled into her chair, and then, almost immediately, said something that contradicted the whole impression: “I wake up sometimes at 2 a.m. and just lie there calculating what would happen to us if Marcus got hurt.”
Marcus is her partner of nine years. He earns $140,000 annually as a senior software engineer. Grace earns roughly $18,000 — split between yoga instruction at two Portland studios and income from her wellness blog. They have a seven-year-old daughter named Wren. They have no life insurance policies on either of them, no private disability coverage, and no will.
The Trade She Made — and What It Cost
Grace spent eight years in corporate HR before leaving in 2022. She managed benefits programs for a mid-size tech firm, which, she acknowledged with a dry laugh, makes the irony of her current situation fairly pointed. “I literally used to explain open enrollment to other people,” she told me. “I knew exactly what short-term disability was, what the elimination period meant, all of it. And then I just… walked away from all of it.”
When she left, she also walked away from employer-sponsored health insurance, a group life insurance plan with a $200,000 death benefit, and long-term disability coverage that would have replaced 60% of her salary. At the time, she and Marcus calculated they could absorb the loss. He had coverage through his employer. They figured her income was supplemental anyway.
The problem, as Grace explained it, is that over three years, the framing never changed — even as the reality did. Marcus’s income now covers 100% of the household’s fixed costs: a $2,400 monthly mortgage, car payments, Wren’s school expenses, and groceries. Grace’s $18,000, after self-employment taxes, contributes to savings and discretionary spending. But there’s no formal cushion beneath any of it.
The Disability Gap Most Families Don’t See Coming
Grace’s anxiety centers less on death — “I try not to go there,” she said — and more on disability. This is actually the statistically more likely scenario. According to the Social Security Administration, more than one in four of today’s 20-year-olds will experience a disability that prevents them from working before they reach retirement age. The figure doesn’t shrink dramatically by age 38.
Marcus has short-term disability coverage through his employer, which would replace approximately 60% of his salary — roughly $84,000 annualized — for up to 12 weeks. After that, long-term disability coverage would kick in at the same replacement rate, but only after a 90-day elimination period. Grace ran through this math for me with the fluency of someone who has done it many times in her head.
The emergency fund question is its own chapter. Grace estimated they have roughly $11,000 in a joint savings account. At their monthly fixed expenses, that’s less than three months of runway if Marcus’s income disappeared entirely. The standard benchmark cited by many financial literacy resources is three to six months of expenses — and Portland’s cost of living means their monthly burn rate is closer to $6,500 when all fixed costs are included.
The Conversation They Keep Not Having
What struck me most during our conversation wasn’t the financial gap itself — it was the reason it hadn’t been closed. Grace and Marcus, she said, have a philosophical difference about money that keeps the conversation stalled.
“Marcus thinks about money in a very protective, accumulate-and-hold way,” she said. “I think about it more like, we have enough right now, and obsessing over what might happen creates anxiety that costs us in other ways. I genuinely believe that. And I also know that belief has left us exposed.”
She paused, looked at her matcha. “Both things are true at the same time, and I don’t always know what to do with that.”
The will is perhaps the starkest example of this. Oregon, like most states, has default intestacy laws that would govern the distribution of assets if Marcus died without one — but those defaults may not reflect what the couple actually wants, particularly regarding guardianship of Wren. According to the Oregon Revised Statutes on intestate succession, a surviving domestic partner’s rights vary depending on whether the relationship is legally recognized, which adds another layer of complexity for unmarried couples.
What the Numbers Actually Look Like Without a Net
I asked Grace to walk me through the worst-case scenario she actually plays out in her head. She didn’t hesitate — she’d clearly thought about it in detail.
If Marcus became permanently disabled and could no longer work, the household income would drop to her $18,000, plus whatever Social Security Disability Insurance he might qualify for after a waiting period. According to the SSA, the average SSDI benefit as of early 2026 is approximately $1,537 per month — but workers must typically wait five months after the onset of disability before benefits begin, and the application and approval process can take much longer. The SSA reports that initial SSDI applications are denied roughly 67% of the time at the first level of review.
“I’d have to go back to corporate,” Grace said flatly. “Which, fine — I could do that. But I’d be doing it in crisis, probably selling the house, and Wren would be seven years old watching all of it happen.” She exhaled. “I don’t say that to be dramatic. That’s just the math.”
Where Things Stand Now — and What Grace Is Sitting With
When I asked Grace where she and Marcus were in actually addressing any of this, she gave me an honest answer: they’d had two conversations in the past year that went nowhere. One ended in a disagreement about priorities. The other got interrupted and never resumed.
She mentioned that a friend had recently gone through the process of getting a term life insurance quote and found it less expensive than expected — somewhere in the range of $30 to $60 per month for a healthy 38-year-old male seeking a 20-year, $500,000 term policy. Grace said she’d looked at similar numbers online and found herself “weirdly relieved” by them, then did nothing with the information.
“That’s kind of where I live,” she said. “Researched and relieved and still not done anything.”
At the end of our conversation, I asked Grace what she’d tell someone in a similar position — a partner who earns significantly less, a household riding on one income, a pile of avoided paperwork. She thought about it for a long moment.
“I’d tell them the avoidance isn’t actually peaceful,” she said. “I feel the anxiety anyway. I just feel it at 2 a.m. instead of in a conversation with my partner. That’s not a better deal.”
She picked up her matcha. “I genuinely don’t know how to fix the philosophical difference. But I think I’m going to try to separate that out from the actual logistics. Like, we don’t have to agree on what money means to both get our names on a will.”
When I left the coffee shop, the April deadline for enrollment in Marcus’s supplemental voluntary life insurance plan — something Grace had mentioned in passing, still unacted upon — was about two weeks away. Whether they’d act on it was something I genuinely didn’t know. Grace didn’t either.
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