Owning your own business is supposed to give you control. That’s the pitch, anyway. What nobody says loudly enough is that control comes bundled with every expense your employer used to absorb quietly in the background — including the full, unsubsidized weight of keeping yourself insured. For Janine Nakamura, that weight has become something she carries every single month without any sign of it getting lighter.
I first connected with Janine through a Kansas City veterans’ support group that hosts monthly small-business panels for veteran-affiliated families. Her partner, Marcus, is a Navy veteran currently finishing a graduate degree in social work, and Janine had been invited to speak about the financial challenges facing small-business owners in the veteran community. When she started describing a cascade of insurance problems that began with a single property claim, the room stilled. I asked to follow up with her later.
We met a few weeks after that meeting at her daycare, Bright Horizons of Westside — a warm, colorful space near Westport that she has operated since 2019. She made coffee and pulled two chairs to a small table surrounded by miniature furniture, and she walked me through the last two years of her financial life with the patience of someone who has rehearsed the story enough times that the sharpest edges have worn down. She was not bitter. She was just tired.
One Burst Pipe, and Everything Shifted
In January 2024, during a sustained cold snap in Missouri, a pipe burst inside Janine’s daycare. The damage was thorough — warped flooring, collapsed drywall in two rooms, mold remediation that had to happen quickly to protect the children in her care. She filed a commercial property claim for $28,400. Her insurer paid it. Then, six weeks later, she received a non-renewal notice in the mail.
“They paid it, and then they said goodbye,” Janine told me, her voice flat. “No real explanation I could use. Just — we’re not renewing you.”
Her broker found a new carrier, but the new annual commercial property premium came in at $4,100 — more than double the $1,850 she had been paying. That single line item increased by $2,250 per year. On its own, it was painful. Layered on top of everything else, it became the thing that cracked the foundation she’d been quietly building.
The Hole Where a Group Plan Should Be
Janine is 54, self-employed, and has four part-time employees at her daycare — not enough to make a traditional small-group health plan financially workable. That means she has been purchasing individual coverage for herself and Marcus through the ACA marketplace, where premiums are shaped by income, location, and the shifting math of premium tax credit eligibility.
In 2023, her monthly marketplace premium for both of them was roughly $640, partially offset by tax credits tied to their reported household income. By early 2026, that premium had climbed to $890 per month — a $250 monthly jump driven by rate increases and a reduction in their tax credit as the daycare’s net income fluctuated upward one year and the subsidy calculation shifted accordingly.
“I keep the plan because I have to,” she told me. “I’m 54 and Marcus had knee surgery two years ago. You can’t just roll the dice on that. But $890 a month is $10,680 a year just to not be uninsured. And that’s not counting the deductible.”
Her plan carries a $3,500 individual deductible. In 2025, Janine estimated that she and Marcus spent roughly $14,800 combined on health-related costs — premiums plus out-of-pocket medical expenses. That money comes directly out of whatever the daycare generates after payroll, rent, supplies, and the elevated property insurance premium she now carries.
The Compounding Math of Doing It All Yourself
When I asked Janine to lay out her monthly fixed insurance costs before and after January 2024, the numbers told a blunt story.
Over $5,000 more per year in fixed insurance costs alone — with no change in what her coverage actually does for her. Janine’s daycare revenue has remained relatively flat during this period. She told me she earns roughly $185,000 in gross revenue annually, but margins in childcare are notoriously thin once payroll, utilities, licensing, supplies, and now sharply elevated insurance are accounted for.
“Parents are stretched, too,” she said. “I know what it costs to raise a kid. I can’t just pass everything along to them.” She hasn’t raised her rates meaningfully in 18 months, and she knows she’s absorbing costs that are slowly shrinking what’s left for her own future.
Her annual SEP-IRA contributions, which she had been building steadily, dropped from $6,000 in 2022 to $1,500 in 2025. The savings earmarked toward eventually purchasing the building she leases for the daycare have essentially stalled. She’s not in crisis — she’s clear about that — but the forward momentum she once felt has gone missing.
What She Looked Into — and What She Found
Janine has not been passive about any of this. Over the past year she explored several alternatives to her current marketplace plan, and the search itself revealed how limited the options are for someone in her specific position.
One avenue Janine hadn’t fully pursued at the time of our conversation was whether Marcus’s university enrollment might give them access to a student health plan that could cover dependents at a significantly lower rate. She mentioned it herself as something on her mental list — but she hadn’t had the time or bandwidth to call the university’s benefits office. That detail stayed with me. Exhaustion, in her case, had become its own obstacle to solving the problem.
According to Medicare.gov, Janine won’t be eligible for Medicare for another 11 years — she qualifies at 65. That’s more than a decade of individual marketplace premiums ahead of her, in a market that has not shown much inclination toward moderation. She’s aware of it. She doesn’t talk about it much.
The Resignation That Comes With Doing Everything Right
What lingered after I left Janine’s daycare that afternoon was the absence of a villain in her story. She did the things the system says you’re supposed to do. She built a small business. She maintained insurance — property and health both. She filed a legitimate claim, received a legitimate payout, and was still penalized for it. She kept her health coverage even when the premiums made it genuinely painful.
She described herself as sitting in a kind of gap — not struggling enough to qualify for meaningful government assistance, not earning enough to absorb rising costs without consequence. According to Benefits.gov, eligibility for most federal assistance programs is determined by income thresholds that self-employed middle-income earners frequently sit just above. The safety net, in many cases, starts just below where people like Janine stand.
Her retirement picture is the part that worries her most quietly. The SSA’s retirement benefit system is built around lifetime earnings — and years where savings contributions stall, or where business income is consumed by insurance overhead rather than invested, leave a mark that compounds over time. Janine is 54. Every year she can’t add meaningfully to her SEP-IRA is a year that will show up in her retirement math eventually.
“I’m not looking for sympathy,” she told me as I was packing up my recorder. “I just want people to understand that it costs a lot to be your own safety net. It really does.”
She’ll keep the marketplace plan. She’ll keep the daycare open. She’ll keep watching the premiums tick upward each year and making the calculation that staying covered is still better than the alternative. And she’ll do it without an HR department, without an employer match, and without anyone absorbing a single dollar of the bill except herself.
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