At your old job, health insurance was just handled. You picked a plan during onboarding, money came out of your paycheck, done. Then you got your real estate license, left the W-2 world — and discovered there's no HR department for independent contractors. This guide is the benefits packet nobody handed you, and it starts with the one deadline that matters most.
The clock is already running: your 60-day window
Losing employer coverage is a qualifying life event. It opens a Special Enrollment Period (SEP): you generally have 60 days from the day your employer coverage ends to enroll in an ACA marketplace plan — no waiting for the annual Open Enrollment period. You also typically have at least 60 days to elect COBRA. Miss both windows and you could be uninsured until the next Open Enrollment, exposed to every medical bill in between.
Step 1: Know your two real options
Option A — COBRA: keep your old plan, pay full freight
COBRA lets you continue the exact plan you had, usually for up to 18 months. The catch is the price: you pay the entire premium — your old share plus everything your employer was quietly contributing — plus up to a 2% administrative fee. Agents are routinely shocked by the number, because they never saw what their employer paid.
When COBRA makes sense: you're mid-treatment with doctors you can't switch, you've already hit your deductible this year, or you need a short bridge before other coverage starts.
Option B — an ACA marketplace plan: usually the price winner
Marketplace plans are real major medical coverage — essential health benefits, pre-existing conditions covered, an annual out-of-pocket maximum. And because premium subsidies are based on income, a lean first year in real estate often means a substantial subsidy. Many new agents find a marketplace plan dramatically cheaper than COBRA for comparable coverage. Compare both with real numbers before you decide; don't default to COBRA just because it's the path of least paperwork.
Step 2: Estimate income you haven't earned yet
Marketplace subsidies key off your estimated full-year household income — and this is where new agents get anxious, because who knows what they'll close in their first year? Three rules keep you out of trouble:
- Count everything for the calendar year: W-2 wages you already earned before leaving, expected net commission income (after expenses), and a spouse's income if you file jointly.
- Make a good-faith estimate, then update it. When a big closing lands, log in and revise your income estimate. Updating mid-year adjusts your subsidy going forward instead of piling up a bill for tax time.
- Understand the reconciliation. Subsidies are reconciled on your tax return. Underestimate badly and you may repay part of the subsidy. The full mechanics — and why lumpy commission checks make this a realtor-specific problem — are in our guide to ACA subsidies on commission income.
Step 3: Pick the plan by the number you could survive
On thin first-year cash flow, the temptation is to sort by lowest premium and click the top result. Resist it. The number that matters most is the out-of-pocket maximum — the worst-case total you'd pay in a bad year. One unexpected hospital visit can wipe out months of commissions; ask yourself honestly which out-of-pocket maximum you could actually absorb, and buy that plan. If you're healthy and building an emergency fund, an HSA-eligible high-deductible plan can pair low premiums with a tax-advantaged savings account — a structure that keeps paying off as your income grows (see the S-corp and HSA strategies guide).
Step 4: Ignore the texts
Within weeks of your license going active, your phone will start buzzing with "as a Realtor, you qualify for special health coverage" messages. Those are marketers scraping license-lookup lists, not NAR, not your board, and usually not real major medical insurance. The full story of what NAR does and doesn't offer — and every legitimate coverage route — is in Where Do Realtors Get Health Insurance?
Your first-60-days checklist
- Confirm the exact date your employer coverage ends — the 60-day SEP runs from that date.
- Get your COBRA election notice and the real monthly price.
- Build a good-faith full-year income estimate (all sources, filing-jointly spouse included).
- Compare COBRA vs. marketplace plans on premium and out-of-pocket maximum, with your subsidy applied.
- Check that your doctors and prescriptions are in-network for any plan you're considering.
- Enroll before day 60. Set a reminder for day 45 as your personal deadline.
- Calendar a mid-year income-estimate review, or after your first big closing — whichever comes first.
Want a second set of eyes before you enroll?
A free 15-minute review with a licensed advisor — your COBRA number vs. your marketplace options, with your real income situation on the table.
Start My Free Coverage ReviewFrequently asked questions
How long do I have to get health insurance after leaving my job?
Losing employer coverage is a qualifying life event that opens a Special Enrollment Period — generally 60 days from the date your employer coverage ends to enroll in an ACA marketplace plan. Separately, you typically have at least 60 days to elect COBRA. Miss both windows and you may be stuck waiting for the annual Open Enrollment period.
Is COBRA or a marketplace plan better for a new agent?
It depends on your situation, but the honest starting point is: compare before you default to COBRA. COBRA keeps your exact plan and any deductible progress, but you pay the full premium with no employer contribution. A marketplace plan with a premium subsidy — especially in a low-income first year — is often substantially cheaper. COBRA tends to win mid-treatment or late in a deductible year; the marketplace tends to win on price.
How do I estimate my income for subsidies if I haven't closed a deal yet?
Make a good-faith estimate of your full calendar-year income from all sources — W-2 wages already earned this year, expected net commission income, a spouse's income if you file jointly. Then update your marketplace estimate whenever reality changes, such as a big closing. Subsidies reconcile on your tax return, so a badly low estimate can mean repaying part of the subsidy later.
What should I look at first when choosing a plan on thin cash flow?
The out-of-pocket maximum, not the premium. Ask: if the worst year happened, could I survive this number financially? A slightly higher premium with a survivable out-of-pocket maximum usually beats the cheapest plan whose worst case would wipe out months of commissions.