Your Four Doors

Every quit conversation about health insurance is really a conversation about four doors. You will walk through exactly one of them, and choosing well is mostly a matter of knowing which doors are even open to you before you fall in love with one. And if income has to start moving while you price them, bridge income while the doors are priced is a question with its own guide; this one owns only the coverage.

Door one: COBRA, the same plan at full freight

COBRA is the law that lets you keep your exact employer plan after you leave, at your own expense, generally for up to 18 months. Your doctors stay. Your deductible progress stays. Your formulary stays. The price of that continuity is that you start paying the whole premium, the part your employer used to pay plus a 2 percent administrative fee.

COBRA fits a narrow slice of quitters well: people mid-treatment with a specialist network they cannot leave, people with a surgery already scheduled, and people who want a bridge of a month or two with zero surprises. For everyone else it is usually the most expensive door, and the single most common mistake is electing it by reflex on the way out. We price it to the dollar later in this guide.

Door two: the marketplace, your own plan with subsidies

The ACA marketplace is where you buy your own coverage, and the reason it deserves first attention is the subsidy. Depending on your income for the calendar year, the government pays part of your premium directly to the insurer, and can also shrink your deductible. A marketplace plan is the default door for most people leaving employment, which is why this guide spends more time on it than on any other door.

Door three: somebody else's plan

If a spouse's employer offers family coverage, losing your own coverage opens a 30-day window to join it. If you are under 26, a parent's plan is legally required to take you back. This door is often the cheapest and always the least paperwork, which is why it deserves a phone call before anything else. It also carries a trap: a spouse's plan that passes the federal affordability test can disqualify you from marketplace subsidies even when you decline the coverage. That trap gets its own treatment later in this guide.

Door four: Medicaid, the income door

In most states, an adult with low income qualifies for Medicaid at essentially no premium. For a founder living on savings while a business ramps, this door is more relevant than corporate employees ever expect, because what matters is your taxable income for the year, not your net worth or your dignity. In ten states this door is nailed shut for most adults, and the gap it leaves is the ugliest fact in American health coverage. Who qualifies where, and what counts as income when your income is a brand-new business, gets its own treatment later in this guide.

The fake fifth door

You will see ads for short-term health plans promising major-medical coverage at a third of the price. These are not the fifth door. They are a different product wearing insurance clothing: no guarantee of covering what you already have wrong with you, dollar caps on what they will pay, and in several states a flat ban on selling them to you at all. Their federal rules have also been in flux since 2025, which tells you something about what you are buying. I do not tell you never to buy one. I tell you to buy one only after reading what these plans actually are, a subject this guide returns to later, because the pitch never includes the exclusions.

The doors at a glance

| Door | Typical fit | Typical monthly cost, single, 2026 | The way it traps you | |---|---|---|---| | COBRA | Mid-treatment, need the same network | About $793 | Priciest default; locks you out of marketplace until it ends or open enrollment | | Marketplace | Most people leaving a job | $0 to $625 depending on income | Subsidy cliff just over 400% of the poverty line | | Spouse or parent plan | Anyone with access | Varies by plan; often $300 to $600 | 30-day window; can block marketplace subsidies | | Medicaid | Low taxable income, expansion states | Near $0 | Not available to most adults in 10 states |

Those four cost figures are each derived and sourced in the lessons that own them. The table is a map, not a verdict.

Here is the sequence I recommend, and it is the sequence the rest of the guide follows. Call the spouse's employer first, because a yes there ends the conversation. Run your marketplace numbers second, because subsidies make it the usual winner. Hold COBRA as a decision you are allowed to defer for 60 days rather than make on your last day. And know your state's Medicaid line before you assume anything about it.

The first door to price properly is the one everybody overpays for: COBRA.