Your Thirty-Day Coverage Plan

Knowledge without a sequence decays into anxiety. This lesson is the sequence: thirty days from deciding to leave, or from the layoff you did not choose, to coverage that is running and a file that proves it. Work it in order and the guide compresses into an afternoon, a phone call, and a screening session. If you are leaving on purpose, this sequence nests inside a bigger one: sequencing the quit owns the whole leave-well calendar, severance to runway to the fork, and this lesson is the coverage slice of it.

Days one to three: establish the anchors

Before anything else, get the two dates everything hangs on. Ask HR in writing:

Please confirm in writing: the exact date my health coverage ends, the date the COBRA election notice will be mailed, and my plan's total monthly premium, employee and employer shares combined.

The first answer anchors every window in "Every Deadline in One Place." The third number is your COBRA price from "COBRA, Priced Honestly" before the paperwork exists. While you are in the conversation, ask whether payout of unused PTO extends the coverage end date, because sometimes it does.

Put both anchor dates in your calendar with three alarms: the marketplace 60-day close, the COBRA 60-day close, and a day-40 checkpoint before either expires.

Days four to seven: price the doors

One evening, in this order. First, the spouse-plan call from "The Spouse or Parent Plan": 30-day window, incremental cost, in writing. Second, the marketplace screener with your income estimate from "Estimating Income Without a Job" built honestly, whole calendar year, net of business expenses. Third, write the three results on one page: spouse tier, marketplace premium at your metal choice, COBRA at 102 percent.

The lanes now sort themselves.

If your income is under your state's Medicaid line from "Medicaid and Your State's Line", lane one: apply for Medicaid this week. It is the only door with no window, the cheapest by far, and the application is its own answer.

If your income is between roughly $16,000 and $62,600 and no spouse plan beat the price, lane two: enroll in the marketplace plan now, this session, and upload the proof of coverage loss. Pick silver if you are under 250 percent of poverty for the cost-sharing reductions. Do not elect COBRA yet, and keep its notice in the file for the backstop play from "The Sixty-Day Decision."

If your income is over the cliff, or a spouse's affordable offer blocks subsidies, lane three: choose deliberately between full-price marketplace, the spouse tier, and COBRA on total value, network, and deductible, not premium alone. COBRA earns its premium only when your treatment or your plan's richness justifies it, and now you can prove which is true.

Days eight to fourteen: enroll and document

Whichever lane, this week is enrollment week. Marketplace: select the plan, upload the loss proof the same day, screenshot the confirmation page with the effective date. Spouse plan: the form goes in, with the email confirming the per-paycheck cost and the effective date. Medicaid: application submitted, documents uploaded, confirmation number saved.

Start the file. It holds: the coverage termination letter, the COBRA election notice, every enrollment confirmation, the premium number, and the income estimate with its pieces. This file is what turns any future dispute from your word against a bureaucracy into a settled question. It takes twenty minutes to maintain and once, maybe twice, it is worth thousands.

Day forty: the checkpoint

The calendar alarm fires. Marketplace enrollment done and coverage started, or on a known start date. COBRA window still open for its remaining weeks if you are running the backstop. Spouse form cleared with the effective date in hand. Income estimate still honest against what the business has actually done, and updated on the marketplace if it has drifted.

November, every year

Open enrollment is your annual repricing, and a founder's income moves more than an employee's, so treat it as a standing appointment: re-run the screener with the year's real numbers, re-check the metal choice against the business's trajectory, and re-file the estimate for the new year. The system resets every November 1, and so does your power to reprice.

One lesson remains: where this guide ends and deeper help begins.