Just Lost Your Employer Coverage?

Ryan Michalek, Licensed Health & Life Insurance Agent, NPN 21043091. Last updated November 8, 2026

Just got laid off, or your last day is set and your benefits end with it? If COBRA is on the table, the COBRA cost and deadline calculator shows what keeping your old plan would run and when your election window closes. Then call or text me at (813) 833-7448, book 15 minutes, or send the short form, and I'll compare your routes before a gap starts.

I answer my own phone, evenings and weekends.

Your 60-day window

Whether you were laid off, quit, had your hours cut, or retired early, losing employer coverage is generally a qualifying life event. That typically opens a special enrollment period of about 60 days to pick a new plan, and coverage can often start the first of the following month. Miss the window and you may have to wait, so it's worth acting early.

COBRA isn't your only option

COBRA lets you keep your old plan, but you pay the full premium yourself, which is often a shock. As an independent broker, I compare COBRA against ACA marketplace plans and private under-65 coverage side by side, so you can see the real trade-offs instead of defaulting to the most expensive one, and there's no fee to work with me. If you've never had to buy health insurance on your own, here's how the marketplace and private plans compare. If your COBRA election notice has arrived, you can work out your COBRA cost and election deadline in about a minute.

Not long ago a family came to me through an existing client, right after the husband was laid off from a role in the legal field. His wife is self-employed, so there was no spouse's plan to fall back on, and the COBRA quote to keep the whole family covered was brutal. Because they were healthy, we were able to put them on a private plan that cost a good deal less than COBRA and carried them through the gap, until he landed a new firm position that came with benefits. That's the whole idea: keep the family covered well, without overpaying, for exactly as long as you need the bridge.

• A clear comparison: COBRA vs. marketplace vs. private coverage
• Move quickly to line up coverage before a gap
• PPO-style options so you can often keep your doctors
• One licensed advisor who handles the paperwork with you

A plain-English summary, not a quote, a promise of coverage, or tax advice, so confirm anything tax-related with your CPA. What fits depends on your health, income, doctors, and state, and I’ll walk through your real options with you at no cost.

What do wealthy people do for health insurance when they’re unemployed?

Most buy their own coverage rather than go without. If severance or investment income keeps your household income for the year above the subsidy line, the usual choices are COBRA, which keeps your old plan for up to 18 months after a job loss at up to 102% of the plan’s full cost, or a private under-65 plan, which is medically underwritten and often comes with PPO-style networks; a marketplace plan stays open to you too, at full price, or with a subsidy if your income for the year lands under the line. I set all three side by side on your numbers, and the COBRA cost and deadline calculator shows what keeping your old plan would run.

The weeks after your last day: what arrives, and when

Losing employer coverage comes with a paper trail, and knowing what's supposed to show up, and when, keeps you from waiting on a letter that's running late. These are the federal deadlines as I checked them on November 8, 2026:

• Your employer tells the plan. After a job loss or a cut in hours, the employer has 30 days to notify the plan administrator (29 U.S.C. 1166).
• The plan tells you. The administrator then has 14 days to send your COBRA election notice. Add those together and the notice can take about six weeks to arrive, which is why I'd never let the mailbox set your schedule.
• You decide. You get at least 60 days to elect COBRA, counted from the later of the day coverage ends or the day the notice comes. Your marketplace window runs on its own clock: 60 days after coverage ends, and on HealthCare.gov you can apply up to 60 days before.
• You pay. The first COBRA payment is due no earlier than 45 days after you elect, and after that a premium paid within 30 days of its due date counts as on time (29 U.S.C. 1162).
• A spouse's work plan closes first. If you'd rather join a spouse's employer plan, federal rules only require it to give you 30 days after your coverage ends to ask (29 CFR 2590.701-6). Call their HR in week one.

Why the COBRA number looks so big

The plan didn't get worse, you're just seeing its real price for the first time. In KFF's 2026 Employer Health Benefits Survey (published October 22, 2026), the average family premium was $28,303 a year and the average worker paid $7,471 of it, about 27%. Single coverage averaged $9,804, with workers paying about 18%. COBRA hands you the whole premium plus up to 2%. So if you're comparing ACA plans after losing employer coverage, or a private plan, that full price, not your old paycheck deduction, is the number to set them against.

If you lost coverage when your spouse passed away

First, I'm sorry. Health insurance is the last thing anyone wants to sort out in that stretch, and you shouldn't have to figure it out alone.

If your coverage came through your spouse's job, or you were both on the same plan, losing it is generally a qualifying life event. That typically opens a special enrollment period of about 60 days to choose a new plan. If it was an employer plan, COBRA generally lets you keep that same coverage for up to 36 months after the covered employee's death, though you'd usually pay the full premium yourself.

A few dates are worth knowing, even if you don't act on them right away:

• The employer has 30 days after the death to tell the plan, and the plan then has 14 days to send you a COBRA notice (29 U.S.C. 1166, checked November 8, 2026).
• You have at least 60 days to elect COBRA, counted from the later of the day coverage ends or the day the notice arrives. If you elect and pay, coverage reaches back to the day it ended.
• Your marketplace window is 60 days from the loss of coverage. HealthCare.gov also counts a death in the household as a qualifying event when it ends your marketplace plan.
• If you're 65 or older, Medicare is the conversation, and I'll connect you with a Medicare partner I trust.

You don't have to decide everything this week, but it's worth one calm conversation before the window closes, so you know your real options side by side: COBRA, a marketplace plan, or private coverage. There's no fee, and if keeping what you have or a marketplace plan is the right call, I'll tell you so. It's my own phone you'll be calling, evenings and weekends included, because none of this happens on a schedule.

Leaving the military: TAMP, then what comes next

When you separate from active duty, regular TRICARE ends. If you qualify, TAMP gives you and your family 180 days of transitional TRICARE coverage, starting on your separation date (TRICARE, page updated May 15, 2025). After that you need a plan of your own, and the time to set it up is before day 180, not after.

TAMP isn't automatic for every separation. TRICARE lists who qualifies, including involuntary separations under honorable conditions, members taking separation pay, and Guard and Reserve members leaving after more than 30 consecutive days of active duty for a contingency, so confirm your status with your personnel office before you count on it.

Your options when TAMP ends

• CHCBP. TRICARE's Continued Health Care Benefit Program is premium-based, lasts 18 to 36 months depending on who you are, and has to be bought within 60 days of losing TAMP (TRICARE, page updated September 21, 2026). Guard and Reserve members may be able to buy TRICARE Reserve Select, which starts after TAMP.
• A new employer's plan, if your next role is a W-2 job with benefits.
• A marketplace plan. TRICARE counts as qualifying health coverage (HealthCare.gov), and losing qualifying coverage generally opens a 60-day special enrollment window. My marketplace partners handle that enrollment.
• A private under-65 plan, often worth pricing for officers and families moving into consulting or their own business who are healthy and expect to earn above the subsidy line. It's medically underwritten, so approval isn't automatic.

If you're heading into 1099 contracting or starting a company after you get out, your first year's income is often hard to predict, which makes a subsidy estimate tricky; the self-employed guide walks through that part. VA health care eligibility is a separate question for the VA. I'm glad to map the whole handoff with you before your separation date, at no cost.