Woman-owned · Independent · Licensed in 11 states
Nobody wakes up wanting an HMO. They turn 26, change jobs, have a baby, retire. Find what's happening in your life below and we'll show you what changes for your coverage, which windows open, and where to go next.
Each card below starts with an "I'm ..." statement. Find the one that sounds like you, read what changes for your coverage, and follow the links for the details. Most life changes open an enrollment window that closes on a schedule, so the worst move is usually waiting. If two cards apply at once, retiring and moving, say, just call us and we'll untangle the overlap for you.
Aging off a parent's plan is a qualifying life event, so you do not have to wait for Open Enrollment. You generally get a 60-day window to pick your own plan on the ACA Marketplace, and depending on your income you may qualify for premium help that makes coverage cheaper than you expect.
Marriage is a qualifying life event with a 60-day enrollment window. You can join one spouse's plan, keep separate coverage, or shop the Marketplace together. If either of you gets a subsidy, the math changes, because your household income now includes both paychecks.
Birth and adoption are qualifying life events, and coverage for the baby can start the day they arrive. You have a window, generally 60 days, to add them or change plans. It is also the moment most parents get serious about life insurance, because someone now depends on your income.
Leaving a W-2 means leaving employer benefits, and replacing them yourself. Marketplace subsidies are based on your estimated self-employment income, which most new 1099 workers overestimate. Depending on your situation, your health premiums may also be tax-deductible, which changes the real cost.
Losing job-based coverage opens a Special Enrollment Period, generally 60 days. Before you sign the COBRA paperwork out of reflex, compare it to a subsidized Marketplace plan. With no paycheck, your income estimate may qualify you for significant premium help, and sometimes COBRA still wins. Run both.
The moment you hire, benefits become a recruiting tool and a budget line. Depending on your headcount, the right answer might be a small group plan, a level-funded plan, or handing HR and benefits to a PEO. Each has a different cost curve, and the wrong fit is expensive to unwind.
Your Medicare decisions start before your birthday: the Initial Enrollment Period spans seven months around the month you turn 65. If you fund an HSA, timing matters even more, because contributions must stop before Medicare starts. Starting the homework a few months early is the difference between choosing and scrambling.
Retirement runs on two clocks. Medicare: once your employer coverage ends, you generally get an 8-month Special Enrollment Period to pick up Part B without penalty. Social Security: full retirement age is 67 for most people retiring now, and the age you claim changes your check for life. Decide both on purpose, not by default.
Eligibility can arrive at 65 or earlier through disability, and the first plan you pick is not a forever decision. Every year, the Annual Enrollment Period runs October 15 through December 7, when you can switch Medicare Advantage or drug plans for the following year. Networks and drug lists change annually, so an unreviewed plan quietly drifts.
Helping a parent usually means three jobs at once: reviewing their Medicare plan each fall against their current doctors and prescriptions, getting the legal paperwork in order so you can act for them, and finding a team you can call when something breaks. You do not have to be the expert. You just need one on call.
A move to a new coverage area is a qualifying life event for Marketplace plans and can open a Special Enrollment Period for Medicare Advantage and Part D too. Networks and plan menus are county-specific, so the plan that fit perfectly in one ZIP code may not exist in the next. Check before the boxes are unpacked.
For most Marketplace qualifying life events, marriage, a birth, a move, losing coverage, the Special Enrollment Period is 60 days from the event. Some windows also open 60 days before a known loss of coverage, so you can line up the new plan with no gap. The clock starts whether or not you notice it, which is why the first call should happen the same week as the life change.
No. Losing job-based coverage is a qualifying life event, so you get your own 60-day Special Enrollment Period and can enroll right away. Open Enrollment, which for 2026 federal Marketplace coverage ran November 1 through January 15, is only the window for people without a qualifying event. Just do not let the 60 days lapse, because then you generally are stuck waiting.
If you kept working past 65 with employer coverage, you generally get an 8-month Special Enrollment Period for Part B, starting when the employment or the coverage ends, whichever comes first. Drug coverage runs on a shorter clock, so do not use all eight months before sorting out Part D. And COBRA does not count as employer coverage for this purpose, a detail that catches people every year.
For Marketplace coverage, you generally wait for the next Open Enrollment unless another qualifying event comes along. For Medicare, missing your window can mean late enrollment penalties that, depending on the part and how long you waited, may last as long as you have Medicare. The fix is cheap: one call when life changes, so the windows get used instead of missed.
Marriage, kids, a business, aging parents: Kate has planned coverage through her own family's life stages, not just her clients'. Whatever is changing in your life, she has probably walked someone just like you through it.
Tell us what's changing, a birthday, a job, a move, a retirement date, and we'll map the windows that open, the deadlines that matter, and the options that fit. One free conversation, no pressure.
We do not offer every plan available in your area. Currently we represent 10 organizations which offer 90 products in your area. Please contact medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.
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