The holidays are nearly here, and while some people dread fruitcake and family small talk, nothing spikes the blood pressure quite like open enrollment. Whether you’re at a Fortune 500 with an org chart longer than a CVS receipt or clocking in at a rom-com-worthy, locally owned flower shop, this is the moment when HR (if you have one) starts sending links and forms and expects you to know your PPOs from your HMOs.
For family caregivers, open enrollment isn’t just about finding the cheapest health plan or deciding if you’ll finally spring for vision coverage. It’s the once-a-year chance to peek under the hood of your benefits and plan for what’s coming — including the very real possibility of caring for aging parents (if you aren’t already).
Consider this our company-wide memo to move your well-being to the top of the to-do list. Caregiving usually doesn’t send a calendar invite and if and when the time comes, you don’t want to be left scrolling through your HR portal decoding acronyms. Open enrollment is your chance to prepare now so you already know which benefits have your back.
Unlike the colleague who keeps setting meetings that could’ve been emails, we actually help. The Gray Monster team spoke with the HR experts (you know, the humans who actually are resources) and pulled together some good-to-knows and caregiver centric questions to help you make informed enrollment decisions.
Got questions about Medicare’s open enrollment period that kicks off October 15th? Hold your alphabet soup horses — we’re roping in that Q&A next week. This Sunday is all caregiver core.
ICYMI (in case you missed it)
🎤 At his Santa Barbara show, Paul McCartney turned back time with a virtual duet of “I’ve Got a Feeling” alongside a projected image of John Lennon, reminding us that some friendships, and some songs, never really end.
📜 Just in time for open enrollment, the Medicare & You 2026 has hit mailboxes across the United States. Jump scare, it’s 125 pages long, making it the most comprehensive resource guide out there.
▶️ Dr. Jane Goodall, founder of the Jane Goodall Institute, UN Messenger of Peace and world-renowned ethologist, conservationist, and humanitarian, passed away from natural causes at the age of 91.
Benefits Maxing
Sure you know everything about Mom’s Medicare but are you as familiar with your own employer-sponsored benefits? Outside of the “two annual cleanings with an in-network dentist” most of us don’t know what’s hiding in our HR portals until we desperately need it. Here’s a rundown of what to look for and how to ask about the potential support you might need. Reading the below feels like another job? Skip the bottom for Gray Monster’s HR for caregivers checklist.
📊 The Stats (a.k.a. Why This Matters)
53 million Americans provide unpaid care to family, friends, or both.
60% of them are working while they do it.
The Family and Medical Leave Act (FMLA) covers about 56% of U.S. workers — but only offers unpaid leave. That’s up to 12 weeks off with job protection, but no paycheck. Military caregiving gets up to 26 weeks.
Thirteen states + D.C. now offer mandatory paid family leave systems. Another 10 allow voluntary plans through private insurance. Translation: depending on where you live, you might have wage replacement to soften the blow.
🧾 Your Employer-Sponsored Benefits: What to Look For
FMLA & State Leave Laws
Confirm if you’re FMLA-eligible (company size, hours worked, tenure matter).
If your state offers paid family leave, figure out how much wage replacement you’d get — and for how long.
Employee Assistance Programs (EAPs)
These aren’t just for counseling. Many include caregiver resources, referrals, and legal/financial consults. Ask your HR team what’s included and how to access it.
Flexible Work Options
Can you flex hours, shift to remote, or compress your week? Even partial flexibility can keep you afloat during high-care months.
Health & Insurance Perks
Others offer dependent-care FSA dollars or stipends you can redirect toward eldercare.
Many companies offer employer-paid long-term care insurance. A meaningful benefit worth learning more about should the caregiver become the patient.
🧠 What to Ask HR (Before You Need It)
“What caregiving benefits does our company offer — beyond the basics?”
“Does our insurance cover eldercare resources or care navigation platforms?”
“What’s the process for requesting flexible work tied to caregiving?”
“If I need to take leave, how much notice do you require and what documentation do I need?”
Remember, HR stands for human resources but if you don’t communicate with them, they won’t feel human nor resourceful. HR can’t help if they don’t know what you’re managing. Caring for aging parents while working is hard enough without adding “benefits detective” to your résumé. Do yourself a favor: audit your employer perks now. Screenshot policies. Save HR’s number. Ask the questions you want to know. Because when the call comes — and it likely will — you’ll want to be spending time with your Dad, not deciphering Section 3, Paragraph 4 of your employee handbook.
What’s Good
Helpful care-focused finds we’ve identified and researched so you don’t have to.
No job-based insurance plan? You’ve still got options. If you or the person you’re caring for don’t have health insurance through an employer, HealthCare.gov is where you go to find coverage that fits your life (and your caregiving reality).
The site walks you through Marketplace plans, Medicaid, and CHIP — and helps you compare costs, subsidies, and coverage in just a few clicks. You can even preview plans and see if you qualify for financial assistance before you apply.
Why it’s Gray Monster-approved: For caregivers, the Marketplace can uncover plans that make a difference — like ones that include mental health visits, telehealth, or home health services. And if you’re helping a parent, spouse, or loved one apply, HealthCare.gov makes it possible to fill out applications on their behalf (with their consent).
Try this:
Use the “See Plans & Prices” tool before you apply — it’s the easiest way to estimate what you’ll actually pay each month.
Call the Marketplace Call Center (1-800-318-2596) if you get stuck; they have live help 24/7 in multiple languages.
And if you prefer face-to-face guidance, check the “Find Local Help” tool to connect with a certified enrollment counselor nearby.
