Insights
Updates on COBRA, Marketplace, Medicare and all things healthcare.
Every day, employees reach moments that change everything. They retire. They turn 65 and face Medicare for the first time. They lose employer coverage after a layoff or a job change. More and more, they also step into caregiving for an aging parent while still showing up for work.
These moments are deeply personal, and they often come with uncertainty, stress, and a few sleepless nights. MyCarePro was created to make sure no one has to face them alone. That's why we're especially grateful for the chance to join Michigan's HR community this year, both on the expo floor and on the speaker's stage.
The 2026 MISHRM State Conference takes place October 21 to 23 at DeVos Place in Grand Rapids, under the theme Culture Catalysts. The theme celebrates HR professionals as the people who shape what work actually feels like, turning company values into everyday practice.
We love this theme, because culture isn't only built in how people are welcomed and developed. It's also revealed in how they're supported when life changes and in how they're treated on the way out the door. A retiree who leaves feeling respected, or an employee who gets real help sorting out coverage after a layoff, becomes a lasting reflection of an organization's values.
At MyCarePro, we see these transitions as culture-defining moments. Handling them with care is one of the most powerful ways HR can turn values into action.
Elizabeth Robinson, Agency Director of MyCarePro, and Kristopher Powell, President and CEO of MyCarePro, will lead a Total Rewards breakout session on Friday morning.
Date: Friday, October 23, 2026
Time: 9:15 to 10:15 AM
Room: River Overlook C/D, Breakout Room 8
Employees are preparing for retirement, becoming eligible for Medicare, navigating changes in healthcare coverage, and adjusting to shifts in employment from organizational changes. Many are also stepping into unexpected caregiving roles for aging family members, adding emotional, financial, and logistical weight to an already demanding season of life.
These realities affect HR teams too. Uncertainty around healthcare decisions, benefits transitions, and caregiving can ripple into productivity, morale, engagement, and compliance.
In this session, Elizabeth and Kristopher will introduce the Workforce Transition Mindset: a practical, human-centered approach that helps organizations proactively support employees through benefits-related life transitions such as Medicare eligibility, coverage changes, and workforce exits. They'll also explore how HR leaders can design compassionate offboarding experiences, including retirements and organizational transitions, that treat employees with dignity while protecting culture and reducing organizational risk.
At its heart, the session asks HR professionals to lead with both strategy and empathy, because how an organization supports people during transitions is a defining part of the employee experience.
Attendees will leave with real-world insights and practical frameworks they can put to work right away, including:
• A clearer picture of what employees face during retirement, Medicare eligibility, coverage changes, and caregiving
• The role HR can play in providing education, resources, and support during these moments
• Ways to design offboarding and retirement experiences that are compassionate, consistent, and protective of culture
• Strategies that strengthen engagement, trust, and organizational effectiveness through every stage of the employee journey
Between sessions, stop by Booth 77 for our Slumber Party. We know the challenges of supporting people through change can keep HR leaders counting sheep at night, so we've created a cozy spot to relax, count a few sheep with us for a chance to win prizes, and pick up a sleepover giveaway.
Most of all, we'd love to hear from you. Tell us about the transitions your employees are facing and what keeps you up at night, and we'll share how MyCarePro helps.
MyCarePro connects individuals, employers, and brokers with licensed insurance professionals who provide guidance on COBRA alternatives, Medicare, and individual and family coverage. Our support is offered at no cost to employees, employers, or brokers, and there is never an obligation to enroll through a MyCarePro agent.
We can't wait to see you in Grand Rapids. Learn more at mycarepro.net or reach us at info@mycarepro.net.
We do not offer every plan available in your area. Currently, we represent 11 organizations that offer 47 plans in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
Looking to help my clients reduce COBRA burden and offer off-boarding support.
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Looking for Medicare or Individual/ Family plans, or COBRA alternatives.
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Compassionately off-board employees and offer them alternatives to COBRA.
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Medicare Annual Enrollment runs from October 15 through December 7, and it's the one window each year when you can change your Medicare Advantage or Part D plan for 2027. Most people don't need to switch anything, but everyone should spend a few minutes checking what's changing. Here's what to look at, in the order we'd look at it with you.
Medicare Open Enrollment has a way of sneaking up on people. One minute it's summer, and the next your mailbox is stuffed with postcards promising the "best plan for 2026," your TV is running the same three commercials on a loop, and you're left wondering if you should actually be doing something about it.
When employees leave an organization — whether through resignation, retirement, restructuring, or unexpected life changes — the loss of health benefits can create uncertainty during an already stressful transition.
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We do not offer every plan available in your area. Currently we represent 11 organizations which offer 47 plans in your area. Please contact Medicare.gov or 1 800 MEDICARE to get information on all of your options.
No cost. No obligation. Just support when you need it.