It is that time of year again. The email has been sitting in my inbox for a week, quietly waiting for me to deal with it. I keep flagging it, moving it to another folder, telling myself I will come back later. But the truth is, I already know what it says.
Open Enrollment.
Time to choose my insurance plan. And just as I finally got comfortable with the one I have, I learned in a recent webinar that the company has switched providers again. Right when I was breathing easy, the rug gets pulled.
Sound familiar?
For many of us, open enrollment feels like a yearly exercise in frustration. Some of us rush through it. Some of us don’t touch it at all, because if we do nothing, the company assumes we’ll just keep the same plan. That feels easier, doesn’t it? Stick with what you know.
And yet, here’s the catch: sticking with the same plan might mean you’re paying for benefits you’ll never use. Or you might be missing out on options that would save you money in the long run.
Why It Feels So Hard
The language alone can make your head spin: PPOs, HMOs, HSAs, FSAs, open access, deductibles, out-of-pocket maximums. It’s enough to make anyone want to shut the laptop and walk away.
And you’re not alone in feeling that way. In fact, entire industries and professions exist just to help people choose insurance plans, because it really is that confusing. Seniors often struggle the most, whether navigating private insurance or state options, and many simply don’t have the time, energy, or patience to figure it all out alone.
Practical Tools to Move From Overwhelm to Empowerment
• Audit your current plan. Before clicking “renew,” take a hard look at what you used (and didn’t use) in the past year. Did you pay for a vision plan you never touched? Are you shelling out for coverage you don’t need? Reviewing your actual usage can help you spot what’s working and what’s just extra weight on your paycheck.
• Compare for cost and care. Don’t just look at monthly premiums. Lay two plans side by side and compare: What are the copays? The deductible? The out-of-pocket maximum? If you have a big procedure or regular prescriptions, these details matter more than the monthly price tag.
• Ask for help, use the tools. This is not a solo sport. HR departments, benefits webinars, and even independent advisors exist for a reason. Ask questions until you understand the answers. If your employer offers decision-support tools, use them. They’re designed to make the maze navigable.
• Translate the jargon. If the language feels like Greek, use the tools you already rely on , AI, Google, or even a trusted colleague to translate acronyms and terms into plain English. Insurance shouldn’t feel like a secret code.
• Put it on your calendar. Don’t leave this for the last minute. Schedule open enrollment the way you would any other important appointment. Block off a couple of hours to review, compare, and decide. When you schedule it, you’re programming your head and your heart to treat the process with intention instead of avoidance. That mental shift makes all the difference.
Leadership Beyond Insurance
The way we face open enrollment is often the way we face other overwhelming decisions. Do we ignore them? Do we rush? Or do we pause, reflect, gather information, and make empowered choices?
Pausing before you decide. Breaking complexity into smaller parts. Asking for help when you need it. Translating what feels impossible into what’s understandable. Scheduling with intention instead of procrastinating.
These aren’t just open enrollment strategies, they are leadership practices that will strengthen you in work, in life, and in every big decision ahead.
Give yourself room to choose. Don’t leave it to the last minute. And remember: whatever plan you select, you’ll live with it for the year ahead. You deserve health insurance, and if you’re in a position to have it, make sure you’re covered.
Because this isn’t just about benefits. It’s about practicing empowered decision-making in the places that matter most.
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Quackenbush Coaching LLC 