Let’s be real, open enrollment season shows up like a pop quiz no one studied for and most people scroll through their options the way they scroll past contract terms and conditions.

Fast. Half-distracted. And with zero idea what they just agreed to.

If that’s you, you’re not alone. If your life is anything like mine, you’re juggling toddler tantrums, work meetings, endless piles of laundry, and finding leftover Halloween candy in the oddest places. (I found one in my shoe the other day.) So it’s no wonder why you’d just pick the same plan you had last year, cross your fingers, and move on.

But that “click and forget” moment?
It could end up costing you thousands — or worse, leaving your family uncovered when you need it most.

So let’s walk through the most common mistakes families make during open enrollment and how you can avoid them this year (without needing a PhD in insurance or suffering a panic attack).

Mistake #1: Defaulting to last year’s plan without reassessing

I know — the idea of reviewing all those benefit PDFs makes your brain leak out your ears.

But here’s what most folks don’t realize: just because it has the same name, doesn’t mean it has the same coverage.
Insurance plans tweak networks, adjust premiums, raise deductibles, and slide new limitations into the fine print all the time — even when the plan name stays identical.

And if your life has changed (had a baby, got married, switched jobs, added a side hustle), your plan needs to reflect that too.

👉 According to a 2023 study, 90% of people stick with the same plan every year — even when better (or more fitting) options are available.

So don’t assume last year’s “pretty good” plan still works.
Your family isn’t the same this year. Your coverage shouldn’t be either.

Mistake #2: Choosing the lowest premium without looking at the full picture

That low premium is tempting, right? Especially when you’re already stretched with daycare, groceries, diapers, and that random subscription to something you can’t figure out how to cancel.

But here’s where people get burned:
They grab the “cheapest” plan… and then get smacked with sky-high deductibles, out-of-network costs, and out-of-pocket expenses when something happens.

The low monthly premium feels like a win, until your kid needs surgery or you need an MRI and suddenly you’re out $4,000 before coverage kicks in.

👉 In 2025, the average family premium hit $26,993 — with employees footing more than $7,400. It’s more important than ever to understand what you’re actually buying.

Your best bet? Look at:

• Your deductible
• Your max out-of-pocket
• Who’s in-network
• How often you actually go to the doctor

The goal isn’t “cheapest.”
It’s the smartest. (And least likely to turn that ‘great deal’ into a mid-year money pit.)

Mistake #3: Forgetting to update your dependents or account for life changes

Life moves fast. Babies arrive. Jobs change. You get married. You move across the state for more space (and cheaper daycare).

If anything in your life looks different than it did last open enrollment season — your coverage should look different too.

But most folks just… forget.

👉 One study showed that 25% of people who regretted their benefits choices did so because they failed to adjust their plan after a life change.

That includes:

• Not adding new dependents (like a new baby)
• Not switching from single to family coverage
• Not checking if your new job qualifies you for something better
• Not updating coverage after a new health diagnosis or new treatment plan

Your insurance needs to match the actual people, income, and health risks in your home — not just what worked back when it was just you and your dog in a studio apartment.

Mistake #4: Ignoring supplemental benefits and tax-advantaged accounts

Let me guess: you picked your health plan, clicked past the rest, and called it a day?

Totally get it. But here’s the deal…

Supplemental benefits (like disability insurance, accident plans, hospital cash coverage, etc.) and tax-advantaged accounts (HSA, FSA) are where a lot of families miss out on serious value.

These aren’t “extras” — they’re financial shock absorbers.

Especially if you:

• Have a high deductible plan
• Are self-employed or have variable income
• Are paying for things like chiropractic care, acupuncture, or therapy out of pocket (most HSA/FSA accounts cover these!)

And don’t forget: HSAs and FSAs let you use pre-tax money.
So if you’re spending $1,500 a year on healthcare costs, wouldn’t you rather do it with tax-free dollars?

👉 And yes, “forgetting about supplemental benefits” made TIME’s list of top open enrollment mistakes.

Think of these like the airbag system in your financial car. You hope you never need ’em. But when you do — they give you an extra layer of support when things go sideways.

Mistake #5: Waiting until the last minute and rushing the decision

Listen, I’ve been doing this a long time — and I’ve seen it all:

📆 People logging into their benefits portal at 11:58pm the night it closes.
🤯 People forgetting their login info, panicking, and just clicking “whatever.”
😬 People guessing which plan to pick because the baby woke up mid-decision.

And I get it. You’re juggling a lot. Open enrollment feels like one more thing.

But this isn’t a “figure it out later” moment.

👉 Surveys show that over 50% of employees regret their benefits decisions — mostly because they didn’t take enough time to understand them.

This is a once-a-year window to get it right.
And “winging it” could cost you thousands — or leave you exposed when you thought you were covered.

Block an hour. Ask for help. Make the decision with a clear head.
Future You will thank you.

Real Talk: You Don’t Have to Guess Your Way Through This

Here’s the thing:

If you’ve ever stared at your insurance options and thought:
”I have no clue what any of this means… but I guess we’ll go with Plan B again,” —  you’re not alone. 

Sometimes it feels like insurance jargon is made confusing on purpose and if you’re not an insurance broker, it’s easy to get lost in the terminology.

Open enrollment wasn’t built for real families with limited time, a lot on their plate, and zero desire to read through a 47-page benefits guide.

But this is your shot.
To finally know your plan covers what you need.
To finally feel like you’re not winging the whole “adulting” thing.
To finally stop worrying if one accident or hospital visit might hit your savings harder than you expect.

If anything in this post made you think, “Oh crap… that might be us,” — don’t panic. Just act.

Get someone in your corner who can explain things in plain language.
Who gets where you’re coming from.
And who’ll make sure your plan actually fits your life right now.

Because protection shouldn’t be a guessing game.

👋 I’d be honored to be that person for you.

Ready to make sure your coverage actually covers your real life?

Book a free, no-pressure clarity call with me.
Just answers, clarity, and maybe a few dad jokes.

👉 Schedule your call now

Because I Believe in Using Stats Responsibly…

Look, I’m not out here making up numbers to sound smart. (My kids do enough made-up math at bedtime — I don’t need to join in.)

If I’m throwing stats your way, I want you to know they’re legit. So here’s exactly where I pulled the data you saw in this post:

• 90% of people stick with the same plan year to year:
  Source: Benefit News
• 25% of employees regretted their plan choice due to life changes:
  Source: Benefit News
• Over 50% of people spend 30 minutes or less reviewing their benefits:
  Source: Benefit News
• Average family premium hit $26,993 in 2025:
  Source: Washington Post
• “Forgetting about supplemental benefits” made TIME’s top open enrollment mistakes list:
  Source: TIME Magazine

If you ever want me to break down what any of these mean — or how they impact your situation specifically — I’m your guy.

P.S. If you liked this blog post, you might also like my “What’s a Deductible?” Blog Post.

Disclaimer: Stephen Marker is a licensed insurance producer. Products, plans, and availability may vary by carrier and by state. Benefits, premiums, costs, and rules vary by plan, carrier, and location. Review each plan’s official documents before making a decision.
This information is provided for educational purposes only and is not intended as a guarantee of coverage, pricing, eligibility, or benefits. This content does not constitute a complete description of available Medicare coverage options. Stephen does not offer every plan available in all areas. Information shared is limited to plans he is appointed to offer.

Calling this number or attending an educational event does not obligate you to enroll in any plan.
For complete Medicare information, beneficiaries may also visit Medicare.gov or call 1-800-MEDICARE.

Stephen Marker is not a licensed tax or legal professional. For tax or legal advice, please consult a qualified professional.
Free language interpreter services are available. Contact us for assistance.