The 5 Mistakes People Make During Open Enrollment (and How to Avoid Them)

Sep 9

Open Enrollment rolls around every year like a dentist appointment nobody really wants to go to. You know it’s important. You know ignoring it will cost you more later. But the process feels like a confusing mashup of legal jargon, hidden fees, and choices you’re supposed to make without any real guidance.

If you’re reading this, chances are:

You’re staring at a stack of options from your employer or the marketplace.
You’ve tried to Google “best health insurance plan” and had your phone blow up with spam calls.
Or you’re just praying you don’t screw this up (again).

I’m here to tell you: most people do screw it up. But not because they’re dumb, but because the system is designed to be confusing. And when you’re confused, you end up overpaying, under-insuring, or both.

So let’s cut through the frustration. These are the five biggest mistakes people make during Open Enrollment and how to dodge them like a pro.

Mistake #1: Picking the Cheapest Premium Without Looking at the Whole Picture

This one’s a classic. People see a plan that’s $200 cheaper a month and think, jackpot. But here’s what they don’t realize:

That “cheap” plan has a deductible so high you’ll never meet it.
The copays are brutal.
The network is so narrow you’ll end up driving across town for care.

Example: I had a client who switched to the cheapest option at work because it looked like a good deal. First doctor visit? Out of network. First prescription refill? Not covered. By March, they’d already paid more out of pocket than if they’d stayed on their higher-premium plan.

How to Avoid It:
Don’t just look at the monthly premium. Compare:

Deductible
Max out-of-pocket
Copays for primary care, specialists, ER visits
Prescription coverage
Whether your doctor/hospital is in-network

That’s the real cost picture. Premium is just one piece.

Mistake #2: Assuming Your Employer Plan is Automatically the Best Deal

This one hits especially hard for high earners. You get the email from HR, you check a box, and you think you’re done. After all, if it’s coming through your job, it must be the best deal… right?

Wrong.

Employer plans are designed for the group, not the individual. Which means if you’re making $100k+ per year, you might be subsidizing everyone else in the pool. Worse, you’re paying full-price for your family to be included on your plan.

I’ve worked with dozens of professionals who thought they were getting a bargain at work, only to find out they were paying 20–40% more than they needed to for less flexible coverage.

How to Avoid It:
Always compare your employer plan to private or marketplace alternatives. Especially if:

You’re covering a family
You’re a dual-income household
You want specific doctors or hospitals that aren’t fully covered by your employer plan

An independent review takes 15 minutes and could save you thousands.

Mistake #3: Ignoring Your Actual Health Needs

People tend to shop for insurance like they shop for gym memberships. Hope, not reality. They pick plans assuming they’ll be perfectly healthy all year, then life happens.

That one urgent care visit for your kid’s broken wrist? Out-of-network.
That new prescription you didn’t see coming? $200 a month.
That follow-up specialist? Not covered before a $7k deductible.

Insurance isn’t about guessing. It’s about matching your plan to your actual probable needs.

How to Avoid It:
Take stock of the last 2–3 years:

How often do you see the doctor?
Any recurring prescriptions?
Specialists you rely on?
Kids who love ER trips like it’s a hobby?

Build your plan around reality, not wishful thinking.

Mistake #4: Forgetting to Update for Life Changes

Big life events change everything in insurance world:

Marriage or divorce
Having a baby
Kids turning 26 and aging off your plan
Moving to another state
Income changes (especially around subsidy eligibility)

If you don’t factor these in during Open Enrollment, you’ll either overpay or get stuck with gaps.

Example: I had a client who forgot their taxable income included their side hustle. Mid-year, they owed thousands back in subsidies. Ouch.

How to Avoid It:
Sit down and update your “life math” before you pick a plan. Income, household size, dependents, all of it. If you’re unsure, this is where a pro can walk you through what counts and what doesn’t.

Mistake #5: Waiting Until the Last Minute

Listen, I get it. Health insurance feels like homework. Nobody wants to deal with it. But if you wait until the final week of Open Enrollment, you’re in panic mode. And panic mode leads to bad decisions.

You’ll pick the first plan that looks okay.
You won’t double-check networks.
You won’t have time to compare alternatives.

And once you’re locked in, you’re locked in until next year (unless you have a qualifying event).

How to Avoid It:
Start early. Give yourself time to actually compare plans, run the numbers, and ask questions. Even one extra week can save you thousands in mistakes.

How to Actually Get This Right (Without Losing Your Mind)

This is the part where most blogs would tell you to “do your research” and leave you hanging. But that’s not helpful when you’re already overwhelmed.

Here’s the better path:

Get clear on your needs. Doctors, prescriptions, family changes, income.
Compare apples to apples. Look beyond the premium to the full cost picture.
Have someone independent check your options. Not HR. Not a call center. Someone who can actually compare multiple companies and plans for your situation.

And hey, guess what? That’s literally what I do every day.

Your Tools for Open Enrollment

I don’t just help clients one-on-one. I’ve also created resources to make this less painful for you.

📘 My Book: The Health Insurance Solution: a plain-English guide to navigating this crazy system without feeling like you need a second degree in finance.

📓 My Workbook: The Open Enrollment Survival Workbook: fill-in-the-blank pages that walk you through your household snapshot, plan comparisons, and even space for notes/questions so you don’t forget what matters when you’re comparing options.

Final Thoughts

Health insurance is one of the biggest expenses for families and small business owners. And yet most people spend less time choosing their plan than they do picking a Netflix show. No wonder the system wins and consumers lose.

But it doesn’t have to be that way.

Avoid these five mistakes, arm yourself with the right info, and you can walk into Open Enrollment confident you’re not getting fleeced.

And if you want someone to double-check your options, I’m here. Send me a quick message and I’ll walk you through it in plain English.

TL;DR (for the skimmers)

Mistake 1: Picking the cheapest premium without comparing deductibles, networks, or copays.
Mistake 2: Assuming employer plans are always the best deal (they’re not, especially for high earners).
Mistake 3: Ignoring your real health needs and hoping for the best.
Mistake 4: Forgetting to update for life changes (marriage, kids, income).
Mistake 5: Waiting until the last minute and panic-picking a plan.
Solution: Start early, compare properly, and work with an independent specialist (like me) to avoid paying thousands more than you should.

👉 Grab the book. 👉 Grab the workbook. 👉 Or just message me and let’s make sure you’re covered. The right way.

McGarrity Harney