Open Enrollment: Don’t Just Click “Repeat” This Year
Every fall, millions of employees (and retirees) face the same task: reviewing their benefits during open enrollment. And if you’re like most people, you might be tempted to check “same as last year” and move on.
We break down open enrollment with a practical, no-fluff framework: protect against the big risks, pay cash for the small ones, and route every eligible dollar through the most tax-efficient account.
I get it—benefits paperwork isn’t anyone’s idea of fun. However, the truth is that these choices can have a significant impact on your finances and overall peace of mind for the year ahead. Spending even an hour thinking them through can pay off in real dollars.
Here’s a summary of how to approach open enrollment with a clear framework so you can make smart, confident choices. If you want to dig deeper, check out our latest podcast on the subject here, or wherever you get your podcasts.
1. Health Insurance: The Big One
This is usually the most important and most confusing decision you’ll make. Whether you get insurance through your employer, Medicare, or the ACA marketplace, open enrollment is your once-a-year chance to review your coverage.
A few rules of thumb:
Think about usage. If you expect frequent doctor visits or ongoing prescriptions, a lower-deductible, higher-premium plan may make sense. If you’re generally healthy and don’t anticipate much care, a high-deductible plan with an HSA could be the better financial fit.
Check your network. Make sure your preferred doctors and specialists are still in-network. This one step can save you from costly surprises.
Review prescriptions. If you take brand-name or specialty medications, confirm how each plan covers them—pricing can vary dramatically.
Even if you think you “never go to the doctor,” make sure you can afford the deductible if something unexpected happens. Saving the premium difference in an HSA or dedicated account can give you a financial cushion for that “what if” moment.
2. Dental and Vision: Worth It?
These benefits feel like health insurance, but they’re actually separate—and often less critical.
If your employer pays most or all of the premium, sign up. If you’re paying out of pocket, recognize that dental and vision plans mostly prepay for routine care. They rarely cover significant expenses like implants or eye surgery.
In other words:
It’s great if it encourages you to keep up with checkups.
But skipping it won’t blow up your financial plan the way skipping health insurance could.
3. Life and Disability Insurance: Good to Have, But Not Always Enough
Many employers offer group life and disability insurance. It’s a great perk, but it’s not a full solution.
Group life insurance can be an easy, inexpensive way to get coverage—especially if you have health conditions that make private insurance costly or unavailable. But if you have family depending on your income, you likely need more coverage than your employer provides. Plus, if you leave your job, that coverage usually ends, and if you’ve developed a health condition or other risk factors, you may no longer be insurable on the private market.
Disability insurance (DI) is often overlooked, but it is arguably just as important. After all, your future income is probably your most significant financial asset. Group policies can be a good start, but benefits are taxable if paid by your employer or with pre-tax dollars. Group plans usually have stricter definitions of “disability,” meaning it’s harder to qualify for benefits if/when you need them. A private policy can provide more flexible, tax-free coverage.
If you can, review both and consider layering coverage to fill any gaps.
4. The “Checkout Aisle” Add-Ons
Critical illness, accidental death, legal assistance—these benefits often appear at the end of your enrollment form. They can sound useful but are usually low-probability, low-impact coverage.
If your employer pays for them, great. If not, think of them like impulse buys at the grocery store checkout: not harmful, but not essential either.
5. Flexible Spending Accounts (FSAs) and Dependent Care
If your employer offers a dependent care FSA, and you’re paying for childcare, this one’s almost a no-brainer. You can pay up to $5,000 per household in childcare costs with pre-tax dollars, which can easily save hundreds on taxes.
Just remember: FSAs are “use it or lose it,” so only contribute what you’re confident you’ll spend.
6. Coordinating with a Spouse’s Plan
If both spouses have employer benefits, compare plans side by side. It’s often the most cost-effective for each person to stay on their own employer’s health plan while the kids go on one. The difference can be hundreds per month, so it’s worth the spreadsheet exercise. Additionally, note that contribution limits for certain benefits, such as dependent care FSA accounts or HSA contributions, may be combined for married couples.
Final Thoughts
Open enrollment isn’t glamorous, but it’s one of the most practical ways to make the most of your money each year.
Even small tweaks—switching to an HSA plan, adding the right coverage, or dropping unnecessary extras—can save real dollars and protect your financial plan.
And if you’re unsure what’s best for your situation, this is exactly the kind of decision a financial planner can help you think through. A 30-minute conversation can bring clarity and confidence to choices that otherwise feel overwhelming.
