As we move into October and November, many employers enter their annual benefits enrollment season. While it’s easy to click through your elections and move on, this is one of the best opportunities of the year to review some important financial and insurance decisions.
Think of open enrollment as a yearly tune-up for your financial protection plan. A few small updates today can help avoid major headaches down the road.
1. Check Your Beneficiaries
This is one of the most overlooked items I see.
Many people set beneficiaries when they first join a company and never look at them again. Life changes quickly. Marriage, divorce, children, grandchildren, or the loss of a loved one can make those old designations outdated. Beneficiary designations also generally take precedence over instructions in your will, so an outdated designation could result in assets going somewhere you no longer intend.
Take a few minutes to review who is listed on:
- Employer-provided life insurance
- Supplemental life insurance
- Retirement plans such as your 401(k)
- Deferred compensation plans
- Stock purchase plans
2. Evaluate Your Life Insurance Coverage
Many employers provide life insurance equal to one or two times your salary. While that’s a valuable benefit, it may not be enough protection for a family that relies on your income. Keep in mind that employer-provided coverage may also end when you leave your job or change positions.
Open enrollment is a great time to ask:
- How much life insurance do I currently have?
- Would my family be financially secure if something happened to me?
- Should I consider supplemental coverage?
The goal isn’t necessarily more insurance. It’s making sure the protection matches your family’s needs.
The Downsides
Despite the attractive features, these accounts are not necessarily the best choice for every family.
The biggest drawback is tax treatment. There is no tax deduction when you fund the account, and withdrawals of the account’s earnings are taxed as ordinary income. That’s less favorable than a Roth IRA, where qualified withdrawals are completely tax-free.
If your primary goal is saving for college, a 529 plan will often be the better option because qualified education withdrawals are tax-free, and you may get a state tax deduction on contributions, depending on where you live.
Investment flexibility is also somewhat limited. Unlike a brokerage account, where you can choose from thousands of investments, Trump Accounts are generally restricted to broad-market index funds.
3. Don’t Overlook Disability Insurance
Your ability to earn an income is often your biggest financial asset.
Many employees focus on life insurance but spend very little time reviewing disability coverage. Yet a long-term illness or injury can have a significant impact on finances during your working years.
Many employer plans replace only part of your salary, and benefits may be taxable depending on who pays the premiums. Understanding what your employer provides can help identify potential gaps.
4. Do You Have Access to an HSA?
If you’re enrolled in a qualifying high-deductible health plan, you may be eligible for a Health Savings Account (HSA).
HSAs are one of the most tax-efficient savings vehicles available because they offer:
- Pre-tax or tax-deductible contributions
- Tax-deferred growth
- Tax-free withdrawals for qualified medical expenses
- Penalty-free withdrawals for any purpose after age 65 (subject to income tax).
Many employers also contribute money to employees’ HSAs, which can make the opportunity even more valuable.
If an HSA is available to you, it’s worth understanding how it fits into your overall financial plan.
5. Review Your 401(k) Options
Open enrollment is a great reminder to revisit retirement savings.
Ask yourself:
- Am I contributing enough to receive the full employer match?
- Should I increase my contribution percentage?
- Does my plan offer a Roth 401(k) option?
- Are my investment selections still appropriate?
A Roth 401(k) may be worth considering for individuals who believe they could be in a similar or higher tax bracket in retirement. Contributions are made after taxes, but qualified withdrawals are generally tax-free later. New for 2026: if you’re age 50 or older and your prior-year wages from the employer sponsoring the plan exceeded $150,000, catch-up contributions generally must be made as Roth contributions.
There’s no one-size-fits-all answer, but this is a conversation worth having.
6. Check Other Benefits You May Be Ignoring
Many benefit packages include valuable programs that employees rarely use.
Look for:
- Employee Assistance Programs (EAPs)
- Legal assistance benefits
- Identity theft protection
- Accident insurance
- Critical illness coverage
- Wellness incentives
- Mental health resources
Sometimes the most valuable benefits aren’t the ones with the biggest headline.
A Good Annual Habit
Most people spend more time researching their next phone upgrade than reviewing the benefits that protect their income, health, and family.
This fall, set aside 15 minutes to review your elections before simply clicking “Renew.” A quick review of your beneficiaries, insurance coverage, HSA eligibility, and retirement plan options can help ensure your benefits continue to support the life you’ve built.
The goal isn’t perfection. It’s making sure your benefits still fit your family, your finances, and your future.
As always, if you’d like help reviewing your workplace benefits and understanding how they fit into your overall financial picture, don’t hesitate to reach out. Sometimes a second set of eyes can help identify opportunities that are easy to overlook.