10/15/25
"Your benefit selections can significantly impact your paycheck, taxes, savings, and long-term financial security."
SENIOR ADVISOR, DIRECTOR OF FINANCIAL PLANNING
Every year, I get the same calls around this time:
“Should I change my health plan?”
“Do I really need disability insurance?”
“What’s this HSA thing again?”
That’s right—it’s open enrollment season, the few weeks each year when you can make changes to your employer-sponsored benefits. While it might feel like just another HR task, open enrollment is actually one of the most critical financial planning opportunities of the year. Your benefit selections can significantly impact your paycheck, taxes, savings, and long-term financial security.
Let’s walk through a few key areas to focus on—through the lens of a financial advisor.
1. Revisit Your Health Insurance Plan
Health coverage is usually the biggest decision during open enrollment. Most employers offer several options: PPOs, HMOs, or high-deductible health plans (HDHPs).
If you’re generally healthy and can afford higher out-of-pocket costs, a HDHP paired with a Health Savings Account (HSA) can be a powerful wealth-building tool. HSAs offer triple tax advantages—contributions are pre-tax, growth is tax-free, and qualified withdrawals are tax-free. For many clients, I even treat the HSA as an additional retirement account.
However, if you or your family expect significant medical expenses next year, a lower-deductible PPO might make more sense. The right choice often comes down to comparing total annual cost (premiums + expected out-of-pocket expenses), not just the monthly deduction from your paycheck. It’s also important to factor in the tax savings of HSA contributions as you compare your options.
2. Don’t Overlook Disability and Life Insurance
Many people skip these options because they feel abstract—until something happens. Disability insurance is essentially income protection, and it’s one of the most important benefits you can have. I typically recommend clients aim for at least enough coverage to replace 60–70% of after-tax income if offered through work.
Employer-provided life insurance is often inexpensive, but usually limited (typically one to two times your salary). If you have a family or significant financial obligations, consider supplementing with an individual policy outside of work.
3. Take Advantage of Flexible Spending Accounts (FSAs)
FSAs let you use pre-tax dollars for medical or dependent care expenses. While you have to “use it or lose it” by year-end (or within a short grace period), these accounts can still offer meaningful tax savings.
Pro tip: Run the numbers on your average annual out-of-pocket medical or childcare expenses. That’s a smart place to start when deciding your contribution amount.
4. Review Your Retirement Contributions
Open enrollment is also a good reminder to revisit your 401(k) contributions.
Ask yourself:
- Am I contributing enough to get the full employer match?
- Can I afford to increase my contribution by 1–2% this year?
- Should I be using the Roth option (after-tax contributions for tax-free withdrawals later)?
Even small annual increases can make a big difference over time.
5. Update Your Beneficiaries and Emergency Contacts
This is the step most people skip—but it’s critical. Make sure your beneficiary designations on your retirement accounts and insurance policies reflect your current wishes. Life changes like marriage, divorce, or new children often mean it’s time for an update.
6. Need an Estate Plan? Get one here…
Some companies provide a legal benefit. Many people miss out on a great usage of this inexpensive coverage – creating an estate plan. Instead of the $1,000+ to create an estate plan, you can enroll in the legal plan (usually for less than $10/month) and use their network of attorneys to establish this important, and often overlooked piece of your financial plan.
Final Thoughts
Open enrollment is more than just selecting health insurance—it’s about aligning your benefits with your financial goals and life stage. As a financial advisor, I encourage clients to approach these decisions with the same intentionality they’d bring to an investment or tax strategy.
Take the time to review, compare, and ask questions. The right choices now can save you money, reduce stress, and build a stronger financial foundation for the year ahead.
Need guidance?
If you’re unsure which options best fit your financial plan, consider setting up a time to talk to one of our advisors.
The views and opinions expressed in this blog post are those of the author, an Investment Adviser Representative (IAR) of Greenway Wealth Advisors, LLC, an SEC-registered investment adviser. The information provided is for educational and informational purposes only and does not constitute investment advice. This content is not an offer to buy or sell any security. All investing involves risk, including the potential for loss of principal. Past performance is not indicative of future results. It is important to consult with a qualified financial professional before making any investment decisions. Greenway Wealth Advisors, LLC is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. Greenway's Form ADV Part 2A is available upon request and provides additional information about our services, fees, and conflicts of interest. The information contained herein is as of the date published and may be subject to change without notice.
Easily (and securely) access your account information from anywhere, on any device, at any time.