Making the Most of Open Enrollment: A Guide for Working Professionals
Fall isn’t just about cooler weather and shorter days—it’s also open enrollment season for many workplace benefits. For a few short weeks each year, you get the chance to review and update the benefits you’ll carry into 2027.
It can be tempting to simply check the same boxes you checked last year, especially if nothing major has changed. But benefits, costs and tax rules change—and sometimes your own life has changed more than you realize. A raise, a new medication, a child leaving home or simply getting a little closer to retirement can all change which benefits make the most sense.
Why Open Enrollment Matters
Your employer’s benefits package is about much more than health insurance. It can be an important part of your retirement savings, tax planning, insurance protection and overall financial plan.
To help you navigate the process, we’ve included a simple Open Enrollment Checklist highlighting some of the key issues to review with your employer-provided benefits.
Start With Your Health Insurance
Don't compare health plans based on the monthly premium alone. Look at the deductible, copays, coinsurance, prescription coverage, provider network and maximum out-of-pocket costs. Think about how you actually used health care this year and whether you expect anything to change in 2027.
If your employer offers a High Deductible Health Plan (HDHP), also consider whether it makes sense to pair it with a Health Savings Account.
For 2027, the HSA contribution limit is $4,500 for self-only coverage and $9,000 for family coverage. The minimum HDHP deductible is $1,750 for self-only coverage and $3,500 for family coverage, while maximum out-of-pocket expenses are $8,700 and $17,400, respectively. If you're over age 55, the contribute limit increases by an additional $1,000.
Remember that employer contributions generally count toward your annual HSA contribution limit, so check how much your employer plans to contribute before deciding how much to contribute yourself.
For people approaching retirement, we also like HSAs because the money doesn't have to be spent in the year you contribute it. Unlike a health FSA, unused HSA dollars can remain in the account and potentially be invested for future health care expenses.
Review Your Retirement Plan Contributions
Open enrollment is also a good reminder to check your 401(k) or 403(b). Are you contributing enough to receive the full employer match? If your income has increased, could you increase your contribution without significantly affecting your day-to-day spending?
If you're approaching retirement, this is also a good time to look beyond simply how much you're contributing. Consider whether you're contributing on a pre-tax or Roth basis and how that fits into your broader tax and retirement income strategy.
There is another change higher earners should have on their radar. Beginning in 2026, certain employees with higher prior-year FICA wages who make age-50 catch-up contributions are generally required to make those catch-up contributions on a Roth basis. Check how your employer's plan is implementing the rule, particularly if you're over 50 and maximizing your retirement plan contributions.
The IRS typically announces the following year's 401(k), 403(b) and related retirement-plan contribution limits later in the year, so check the final 2027 limits when they become available.
Don't Overlook FSAs and HSAs
If your employer offers a Flexible Spending Account, estimate your expected expenses before making your election.
A health FSA allows you to set aside pre-tax dollars for eligible health care expenses, while a dependent care FSA can help cover eligible child or dependent care costs. Pay attention to your employer's specific rules regarding unused balances, including whether the plan permits a carryover or grace period.
An HSA works differently. The account belongs to you, the balance rolls over from year to year, and eligible funds can be used tax-free for qualified medical expenses. That combination can make an HSA useful for both current expenses and longer-term health care planning.
Revisit Your Insurance Coverage
Employer-provided insurance is another area that's easy to put on autopilot.
Take another look at your life insurance coverage, especially if your family circumstances, mortgage or other financial obligations have changed. Employer coverage may be enough for some people, while others may want additional coverage outside of work.
We also think disability insurance deserves particular attention. Your future income is one of your biggest financial assets, especially during your peak earning years. Consider what would happen to your financial plan if your paycheck suddenly stopped for an extended period.
And while dental and vision coverage may feel like smaller decisions, compare the premiums with the benefits you realistically expect to use rather than automatically enrolling or declining.
Look Beyond the Basics
Open enrollment materials can be long, which makes it easy to focus on health insurance and ignore everything else. Take a few minutes to look through the full benefits package.
Depending on your employer, you may have access to an employee stock purchase plan (ESPP), legal benefits, tuition reimbursement, wellness benefits, commuter benefits or other programs you haven't been using.
Also check your beneficiaries on employer-provided life insurance and retirement accounts. Open enrollment is a natural time to make sure those designations still reflect your wishes, particularly after a marriage, divorce, birth, death or other major family change.
A Few Common Open Enrollment Mistakes
One of the biggest mistakes is simply defaulting to last year's elections without looking at what changed. Premiums, deductibles, provider networks and prescription coverage can all change from one year to the next.
It's also easy to overlook the tax side of your benefits. HSAs, FSAs and retirement accounts can all affect your taxable income, while the choice between traditional and Roth retirement contributions can have implications well beyond the current year.
Finally, don't evaluate each benefit completely on its own. Your health insurance, HSA, retirement contributions, disability coverage and other benefits are all pieces of the same financial picture.
How Birch Street Can Help
Open enrollment is more than checking boxes—it's an opportunity to make sure your workplace benefits still fit your life and your larger financial plan.
At Birch Street, we can help you evaluate how your employer benefits work alongside the rest of your finances. That may include reviewing health plan and HSA choices, retirement plan contributions, traditional versus Roth contributions, insurance coverage and other workplace benefits, particularly as you get closer to retirement.
Sometimes the best choice is exactly what you already have. But we think it's worth taking a fresh look each year rather than assuming last year's decisions are still the right fit.
