Retirement Planning
A plain-language open enrollment checklist covering retirement contributions, the health plan, HSAs and FSAs, workplace life and disability, and beneficiaries.
By Lifeway Financial · October 21, 2026 · 4 min read
How should you approach open enrollment this year?
Instead of rolling last year's elections forward, check the handful of choices that shape most of your year: retirement contributions and the match, the health plan, HSAs and FSAs, workplace life and disability coverage, and beneficiaries.
Key takeaways
Gather your benefits summary, your current elections, and a note on what changed at home before you log in.
Make sure you are contributing enough to receive the full employer match, at a rate that fits your cash flow.
Compare health plans against how your household actually uses care, including doctors and prescriptions.
Confirm beneficiaries on every workplace account and policy, including plans from previous jobs.
Save your confirmation page. It is your record of what you chose and when.
Open enrollment shows up every year like a houseguest with a very short visit and a very large suitcase. The benefits guide is thick, the deadline is close, and the sensible response is to log in, keep what you had last year, and click submit.
That is understandable, and it is also how an election made years ago can turn into a decision nobody has looked at since. The checklist below is for people who would rather not read the whole benefits guide, and it is organized around the elections that shape most of your year.
Before you log in
Gather this year's benefits summary, a screenshot of your current elections, and a short note about anything that changed at home this year. A new dependent, a spouse changing jobs, a planned retirement date, or a parent who needs more help can all change what makes sense.
If you are married and both of you have benefits at work, sit down together. Two separate portals make it easy to miss overlap or gaps.
The checklist
Retirement contributions and the match
Do you know your employer's matching formula and vesting schedule?
Are you contributing enough to receive the full match, and does that rate fit your cash flow?
Has your contribution rate kept pace with raises? If your plan offers automatic increases, is that feature on?
Contribution limits are set by the IRS each year. If you are near the maximum, check the current limits before changing anything.
Many plans let you change retirement contributions at other times of year too, but enrollment season is a natural moment to check.
The health plan
Does last year's plan still fit how your household actually uses care?
Have deductibles, premiums, or networks changed for next year?
Are your doctors and prescriptions still covered?
If you and a spouse both have access to coverage, have you compared the plans side by side?
Health savings and flexible spending accounts
If you have a health savings account, how do you plan to use it this year, and possibly in later years? Unused HSA funds generally roll over, and the account stays with you if you change jobs.
HSA eligibility depends on your health plan and other IRS rules, so confirm yours before you enroll.
If you use a flexible spending account, how much do you realistically expect to spend? Rules on unused balances vary by plan.
If you are considering a dependent care account for a parent's care, confirm with your CPA that your situation meets the IRS dependent rules.
Life and disability coverage through work
How does your group life coverage fit alongside any policies you own?
What would your disability coverage through work actually pay, and for how long?
Would any of this coverage continue if you left the job?
Beneficiary lines
Is the beneficiary current on every workplace account and policy, including old plans from previous jobs?
If you are married and naming someone other than your spouse on a 401(k), has your spouse signed the witnessed consent most 401(k) plans require?
After you submit
Save the confirmation page. It will probably be the least exciting screenshot you take all year, and one of the more useful ones. If an election does not show up correctly on a paycheck in January, that page is your record of what you chose and when. Store it in a folder labeled with the year. Then put next year's enrollment on your calendar, with a reminder a week before the window opens.
A note on Medicare
If you or a spouse already has Medicare, the yearly open enrollment period runs October 15 through December 7. It is the time to review health and drug coverage for next year. If you are approaching 65, your first enrollment happens on its own timeline, during a seven-month window around your 65th birthday month. Either way, Medicare decisions fit best inside the larger retirement plan.
How we approach it
At Lifeway, open enrollment is part of the fall service calendar. We review benefits as part of the financial plan and coordinate with your employer's benefits team where it helps. We help you line up your options next to your goals, your other coverage, and the rest of your year, and the choice itself stays yours.
Common questions
Frequently asked questions
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It is the easy choice, but an election made years ago may no longer fit. Check the decisions that shape most of your year: retirement contributions and the match, the health plan, HSAs and FSAs, workplace life and disability coverage, and beneficiaries.
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Many plans let you change retirement contributions at other times of year. Check your plan's rules, and use enrollment season as a natural reminder to review your rate.
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No. Medicare's yearly open enrollment runs October 15 through December 7 and is for people who already have Medicare. Employer windows are set by each employer. If you are approaching 65, your first Medicare enrollment follows its own seven-month window around your 65th birthday month.
Sources and further reading
Where these figures come from
Rules, thresholds, and figures change. Confirm current details with the primary source for the year you are planning.
Retirement Topics: 401(k) and Profit-Sharing Plan Contribution Limits
Internal Revenue Service
Publication 969: Health Savings Accounts and Other Tax-Favored Health Plans
Internal Revenue Service
Publication 503: Child and Dependent Care Expenses
Internal Revenue Service
FAQs about Retirement Plans and ERISA
U.S. Department of Labor
Medicare.gov
When can I sign up for Medicare?
Medicare.gov
Insights are educational and are not investment, tax, or legal advice. See our Form ADV Part 2A and Form CRS for important details.
More insights
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The Years Between Your Last Paycheck and Medicare
Your Beneficiary Form Can Override Your Will
Can You Retire? The Question Behind the Question
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