Open enrollment checklist

It's easy to treat open enrollment as a once-a-year box to check: log in, pick a plan and move on. But the choices made during this window don't just cover the coming year; they can shape healthcare costs, retirement savings, and long-term financial security for years or even decades to come. Whether you're early in your career, in your peak earning years, or approaching retirement, open enrollment is a natural moment to pause and ask whether your current elections still fit where you are.

As open enrollment approaches, here’s a helpful checklist to organize the key steps you should consider taking.

1. Revisit healthcare elections and savings accounts

Health plan selection is often the first decision employees think about during open enrollment, but it shouldn't be made in isolation. Rather, it should be part of your broader financial picture.

One of the most common things we see during open enrollment is people simply sticking with the same health plan, year after year. It's easy to think that may be the simplest path to meeting your open enrollment deadline. But healthcare needs, family situations, plan details and costs all change. So, open enrollment is an important opportunity to take a fresh look at the options available to you and ask yourself if your current plan still makes the most sense.

Two common types of plans you may see include a PPO and a high-deductible health plan (HDHP). Each has their benefits, so choosing the best one for you depends on your individual circumstances and of course, the specific plans available to you. PPOs generally have higher premiums and a lower deductible while HDHPs have lower premiums and a higher deductible. So, with a PPO, you may pay more each month in premiums in exchange for potentially more predictable healthcare costs. On the flip side, with an HDHP, you may pay less in monthly premiums but you could potentially have greater upfront costs for healthcare services. Making a reasonable estimate of your anticipated healthcare needs for the upcoming year is a key step in choosing which plan may suit you best.
 

Beyond the medical plan itself, it's worth revisiting the savings vehicles built around it: a Health Savings Account (HSA) for those enrolled in an eligible high-deductible plan, or a Flexible Spending Account (FSA) for employees who don't qualify for an HSA. Both are designed to help manage healthcare costs today – and, in the case of an HSA, potentially into retirement as well. 
 

It’s important to recognize neither account type is better than the other; each is a different tool for a different purpose. So, it’s important to consider your needs and determine which is best for you. Take time to compare plan options, evaluate whether an HSA or FSA better fits your situation, and align your health plan choice accordingly.

2. Match your retirement planning strategy to your career stage

Retirement planning looks different depending on where you are in your career – and open enrollment is a natural time to check whether your strategy still matches your stage.

Early career: Build the habit, capture the match

The biggest advantage early-career employees have is time. Starting early and staying consistent matters more than the dollar amount at first, thanks to compounding – money which has earned returns and interest and can then earn returns and interest of its own, so an account’s growth can snowball over time.

Two concrete moves to consider:

1. Contribute enough to your 401(k) to capture your full employer match (skipping it means leaving money on the table)
2. Consider whether making Roth contributions makes sense while you're potentially in a lower tax bracket

Mid-career: Increase contributions as income rises

Established employees are often juggling competing priorities – a mortgage, a family, aging parents – alongside saving for retirement. A simple habit worth building: Raise your contribution rate each time you get a raise, since the increase is easy not to notice in your paycheck but could add up meaningfully over time.

Two concrete moves to consider:

1. Revisit your investment allocation (Has it kept pace with how close you are to retirement?)
2. Reconsider your Roth-versus-pretax split as your tax picture shifts

Nearing retirement: Make catch-up contributions and plan withdrawals

Employees age 50 and older have more options available to them for boosting their savings in preparation for retirement. Within 5-10 years of retirement, the focus shifts from accumulation to preparing for withdrawals.

Two concrete moves to consider:

1. Make catch-up contributions above the standard limit and explore a newer "super catch-up" provision that allows an even higher limit for those ages 60-63.
2. Start thinking about tax diversification – having both tax-deferred and Roth assets gives you more flexibility to manage your tax situation once you start drawing down retirement income.

3. Understand Roth vs. Traditional contributions – and consider using both

A pretax (traditional) 401k contribution reduces your taxable income this year, with taxes due when you withdraw in retirement. A Roth contribution is taxed now, but qualified withdrawals in retirement are tax-free. Neither is universally "correct" – it depends on your current tax bracket versus what you expect in retirement, and there's no rule against splitting contributions between the two. Younger employees, often in a lower tax bracket early on, may lean Roth; the right mix comes down to your individual situation and how you expect your taxes to trend. Consulting with financial and tax professionals can help you determine the right fit, or when to consider a mix.

4. Take five minutes to do a beneficiary check

This may be the highest-impact, lowest-effort action you can take during open enrollment. Review beneficiaries on your:

• 401(k) and other retirement accounts
• HSA
• Life insurance policies

Why it matters: Beneficiary designations generally override your will. An outdated designation – an ex-spouse or a deceased relative – can direct your assets to the wrong person, regardless of what your will says. Run this check every time you experience any major life event – marriage, divorce, a new child or the loss of a loved one.

5. Confirm your estate planning basics are in order

Estate planning isn't the first thing people associate with open enrollment, but having a few key elements in place can prevent some costly headaches later.

Four foundational documents are worth having in place:

• A will directs where your assets go and names guardians for minor children
• A durable power of attorney authorizes someone you trust to manage financial matters (paying bills, managing accounts) if you're unable to
• A health care power of attorney names someone to make medical decisions on your behalf if you can't
• An advance health care directive (living will) documents your care preferences ahead of time, so your family isn't left guessing during a difficult moment.

When to revisit your plan: Review beneficiaries annually – open enrollment is a convenient trigger. Revisit the full estate plan after any major life event, and in the absence of one, aim for every 3-5 years. Estate planning isn't a one-and-done task; it's an ongoing check-in.

6. Approaching Medicare age? Plan ahead for your HSA

If you have an HSA, be careful about the transition into Medicare – you can't contribute to an HSA once you're enrolled. Because Medicare enrollment can apply retroactively, it's worth stopping HSA contributions about six months before you enroll to avoid a conflict.

Medicare Part B enrollment timing depends on your employment situation. If you or your spouse are still working and have creditable coverage through an employer plan, you may not need to enroll in Medicare right at your eligibility age. Check with HR to confirm whether your employer’s plan qualifies. If you don't have that coverage, enrolling at your Medicare eligibility age matters, since missing the initial window can lead to lasting penalties. Given how many decision points are involved, it's worth starting to research your options around age 63, well before you need to decide.

7. If you’re part of a couple, plan together

If both partners are working, it's worth comparing benefits side by side – determine who has the stronger health plan, whether family coverage makes sense, and who should be listed as beneficiary or power of attorney on shared accounts. It's also worth aligning on the retirement picture itself – what retirement looks like for each of you, and whether you're on the same page about when and how you want to get there.

Making the most of open enrollment

Open enrollment decisions rarely stay in their own lane: a Roth choice shapes your tax picture, a beneficiary designation shapes your estate plan, and an HSA election shapes your options heading into Medicare. Financial professionals can help connect these choices into one strategy instead of a set of one-off decisions, which is especially useful if you're weighing Roth versus pretax, approaching retirement, or navigating a recent life change.

Frequently asked questions

Why should I treat open enrollment as more than just an administrative task?

Open enrollment is one of the few times each year when you're prompted to review decisions that affect your healthcare costs, retirement savings, financial security and long-term goals. The choices you make don't just affect the coming year – in some cases they can influence your financial future for years or even decades.

What should I consider when choosing a healthcare plan?

Don't make this decision in isolation. Consider it as part of your broader financial picture. Evaluate:

• Your expected healthcare usage for the year
• Premium costs versus deductibles and out-of-pocket maximums
• Whether a plan pairs with an HSA
• How the plan fits with your savings goals and paycheck impact

What's the difference between an HSA and an FSA?

• HSA (Health Savings Account): A powerful long-term savings vehicle available to employees enrolled in an HSA-eligible high-deductible health plan. Funds roll over year to year.
• FSA (Flexible Spending Account): An alternative for employees who don't qualify for an HSA. Helps manage healthcare expenses tax-efficiently, though generally with "use it or lose it" rules.

How should my spouse or partner factor into open enrollment decisions?

If both members of a couple work, compare benefits between employers to decide:

• Which healthcare plan best fits your family's needs
• Whether family or individual coverage makes more sense
• Whether beneficiary designations, powers of attorney, and healthcare directives properly reflect your current wishes
• Whether you're aligned on retirement goals (timing, lifestyle, savings targets)

Retirement planning as a couple means making sure you're on the same page for what retirement will look like for both of you.