Every fall, I have some version of the same conversation with clients: “I got an open enrollment packet from work, and I also keep hearing about Medicare enrollment. Which one applies to me?” The honest answer is that it depends on where you sit in the transition from working to retired, and getting it wrong, even for a short window, can be expensive.

For pre-retirees and retirees in Pasadena and the surrounding area, many of whom are former or current employees of organizations such as JPL, Caltech, Kaiser Permanente, etc., healthcare open enrollment is not a single decision. It is several overlapping decisions depending on your age, your employment status, and how close you are to drawing retirement income. This blog walks through the questions I ask clients each fall to help them optimize their choices rather than default into whatever plan they had last year.

Three Enrollment Windows, One Overlapping Calendar

Broadly, three healthcare enrollment windows can affect a retiree or pre-retiree in a given year:

• Employer open enrollment: typically held in the fall for coverage starting January 1
• Medicare’s Annual Election Period: running October 15 through December 7 each year, during which you can change Medicare Advantage and Part D drug plans
• ACA Marketplace open enrollment: for those retired before 65 and not yet Medicare-eligible, typically running November 1 through January 15

Depending on your situation, you may need to consider only one of these. But for clients navigating the transition out of full-time work, more than one can apply in the same year, and the decisions interact.

Still Working: Comparing Your Employer Plan to Medicare

If you are approaching 65 but still employed, and your employer has 20 or more employees, you generally have a real choice each fall: stay on your employer plan, or enroll in Medicare and potentially drop the employer coverage.

The right answer depends heavily on the specifics of your employer plan compared to Medicare Part B plus a Medicare Supplement or Advantage plan. I worked with a client who had spent his career at JPL and was still on staff at 66. His employer plan had a strong network and a manageable premium, so for him, delaying Medicare Part B enrollment made sense. Another client, working part time for a smaller employer with a thinner plan, found that enrolling in Medicare and dropping the employer coverage saved real money.

A detail worth confirming, not assuming: if your employer has fewer than 20 employees, Medicare often becomes your primary coverage automatically once you are eligible, and delaying enrollment can leave you with unexpected gaps or a permanent late enrollment penalty on Part B.

Already on Medicare: Reviewing Part D and Advantage Coverage Every Year

If you are already retired and on Medicare, the Annual Election Period is your one chance each year to change Medicare Advantage plans or switch your Part D drug plan without a qualifying life event. Plans change their formularies, premiums, and provider networks every year, which means a plan that fit well last year may not fit as well this year.

I encourage clients to actually run their current medications through Medicare’s Plan Finder tool each fall rather than assuming last year’s plan is still the best option. It takes twenty minutes and can meaningfully change what you pay out of pocket for prescriptions over the coming year.

Retired Before 65: Navigating the ACA Marketplace

For clients who retire before Medicare eligibility, often a deliberate choice for those who are financially on track for an earlier retirement, healthcare coverage typically comes from COBRA, a spouse’s employer plan, or the ACA Marketplace. Marketplace open enrollment is the window to shop plans and, depending on income, to claim premium tax credits.

This is an area where your broader retirement income plan and your healthcare decision are tightly linked. The income you report, including how much you choose to withdraw from retirement accounts in a given year, directly affects your eligibility for premium subsidies. This is exactly the kind of decision that benefits from being made alongside your financial plan, not in isolation.

Coordinating Open Enrollment With Your Retirement Income Plan

Whichever category you fall into, the healthcare decision you make each fall does not exist in a vacuum. It interacts with:

• How much taxable income you plan to realize this year, which affects Marketplace subsidies and future Medicare premiums through IRMAA
• Whether you are taking Social Security yet, since Part B premiums are often deducted directly from a Social Security check
• Your broader retirement income sequencing, particularly in the years just before and after you become Medicare-eligible

What This Means for You

1. Identify which enrollment window or windows actually apply to your situation this year
2. If you are still working near 65, confirm your employer’s size and how it affects your Medicare enrollment timeline
3. If you are on Medicare, run your medications through the Plan Finder tool before assuming your current plan is still the best fit
4. If you are retired before 65, review how this year’s income affects your Marketplace subsidy eligibility
5. Loop your financial plan into the healthcare decision rather than treating them separately

A Decision Worth Making Deliberately

Open enrollment often falls during a busy time of year, and it is tempting to let coverage renew automatically rather than actively review it. For most of the retirees and pre-retirees I work with, an hour of attention during this window is one of the higher-value hours they will spend all year, both financially and in terms of the coverage they will actually rely on.

If you would like help thinking through your specific healthcare and retirement income picture together, I would be happy to have a conversation. Schedule a discovery call, and we can walk through it.