HR departments can sometimes present open enrollment as a mundane, business-as-usual exercise, but at home, it’s often anything but. Feeling good about your selection requires time and thought.‍

• Predicting isn’t easy: Choosing benefits each year is an act of prediction. And humans are remarkably bad predictors. In fact, a recent survey by Equitable says more than half of employees regretted their health plan decision last year.
• Sit-down time required. Choosing a healthcare plan, how much to contribute to healthcare accounts, whether to use disability insurance—comparing all those option across two people’s options (if you’re partnered) requires some reflection time — time that can be hard to find.
• Changes can create work and emotion. The other thing buried in the logistical notion of “open enrollment” is the real possibility of changed providers. That can be hard to deal with—even frustrating or saddening. Plus, it creates a whole slew of new work to attack for the new plan year.

Here are few stories from real people on how open enrollment has gone for them in the past:

• Woman, 40s — married with 3 children. In recent open enrollments, she’s taken the initiative of getting her husband’s benefit credentials, so that she can compare across and get the best deal for the family across both plans. Usually happens late at night because there’s no time otherwise to do this analysis. Even with that work, she describes only feeling like she got it right once or twice.
• Couple, 30s. They described the frustration of finding the actual coverage details for fertility treatment in each of their plans before actually selecting one. It turns out the detailed benefit coverage brochures were only delivered via the company wiki instead of being available in the online enrollment portal.

Is it just me or does the window of open enrollment feel incredibly brief and full of pressure? November always tends to sneak up with open enrollment, asking for sudden and immediate demands on my time.

The challenge of predicting what I’m going to need in terms of healthcare for the next year—what my household is going to need—feels like a finger in the air measurement. Impossible to predict.

And yet, the window comes. Choices have to be made by the deadline. And there’s no going back.

It raised for me two key questions for this deep dive:

• First, why is open enrollment this way? Is there an alternative? Should we be trying to change it?
• What does it really mean to “do well” in open enrollment?

Why is open enrollment the way it is?

If you feel the grind of open enrollment the way many people do, it may help to know that this once-per-year high-pressure tradition was never trying to solve a human problem. It was solving an insurance problem.

In 1949, after President Harry S. Truman proposed a national healthcare system, employers nationwide reacted to that effort and a high demand for labor by using health insurance to attract talent. The result was that more and more people starting signing up, expanding the risk of health insurance plans.

Health insurance companies wanted to control prices and premiums based on new annual expectations, and so rather than allowing changes throughout the year, they limited down the window and set a uniform period.

Since then, Medicare and Medicaid work the same way, and in the past decade, the annual tradition of has been expanded to Affordable Care Act plans too.

Could it work differently? Maybe. Will it change — probably not. Open enrollment has become a nationwide life admin tradition, just like March-April’s tax season.

What does it mean to “do well” in open enrollment?

In gathering my research on how deal with open enrollment, I had to wrestle with a core question: What does it mean to do well with open enrollment? Assuming you’ve gone through it before, you’ve maybe experienced regret a few months into the new year — you wish you had made different decisions.

But I wonder... Is insurance plan regret inevitable? Is FSA contribution regret inevitable? According to Equitable’s survey this year, it’s at least very common — 53% of those surveyed said they regretted the plan they choice. But maybe that’s just human nature? Hindsight is truly 20/20, and open enrollment asks us to have foresight.

Consider this — especially if you’re part of a couple selecting your healthcare plans together — it may be better to focus less on predicting the perfect healthcare choice and instead control what you can control: the time, pace, and emotions surrounding your open enrollment.

Doing well in open enrollment might simply mean feeling like you made the choice with more confidence than last year. And, if you’re partnered, feeling closer to them. Endlessly trying to make the optimal choice, while admirable, may have its emotional costs when the year ahead is full of unknowable possibilities.

If you shift your focus away from focusing on predicting which plan will be the absolute most optimal for you and orient more toward creating you own definition “doing open enrollment well,” I think it opens up several helpful changes to how you handle open enrollment.

1. Put open enrollment season on your calendar — for every year moving forward.

This sounds simple, but be honest, do you have open enrollment season on the calendar for 2025? And 2026? And so on? If it’s so predictable and entrenched in our healthcare system, what if you got an alert in early October to ensure you have a somewhat clear window during your expected window to spend some time on it?

We say it a lot on Wayshaping, but “put it on a calendar” — ideally an electronic one that can alert you — can be a huge help for getting in the right mental state to address open enrollment.

2. Before you log into your enrollment portal, try writing out what you anticipate for the year

It’s impossible to predict the year ahead. But often, we try to predict life just by thinking. What if you wrote instead? Or drew it? Enrollment portals don’t necessarily help you envision and anticipate what your household could go through. But if you are trying to predict the year ahead, then almost certainly, life decisions are going to come up; life worries are going to appear.

Whether you’re doing it alone or solo, the key is to put some time aside and let yourself consider the possibilities before diving into the choices.

3. Instead of worrying about the best possible plan, focus on understanding your choice fully

While open enrollment ends with your selection, it’s really the start of your health insurance as its been set for the year ahead. So, while you’re making your choice, treat it as a moment where you collect all the docs provided by the plan — the benefits coverage summary, the full coverage details, and any other fine print — and store them in an easy to access place.

You may be completely healthy and not expecting much of anything in the year ahead. If that’s you, it means that the (unfortunate) surprise causing you to use your insurance probably won’t be a time when you want to have to review coverage details.

4. Treat enrollment as a kickoff rather than just a selection process. Consider yourself done when you’re ready to use it.

While your employer has everything they’ll need the moment you choose your plan details, you can save yourself some rework if you really take some time to save details down and get set up with any new apps or websites you’ll use.

• As I mentioned, save down your coverage docs. Perhaps in a cloud storage solution that other members of the family can have access to.
• Download any apps and bookmark websites for new providers or insurance providers
• Set a reminder for family members on your plan to replace their insurance cards when the new plan year starts.