How to Tackle Open Enrollment with Confidence

How to Tackle Open Enrollment with Confidence

Open enrollment is just around the corner. Do you have what you need to make critical choices at this vital time of the year? 

Now, while benefits elections might seem like a routine administrative task, the decisions you make during this crucial election period could significantly impact your finances for years to come.

But for many of you out there, open enrollment might feel like a maze of features and benefits that can leave you feeling so confused and overwhelmed that you resort to box-ticking just to get it over with. 

And so, what if we could change the narrative this year?

What if this year was the year where you finally stepped off the default path, and made your benefits elections with confidence?

What if this year, instead of rushing through the enrollment process, you mindfully took your time and opted into coverages that align with your lifestyle needs?

And, so, how do you achieve this outcome?

Well, this approach begins with following a game plan for navigating the maze of healthcare choices, insurance options, and fringe benefits that are available to you.

More specifically, when you know how to approach your benefits book, which common pitfalls to avoid, and how to select your coverage options, you can make wise choices this benefits season without being overwhelmed.

Before You Open the Benefits Book

Alright, now the first step to making wise choices with your benefits this year so that you don’t get overwhelmed is to take some time to evaluate your current needs. Now, it might be tempting to dive into your benefits elections, check the boxes, and just get the process over with. 

With that said, and as counterintuitive as it may seem, taking time for reflection can make the process go faster than digging through the benefits book and making your elections as you go.

And so, why is this self-assessment so vital to the process? Well, it’s pretty simple. And that’s because, from one year to the next, your and your family’s lives evolve, whether we’re talking about changes in health statuses, family compositions, or retirement plans. 

So then, from this perspective, ask yourself: How has my health fared over the past year? Have any significant health challenges reared their heads in my family? And because of these changes or other developments, am I anticipating any major life events, such as surgeries or pregnancies, in the coming year?

More specifically, let’s say that you just discovered that you’re about to become a parent. Now, this year’s health plan might have sufficed for your individual or couple’s needs, but with baby on board, now may be the time to make some plan changes. 

Certainly, thinking down the road, having a baby is a qualifying event that would allow you to make changes to your plan after your child is born, but different health plans offer different maternity or pediatric benefits, which could be a more fitting choice for the year ahead before the baby arises.

Either way, it’s essential to start by evaluating your needs for the year ahead. Indeed, without this self-evaluation, you could end up overlooking a pivotal shift in your needs and, as a result, in your benefits selection for the year ahead.

Review Your Usage

Now, another thing you’ll want to do before cracking open that benefits book is to consider your past year’s benefits usage. More specifically, this process involves taking the time to reflect on your interactions with various benefits providers over the past year or so. And as you do, ask yourself, “did my current plan meet my needs, or were there gaps?”

Here again, understanding your past usage is key to anticipating your future usage needs and hence, your insurance coverage needs. So then, take a moment to review how your existing benefits have performed and how you’ve utilized them.

For example, let’s say that over the past year, you’ve seen several doctors and specialists due to the sudden onset of a chronic health condition. Now, in this case, your current plan may have burdened you with hefty out-of-pocket expenses. 

So then, if you anticipate your health condition to persist for some time, then you might choose a plan with higher premiums but lower deductibles in the year ahead, which could significantly minimize your out-of-pocket expenses.

Either way, take some time to ask yourself whether there have been instances where out-of-pocket expenses soared due to inadequate coverage. Did your network of healthcare providers meet your needs, or did you have to go out of network? And were there any benefits you paid for but did not utilize, like your flexible spending account (or FSA)? 

Indeed, a candid review of these and similar questions will likely shape your understanding of what worked and what fell short and likely equip you with insights for effective benefits elections decisions in the months ahead.

Don’t Just Look at Costs, Consider Value

Okay, so now that you have a solid grasp on your health experiences over the past year and what you might anticipate with respect to medical needs in the coming year, it’s now time to crack open that benefits book and begin reviewing your options.

So then, the first thing you’re likely to do as you review your benefits choices is to look at costs. With that said, however, the process of selecting your benefits shouldn’t be just a mere financial comparison. Indeed, you need to look beyond the dollar figures to appreciate each plan’s holistic value.

And so, why shouldn’t we look just at the cost of services offered? Well, the rationale here is simple: low cost doesn’t always translate into the best value. 

That’s because a seemingly cheap plan could leave you grappling with sizable bills for certain services later on, while a seemingly more expensive plan might offer better coverages, leading to lower out-of-pocket expenses over the coming year.

Indeed, making your benefits elections based on low premiums and thinking that you’re making the most economical choices could leave you in a lurch if your plan offers limited coverage or a restrictive network of providers. 

To be sure, because of your cost-effective choices, you could even find yourself burdened with high out-of-pocket costs for procedures not covered or for seeing providers outside of your network, which likely will negate your cost savings altogether.

So then, as you’re reviewing your options this benefits season, don’t get hung up on the upfront costs only to get caught with hidden expenses on the back end. Indeed, take a moment to think through the value of the services offered through each plan beyond its price when choosing your benefits options.

How to Avoid Common Potholes

Alright, so now that we’ve talked through the importance of understanding your current needs, reviewing your past benefits usage, and taking a comprehensive look beyond mere costs, let’s take some time to talk through some ways to identify and avoid common pitfalls that you may encounter when navigating the benefits selection process.

Now, no matter how well-prepared you are, the road to choosing your benefits can be filled with unexpected twists and turns. For example, you could come into this benefits season and just stick with what’s familiar. 

Indeed, you might even think to yourself, “Well, why shouldn’t I just renew my current healthcare plan? It’s worked fine for me until now.”

Well, maybe that’s true, but there’s an issue here.

More specifically, each open enrollment period brings with it not just an evaluation of changes in your own life, but also changes to your benefits as a whole! Keep in mind that employee benefits are one of the most significant costs many employers face outside of employee salaries. 

And so, given changes in the marketplace, your costs and benefits coverages from one year to the next could experience changes ranging from minor adjustments to a major benefits revamp.

For example, let’s say that you opt to click through the defaults this year, only to discover a few months later that a procedure that was covered in last year’s plan is now a hefty out-of-pocket expense. In this situation, you’d likely be stuck with your current coverage until a qualifying event or next year’s open enrollment period before you could make any changes to your plan.

So then, as you gear up for open enrollment, don’t allow the allure of the known to blind you to the potential benefits of what’s changed. That’s why it’s essential to take the time to dive deep into the specifics of each plan every year, even if you anticipate that nothing has changed.

The Hidden Treasures of Benefits

Now, the next thing you want to pay extra attention to is the not-so-obvious benefits that many employers offer. To be sure, your focus might naturally drift towards the big three coverages like medical, dental, and vision, and then you’re done, right? 

Well, it’s critical to note that your employer’s benefits package might offer coverages that could leave you with unnecessary lost opportunities.

How so?

Well, let’s say that you decide to opt out of short-term disability insurance, only to face an unexpected incident that leaves you wishing you had that safety net as you burn through savings during your long-term disability waiting period. 

Or maybe, as you approach this year’s benefits season, you realize that your employer could have deposited thousands in free money to your HSA (or health savings account) had you simply taken a few minutes to participate in your plan’s wellness programs.

And let’s not forget about the legal assistance benefit that might seem irrelevant now but could prove invaluable during significant life events like buying a home or drafting a will. 

So then, as you navigate through your benefits book this open enrollment season, take some time to expand your thinking beyond the conventional because you never know what you might miss.

The Clock is Ticking

And now, as we’re thinking through common pitfalls and mistakes during open enrollment season, it’s crucial to not miss out on the big one this year: get clear about your enrollment deadline. 

Now, this might point seem like an insignificant administrative detail, but it carries significant consequences.

How so?

Well, imagine that you’ve invested significant time and energy into reviewing your options, weighing the benefits and costs, and finally landing on an ideal mix of healthcare and fringe benefits. But the trouble is that you spent all that time completing your analysis and yet missed your deadline, and now you’re stuck with last year’s choices.

Now, this might not be the end of the world, but it is a crucial point nonetheless.

And why’s that? 

Well, here again, outside of any qualifying life events like getting married, having a child or changing jobs, you’ll likely be stuck with your benefits for an entire year. 

So then, remember that open enrollment is, in a way, a race against time. And yes, while all those emails from HR reminding you of the deadline are annoying, they’re there for a reason.

And, as you review your benefits options, take the time to make a note of key dates, set your own alerts, don’t rely on management for reminders, and secure your chosen coverage without feeling overwhelmed this open enrollment season.

How to Evaluate Tradeoffs Between Various Benefit Options

Alright, so now that you have a basic understanding of some things to consider before diving into your benefits book, let’s talk a little about an approach you can take to wade through the various options you have available to you.

Now, for many of you out there, the mere thought of looking through your benefits could fill you with a sense of dread as you consider all the options available. 

In fact, you might take one look at that benefits book and be tempted to go with the default options from last year instead of working through this seemingly arduous process.

And yes, you likely already know how not being mindful of your options can either cost you money or mean leaving money on the table. 

So then, what can you do to explore all of your options without getting bogged down in analysis paralysis?

Well, this year, you can try using a four-step approach to help you more effectively decide on benefits that best match your needs. 

And, so, what does this look like? 

Step 1: Prioritize

Well, at a high level, this means starting by prioritizing your key healthcare needs and preferences so that you can focus on what matters most to you.

Now, this might mean identifying plans that offer lower monthly costs, flexibility in choosing your healthcare providers, or ones that allow you to gain access to a wider network of medical facilities. 

Either way, knowing your priorities ahead of time can help you find a plan that aligns with your specific needs and circumstances.

Step 2: Evaluate

The next step you’ll want to take in our four-part process is to evaluate your options and compare features like costs, premiums, deductibles, and out-of-pocket expenses for each healthcare plan.

For example, a high deductible health plan (HDHP) gives you the ability to contribute to an HSA that offers a triple-tax savings. Now, this option might be a solid choice if you’re in good health, but if you’re dealing with a pre-existing or chronic condition, then the long-term savings advantage might not outweigh the out-of-pocket costs from a high deductible health plan.

Either way, this approach is critical because it can allow you to strike a balance between short-term affordability and long-term protection while, at the same time, allowing you to make sound financial decisions while safeguarding your health needs.

Step 3: Research

And whether you’re starting out at a new company, your benefits have changed recently, or you simply have never explored your benefits before, then the next thing you’ll also likely want to consider is your provider network. 

Now, the objective of this step is to allow you to gain some insights into the various healthcare options available to you to ensure that your preferred doctors and medical facilities are covered under the plan you choose.

And why is this important?

Well, this approach likely will minimize the risk of surprises or inconveniences when it’s time to get medical care or work with a specialist down the road.

Step 4: Select

And finally, now that you’re armed with your priorities, evaluations, and research, you can confidently choose a benefit that best suits your needs and financial situation. 

Now, it’s one thing to think about the coverage you need. Ultimately, you’ll need to select your coverages. So then, take the time to go back and review your selection to ensure that you’re not leaving money on the table.

The Four-Step Approach in Practice

Alright, so now that we’ve talked through this four-step approach, what exactly does it look like in practice? Well, let’s take a look at it from the perspective of choosing a healthcare plan.

Healthcare Plans

For example, during open enrollment, you’ll likely have the opportunity to choose from different healthcare plans, such as HMOs, PPOs, HDHPs, and others. 

So then, the big question for you here is, which one should you choose? 

Well, here again are the four points you may want to consider as you go through the election process:

  • Step 1 – Prioritize: Identify your key healthcare needs and preferences. Are you looking for lower monthly costs, greater flexibility in choosing providers, or a plan with a more extensive network of medical facilities?
  • Step 2 – Evaluate: Compare the costs, premiums, deductibles, and out-of-pocket expenses for each plan. Balance short-term affordability with long-term protection.
  • Step 3 – Research: Examine the provider networks to ensure your preferred doctors and medical facilities are covered under the plan you choose.
  • Step 4 – Select: Make an informed decision based on your priorities, evaluation, and research, and don’t forget to select the plan that best suits your needs and financial situation.

**Now, it’s essential to note here that this is just one example of options you may want to consider. We offer more detailed guidance on how to use prioritize, evaluate, research and select various coverage options in this month’s FI Mastery journey, available at

Tackle Open Enrollment with Confidence

Now, as the open enrollment period kicks off this year, it’s crucial to remember that picking your benefits isn’t just a routine, administrative task. In fact, it’s an opportunity to shape the foundation of your financial wellness for the entire year ahead.

That’s why, as you go about reviewing your benefits book this year, it’s vital to be deliberate and proactive throughout the process. And to do this, you can start by assessing your current and future needs, understanding the options available, and then making informed decisions.

Now, if you’ve avoided giving this critical process your attention in years past, then overcoming the inertia and confronting the complexity of employee benefits might seem daunting at first, but the payoff can be significant if you put in the effort.

Indeed, the process, while seemingly meticulous, not only offers you immediate benefits that help align your needs with benefits offered, but the process itself can also help you build a habit of mindful financial decision-making that ultimately can help you tackle open enrollment with confidence and take you one step closer to becoming the master of your own financial independence journey.