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Open Enrollment: Navigating Employer Benefits

Open Enrollment: Navigating Employer Benefits

| September 22, 2021

There are a lot of things that remind us that we are entering into the Fall season. Starbucks releases the Pumpkin Spice Lattes, everyone starts posting pictures on Instagram in the woods, at an apple orchard, or pumpkin patch, scary movies start playing on TV, and the holidays are right around the corner!

In addition to that, it's group benefit enrollment season! That's what everyone really gets excited about, right?


I figured; however, the decisions you make during open enrollment can have massive consequences (good or bad) on your finances. So this year, instead of just checking the boxes to "get it done", let's take the time to review how your benefits actually work.

First, health insurance.

  • How many different options do you have? 
  • How often do you go to the doctor?
  • Are you planning to have a child next year?
  • What are the monthly premiums for each plan?
  • What is the deductible and out-of-pocket maximum for each option?
  • Do you have a high deductible health plan that gives you access to a health savings account?
  • Does your company make contributions to a health savings account for you (free money like a 401(k) match)?

Answering these questions about your health insurance options will start to give a clear picture on where you can recapture dollars that may have otherwise been lost. Be strategic.

Next, disability insurance.

This may be one of the most important insurance items of all that are offered. It protects your paycheck and provides income in the event you get sick or hurt. Until you have significant assets on your balance sheet that can reproduce your income, owning disability insurance is a must because if something happens that takes you out of work, you face a systematic liquidation of all of your assets until you get back to work. It can lead to financial failure faster than anything else in life.

  • Who pays for the disability insurance premium?
  • If it's you, do you pay with before- or after-tax dollars?
  • What is their definition of "total disability"?
    • Most employer plans pay you for 12 or 24 months if you can't do your job, then stop paying you if they can prove you can do "any other occupation". If you answer their phone call, do they now have proof you can be a telemarketer?
  • How long do they pay for claims of stress, anxiety, depression, sleep disorder, etc? 
  • How much of your income is protected, and is the benefit then taxable to you when you receive it?
  • Will they pay benefits if you are only partially out of work?

We are talking about the difference of potentially hundreds of thousands, or even millions, of dollars on or off your balance sheet in the event something happens that prevents you from working at your full potential. There are simple ways that we can fix this, let's schedule a time to talk more.

Next, life insurance.

  • How much can you get?
  • How often do they increase the price?
    • Usually in 5 year increments
  • Can you take it with you if you change jobs?
  • What would you want life to look like for your family if something happens? What amount is appropriate based on like today and in the coming years?
  • What if you can get something outside of work that is cheaper over time?

Life insurance has a lot less moving parts than health and disability insurance. There's a lot of "gray" areas in the former two benefits.

Lastly, retirement options.

  • Do you get a pension, profit-share, 401(k), 403(b), 457(a)?
  • Do they offer a roth portion? What's the difference between roth and pre-tax?
  • How much is the company match? Is that dollar for dollar?
  • Is it better to pay off high interest debt first and contribute up to the match, for now?
  • Should you start maxing out the plan?
  • What are the investment options they provide?
  • Should you do a target date fund or allocate the dollars yourself?
  • If you allocate dollars yourself, how much equity vs bonds should you have? US vs International? Large-cap vs mid-cap vs small-cap? Growth vs value?

This is your future we are talking about. The money that you are hoping to build in order to provide an income stream in retirement. Don't leave that up to "chance". Remember, what has done well the last few years might not continue to do well in the future. There is enough data out there now that can help you craft a very strategic portfolio, depending on the options that your company provides.

Now there are plenty of other benefits provided through work as well, like Paid-Time-Off, Dental, Vision, Accidental Death & Dismemberment, Critical Illness, Accident Insurance, etc.

Just because they offer a benefit and just because it may be cheap today, doesn't mean you have to enroll. There are a lot of good things to have through work, but there are some items you should consider getting outside of work.

The insurance that is provided through work should be supplementing your individual coverage. Individual coverage follows you no matter your job, and covers you specifically, not a blanket plan that is trying to cover 100 or 10,000 employees. Blanket plans have a lot of loopholes that you may soon realize if you find the answers to the questions above.

Now if you're like most people and don't have the time or bandwidth to dive into all of those items, send me an email at or book a meeting here and I would love the opportunity to help.

All of my initial meetings are complimentary in the hopes I can provide a ton of value, you enjoy the conversations, and we can continue them from there. 

I hope to speak soon!