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Open Enrollment: Medicare and Health Savings Accounts

We know selecting Medicare and a healthcare plan can be stressful due to the many choices and increasing healthcare costs. Your Charter Oak advisor will gladly assist you in this process, whether it be Medicare or during your open enrollment period.

Let's start with a quick refresher on Medicare, its various parts, and some available resources. 


  • What is Medicare? It is the federal health insurance program created for individuals aged 65 and older and certain younger people with medical conditions or disabilities. 
  • When do I enroll? For those over 65, the open enrollment period is October 15 to December 7.
  • What are the parts of Medicare? See chart below. 

  • What plan do I choose? What plan do I choose? One of the biggest questions is whether to choose Original Medicare (and buy a Medigap policy) or a Medicare Advantage plan (often viewed as an all-in-one alternative to Original Medicare). 

Your Charter Oak advisors are here to assist. Still, at the highest level, Original Medicare with Medigap Plan G is our preferred choice, as it gives participants more flexibility in seeing any doctor or specialist who accepts Medicare. It also is one of the most comprehensive plans. 

Below are additional resources to help educate yourself and your family members.

  • For most Marketplace participants, Healthcare.gov is your starting point. 
  • For Maine residents, the state-based marketplace can be found at Coverme.gov 
  • Medicare’s online Finder tool or by calling 1-800-MEDICARE

Medicare Resources 

Health Savings Accounts

An increasingly popular option, due to its triple tax advantage, is Health Savings Accounts. Once again, there are many decisions to make on health care plans through employers, and your Charter Oak Advisors are here to help. Here is an overview of Health Savings Accounts.

  • A health savings account (HSA) is a tax-advantaged way to save for qualified medical expenses.
  • HSAs pair with an HSA-eligible health plan. This is generally a high-deductible health plan.
  • Because it offers potential tax advantages and money within the account can be invested, an HSA can be used to pay for both near-term medical expenses and expenses in retirement.

The triple tax advantage of HSAs can allow for a sizeable account balance. Triple tax advantage means your contributions go in with pre-tax dollars, your account grows tax deferred, and your withdrawals from the account are tax free (for qualified expenses). HSAs are the only type of savings account that receives this kind of preferential tax treatment!

The tax benefits can help your account grow, even beginning at age 50 as the chart below illustrates. 

We understand how daunting selecting health care plans can be. This was a high-level overview of both Medicare and Health Savings Accounts. As this is a highly personal decision, please contact your Charter Oak Advisor for further assistance. 

It is a pleasure and a privilege to serve you, and we wish you a peaceful and relaxing Thanksgiving holiday.