Norm Grill: How to prepare for a comfortable retirement

If you are considering retirement, here are five financial issues to focus on to help make a successful transition:

Health insurance

Are you among the lucky few who will continue to be covered after retirement? If not, you’ll need to replace your health coverage.

If you will be eligible for Medicare at the time of your retirement, you may want to start checking into “Medigap” coverage. Medicare pays for much, but not all, of the cost for covered health care services and supplies. Medigap is Medicare Supplement Insurance that helps fill in “gaps” and is sold by private companies to individuals age 65 and older.

If your employee plan coverage is broader than Medicare, consider taking care of nonemergency medical, dental, or eye care needs before you retire.

Other insurance

Once you retire, and depending on individual circumstances, you may need to replace employer-provided life insurance with extra coverage. You should also consider purchasing long-term care insurance in case of a lengthy nursing home stay in the future. Premiums for qualified long-term care insurance policies are tax deductible to the extent that they, along with other unreimbursed medical expenses (including Medicare premiums), exceed 10 percent of the insured’s adjusted gross income in 2020.

Social Security

Decide whether you want to take early Social Security benefits if you’re retiring before your full retirement age, which is currently 66 years of age for people born between 1943 and 1954 and age 67 for those born after 1960. The years in between are prorated accordingly. If you choose to retire as early as age 62, doing so may result in a reduction of as much as 30 percent of your full benefits. Conversely, starting to receive benefits after normal retirement age may result in larger benefits.

Taking Social Security benefits at full retirement age makes financial sense for most people, but if you think you might need to take early benefits, it would be prudent to talk with a financial professional first.

Pension plan or 401(k) retirement plan payout

Plan well in advance how you’ll take the payout from your pension plan or 401(k) plan. For example, will you transfer the funds to a conventional or Roth IRA? How will the funds be invested?


If you’re planning a move to another state or country, make sure that you fully explore the financial ramifications of living there before you move. Cost of living as well as rates of taxation can vary significantly from one region of the country to another.

This writeup does not cover all the elements for a comfortable retirement and should not be taken as advice. Consider consulting a financial professional to develop a plan specific for your circumstances.

Norm Grill, CPA, ( is managing partner of Grill & Partners, LLC (, certified public accountants and consultants to closely held companies and high-net-worth individuals, with offices in Fairfield and Darien, 254-3880.