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Wednesday, June 14, 2023

Are You Really Ready to Retire?

It’s easy to think that reaching retirement age will automatically usher you into a happier time of life. Not so – check out these considerations before you quit work.

Ah, retirement. You’ve been working your whole life to get here. What a relief not having to work! Well, it’s not quite as simple as that. Let’s talk about what you need to consider well ahead of this transition.

Look Ahead, Not Behind

We tend to think of retiring as leaving work behind. Instead, consider what you will be retiring to. Try and get specific to visualize what your days ahead will hold. 

Is travel a top priority? Which countries or areas are at the top of your list? How long do you want to be on the road for each trip? In a year? Do you want to travel in an RV, camp, stay at hotels or some combination of those? You can always change your mind, but it can be helpful to start with some ideas. Take an RV on a test run by renting one for a short trip before committing to a purchase. 

Will you spend more time with the grandkids? How much? Will you take Susie to dance lessons or watch the baby three days a week? Do you want to volunteer for single charity events, or become a regular volunteer where you might form friendships with others? Is gardening an interest? Do you want to landscape the front yard, or just plant some sunflowers on the south side of the house? 

Blocking Out Time

You don’t have to make a firm plan for anything; part of the joy of retirement is that you’re allowed to change – again and again – how you spend your days. But it is helpful to have some sort of structure, at least at the beginning, as you transition into your new life.

You may need, or want, to build your days around a part-time job. You could join a reading group that meets once a month or have a weekly golf game with your best friend. You might commit to exploring a new opportunity with MeetUp every couple of weeks until you see what sticks or attend a few meetings of a local history club or game night at your library. 

Having some scheduled outings can help you fill chunks of time, which may ease the transition from days filled with work projects to days that may be unnervingly open. Take an hour for coffee and scrolling through news every morning if it helps and spend a couple of hours walking or at the gym every afternoon. Bake a treat for the neighbors every Saturday. Whatever activities float your boat, early retirement is a time to schedule them in so you can continue to feel productive.

Social Security and Medicare

There can be severe penalties for failing to enroll on time or electing the wrong program/age to begin receiving payments. Go to an informational session at your local library or consult your finance professional about when to claim Social Security and Medicare benefits. They will not start automatically.

Although you will often see recommendations online to wait until age 70 to take Social Security, and that is often wise advice, there are a host of personal circumstances when starting Social Security at an earlier age may be best. Start by reading this guide to Social Security to determine how to optimize your own situation.

Medicare is wonderful to have, but it is a complicated healthcare system with outsize implications for missteps. Start by reading up on how to get started with Medicare. Read articles about the pros and cons of Original Medicare and Medicare Advantage and consult the State Health Insurance Assistance Program in your state for more information about Medicare in general and the plans available in your area.


Before you retire, it’s crucial to know how much you will spend every month to make sure your income will cover your needs, and hopefully, your wants. Your financial situation will largely dictate your retirement lifestyle. Work with a financial professional closely to make sure you don’t get hit by unpleasant surprises. 

Start by making a budget of current expenses, then remove items you will no longer need to spend on, such as a work wardrobe or a mortgage that will be paid off. Add in expenses that may increase, like traveling more or funding college for the grandkids.

Take a look at what income you can expect in retirement. You may have a pension, Social Security, a 401(k), IRA, and brokerage investments. Work with an advisor to ensure that your investments are properly diversified and understand how much you’ll be able to safely use without depleting your accounts. 

Plan on unexpected expenses. Have a fund available for the inevitable surprises, such as needing a new roof, car repairs, a health emergency, or helping family members through tough times. Many of us will need long-term care, which is not covered by Medicare. Do you have insurance to help cover the cost, or will you self-insure? 

Finally, clear up debts that may be depleting your budget. Credit card debt is particularly costly and pervasive. Get rid of it before you quit working. 

Like pretty much everything in life, easing into a happy retirement requires planning and some work on your part to get it right. To make the most of those years, you’ll need to prepare a framework for how you’ll pay for them, and how you may spend them. With that in place, they likely will be golden years. 

This article is not intended to be a substitute for professional financial advice from a qualified financial advisor.