On February 14, 2019

Take retirement for a test drive

There are many reasons why people who could retire are hesitant to do so. Some people think they need to wait until they’re 65 or older. Some are worried about running out of money. Many parents want to keep supporting their children through some major life transition, like college, marriage, or buying a first home.

Maybe the most common reason we see for a retirement delay is folks who just can’t imagine their lives without work. That’s understandable. A routine that’s sustained you and your family for 30 or 40 years can be a hard routine to shake.

But retirement doesn’t have to be all or nothing right away. If just thinking about retiring makes you jittery, use these tips to ease into retirement a little at a time.

1. Talk to your family

Clear, open communication is an essential first step to approaching retirement. Be as honest as possible about what you’re feeling. What worries you about retirement? What excites you? What do you envision your days being like? Where do you want to live? What does your spouse want retirement life to be like?

2. Talk to your employer

Many companies have established programs to help longtime employees transition into retirement. You might be able to trim back your hours gradually to get an idea of what days without working will be like. You’re also going to want to double-check how any retirement benefits you may have are going to work. Discuss any large outstanding projects with your supervisor. Make a plan to finish what’s important to you so that you can leave your job feeling accomplished.

Self-employed? Give your favorite employee (you) fewer hours and clients! Update your succession plan and start giving the soon-to-be CEO more of your responsibilities. Make sure you have the absolute best people working for you in key leadership positions so that your company can keep prospering without your daily involvement.

3. Make a ‘rough draft’ of your retirement schedule

What are you passionate about? What are some hobbies you’d like to develop into a skilled craft? Do you want to get serious about working the kinks out of your golf swing? Are there household projects, repairs, or upgrades you want to tend to? A crazy idea you kicked around at work you’d like to build into a new company? A part-time job or volunteer position you’d like to take at an organization that’s important to you? New things you want to try? New places you want to visit? Grandkids you want to see more often?

Try filling out a calendar with some of your answers to these questions. As you start to scale back your work hours, take a few lessons or volunteer shifts. Sign up for a class. Leave town for a long weekend. See what appeals to you and what doesn’t.

Remember, you don’t have to get your schedule right the first time! A successful retirement will involve some trial and error. Learn from things you don’t like and make a point to spend more time doing the things you do like.

4. Review your finances

Once you and your spouse have settled on a shared vision for retirement, you may want the help of a qualified financial advisor to create a financial plan to help ensure you are financially fit for (semi)-retirement. Go through all of your sources of income, retirement accounts, pensions, savings, and other investments to lay out a projection of where your money is coming from and where it’s going.

With a solid financial plan, you and your advisor can coordinate all aspects of your situation and collaborate with you on the best course of action. You don’t have to face retirement alone and make big decisions without expert guidance. So, if you are dreaming of those days when work is optional, start taking some action steps to help yourself through this phase of life.

Kevin Theissen is the owner of Skygate Financial Group in Ludlow.

Do you want to submit feedback to the editor?

Send Us An Email!

Related Posts

Pies, parades, and porch chats

July 2, 2025
“America is a tune. It must be sung together.”—Gerald Stanley lee The month of July is the height of summer, bringing a spirit of celebration to all of us. Our town of Killington may be small, but we know how to celebrate the 4th of July. We start early with the annual book sale at…

Inventing a better ski day: the innovations that drew crowds to Killington

July 2, 2025
By Karen D. Lorentz Editors’ Note: This is part of a series on the factors that enabled Killington to become the Beast of the East. Quotations are from author interviews in the 1980s for the book Killington, A Story of Mountains and Men. “We’ve got a million dollars that says you’ll learn to ski at…

‘Almost Heaven’

July 2, 2025
The stage was simple, designed to resemble a wooden board that resembled the siding of any barn, anywhere across America. It could have been the barn behind my house, or the one that my cousins have down in Georgia. It could have been a barn in Colorado or even West Virginia.  Nothing remarkable at all,…

Getting away from it all

July 2, 2025
My family and I went to the beach this past week. The temperatures were hot, and the weather was sunny, making for a classic seaside vacation. The house we rented was in the harbor of the town where we were visiting, so while we didn’t stare out at the ocean, we were able to sit…