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Checklist for a Satisfying Retirement

Maybe you’ll play 18 holes every day, throw yourself into volunteer work or finally write that book. Maybe, for you, a satisfying retirement means selling everything and hitting the road with nothing but your dog and a classic car. Your working life was about doing what you had to do, and your retirement should be about enjoying things you want to do… whatever they may be. Though your vision for your ideal future may be unique to you, these are the eight areas I think about as the building blocks for a satisfying retirement.

Financial Security

It’s hard to enjoy a satisfying retirement when there’s a constant nagging worry that you’ll outlive your money. That said, “financial security” means different things to different people. How much you’ll need depends on a number of factors, and how comfortable you are with your assets and investments depends partly on your risk tolerance. Ultimately, do you and your advisor believe that you’ll be able to afford your basic expenses for as long as retirement lasts? Clearing this bar is the bare minimum for a satisfying retirement.

Some Leisure Money

Though making and sticking to a budget is essential once you’re living on a fixed income, a satisfying retirement should include some financial flexibility. Ideally you’ll feel comfortable going beyond your budget if you want to splurge on a vacation rental or throw an extravagant anniversary party. Knowing that you can make those occasional extra purchases, without putting your future at risk, is part of enjoying the fruits of your labor.

Safe, Comfortable Housing

The home that suited your needs while you were working won’t necessarily continue to be comfortable throughout retirement. As you age, downsizing to a single-level home or moving into a retirement community may become appealing. This is why it’s important to factor in future living expenses when you’re planning for retirement. Are you going to want to move somewhere where housing costs are much higher? Do you envision living in a community with luxury amenities? Getting specific about your housing goals is important for making sure your budget will work.

High-Quality Health Care

It doesn’t matter how satisfying every other element of your retired life is, if you’re not well enough to enjoy it. Having continuous and comprehensive medical coverage could prove very important to your general wellbeing over the course of your retirement.

Access to Support and Transportation

The MIT AgeLab identified three questions that are designed to help near-retirees assess how comfortably they’ll live in retirement. They’re simple, but thinking about your answers could be revealing. The first two questions: Who will change my light bulbs? And how will I get an ice cream cone?

As your physical abilities change, how you approach everyday activities will change too. If you’re someday unable to drive yourself to the ice cream parlor or handle home maintenance tasks, will you have access to help with those things? Someday that may be a key element of continuing your satisfying retirement.

Social Connection

Connection with others is absolutely essential for a satisfying retirement. That’s reflected in the third AgeLab question: Who will you eat lunch with? In other words, will you have people around you for companionship? For people with spouses, children, other close family members and lots of local friends, social connection is virtually guaranteed in retirement. For those professionals whose colleagues have been a primary source of connection, enjoying a satisfying retirement may require expanding their social circle.

Meaningful Activity

How will you fill your days? After decades of working and/or raising children, some retirees have a hard time adjusting to so much free time. A big part of having a satisfying retirement is having plenty of fulfilling activities to enjoy. Maybe you’ll continue to work in some capacity at first, but if you eventually retire completely, how will you continue to keep your brain sharp and stay physically active?

Minimal Stress

Stress is bad for everyone. It tends to exacerbate medical conditions, so anyone at risk of poor health should be especially intentional about avoiding stress. And frankly, by retirement you’ve spent decades dealing with stress—it’s time for a break.

Knowing that things are taken care of, and that your estate plans and financial plans are in good shape, allows you to relax and fully enjoy whatever it is that you enjoy the most.

What do you picture when you picture a satisfying retirement? Are you on track to make that vision a reality, or does more financial planning have to happen first? I’ve helped people at all stages of their retirement planning. Wherever you are in your process, I am here to help. The holistic approach we take at Sachetta Callahan means we’re interested not just in your financial life, but in your whole life. Contact me to get started. 


Joseph Sachetta

For over 35 years, Joseph Sachetta has worked in finance and accounting. He is a Certified Financial Planner, and a Certified Public Accountant. Joe’s passion lies with helping his clients strike a balance between living for today and saving for tomorrow.

We’re pleased to announce a growth merger with Wealth Management Advisors, effective January 1, 2022.

Learn more about what to expect.