By: Andrew Dickens, AIF®, CEXP™, CBVS™
Director of Pension Services & Wealth Advisor
Your 50s can feel like standing at the top of a hill, looking both backward and forward at the same time. Behind you are decades of working, raising a family, buying homes, and paying bills. Ahead is the next phase – retirement or semi-retirement – where your time is more your own, but your savings have to do more heavy lifting.
This decade is incredibly powerful. The choices you make now can have more impact than almost anything you did in your 20s or 30s.
The idea starts taking clear shape
Until your 50s, retirement is often an idea: “I’ll stop working at some point.” Now it’s close enough to start taking a clear shape. That means asking yourself when you might wish to slow down, how much you want to work (if at all), where you’d like to live, and what a good day in retirement looks like for you.
Do you picture travel, hobbies, and grandkids? Do you want to downshift to part-time work, consulting, or volunteering? There are no wrong answers, but having a clearer picture helps us test whether your current path aligns with that vision or needs some adjustments.
Peak times
For many people, the 50s are their peak earning years. You may finally be past the most expensive child-raising years, or you might still be helping with college. Either way, this is often the moment when you’re in the best position to make progress.
This is the time to be intentional about where each extra dollar goes. Boosting retirement contributions, especially if you’re eligible for catch-up contributions, can make a meaningful difference in just a few years. Checking that your investment mix still fits your timeline and comfort level is equally important. While it’s natural to want to enjoy the fruits of your labor, letting every raise add more lavishness to your lifestyle can prove to the detriment of your future self.
The 50s are also a good time to clean up. This might mean paying down high-interest debts, coordinating a plan for your mortgage, or consolidating old retirement accounts so you aren’t managing a scattered collection of small balances.
You don’t have to enter retirement completely debt-free, but you should know what you’ll still owe, how it fits into your budget, and whether you’re comfortable with that. Less debt and less complexity often means less stress down the road.
The health angle
As we get older, health moves to the center of the financial conversation. If you plan to retire before Medicare, you’ll want to understand your options for health coverage in the gap years. Disability insurance may or may not still belong in your plan, depending on how close you are to your “enough” number. Life insurance needs may change as children become financially independent and debts are paid down.
Long-term care is another topic that must be part of the conversation in your 50s. You don’t have to buy an insurance policy, but you should have a strategy in case you or your spouse need extended care. That strategy might involve savings, insurance, family support, or some combination of the three.
In the middle
Many people in their 50s feel squeezed between aging parents and nearly grown children. You might be helping your kids with tuition or housing while also worrying about your parents’ health and finances.
It’s generous to want to provide support in both directions. The challenge is doing it without sacrificing your own future. Keep in mind that you can borrow for college, cars, and homes, but you can’t borrow for retirement. Sometimes the most loving thing you can do for your kids and your parents is to make sure you won’t need to rely on them later.
One helpful exercise in your 50s is to “test-drive” retirement before you get there. You might try living for a few months on the income you expect to have later or start leaning into the activities you hope to spend more time on when work becomes optional. This can show you whether your financial plan and lifestyle expectations are in sync.
Don’t panic
If you feel you’re behind, don’t panic – you’re not alone. Many people start serious planning in this decade and still create secure retirements. The most important step is to start the conversation, to turn vague hopes into a concrete, flexible plan for your next chapter.
