Three things you could lose in retirement that you may not expect.
Switching into a new chapter of life—retirement—comes with challenges that are often unseen and unexpected. Today, we’re going to explore some of the biggest ones.
Hi, I’m Devin Choules, founder and CEO of Choules Financial, and on this week’s Key to Yes, we’re going over three things many people lose as they transition into retirement—and what you can do to plan ahead.
The first thing is financial security.
You’ve likely had a steady paycheck for decades. That paycheck created consistency, confidence, and a sense of control. But once that income stops, everything shifts. Now you’re responsible for creating your own income—from your assets, Social Security, and other sources—and making sure it lasts.
This is where a Social Security strategy becomes critical. Whether you take it at 62, 67, or 70 will impact your lifetime benefit, taxes, and how much you may need to draw from other sources. We also look at financial tools that can generate income—like dividends, REITs, annuities, and even CDs. (Although I’ll add an asterisk there—if interest rates go down, CDs may become less attractive.)
But the most important thing is this: don’t hope it works out—know that it will. That confidence comes from having a written retirement income plan. It tells you exactly where your income will come from, how long it will last, and how to adapt when the markets—or life—shift. We update these plans every year to keep our clients on track.
So while your employer paycheck may go away, you can absolutely replace that financial security with proactive, intentional planning.
The second thing people often lose is employer benefits, especially health insurance.
When you leave the workforce, you lose access to employer-sponsored healthcare. If you retire before you’re eligible for Medicare, you’ll need to find a private health plan. That means evaluating costs, seeing if you qualify for subsidies, and making sure your income and cash flow align with those premiums.
Once you’re on Medicare, there are still decisions to make: do you choose a Medicare Advantage plan or go with a Supplement? Do you need vision or dental coverage? What about prescriptions? These are all important factors that affect both your care and your budget.
Just like you once reviewed benefits during open enrollment at work, you’ll now need to take responsibility for those choices—and it’s critical to understand how they fit into your overall plan.
The third thing many people don’t expect to lose is social connection.
You may have spent 10, 20, even 30 years with the same coworkers, eight hours a day. That group becomes your tribe. But when you retire, that tribe disappears—and for many, that creates a real emotional gap.
Whether you retire earlier or later than your peers, that circle starts to shift. If you don’t intentionally replace it, it can lead to isolation and even a decrease in life satisfaction. In fact, a 2024 study found that 8% of retirees reported feeling less satisfied in retirement—largely due to a loss of social engagement.
That’s why we always encourage clients to build a life outside of work. Find community. Volunteer. Get back into old hobbies. Try new ones. Spend more time with kids and grandkids. Take up golf, go to lunch with friends, or just get out and connect with others. Retirement should be meaningful—not lonely.
So whether you’re already retired or preparing for it, make sure you’re thinking about all three of these areas.
Take control of your financial security with a written income plan. Understand your healthcare needs and costs. And don’t underestimate the importance of staying socially active and emotionally fulfilled.
That’s all for this week’s Key to Yes. I’m Devin Choules. Thanks so much for watching. Don’t forget to like, subscribe, and follow—and we’ll see you next time.
