A Tale of Two Sunsets: How Early Retirement Planning Dictates Your Final Chapter

Two Sunsets, One Powerful Lesson

I’ve seen two life sunsets up close — and the difference between them still stays with me.

My grandfather, Harry (HR), passed away in March of 2015, and my mother-in-law, Patricia (Patty), passed away in May of 2014. Both were deeply loved, and the losses were devastating to our family. However, only one had the power of choice. That’s what early retirement planning and strategic long-term-care planning are really about — protecting dignity, reducing stress on your family, and giving yourself a say in how the final chapter looks.

HR’s Story: A Lifetime of Planning Pays Off

My grandfather, Harry “HR” Rosman, lived 92 full years. He was a CPA for over 50 years, an avid fisherman, and loved the outdoors. Married to my grandmother (Gram) for 67 years, they raised two children, traveled the world, and lived conservatively. They were steady savers and careful investors who built security over time. They also believed in insurance. Life, disability, homeowners, auto, and most importantly, long-term-care coverage.

That discipline didn’t mean a joyless life. In fact, my grandparents’ consistency granted them freedom. Even in their 80s, they were still flying to Alaska, hopping on float planes, and spending a week fishing for salmon and halibut at Sportsman’s Cove. A classically-trained French chef cooked the fish they caught, and I still smile at the picture of them on the dock in bright yellow rain gear, holding a massive salmon. 

Careful planning didn’t limit their life — it let them enjoy it longer.

When HR’s health declined in his late 80s, the hospital offered different discharge options, including a facility. HR cut that short with, “I want to go home.” Fortunately, because of decades of preparation, he could. A wheelchair ramp went up, his bedroom was adjusted, and aides provided 24-hour support — all funded by the plan he put in place.

For more than two years, HR lived peacefully in the home he loved, surrounded by Gram and the rest of our family. We were able to spend his last days enjoying his company and reminiscing about his great achievements, without ever wondering, “How will we pay for this?” Lastly, due to good estate planning, Gram (who is now 101 years young!) can live out her days free of financial worry. That’s the power of funding at-home care with foresight.

Patty’s Story: When Planning Is Postponed

My mother-in-law, Patricia “Patty” Calicchio, had a different end-of-life experience. Patty passed away at 62 — exactly 13 months after being diagnosed with pancreatic cancer. She divorced young and raised her two children without support. For more than 30 years, she worked hard in management for a supermarket chain, but she never broke free from debt. She lived paycheck to paycheck, using credit cards and home equity to make ends meet. Saving never became a habit, and insurance was never a consideration.

Then came the diagnosis. Within months, her limited resources were gone. There was no money for private aides, no coverage to fall back on. Medicaid quickly became her only option. That meant the state, not Patty or our family, decided where she would spend her final weeks. Fortunately, she was placed in a facility close to us, but she shared a room where the roommates changed often. 

Unlike Harry, no one ever asked Patty how she wanted her last days to look. Our family was presented with a handful of tough choices and tasked with determining which option was the most compassionate for Patty. Instead of gathering around her to share memories, our conversations often turned to learning the Medicaid system in real time and paying bills. Even her funeral costs fell back on the family. It’s a painful example of what happens when the question of Medicaid vs. long-term-care insurance goes unanswered until it’s too late.

Four Levers That Dictate Your Final Chapter

The difference between Harry and Patty wasn’t luck. It was planning. The truth is, at some point, every family will face these decisions. Whether it’s you, your spouse, or your parents, questions about care, money, and dignity always come up in the final chapter. The only question is whether you’ll face them with a plan — or in crisis.

Four levers can make all the difference:

Consistent Saving & Investing
It’s not about hitting home runs. It’s about showing up year after year. Harry didn’t try to outguess the market. Instead, he saved steadily, invested conservatively, and let time do the heavy lifting. Too many people tell me, “I’ll start saving once the kids are out of college” or “when the mortgage is gone.” But lost time is the one thing you can’t get back. Even small, steady contributions add up to the kind of flexibility Harry’s family had when it mattered most.

Long-Term-Care Coverage — (Or Self-Funding Strategy)
The cost of care can sneak up on families. On Long Island, a private room in a nursing facility or 24-hour in-home aides can quickly deplete savings. Without a strategy, families are left scrambling for Medicaid — and once Medicaid steps in, you lose the ability to choose where and how care is delivered.

Estate Documents & Beneficiary Alignments
You can’t assume paperwork will take care of itself (it won’t). Outdated beneficiaries, missing powers of attorney, or a will that doesn’t line up with your retirement accounts can undo decades of careful saving. Estate documents are more than legal forms; they’re instructions that protect your spouse, your kids, and even your own dignity if you can’t speak for yourself.

Open Family Dialogue Early
This is the lever most people avoid because it feels uncomfortable. But it makes all the difference. Talking about care and end-of-life wishes before a crisis doesn’t make the conversation easier — but it can make the outcome better. It gives your family clarity and a united front when emotions are running high.

End-of-Life Financial Planning Action Checklist: Secure Your Own Sunset

If Harry’s story showed anything, it’s that peace of mind doesn’t happen by accident — it’s the result of decisions made long before the crisis. The good news is, you don’t need to overhaul your entire financial life to head in the right direction. A few intentional steps, taken early, can create the difference between options and obligations when the time comes.

Here are eight ways to start shaping your own “sunset plan”:

1. Review your insurance, especially long-term-care.
Make sure your policies are current and sized to today’s realities.

2. Model the real cost of care.
Know what in-home help or a facility would actually cost so you can prepare.

3. Get your will, trust, and powers of attorney in order.
These documents protect your wishes and spare your family from guesswork.

4. Double-check your beneficiaries.
Outdated forms are one of the most common planning mistakes.

5. Write a “legacy letter.”
Leave guidance, values, or instructions in your own words for loved ones.

6. Talk with family about your care wishes.
Clear conversations now prevent conflict later.

7. Stress-test your plan.
Play out “what if” scenarios—health issues, market dips, or long care needs.

8. Revisit your plan regularly.
Update after big life changes to keep everything aligned.