Landstar System Families: Helping Parents Prepare an Estate Plan with Confidence

Healthcare Provider Update: Healthcare Provider for Landstar System Landstar System, Inc. partners with various healthcare providers to offer health insurance benefits to its employees. While the specific healthcare provider can vary depending on the insurance plan chosen by employees, Landstar commonly collaborates with major national insurers such as Aetna, Blue Cross Blue Shield, and UnitedHealthcare to provide comprehensive health coverage. Healthcare Cost Increases in 2026 As employers brace for steep healthcare cost increases in 2026, the outlook looks particularly daunting due to multiple economic pressures. With projections of medical costs rising by 8.5% and insurers requesting average premium increases of over 20%, workers can expect to see their out-of-pocket expenses soar as enhanced federal premium subsidies expire. The confluence of increased treatment costs, an aging workforce, and overall inflation is exacerbating these challenges, leaving many employees concerned about their ability to afford necessary healthcare services. Without proactive measures, more individuals could find themselves priced out of adequate coverage, emphasizing the urgent need for strategic planning ahead of these changes. Click here to learn more

'Thoughtful conversations about aging and legacy can make a meaningful difference for Landstar System employees willing to engage in early dialogue and clear family communication.' -- Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Open and honest discussions about aging, documents, and family wishes are especially valuable for Landstar System employees, who may want to begin these conversations sooner rather than later.' -- Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. How to begin meaningful estate planning conversations with aging parents.

2. How to organize essential documents and understand state-specific planning needs.

3. How to select the right individuals to help carry out family wishes.

Sharing lessons learned

As a former practicing trust and estates lawyer and advanced planner, I discuss death nearly every day. However, even with professional familiarity, the dialogue was still difficult when it was time to talk about my own parents' end-of-life plan, something many Landstar System families can relate to.

I come from a classic Italian blue-collar family. My sister and I grew up in the same Staten Island home where my parents lived for 40 years. Basic estate planning documents—including a will, powers of attorney, and health care proxies—were created years ago to help others step in if needed. My sister and I discussed how they wanted things handled and who should be responsible for major decisions, an experience similar to what many Landstar System households navigate.

To be closer to me, my parents sold their long-time home and moved to a one-story residence in New Jersey. After their move, I suggested they revisit their estate documents because state-specific laws differ significantly. This also became necessary because my sister no longer wished to manage my parents' affairs, and our family dynamics had changed.

Getting the conversation started

I've learned over the years that many people—especially older generations—are uncomfortable discussing their financial lives with their children. They may hesitate simply because they do not want others to know what they have.

If your parents are unsure about the conversation, start with practical questions about who they want contacted in an emergency and what they would prefer to happen. You can also ask them to create an inventory of their accounts (without balances) so you understand what exists.

Coordinating schedules can be challenging. One of my 80-year-old clients once told me she planned all family financial conversations for Thanksgiving because it was the only time she knew everyone would be in the same room. This is a scenario that may resonate with many Landstar System employees.

Thankfully, my parents are open about their finances, but I still uncovered several things I didn't know. They were unsure about whether they wanted burial or cremation and had strong feelings about their end-of-life preferences. Although cremation was once restricted by the Catholic Church, it has been permitted for decades as long as the choice does not conflict with religious belief. One surprising detail I learned was that my father had long-standing ownership in a small business, something that required additional planning.

The brown accordion folder

When we discussed where their important documents were stored, I realized how vital this knowledge truly is. Too many people create estate documents but leave them hidden away. One client once told me she accidentally kept millions of dollars' worth of original stock certificates in a breadbasket—something any family, including those tied to Landstar System, could experience.

My father, an accountant, has always been meticulous about records, whereas my mother has not traditionally managed household finances. He showed me his brown accordion folder with a purple “Death” tab inside containing all his contact details. Today, families often use cloud-based tools to store documents and allow a trusted person access. No matter the method, the key is that everyone—including those supporting Landstar System families—knows how to locate what is needed.

Locating the appropriate individuals

These discussions are emotionally charged, particularly when determining who will carry out your parents’ wishes. I had to tell my mother that I could not serve as her health care proxy, despite her original designation. Selecting the right individuals for each part of an estate plan is essential.

I currently serve as my parents’ executor and power of attorney, while my husband—whom they trust deeply—will likely act as their health care proxy.

My parents continue to discuss what they want their legacy to look like. They hope to help their grandchildren with education expenses, although they haven’t finalized their approach. My goal is to understand their wishes so I can support them or help find someone who can, just as many Landstar System families aim to do for their own loved ones.

Important Takeaways

While my story is personal, there are larger lessons to share with Landstar System employees. In my experience, I've found that it could be helpful to begin the conversation from an emotional rather than strictly financial angle, especially if your family members are hesitant to discuss end of life matters. 

Since many estate planning laws differ from one state to another, Landstar System employees may want to have their parents' estate planning documents reviewed if their circumstances change, especially after relocating.

Make sure you know where important documents are kept during your conversations, and consider who may be well-suited to help carry out your parents' wishes.

How The Retirement Group Can Assist

Discussing estate planning, family communication, and aging can be challenging, but you do not have to handle it on your own. The Retirement Group helps retirees and their families think through future decisions and understand available options. If you need guidance with retirement or estate planning, you can reach our team at  (800) 900-5867 .

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Sources:

1. Coughlin, Peter. “ How to Organize Estate Documents to Make Life Easier for Your Heirs .”  Berkshire Money Management , 23 Aug. 2024,  https://berkshiremm.com/organize-estate-and-financial-documents/ .

2. Hermance Law. “ Talking with Elderly Parents about Estate Planning .”  Hermance Law , n.d.,  https://hermancelaw.com/blog/estate-planning-for-elderly-parents .

3. Kaminsky, Michelle, Esq. “ Do I Need to Update My Estate Planning Documents if I Move to a New State? ”  LegalZoom , updated 28 Jan. 2025,  https://www.legalzoom.com/articles/do-i-need-to-update-my-estate-planning-documents-if-i-move-to-a-new-state .

4. National Institute on Aging. “ Choosing a Health Care Proxy .”  National Institute on Aging , reviewed 31 Oct. 2022,  https://www.nia.nih.gov/health/advance-care-planning/choosing-health-care-proxy .

5. Nash, Tom. “ The Church’s Cremation Change .”  Catholic Answers Magazine , 4 Jan. 2024,  https://www.catholic.com/magazine/online-edition/the-churchs-cremation-change .