Helping Our Parents Age Gracefully: A Family’s Guide to the Delicate Transition

August 24, 2023

The lifecycle of a family, much like the business it may own, has its ebbs and flows. There’s the rise of the next generation, taking the reins, and the maturation of the older one, requiring new forms of support. Just as we prepare to take over the family business, we must also prepare to step in as caretakers for our aging parents—helping them age with dignity and grace.

The Unspoken Concern About Aging Parents in Family Business

It’s an image few want to conjure: the sprawling family mansion, once brimming with life, now a silent sentinel to a different time. The cracks in the floorboards, the croaking of frogs in the ceiling, and the echoing hallways, are stark reminders of the parents’ advancing years. For a while, these telltale signs go unnoticed, or they are intentionally overlooked; but they represent the impending shift in family dynamics many are too afraid to talk about.

For those leading a family business, admitting the need for help could feel like admitting irrelevance. If the very ones who laid the foundation for the business empire begin to falter, how could they remain influential? On the flip side, for the adult children, acknowledging this change feels like taking on a phase of life they aren’t ready for. Yet, waiting too long can risk the very legacy the aging parents wish to preserve.

The Turning Point

The family mentioned in the introduction here is real. And it took a meeting between the siblings of the aforementioned family and our WillKate team to talk about the signs. Their once-proud family home, valued over $2 million, was crumbling. The signs were subtle at first: a missed appointment here, unpaid bills there, or the house’s condition deteriorating. But as time went on, the signs grew more apparent. The siblings could no longer ignore what was happening right in front of them.

The progression of aging is an inevitable facet of life, and it is often accompanied by a diverse array of emotions and considerations. As individuals advance through their life course, their sense of identity can self-worth can change. What will happen if they can no longer run the family business? From where will they derive their value?

With aging, there may also be a natural decline in cognitive capabilities and an increased probability of health complications, which make the transition even tougher. This is why it is imperative to have the tough conversations early on, before cognition becomes a barrier.

Why Family Businesses Should Engage in Open Dialogue about Aging Parents

Engaging in open dialogue about the aging process has manifold benefits. Addressing concerns early on can prevent monetary losses and helps in maintaining the value of both the business and other family assets, such as the family home(s).  These conversations can also serve as a source of emotional relief for both parents and children, fostering mutual understanding and reinforcing the sentiment that they’re navigating this journey together. Timely conversations, arising from transparent communications, guarantee that parents can relish their golden years in safety and comfort.  Perhaps most crucially, having honest and frequent conversations fortifies the family bond, ensuring alignment in decisions and preserving the unity and values that families cherish.

How to Approach the Conversation About Aging Parents


  1. Pick the Right Setting

Initiating the conversation about the future needs of your aging parents requires a delicate touch. First and foremost, it’s vital to choose the right setting for such a discussion—a neutral, comfortable environment where parents feel relaxed and at ease is probably best.

  1. Be Empathetic

While you may not understand what it feels like to be the aging patriarch or matriarch of your family, you can “walk a mile in your parent’s moccasins” before broaching this conversation. How would you feel in their position? What fears might you have? From where will you derive your value if not as the head of the family and or family business?

As you broach the subject, it’s crucial to remain deeply empathetic, being acutely aware of the myriad emotions in play. When you approach the topic with gentleness, parents are more apt to feel assured that their legacy and dignity will always remain intact and that paves the way for a more receptive dialogue.

  1. Consider Using a Facilitator

The last thing you want to do is create an “us versus them” situation in the family. So, take care not to sideline anyone. It’s best if all relevant family members are part of the discussion. For families finding it tough to navigate these waters, hiring a professional facilitator can be invaluable. Experts, like those at WillKate, are well-versed in guiding these sensitive discussions, ensuring clarity and mutual understanding for all involved.

  1. Create an Action Plan

Lastly, it’s essential to move from discussions to actions by creating a tangible action plan. This might encompass regular check-ins, necessary home repairs, or considering potential relocations to ensure parents receive the care they need as they age.

The Positive Outcomes

In the case of the family mentioned above, much progress was made once the emotional barriers were crossed and open communication was established. The family was able to take the practical steps needed to implement the action plan. The siblings decided to bring in a professional to assess the family home’s condition and make the needed repairs. They hired a daily assistant for the parents’ comfort and to manage the home. They worked closely with us as their wealth management consultants to ensure organized finances. They took turns helping with regular medical check-ups that were scheduled, and they made sure a comprehensive healthcare plan was set up. Estate planning, wills, and power of attorney were discussed openly so everyone knew what to expect once the parents passed.

The parents felt rejuvenated with the care and concern shown. They became more active in family gatherings, shared experiences with their grandchildren, and took on advisory roles in the family business. What’s more is that the family grew closer as an unintended outcome—realizing that things were never going to be quite the same as they were when the parents were in their prime, making everyone even more grateful for the remainder of the time they still had together.

WillKate Can Help Ease the Transition

Ageing is inevitable, but it doesn’t have to be hard. It’s about stepping up alongside our parents, cherishing moments, and ensuring the family tree’s roots remain strong. At WillKate, we guide families through these transitions, focusing on both the business and the heart of the family. If you aren’t ready to have these conversations alone, we can have them alongside you. But, this is just the start. You can learn more about our family-first approach in our popular guidebook, designed exclusively for multi-generational family enterprises, “The 100-Year Plan: How to ensure success and sustainability of your family enterprise over the long-term.”

If WillKate sounds like the type of business advisory team you’d like in your corner, we encourage you to Schedule Your Free Intro Call with us today. We happily serve clients in person in Sioux Falls and Aberdeen, South Dakota and virtually across the country. Or call the offices directly to set up your appointment: 605-275-9181 or 605-262-0308. We look forward to helping you preserve your wealth, your legacy, and your family business over the next 100 years (or more)!