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The art of aging well, with Jennifer Szakaly of Caregiving Corner
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The art of aging well, with Jennifer Szakaly of Caregiving Corner

Expert advice on how families can approach aging with less stress, more understanding and better preparation

This episode of The Charlotte Ledger Podcast is sponsored by Caregiving Corner. Caregiving Corner works with families who are taking care of aging relatives and need assistance navigating the long-term care system. Whether you are planning for aging, or needing help managing a crisis, our team is here for you. For more information, visit CaregivingCorner.com.

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In a recent Charlotte Ledger webinar, Caregiving Corner CEO Jennifer Szakaly shared practical, compassionate advice for families navigating aging and caregiving.

Aging is a stage of life that many of us are either confronting personally or experiencing through the eyes of loved ones. Discussing it can be uncomfortable and overwhelming, especially when there is some resistance or hostility toward extra care as you or your loved one gets older.

This month, The Charlotte Ledger held a webinar titled “The Art of Aging Well” in partnership with Caregiving Corner, which provides care management and counseling services for older adults and their families.

In the webinar, hosted by Ledger managing editor Cristina Bolling, CEO Jennifer Szakaly shared practical strategies to help families prepare for the aging journey with less stress and more support.

Here are five key takeaways — all grounded in experience, empathy and real-life family dynamics:

1. Start the conversation early

Initiating conversations about aging with family members as early as possible can help align expectations and clarify future plans. It provides a chance for everyone to understand the desires and preferences of their loved one well before any decision needs to be made under pressure.

“You really don’t want to wait until you’re in a crisis before you start asking some of these questions,” Szakaly said.

2. Bring a third party in to help with difficult conversations

Engaging a neutral third party such as a medical professional or an aging life care manager can help facilitate challenging or awkward conversations. Third parties can provide unbiased input and help family members confront the realities of aging without family dynamics getting in the way.

“Sometimes bringing a third party in, we find that some people are a lot more forthcoming with us than they are even with their own families,” Szakaly said. “I think it’s because we come to the table with no judgment about what we’re asking and about the answers that they may have to some of the questions.”

3. Plan for uncertainty

Although the future is unpredictable, having a flexible plan that outlines all potential scenarios can alleviate stress, especially as realities unfold. Care managers like Szakaly create detailed care plans that take lots of factors into account, but families can create them on their own, too.

 “We don’t know what’s right around the corner,” Szakaly said, “so when we put a care plan in place for a client, and we’re walking them through the options that they have that are realistic for their situation, for their budget, for their family dynamics, for their care needs — it’s intended to be a fluid document. It’s something that’s going to change and be updated as their circumstances change.”

4. Communicate expectations clearly

Understanding each other’s expectations can prevent misunderstandings and resentment. You’ll want to discuss financial, medical and personal care expectations with your family to prevent any stress or resentment in the future.

“The number one thing that I know affects so many families is, speaking from an adult child’s perspective, a parent who really wants to stay in their home but isn’t maybe realistic about how much care they need or about what kind of care they need,” Szakaly says, which is why it’s important to establish those expectations early on.

5. Support during transitions

Whether transitioning to assisted care or adjusting to new life stages, supporting your loved ones through these changes can improve their adaptation. Szakaly says you have to remember that it’s important for both older adults and their families to manage their expectations during these periods.

Everyone’s experience of transitioning into a care community is different, but “don't write it off yet,” Szakaly said. “You don’t know that it’s not going to work, and we’ve got to give it a shot.”

➡️ 🎥 For more resources and insights about aging well, you can watch the full recorded session of the webinar here (on YouTube).


This podcast was part of a weeklong Charlotte Ledger series called “Retiring Well,” published April 14-17, 2025.

‘Retiring Well’ — a special series

Editor’s note: Retirement isn’t just about stopping work—it’s about starting something new. This week, The Charlotte Ledger is looking at how to make the most of this next chapter, from managing money to finding purpose, staying connected and embracing change. Whether you're close to retiring or just starting to think about it, we hope these articles help you imagine what “retiring well” can really mean.

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