Why estate planning in a tech-driven world still requires a human touch
By Noel D. Villajuan, JD, CFP®, and Catharine Betzig, Diversified Portfolios, Inc.
Key Takeaways
• What is the “sandwich generation”? The group balancing responsibilities for both aging parents and their own children, typically in the Gen X age range of 45-60 years old. These individuals are often managing family priorities while protecting their own long-term financial security.
• How does technology factor into estate planning? Tools like AI can organize information and spark important questions, but they can’t replace human judgment, compassion, and real-world knowledge.
At some point, every family begins to face difficult questions: How will the assets you’ve worked so hard to build be passed along? How can you make sure your loved ones are cared for as life changes? And with technology moving so quickly, you may be wondering what role “artificial intelligence,” popularly named AI, might play in that process. These conversations can feel heavy. They touch not just on money, but on legacy, on relationships, and on the emotions that are hardest to talk about. Many people hesitate to start them at all, and that’s completely natural. But we’ve seen that just beginning the conversation can change everything. It shifts planning from something abstract or intimidating into a way of giving your family clarity, easing future uncertainty, and helping ensure your wishes are carried forward with care. Let’s explore how families are navigating these moments, how technology is starting to shape that process, and why thoughtful preparation now can bring clarity not just for you, but for the people you love most.
Why These Conversations Often Wait
Most families don’t walk into our office asking about estate planning. Instead, it’s something we gently bring up, and the response is usually some version of, “Oh, I didn’t think about that,” or “We’ve been meaning to get to it.” There’s no judgment in that. These conversations require facing things most of us would rather not think about: our own mortality, our parents’ aging, the complexity of family dynamics. There are also assumptions that get in the way. Many people believe estate planning is only for the ultra-wealthy, or that things will simply “work themselves out” when the time comes. Others worry about privacy—who really needs to know what, and when? But here’s what we know: The longer you wait, the fewer options you have, and the more likely your family will face uncertainty at a moment when they need clarity most. One of the easiest ways to begin the estate planning process is by reviewing something straightforward, like the beneficiary designations on your accounts. You’d be surprised how often these are still listing an ex-spouse, missing a child who’s been born, or naming someone who’s no longer the right choice. This step can often lead to bigger, more important conversations, because if your beneficiaries aren’t current, chances are other parts of your plan may need attention, too.
The Appeal of Technology
Not long ago, a client came to us with printouts from ChatGPT. They’d spent time entering their financial details (income, savings, expenses, goals), and asked the AI a simple question: “Will I have enough money?” The AI gave them a thorough answer, but when we ran our own advanced planning analysis, the results were completely different. It wasn’t that the AI was deliberately wrong. It’s that real-world estate planning requires context that’s nearly impossible to capture in a prompt. That isn’t to say that technology should be excluded entirely; but that incorporating these tools requires a nuanced approach.
What AI Gets Right
AI tools are fast, accessible, and can process information in ways that feel almost effortless. For someone just starting to think about their future, AI can help organize the basics and even raise questions that might you hadn’t considered before. We’ve seen clients use AI as a kind of sounding board. While the answers aren’t perfect, they can spark valuable conversations that we can then explore together within a larger context. At its best, AI can help families see patterns, frame possibilities, and begin imagining the bigger picture.
What AI Doesn’t Yet Account For
The biggest challenge is that AI can only work with the details you provide. It won’t automatically factor in your exact tax bracket, the nuances of estate law in your state, or the different ways a trust could be structured for your family’s specific situation. Even more importantly, AI doesn’t capture the human element of your decisions. It can’t sense when family members have competing priorities, or when the right choice is more about honoring values than maximizing efficiency. Estate planning can involve deeply personal decisions: who will inherit, what kind of legacy you want to leave, how to care for loved ones as they age. These factors simply can’t be reduced to an algorithm. AI can lay the foundation, but it can’t finish the house. That final layer, the part that turns concepts into a meaningful plan, still requires human guidance, judgment, and care.
The Human Element: Multiple Generations, Multiple Layers
We’ve had the honor of working with several multi-generational families, and it’s given us a unique view of the complex dynamics surrounding estate planning. Sometimes parents are laser-focused on their children’s futures—college funding, wedding expenses, helping with grandchildren. Other times, the adult children are more worried about their aging parents and whether they’ll have the care and resources they need. We’ve sat with clients who wanted to leave financial gifts to their children, only to find out that what their children really wanted was for them to prioritize their own care. In one case, adult children urged their parents to use nest-egg funds for additional in-home support, saying, “We’ll sleep better at night knowing you’re cared for.” These moments remind us that estate planning is not only financial, but also deeply relational. Sometimes parents and children see things differently, and unless those conversations are facilitated, assumptions can create conflict down the road. Related: How Couples Can Resolve Money Disagreements and Make Better Financial Decisions Together
The “Sandwich” Generation
The relational aspect becomes especially clear when we look at the challenges facing the “sandwich” generation, members of Gen X (ages 45-60) who are balancing care for aging parents while also preparing to support their own children. In this situation, you might be:
- Wondering if your parents’ retirement savings will last
- Considering how to help adult children who are facing high housing costs or student loans
- Trying to maximize your own retirement contributions or thinking about long-term care insurance for yourself
- Managing healthcare decisions for your aging parents
This is where estate planning becomes less about formulas and more about judgment, trade-offs, and deeply personal priorities. Our role is to help you find answers to these questions, creating space for every voice to be heard while building solutions designed to balance financial security across each generation.
Passing the Torch, Honoring the Light
So where does this leave us? The most effective estate planning today combines efficient technology with the values and goals living at the center of you and your family. Depending on your situation, there are many strategies that might make sense, including trust strategies that offer flexibility and control, insurance structures that protect your family, or tax-advantaged approaches designed to preserve more of what you’ve worked for. The key to finding the right path forward is to ask the right questions. What are your values? What are your relationships like? What keeps you up at night? Passing the torch isn’t about having everything figured out perfectly. It’s about meaningful conversations, making thoughtful decisions, and knowing you have trusted partners who understand what’s at stake, not just financially, but personally.
If any of this resonates with you or raises new questions, we encourage you to reach out; we can connect and discuss how your estate plan is designed to support your family across generations. And if you’re not yet a Diversified Portfolios client but you’re curious how your estate plan could adapt to both family and technology shifts, we’d love to help. Our Financial MRI is designed to help you start the conversation and find clarity in all your questions.
