The Conversation That Never Ends
Experience-Based Approaches to Legacy Protection
Here's what I know: talking about legacy protection across generations is hard. It might be one of the hardest things advisors and their clients face together. And here's what makes it even harder—the transactional approach most of us default to doesn't work as well as we'd like, nor does it set clients and advisors up to successfully navigate multi-generational wealth.
We ask: "Do you have your will? Trust? Power of attorney? Healthcare directive?" The client nods (or more likely, avoids eye contact and promises to get on it). We check the box. Move on. But nothing actually happens. Or if it does, it happens once, gets filed away, and becomes this static artifact that everyone hopes they'll never need but also never revisits, let alone actually discusses.
Legacy protection—the real kind—lives squarely in the domain of Security & Freedom, the Beyond the Plan theme Ashley and I have been covering the past few months. And like everything in that domain, it exists in constant tension. Generation one needs the security of knowing their wishes are documented, understood, and protected. They also often need to be given the freedom (permission) to spend. Generation two (and three) need the freedom to have their own relationship with money, without feeling locked into someone else's exact blueprint, but most also consider preservation. All needs are valid. All matter. And, believe it or not, we would argue the goal isn't even to get everyone perfectly aligned—it's to keep the conversation going.
That's the shift advisors can make. Legacy protection doesn’t have to be about getting it right once. It can be about creating ongoing experiences. Where the goal of the experience is to normalize dialogue, allow for evolution, and honor the fact that different generations will always see money differently. And that's okay.
So what does this actually look like in practice?
What Makes This So Hard
Before we get into what advisors can do, let's name a few things advisors are up against. These are the patterns we’ve seen and discussed with advisors:
● Clients stall. They know they need to deal with this. They just… don't. Because thinking about it feels like staring directly into mortality, and who wants to do that?
● The legal documents are cold. A will or trust captures the mechanics—who gets what, when, and how. But it doesn't capture context, intention, values, the "why" behind decisions. There's no space for warmth in legalese.
● Generational divides are real. G1 built it and wants to protect it. G2 inherited it and might want to grow it, risk it, or use it differently. Neither perspective is wrong, but they can feel incompatible.
● No one knows what's age-appropriate. When do you bring the kids into these conversations? What do you tell them at 10 versus 18 versus 25? Older generations and parents are terrified of saying too much or not enough.
● There's no standardized space or structure for talking about money. Families may not know how to have these conversations. Kids grow up thinking money isn’t something appropriate, easy, or interesting to discuss. Then they inherit it and have no framework for navigating it responsibly.
● The fear of getting it "final" is paralyzing. What if circumstances change? What if priorities shift? The pressure to get it perfect makes people freeze rather than start.
All of this is real. All of this matters. And all of it points to the same conclusion: the transactional model doesn't address the actual problem.
From Transaction to Experience
What if instead of treating estate planning as a box to check, we treated it as an ongoing practice? A series of experiences, conversations, touchpoints that evolve as life evolves?
This is where advisors can create real value. Not by pushing harder on the transactional stuff—though yes, the legal documents still matter—but by building structured experiences that make the hard conversations easier. That removes overwhelm. That normalizes talking about money across generations. That honors the tension between security and freedom instead of trying to resolve it once and for all.
Here are a few experiences Beyond the Plan has cooked up.
Experience #1: The Guided Legacy Binder
If you haven’t ever read Mary Beth Storjohann’s Substack, Between Tables, check it out. She recently wrote a wonderful piece we loved at Beyond the Plan about the gap between legal documents and actual intentions. She wrote about the letters we should all write—one to our executor, one to our guardians—that capture the heart behind our estate plans. Not the mechanics, but the meaning. It's beautiful work, and you should read it.
But here's the human problem: asking clients to sit down and write these letters all at once is overwhelming. Mary Beth makes this SAME point. Most people won't do it. The blank page is too daunting. The emotional weight is too heavy. So they avoid it.
But what if you scaffolded it instead?
Send your clients prompts. One question or prompt, every other week. Small, manageable questions that build over time into something comprehensive. You're not asking them to write a novel—you're asking them to answer a single question.
● Week 1: "What's one financial decision you're proud of, and what made it meaningful?"
● Week 3: "If something happened to you tomorrow, what would you want your executor to know about why your accounts are structured the way they are?"
● Week 5: "What values do you want woven through your family's financial decisions, even after you're gone?"
● Week 7: "What do you want your child or kids to know at age X?"
Over four to six months, they build a legacy binder. Not in one agonizing weekend, but gradually. Thoughtfully. And when they're done, you bring them into the office, and you help them compile it all. Organize it. Finalize it. Share it.
But here's the critical part: this isn't a one-time deliverable. It's a living document. As kids age or life trajectories and goals change, you add new sections. As circumstances change, you update old ones. As perspectives evolve, you revisit what was written before. The binder grows with the family.
This removes the paralysis of needing to get it perfect. It creates ongoing touchpoints for your relationship. And it gives clients something tangible—something that feels like love, not just logistics.
Experience #2: Milestone-Based Multi-Generational Conversations
One of the biggest questions parents ask is: When do I bring my kids into the financial conversation? And the answer is: earlier than you think, and more often than you think, but differently at each stage.
What if you built structured touchpoints at key ages? Not lectures. Not boring meetings where kids sit silently while adults talk at them. Actual age-appropriate experiences that normalize you—the advisor—as a safe person to talk about money with.
● Age 10: Bring the kid to the office. Talk about giving. Let them pick a cause the family donates to. Open a custodial account and show them how investing works. Make small financial decisions feel real.
● Age 15: Conversation shifts to car insurance, monthly payments, and what they can actually afford. Maybe they start contributing to the family's charitable strategy. Budgeting becomes tangible.
● Age 18: First solo meeting with you, the advisor. Parents aren't in the room. You talk about student loans, credit cards, and saving for their first apartment. They start seeing you as their resource, not just their parents'.
● Age 22-25: Career launch conversations. Benefits. Retirement accounts. How to think about raises and bonuses. The transition from theoretical to real-world money management.
● Age 30+: Life transitions. Buying a home. Getting married. Having kids. Navigating inheritance. Each stage brings new questions, new complexity.
The importance of this approach is that it creates continuity. By the time these kids inherit, they've been in conversation with you for 20+ years. They're not strangers. They don't leave when their parents pass—they stay, because you're already their advisor.
And critically: there's no expectation that everyone will agree. G1 and G2 can have different perspectives on risk, spending, and giving. That's fine. The goal isn't alignment. It's an ongoing dialogue.
Experience #3: Family Financial Storytelling Sessions
You don't need to plan a family office retreat at a luxury resort to create meaningful multi-generational conversations. You just need structure and intention.
Invite the family in for what I'll call a "financial storytelling session." It could be over dinner. Could be a weekend afternoon at the office with some activities for younger kids. The point is to create space where grandparents and parents share their money stories—not as lectures, but as lived experience.
Use prompts to keep it from becoming preachy or contentious:
● "What's one money decision you're proud of?"
● "What's one money mistake that taught you something important?"
● "What do you want the next generation to know about how you approach money?"
Your role as the advisor is to facilitate. Keep it safe. Navigate moments where tension arises. Make sure everyone gets heard. The goal isn't to have G1 impose their values on G2—it's to surface different perspectives without judgment. And when you create structured space for both to exist, you're doing the real work of legacy protection.
Why This Matters for Your Practice
There's no golden mean here. No perfect balance. Just ongoing calibration. And your job is to normalize that for clients—to give them permission to not have it all figured out, because it's never all figured out.
Shifting from transactional estate planning to experience-based legacy protection, a few things happen:
● You position yourself beyond portfolio management. You're not just the person who rebalances their assets—you're the person helping them navigate the most complex, emotionally charged parts of their financial lives.
● You create stickier relationships. When you've guided a family through these conversations for years, when you've helped them articulate what matters and document it in ways that feel meaningful, they don't leave. They can't imagine doing this work without you.
● You build generational continuity. The kids you bring into the conversation at age 10 become your clients at age 40. That's how you sustain a practice long-term.
● You differentiate through human-centered service. Every advisor can run a Monte Carlo simulation. Not every advisor can facilitate the hard conversations that make the simulation meaningful.
And, most importantly, you address the real fear. Which isn't "do I have the right documents?" It's "will my family be okay? Will they understand what mattered to me? Will they be able to talk to each other about this stuff without falling apart?"
That's what you're solving for. And that's where the value lives.
Getting Started
Pick one experience. Start small. Maybe it's the prompted legacy binder with two or three clients who you think would be receptive. Maybe it's inviting one family in for a storytelling session. Maybe it's scheduling a single 18-year-old for their first solo meeting.
You don't need to overhaul your entire practice tomorrow. You just need to start creating experiences that acknowledge the truth: legacy protection is not a one-time transaction. It's an ongoing practice. And the goal isn't perfect alignment across generations—it's ongoing dialogue that honors both security and freedom.
Because at the end of the day, your clients don't just want their assets protected. They want their families protected. Their values are protected. Their stories told. And they need an advisor who understands that the conversation never really ends—it just evolves.
That's the work.
And if you decide you need some help, Beyond the Plan has you covered. Beyond the Plan has and is currently creating client-facing content, such as a list of questions advisors can email out to clients to serve as their Guided Legacy Binder experience. You can do it on your own, but you do not have to - give us a call.
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Beyond the Plan®
www.beyondthefp.com | hello@beyondthefp.com
Shout-out to Mary Beth Storjohann for her beautiful work on legacy letters. Check out her Substack for more on this topic.
