Cautionary Tales - Online Estate Planning: Helpful Tool or Risky Shortcut? - Episode 211

Hey there, Legal Tea Listeners –This is your host, Jenny Rozelle! Today’s episode of Legal Tea is the “cautionary tales” topic. And on these “cautionary tales” episodes of Legal Tea, we normally talk about real-life cases with real-life clients that are things me or my office have worked on -or they are things that I think are generally good things to be aware of, so you don’t turn into a cautionary tale on my Legal Tea podcast one day! So today I want to chat about something I get asked about SO OFTEN. That’s … “Jenny, what are your thoughts on these estate planning platforms online?” When I say “estate planning platforms online” I’m talking about the websites where you get on, go through their process, and they spit out estate documents like Wills, Trusts, Powers of Attorney, etc. etc. Interestingly, A LOT of the time it’s professionals asking me this questions … mostly financial advisors, who both privately and publicly ask for my thoughts. I’m an open book … I don’t mind sharing my thoughts, so let’s dive in.

So, you have probably seen the ads or scrolled past them on social media or even your advisor recommended one to you: “Create your estate plan online!” …or… “Easy, affordable estate plans!” And listen—I don’t have a serious problem with these platforms. In fact, I do not think they are inherently bad and have actually made estate planning more accessible, and I believe that is a good thing. If these tools are helping people take action where they otherwise would not, I will support that.

But I do wish more people understood—and believed in—two really important risks that often get overlooked. First, when you use a platform instead of working with an attorney, you lose the counseling component—and that’s not a minor thing. Good estate planning is NOT just about documents. Rather, it is about having someone walk you through the legal and personal nuances that come with your family, your finances, and your goals. Especially if you have got ANY kind of complexity—like blended families, special needs beneficiaries, estranged relatives, tax concerns, or even a desire to chat through all sorts of distribution methods for beneficiaries —the insight and strategy that come from a real conversation with a lawyer are irreplaceable.

Second, talking about a second thing that often gets overlooked when using a digital platform, is that there’s often a disconnect between the documents and your assets, which most do not realize. These platforms can help you crank out estate documents like a Will or Trust but they do not ensure your plan is properly implemented. And in many cases, that is where everything falls apart.

One of the biggest misconceptions I see is people assuming that the documents alone will do all the work. But unless you have aligned your assets—like bank accounts, real estate, retirement plans, insurance, businesses, etc. —with your plan, those documents might not have any actual control over what happens. That is how people end up with unintended outcomes: assets bypassing a trust, outdated beneficiaries, or probate surprises that no one saw coming. But an attorney would have discussed it and may have even done the work for you to AVOID those unintended outcomes.

So while these platforms are doing the literal document creation part—which is arguably the easiest part of the process—the real value in estate planning often comes from what is not on the document: it is the counseling, the strategy, and honestly the … accountability.

Let’s break a few things down… by talking about some assumptions. Assumption #1: “My situation is simple.”

Honestly, if I had a dollar for every time someone said their estate was “simple,” I’d be on a beach somewhere. The truth is, even “simple” situations can become complicated quickly—especially when it comes to titling of assets, joint ownership, or beneficiary designations. Without a professional to help you see how all the pieces fit together, you might think you have set up your documents to accomplish ABC, but your plan is actually going to result in XYZ. And that is where online platforms often fall short: they don’t know what questions to ask you specifically. They cannot spot the red flags in your family dynamic or financial structure. So when someone uses a platform to draft their estate documents, thinking it’ll accomplish ABC, they might actually be setting up a plan that does XYZ. And no one realizes it until it’s too late.

Another assumption: “It’s okay, I’ll follow through!”

Estate planning is not just about signing a few documents. If you create a Trust, for example, you have to go through a process of funding the Trust—which means transferring assets into the trust or adjusting beneficiaries so the trust controls them. That step is critical. And yet, so many people never do it.

In fact, we meet with people ALL the time who have existing trusts that were never funded. They come in for help, and when we dig in, we realize the trust owns nothing. It’s just a big stack of paper that probably won’t do what you think it’s going to do.

And you know what … most people need accountability—not because they’re lazy, but because life is busy, and estate planning often falls to the bottom of the list. Online platforms might explain what to do, but they don’t walk you through it. They can’t check your paperwork or remind you three weeks later to call your bank. That’s the kind of support most people actually need to finish the job properly. This is why I have a whole team at my office whose job is to help clients complete that funding process.

Another big assumption: “Documents are enough.”

Hear me loud and clear: estate planning is NOT just about filling in blanks and going through an online prompt. TRUE estate planning is about making sure your plan is right for you—now, and five or ten years down the road. For example, maybe one of your estate planning goals is to shield and protect assets from long-term care or liabilities. Those kinds of plans require irrevocable trusts and other strategies that platforms just flat do not offer—and most people do not even know to ask about those kinds of things. That’s honestly why I say: the documents are the easy part. It is the thoughtful planning, the accountability, and the legal guidance that are harder to replicate—and actually, more important in the long run.

Another important thing to consider—especially if you are weighing whether to use an online platform versus an attorney—is the role of legal ethics rules, especially like the rules around attorney-client privilege. In short, this is a legal protection that ensures anything you share with your attorney stays confidential. It creates a safe space to be completely honest about your goals, concerns, family dynamics, and financial situation without fear that it will be used against you. That kind of candid conversation is absolutely crucial in estate planning, especially when decisions could later be questioned or challenged. If something ever ends up in court or there’s confusion about your intentions, an attorney can stand behind your plan—and explain not just what you did, but why you did it. That layer of protection, advocacy, and clarity simply does not come with a fill-in-the-blank form or an anonymous platform.

So, when someone asks me my thoughts on these digital estate planning document solutions, it’s such a hard question … because my brain thinks about all of this. They ARE getting documents in the hands of more people, but I also have a lot of CONCERNS about those documents going in those hands without legal counseling and legal advice. And all the folks that sacrifice all the GOOD that comes out of working with an attorney – of course the counseling and advice, but also the ethics rules that I just talked about that will PROTECT your plan.

So, here’s where I land. Online estate planning platforms do serve a purpose. If they help someone take that first step who otherwise wouldn’t, that’s a win. But we have to be honest about what they cannot do, too. They cannot walk you through complex family situations. They cannot help you avoid legal missteps. And they definitely cannot hold your hand through funding a trust or aligning your assets with your plan. The documents are just one part of the equation—it is everything around it that actually makes it work.

And here’s what sort of worries me most: we may not see the harshest consequences of these quick, fill-in-the-blank plans for many, many years. It is often not until someone passes away or incapacity surfaces that problems arise—documents get challenged, family conflict erupts, or the legal intentions simply do not hold up because they were not well thought out in the first place. THAT is when the lack of personal advice, strategy, and proper execution may really show. And by then, it is probably going to be too late to fix it.

At the end of the day, estate planning is not just about checking a legal box—it is about your people, your values, and the legacy you want to leave behind. It is about making decisions today that will protect the people you care about most tomorrow. No matter which path you choose between an attorney or a digital platform, the key is to be thoughtful and intentional. Your estate plan should be more than just a set of documents—it should be a clear and coordinated reflection of your goals, supported by the right guidance and structure to carry those wishes forward when it matters most.

Alrighty, let’s shift to a sneak peak of next week, which we’re circling back to the “current trends” topic where we talk about things that are going on currently that impact my estate and elder law world – or maybe, things that I have stumbled upon on the news or social media that is relevant to this podcast. Next week is going to be about the major estate and elder law things within the One Big Beautiful Bill that was recently passed and signed … it was a gazillion pages long, so we are not going to go into all of it, but the things that are extra pertinent to what we focus on on this podcast – estate and elder law things. So, that’s what next week will be about, Legal Tea Listeners, so until then, be well and talk soon!

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