Your Will Shouldn’t Be a Mad Lib: The Case for Quality Estate Planning

Make a high quality Will and Trust with Herbie, which is much more than just a fill-in-the-blank document generator.
Published on
August 1, 2025

Remember Mad Libs? Those word games where you drop random nouns, verbs and adjectives into blank spaces, then read the results aloud for a good laugh. But what’s funny in a kid’s game becomes a disaster when applied to something as serious as your Will.

And yet, that’s exactly how many online estate planning tools work. They give you a bunch of blank text boxes and let you “fill in the blanks” however you want. The result? A legal document that reads more like a bedtime joke than a binding declaration of your wishes.

You deserve better.

Blank Boxes Are Scary

When you write a Will using open text boxes, it’s like trying to draft your legacy by playing word salad. For example:

“I leave my [thing] to [person] because they are [adjective] and always made me [verb].”

It might feel expressive and personal, but the law doesn’t reward creativity, it rewards clarity. Judges, executors and family members need to know exactly what you meant, with no guesswork. Freeform entries are ripe for misinterpretation, contradiction and even courtroom disputes.

Typos and Vagueness Can Destroy Your Best Intentions

In Mad Libs, getting a silly or strange result is part of the fun. But in a Will? A single typo or ambiguous phrase can have major consequences:

  • “John Smyth” instead of “John Smith” could mean your assets go to the wrong person.
  • “My children” — does that include stepchildren? Biological kids only? What if you list different names elsewhere?
  • “The house goes to my niece” — but you have three nieces. Which one?

When platforms let you write whatever you want, without context or guidance, they’re setting you up to create a document full of holes.

Herbie Makes Wills Better than “Good Enough”

Estate planning is an important endeavor. It’s about protecting your loved ones from stress, confusion and unnecessary legal bills.

Herbie is founded by lawyers who understand the complexities of estate planning and the importance of clarity. For that reason, with Herbie, you know you'll get a high quality Will that:

  • Uses tested, precise language
  • Doesn't allow you to fill in the blanks
  • Accounts for the “what ifs” you may not have considered

It’s not just about who gets what — it’s about making sure your family has peace of mind, not a mess to solve.

At Herbie, we're all for doing it yourself. You can do it! But we don’t believe in “winging it” blindly when it comes to your legacy. That’s why we’ve eliminated risky open text boxes for anything important. Instead, we guide you through smart, structured choices — backed by legal logic and clean formatting.

You won’t have to write your own legal language or guess how to phrase things. We make sure everything is organized, consistent and written to actually work, not just exist.

Don’t Let Your Legacy Be Someone's Joke

A Will is one of the most important documents you’ll ever create. It’s not a party game. It’s not a “just in case” side project. It’s your voice, your values and your last word. It deserves more than a fill-in-the-blank approach.

You still can do it online. But skip the Mad Libs. Choose a platform that takes your wishes seriously and gives your family the clarity and care they deserve.

Ready to take the next step? Start your plan with Herbie.

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