Meet the Minnesota lawyer prepping people for death through humor and a little Taylor Swift

Lawyer Jen Gumbel wants to talk to you about the stuff you probably don’t want to talk about.

“Law, death, money. All of everyone's favorite topics,” she said.

And she doesn't just want to talk to you. She wants to make these hard topics funny and relatable. Her hope is to make them so entertaining they stick in your brain and spur you to create a good plan for your death.

So that's why Gumbel, who lives in LeRoy a small town south of Rochester, often finds herself in her kitchen, or the front seat of her car, or on this particular day, in her living room, making short, easy to understand videos about estate planning that she circulates on TikTok and Instagram.

“It's really important that you know what beneficiary designations are,” she said into her the camera on her phone. “I'm Jen Gumbel a probate attorney that wants you and your loved ones to need people like me less.”

Big questions

Gumbel said we need to remember, death is the thing that affects us all.

“Not everyone is going to need a criminal defense attorney or a divorce attorney. But everyone is either going to deal with moving assets after someone dies, or leaving assets that have to be dealt with, you know, after they die,” she said.

Gumbel said years ago she wanted to be a teacher. That a skill dovetailed naturally with the area of law she eventually practiced. She found herself trying to help family members who were not only grieving the loss of a loved one, but also stuck trying to figure out the details of their inheritance.

“Not only is someone else going to have to deal with it, someone else who's grieving you is going to have to deal with it in like, the literally the worst possible time, and you're going to add on top of it dealing with legal issues and getting up to speed and learning,” she said.

Her passion for preparation led to creating a blog and virtual estate planning classes, touching on all aspects of the process.

She answers the big questions. What's probate? How do assets move around once someone dies? How to have hard conversations with parents about planning for their death.

And more recently, she started bringing bite-sized tips to TikTok, Instagram and Twitter, using the @jengumbel handle. She also writes a blog, the Organized (After) Life.

Taylor Swift helps out

Gumbel is a big scroller and it shows. Her videos combine the complexities of estate planning with the music and memes that thread through social media — the inside jokes only those of us who watch Instagram reels instead of TV would understand.

Like the always relevant Taylor Swift reference.

Just after Swift's latest album dropped, Gumbel videoed herself — in her car, no less, where probably half of Instagram's content is shot — giving the popular track “Anti-Hero” a listen.

As it played, one line stuck out.

"The family gathers 'round and reads it and then someone screams out/She's laughing up at us from hell..."

In the video, Gumbel laughs out loud. “Oh that's funny,” she says.

But why?

“It's importance of understanding that the possibility of an inheritance is not something that you should count on or expect,” she explained. “Like, that's not yours."

This idea that nothing is guaranteed is central to Gumbel's work. Her deep ties to her Lutheran faith give her particular point of view on death, one that acknowledges that we aren't in control.

“Our typical American optimism is this very bright and shiny, 'go-get-em' positive. And so death is a very difficult topic. It's like a failure,” she said. “And that leads to a lot of dysfunction.”

We're not going to be masters of our own destinies forever. Gumbel says that good estate planning starts with that understanding.

Or as Taylor Swift sings: “It's me. Hi. I'm the problem. It's me...”