For the next week (or two), we’ll be sharing “audition” pieces from folks interested in being new staff writers at Get Rich Slowly. Your job is to let us know what you think of each of these writers. Pay attention, give feedback, and after a couple of weeks we’ll ask which writers you prefer. This article is from Jennifer Rose Hale. Jennifer’s first audition piece was about what to expect when settling an estate.

Big life experiences: If you haven’t been through them, I wrote earlier, then images from movies and TV will shape your expectations and may leave you confused. No, you (or your partner) won’t give birth on an elevator or in the backseat of Brooklyn taxi accompanied by a witty but kindhearted cabbie.

And, chances are, in estate settlement, you won’t experience scenes like the two pop-culture references that came to my mind in younger years:

  • Jane Eyre (or anyone in pretty much any novel or movie ever) surprised by a long-lost relative leaving her a fortune.
  • Christina Crawford in the camp classic “Mommie Dearest,” shock frozen on her face as she learns, from mother Joan’s will, that she’s been completely disinherited.

Yes, I’m female. Still, no matter your gender, chances are you can picture your own television or movie scenes, grieving family crowded into a wood-paneled office, either satisfied or shocked by what they’re hearing. (In a soap opera, this is usually where the never-acknowledged son or daughter comes out of the woodwork.)

Last message from Dad
As I described earlier, the first communication I received from the attorneys representing the trust was a legal document I was expected to sign — but didn’t. After my siblings and I returned the forms, we received an email from the firm’s representative, introducing himself and expressing sympathy for our loss.

A few weeks later, I got a large envelope in the mail with a copy of the will. (For those who commented on this after the previous piece: No, it didn’t arrive immediately, and we had to pointedly ask for it to find out when to expect it.) I took one look at the envelope, set it carefully on the table and made dinner for my little boy. After he was in bed, I poured a glass of wine, gritted my teeth and finally started reading at the dining table.

No wood-paneled office, no gasps of surprise … but still one of the weirder experiences of my life. It felt like hearing my dad’s voice, but filtered through a cold interpreter who only has an outdated grasp of English — a more severe Shakespeare.

Everyone has a “crumpled second page”
Setting aside movie comparisons, one of the issues most families will struggle with is secrecy — for many reasons, children don’t want to talk to parents about money. I discovered in the early weeks of this process that my siblings and I had different levels of understanding about Dad’s plans, and that my older siblings, who knew more, were still hamstrung by out-of-date information — plans Dad made that later changed or just vague descriptions of assets that are now proving difficult to track down.

One conversation with the attorneys turned up a “crumpled second page” of a life insurance policy, creating a need for legal detective work. (If you looked in your filing cabinet now, do you think you’d have something equivalent to a crumpled second page of something? I know I would. Dave Ramsey writes about organizing documents for your loved ones in a Legacy Drawer.)

Plan A: “Don’t die”
I can understand why the secrecy — or at least reluctance to have the conversation — happens. I created a will after my son was born, making the big choice, among others, about who would get custody of my son in the event of my passing. These are choices I don’t necessarily want to have to explain or defend to anyone not named in my plans.

I’m also hoping it’s all moot and we never have to implement “Plan B.” (As I always say, “Plan A is ‘Don’t die.’”)

We also, of course, don’t want to think about dying (see “Plan A”), and we certainly don’t want to suggest to our older relatives that we think about their ends. It’s an awkward conversation to have. I will join the chorus of voices advising you to have the conversation about estate planning, no matter how awkward.

The big reveal
You can understand why I won’t go into details about what my dad had or what he left; I know J.D. has worked through his own issues about what to share and not share publicly, and I have my own privacy as well as my family’s to consider and respect.

I ended up reading through the multiple estate documents once that night — and again the next day. Just like with Shakespeare, eventually I got it. And what the paperwork left me with was a sense that Dad had done a Herculean job of being equitable — to his wife (our stepmother), my three siblings and me. He was pretty smart with his money throughout his adult life, and he was smart with it at his passing.

It was also, strangely, sweet. While some assets exist in the trust, certain items are to be disbursed through the will — special coins he purchased (one for each child, of course), a car, a boat … and two electric bicycles. I remember hearing about the coins from my stepmother, and the bicycles, which he was quite proud of, from my dad.

The will, though, only answered a few questions, and three months later, we’re still looking for all the answers.

…to be concluded…

This article is about Planning, Real-Life, Relationships