You know what’s harder than managing your finances?
Managing your finances while grieving.

I just read a story about a woman named Alice. For nearly 50 years, her husband Sasha handled all their finances. He kept a spreadsheet only he could understand. He talked to advisers she’d never met. He bought individual shares of what seemed like every stock in the S&P 500—and never explained the why.

Then one morning, he didn’t wake up.

And Alice—a retired professor who wrote 11 books and reads Russian and Yiddish—was left staring at a pile of unopened mail on her dead husband’s desk, screaming to herself in frustration.

She had over a million dollars. And no idea what to do with it.

This Didn’t Have to Happen

Once or twice a year, Alice would feel a jolt of panic and ask Sasha to walk her through their finances. He’d start explaining. Her eyes would glaze over. He’d lose patience. They’d both figure they could do it another time.

Until there was no other time.

I think about this a lot. Because I watched my own mother go through something similar—except she got lucky.

My father died in 1990. He was 45. I was a teenager.

But here’s the thing: he was sick for a while before he passed. And he used that time. He didn’t just hand my mother a spreadsheet and a password manager. He walked her through everything. The accounts. The business. The books. The why behind the decisions.

By the time he died, she knew everything about the finances (and it was still scary for her).

Not everyone gets that gift. And most people don’t realize they could give it.

The Elephant in the Room 🐘

Most couples don’t talk about this stuff.

Not because they don’t care. Because it’s uncomfortable. Because it feels like you’re planning for disaster. Because there’s always something more urgent — work, kids, life.

And so, a system develops. One partner handles the investments. The other handles… other things. And everyone assumes it’ll all work out.

Until it doesn’t.

And then the person left behind isn’t just grieving the love of their life. They’re drowning—in jargon, in stacks of paper, in decisions they were never taught how to make.

What “Being Empowered” Actually Means

Here’s what I’ve learned from my own life and from my clients:

Being financially “ready” isn’t about having a perfect, color-coded spreadsheet. It’s not about having all the passwords stored in a vault. It’s not even about knowing every single account number by heart.

It’s about understanding.

It’s about having the insight to answer these questions:

• Why do we own what we own?
• What’s the plan when things go sideways?
• Who do we trust to help us if we get stuck?
• What would you want me to do if you weren’t here?

These aren’t easy conversations. They are awkward and a little morbid. But they are a gift. Maybe the most important financial gift you can ever give your partner.

You don’t need a terminal diagnosis to start having them. You don’t need to wait for a “good time.”

You just need a conversation. Maybe a few of them. Ongoing. Uncomfortable at first, and then, eventually, less so.

Because the alternative is a pile of mail on a desk and a spouse screaming into the silence, wondering what on earth you were thinking.

Don’t leave them guessing. Don’t make their grief harder than it already will be.

Avraham
Your Financial Coach