The Hardest Part of Inheriting Isn’t the Money

We think the hard part of inheritance is dividing money. But the real challenge is speaking up before things fall apart—and living with the discomfort of being the one willing to do it.

Lou LaMedica

Jul 24, 2025

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The Hardest Part of Inheriting Isn’t the Money

People assume the hard part of inheritance is about the money. The will. The percentages. The lawyer’s office and the signatures. But that’s just paperwork. The real tension starts long before that—when someone in the family tries to keep things from unraveling by speaking up early.

I wasn’t looking for control or trying to play favorites. I just saw the future clearly. And what I saw was the potential for a mess if we didn’t put some structure around what would eventually be passed down.

My parents worked for decades to build their legacy. Like a lot of families, they’ve quietly helped their kids along the way. Groceries here. A loan there. But some of us have learned from those moments, and some haven’t. That’s just the truth. Pretending it’s all equal when it hasn’t been only makes the fallout worse when real money is involved.

So I asked for what I thought was fair, and honestly, necessary: that the inheritance not be paid out in one lump sum. This wasn’t about punishing anyone. It was about protecting the family from future stress and conflict.

We all agreed it would apply to everyone. Equal terms, same structure. It wasn’t personal. It was just smart.

Because when people have shown you, repeatedly, that they struggle to manage what they have, you don't hand them more and hope for the best. Hope isn't a plan.

Still, bringing it up didn’t go over well.

I was accused of overstepping, of meddling in something that wasn’t mine. And maybe that view would’ve stuck—me as the problem—if more facts hadn’t come to light. Like a large amount of credit card debt. Like patterns that were hard to ignore. Eventually, my parents came to the same conclusion. They changed the will. They named me as executor.

That shift caused even more tension. But here’s the part people don’t always want to admit: when you speak plainly about uncomfortable truths, you become the villain in someone else’s story. Especially if they benefit from things staying vague.

No one in the family is a bad person. But one part of the family still lives very paycheck to paycheck. There’s no shame in that. But there also hasn’t been much intentional effort to change it.

Not everyone grows into planning ahead. Some stay stuck in survival mode, even when the crisis has passed. That’s their right.

But when it comes to inheriting a large sum of money, it’s my job to recognize that those habits could create real problems for the family down the line.

Native communities often made decisions with one generation behind and one ahead in mind. And when you look at it through that lens, a few guardrails don’t seem harsh—they seem necessary.

That’s why I pushed for structure. Not out of judgment, but out of realism. If someone has struggled with money for most of their adult life, it’s unlikely they’ll suddenly become a disciplined long-term planner without support. Not impossible. Just unlikely.

It’s not about blame. It’s about patterns. And unless someone is willing to break those patterns—with discipline, with humility, with sustained effort—nothing changes. The past becomes the future on repeat.

And if I’m honest, this whole process hasn’t made me sad. It’s made me sharper. It hasn’t broken my heart—it’s hardened it a little. I see some people differently now. Not with anger, just with clarity. When push came to shove, they cared more about what they believed they were owed than what it actually took to build that legacy in the first place.

My dad missed a lot of dinners and weekends to earn that money. That wasn’t just work—it was sacrifice. And I won’t let that sacrifice become fuel for resentment, chaos, or entitlement.

I didn’t take on this role because I wanted control. I took it on because someone needed to protect what mattered.

Because honoring a legacy isn’t just about dividing it fairly. It’s about making sure it lasts.

“Know what’s enough. Build what matters.”

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Lou LaMedica