My Parents Want to Leave Everything to My Brother

Money Dilemmas is where we talk about the tricky stuff - the conversations about money that live in the grey area between love, power, fairness, and everything in between.

Each story starts with a real member dilemma, the kind many of us have quietly wrestled with but rarely said out loud.

Because money isn’t simply transactional; it’s about what we value, what we tolerate, and what we’re taught to accept.

And at the end of every story, one of our co-founders weighs in — offering her two cents and best advice on how to navigate the dilemma.

The Dilemma:

I grew up in a very ordinary, middle-class family where doing well was kind of the whole point.

My parents will swear up and down that they never pressured me, but somehow it was always clear that achievement was the family currency — the thing that made you matter.

So I worked. Constantly.

I learned pretty early that being the “good” one meant being the one who achieved things.

I got into Duke, which was a huge deal for us.

From there, the path sort of wrote itself: everyone around me was trying to get into consulting, so I did too.

Now I’m 32, a senior consultant at Deloitte, and doing objectively well. But if I’m honest, my whole sense of self-worth still comes from ticking boxes. I don’t really know who I am without the next goal to chase.

My brother’s a different story.

He’s 29, smart as hell, but school was never his thing. He barely finished high school, didn’t get into any of his dream colleges, and ended up dropping out of a safety school.

For years, he was the one my parents worried about - the “lost” one. But recently, he’s completely changed.

He’s studying to become a carpenter, lives simply, and genuinely seems happy.

He says he wants a life that isn’t about achievement, and I honestly respect that.

A few weeks ago, my parents sat me down and told me they’ve decided that when the time comes, they want to leave everything to him.

They said I’m so successful that I’ll be fine, that he needs the help more. I just sat there, trying to smile and nod, but inside I felt like the air went out of the room.

On one level, I get it. I have a career, savings, options - all the things they hoped for me.

But it still hurts.

I’ve spent my entire life working for security, and now it feels like that’s exactly what I’m being denied.

I keep thinking: what if something changes?

What if I lose my job to AI or my industry shifts? What if I get sick or burned out or just… stop wanting this life?

Why is my safety being treated as guaranteed, just because I earned it?

And honestly, it just feels unfair. Like I’m being punished for doing everything right. I love my brother, and I know this isn’t about him.

But I can’t shake the feeling that the very thing that made my parents proud of me — all that hard work — has somehow made me less deserving in their eyes.

Camilla’s Take

I think what you’re feeling is a kind of betrayal that’s hard to explain to anyone who hasn’t been “the good child.”

You spent your life doing everything right - chasing the grades, the career, the stability - because that was the invisible deal.

If you worked hard, life would be fair.

Your parents would be proud. You’d be safe.

And now, suddenly, it feels like that deal has been rewritten without your consent.

The logic your parents are using makes sense on paper: you’re secure, your brother isn’t, so they’re helping him.

But what they don’t understand is that this isn’t just about money. It’s about recognition.

It’s about wanting your effort, your discipline, your years of striving to mean something.

They think they’re being practical - but what you’re hearing is, your success no longer counts as struggle.

I can relate to this more than you might think. I’ve also spent most of my life measuring my worth through achievement and external validation.

And the truth is, even when things look solid on the outside, there’s always a quiet fear underneath: that it could all change. That one bad year, one wrong call, one twist of luck could undo everything.

Your parents might have forgotten that part - how long and unpredictable life really is.

Success can give you stability, but it doesn’t make you immune to uncertainty.

You’re right to question the assumption that you’ll “always be fine.”

No one’s future is guaranteed, no matter how polished it looks right now. But beyond that, I think there’s something deeper at play: your parents are trying to fix something in themselves.

They see your brother as the fragile one, the one who needs redemption, and giving him everything is their way of making peace with their own guilt for how things turned out.

It’s not really about you - even though it affects you most.

My advice? Don’t try to convince them they’re wrong. You probably won’t change their minds, and it will only drain you.

Instead, draw the boundary between their story and yours.

Their decision says nothing about your worth, your effort, or your right to feel hurt.

I understand why this decision might feel painful or unfair, but at the end of the day it’s their money and they get to do with it what they want.

We never have a claim to our parents wealth. At the same time try to be grateful what you do have - grit!

And I honestly believe that grit and passion - and everything that comes with that is one of the biggest blessings you can get in life.

What do you think?

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