Dear Penny: Can I Disinherit My Kid for Repeating My Career Mistake?

A businessman sits in a cardboard box with a rain cloud over him. A little girl wears googles and she tries to fly high in the sky while wearing airplane wings on her back.
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Dear Penny,

Can I write my children out of my will for doing something against my wishes? Specifically, if one of them wants to start a business, but I would rather them work a steady job for someone else? 

I am a failed entrepreneur myself but have since gotten back on my feet. It would pain me for my children to fail at something they worked so hard at. I don't want them to make the same mistakes I did.


Dear T.,

Let’s be clear about what your mistake was: You took a risk and built something. You worked really hard, but you still failed. And yet in spite of all that, you’re still standing.

You can write your kids out of your will for any reason (or no reason at all). But that’s not something I’d advise unless they’ve done something truly egregious.

Dear Penny

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Think about the message you want to send your kids. Is it to never take risks? Is it to never try too hard at something because you might fail? Is it that failure is so shameful you can never recover from it?

It doesn’t matter how great your relationship was with your kids while you were alive. The reality is that if you disinherit your child because you disagreed with their career choices, it will forever taint their memory of you. Plus, if you write one child out of the will while leaving the other kids an inheritance, the odds of family disputes become especially high.

There’s a lot I wish I knew here, including how old your kids are and whether they’ve actually caught the entrepreneurial bug or if you’re just hoping to pre-emptively squash it. But I think you can set up your estate in a way that puts some safeguards in place for your children without cutting them out altogether should they choose to start a business.

One option would be to set up a revocable living trust for the assets that you planned to distribute through your will. Doing so would give you greater control over how your property is distributed when you die.

For example, you may be worried that one of your children would pour their entire inheritance into a harebrained business venture if they received a large lump sum. You could set up a trust so that they’d receive annual distributions after your death instead of getting all the money at once.

Maybe that won’t stop them from becoming entrepreneurs. But at the least, they wouldn’t have access to lots of cash at once. They’d probably have to keep working traditional jobs for at least a while to establish a safety net. That may make them less likely to take big risks. People tend to be a lot more cautious with money they’ve actually had to work for.

Some people go even further by attaching specific strings to distributions. For example, if your children are still young, you could require that they earn a college degree to get a payout. This wouldn’t rule out the possibility of entrepreneurship, but at the very least, having a degree makes it easier to find gainful traditional employment.

Even the best parenting and estate planning won’t protect your kids from failure, though. We’ll all fail many times over during our lifetimes. What stands out about the most successful people isn’t their lack of failure. It’s that they fail fast. They learn from their failures.

Think about whether there are any specific mistakes you think your kids could learn from. Maybe the lesson isn’t to avoid risk, but to manage risk carefully. Or perhaps you can shed light on the realities of being a business owner. Many people learn the hard way that being your own boss isn’t so glamorous.

A heavy-handed approach is likely to backfire. Think about what you want your legacy to be. Do you want your kids to remember you as the parent who, even in death, controlled their career choices? Or as a human who made mistakes and earned wisdom in the process?

The instructions you leave in your estate plan will become your final words. Choose them carefully. The lessons you can teach your kids now are far more valuable than the ones you send from the grave.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].