Talking About Money, Success, and the Things That Shape Us
The holiday season has a way of putting us back in close proximity with our nuclear and extended families. Old stories resurface. Familiar dynamics reappear. We’re reminded, sometimes subtly and sometimes very directly, of the beliefs we grew up with and the ones that shaped us.
It can also be a quiet opportunity to pause and ask a different set of questions.
What did we inherit emotionally, culturally, or practically?
What do we want to carry forward?
What do we want to pass on, more intentionally, to our children?
For parents raising children in any kind of privilege, these questions matter, and they often benefit from being addressed earlier rather than later.
I regularly work with next-generation adults who are capable and motivated, but feel stuck or second-guess themselves because money, success, and expectations were never clearly named in their families. The confusion shows up years later, in their careers, relationships, and sense of confidence.
The families who seem to navigate this best tend to focus on a few shared conversations early on.
Acknowledge wealth and privilege, without shame or secrecy.
If children don’t know they are wealthy, it becomes very difficult for them to be emotionally prepared for wealth, or to grow into confident, responsible stewards of it.
Explain what wealth actually means, in practical terms.
That includes:
Naming that privilege does not make someone better than anyone else, just extremely lucky
Being clear that having means allows access to experiences others may not have, such as:
educational opportunities
time and resources to explore interests and passions
travel and exposure to different ways of living
capital that can enable entrepreneurial risk, flexibility in career paths, or meaningful philanthropy
It also means helping children understand that money is a tool they have been, or will be, given. One that deserves gratitude, respect, and thoughtful consideration in how it’s used.
Define what “success” and expectations actually mean in your family.
Talk about it explicitly.
If children are likely to inherit money, clarity around expectations matters more than reassurance.
In many families, there may be substantial trust funds or inheritances, and at the same time, it may not be enough for future generations to fully sustain the lifestyle they’ve grown up with unless they also earn. Naming this clearly is an act of kindness.
For example:
Will they need to earn in order to maintain something close to the quality of life they were raised in?
If so, what level or kind of earning is realistically required?
Is the goal preservation of capital, continuation across generations, or something else?
Avoiding these conversations often leads to mixed messages, where children are told money “doesn’t matter,” while quietly sensing that it very much does. That ambiguity can leave next-generation family members playing small, opting out, or feeling unsure how ambitious they are allowed to be.
More broadly:
Does success mean preserving capital?
Does it mean earning a certain amount of money?
Does it mean independence and the ability to support oneself?
Does it mean contributing to society in a meaningful way?
Does it mean curiosity, confidence, and a willingness to take risks, knowing that failure is normal and survivable?
Clear expectations don’t limit children. They free them. They replace guesswork with agency and allow next gens to pursue ambition without shame, confusion, or quiet self-censorship.
If these conversations feel hard, start with yourself. Reflect on your own beliefs and where they came from. Talk them through with your partner. Write down what matters to you now, not just what you inherited. That clarity makes conversations with children, both young and grown, far easier and more grounded.
And if your children are already adults, it’s not too late. These conversations can still be meaningful, connective, and clarifying at any stage.
Sometimes the most valuable thing we pass on isn’t certainty, but shared understanding and the permission to talk openly about the things that shape our lives.