If you had five minutes face-to-face with someone worth $50 million or more, what would you ask them about money? Not just about how they got rich—but how they actually live, spend, and plan now. What they regret. What keeps them up at night. What they teach their children. What, in all their wealth, still feels uncertain.
At Open Privilege, we’re putting out a call to readers: What would you ask a mega-millionaire if you had the chance? Because behind every financial milestone is a decision, and behind every decision is a mindset. And it’s the mindset—not just the bank balance—that we’re hoping to better understand.
Most of us grow up learning how to make our paychecks stretch. We plan for retirement in terms of “if I can afford it,” not “how do I shape it.” We spend our adult lives trying to find balance between enjoyment today and security tomorrow. But for someone with enough money to cover five lifetimes, what does balance even mean? That’s where your questions come in.
Money is often talked about in abstract terms: savings rates, market returns, inflation hedges. But when you ask a person who has more than enough, you get answers that reveal emotional truths, value systems, and long-term clarity. That’s what we want to tap into—your most thoughtful, grounded, or even quirky questions about what it actually feels like to live with that kind of wealth.
Some questions will be practical: How do the wealthy approach investing after they’ve already “won”? Do they still budget? How do they decide how much to give to their children—and how much to withhold? Other questions are more philosophical: What does “enough” feel like? Does wealth create more peace or more pressure? Does it isolate, or does it empower?
Let’s walk through a few of the themes that might inspire your own question—each rooted in the kinds of planning, tradeoffs, and values that we all wrestle with, no matter the size of our account balance.
Many people assume that once you’re wealthy, budgeting stops being necessary. But in truth, budgeting doesn’t disappear—it evolves. For a high-net-worth individual, a budget isn’t about restriction; it’s about intentionality. They still track categories like philanthropy, household costs, investment rebalancing, and family trusts. But the goal isn’t to stay within a fixed number—it’s to make sure their money supports the kind of life, impact, and legacy they want. One of the most valuable questions here might be: What does your financial planning process look like now, and how is it different from when you were still building wealth?
That’s a very different lens from asking someone how they got rich in the first place. Building wealth is often fueled by risk-taking, time leverage, and sometimes luck. But managing wealth—especially across generations—is quieter. It involves structure, governance, and purpose. It’s about learning how not to erode what’s been built. And that shift—from growth to stewardship—is often overlooked in everyday conversations.
Some of the most poignant insights come from asking about what wealth doesn’t solve. We’ve heard from wealthy individuals who say they underestimated the emotional tradeoffs that come with success: the tension in family relationships, the skepticism from old friends, the burden of privacy and safety. When you have significant wealth, people often stop being honest with you. Children may feel confused about what’s expected of them. Partners may have different comfort levels with lifestyle choices. These are not just money issues—they’re human issues, refracted through the lens of abundance.
That’s why a question like “What surprised you most about being wealthy?” can open the door to deeply honest answers. Some may admit to guilt. Others to regret. Some will share how they redefined purpose once money stopped being a barrier. And others will tell you they still worry—just about different things. For some, it’s geopolitical risk. For others, it’s whether their heirs are ready for responsibility. Wealth shifts your focus, but it doesn’t erase uncertainty. It just moves the goalposts.
Another area worth exploring is how wealth changes risk tolerance. For someone in a high-growth phase, taking risks may feel essential—career pivots, startup investments, aggressive market positions. But once you’re managing wealth rather than accumulating it, your approach to risk changes. Some become more conservative, focused on preserving capital and maintaining lifestyle continuity. Others see wealth as a cushion that allows them to take bigger swings—whether that’s funding a moonshot idea or supporting political causes. Understanding how the wealthy reframe risk can be helpful for anyone trying to plan for different life stages.
And then there’s the question of family. One of the most consistent concerns among wealthy individuals is how to raise children who are grounded, grateful, and driven. It’s not easy. Handing over money can create passivity. Withholding it can create resentment. The most thoughtful wealth holders don’t just set financial rules—they shape family narratives. They define what their money means, what it’s for, and what values should guide its use. That’s why a deeply useful question might be: How do you talk to your children about money and privilege? And what do you hope they learn from your example?
Many readers are also curious about giving—how wealthy people decide when and where to donate, how much to allocate, and how to measure impact. For someone who wants to give back but isn’t sure where to start, hearing how the ultra-wealthy navigate this process can be illuminating. Some work with philanthropic advisors. Others involve their children in choosing causes. And still others give anonymously, believing that generosity doesn’t need to be recognized to be meaningful. The right question here might be: What’s been your most fulfilling use of money beyond your own needs?
But not every question needs to be serious or strategic. Some of the most revealing answers come from lighter, personal queries: Do you fly first class or own a jet? Do you still cook your own meals? What’s the last thing you bought that brought you joy? These kinds of questions remind us that no matter how much someone has, they still live real lives—full of habits, quirks, and emotional tethers. Money may expand your options, but it doesn’t replace taste, preference, or identity. And understanding how wealth shows up in the everyday can be just as insightful as dissecting an investment portfolio.
If you’re still not sure what you’d ask, start with this: What do you wish someone had told you about money ten years ago? This question strips away status and success and brings the focus back to learning. Because ultimately, that’s what all financial inquiry is about—gaining wisdom you can apply, whether you have $10,000 or $10 million.
So we ask you now, sincerely: What would you ask a millionaire?
Not because you want to copy their life. Not because you believe wealth makes someone smarter or better. But because you’re curious about how money—once unbounded—changes the way people think, plan, and live. And because their answers might offer a mirror. A moment to reflect on what you want your financial decisions to mean.
To submit your question, simply email us with the subject line “Millionaire Question” or reply in the comments section below. We’ll be compiling reader questions for an upcoming feature where real high-net-worth individuals respond with candor, strategy, and, we hope, a little humility.
Your curiosity might be personal. Or practical. Or philosophical. That’s the beauty of it. In a world where money is often talked about with either envy or shame, this is your chance to ask with sincerity. And perhaps hear something real in return.
Because sometimes the best financial advice doesn’t come from an app or a planner. It comes from a moment of human honesty—between someone who’s still figuring it out and someone who’s learned to live with more than enough.
And when that conversation happens, we all get a little closer to understanding what wealth really means.
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