By Zach Whitchurch, President | Wealth Advisor, Certified Private Wealth Advisor®, CFP®
Something interesting happens when you spend enough time around money. You start to notice patterns. Not just in the market, but you also see patterns in people. Specifically in who seems genuinely happy versus who is still searching for something they can’t quite name.
Some of the most accomplished people I’ve met (founders who built something real, executives who earned every bit of their success) carry a subtle restlessness that their net worth never quite resolves. And some of the most content people I’ve met aren’t always the ones with the most. They’re the ones who figured out, at some point, what they were truly after.
I started paying closer attention. What separates people who feel free from people who feel trapped by their own success?
The Vanderbilt Problem
The Vanderbilt family built one of the great American fortunes. They also built an estate so vast it required roughly 400 people just to keep it running. They had more than most people could dream of.
The scale itself wasn’t what went wrong. Plenty of people have managed estates just as large and lived with genuine contentment. For the Vanderbilts, the problem ran deeper: money had become the organizing principle of their entire existence, and somewhere along the way, it stopped creating anything meaningful.
The family’s story became one of generational wealth squandered across lawsuits, estrangements, and a long, slow unraveling.
I think about this a lot. When does money shift from a tool that gives you options and allows you to fulfill on much larger goals to a force that runs your life?
What Wealth Can’t Fix
The case that money buys happiness is easy enough to make, and there is real evidence behind it. But spend enough time looking, and you’ll find just as much pointing the other direction.
Look at the list of the world’s wealthiest people. Many who reached the very top spent their lives in relentless pursuit of more and yet, by their own accounts, found themselves feeling strangely empty once they got there. When someone has more resources than anyone could possibly need and still seems to be searching for something, it’s worth asking what all that striving actually failed to provide
Money solves a lot of problems, but loneliness isn’t really one of them. Neither is presence, or patience, or the ability to show up fully for the people who matter most to you.
What the Happiest People Actually Have
The genuinely content people I’ve worked with over the years share a few things that have nothing to do with their account balance.
They know what they’re building toward. Not in vague terms (not “I want to be comfortable” or “I want to leave something for my kids”) but with real clarity. They can tell you why they’re making the choices they’re making, and those reasons connect back to something that matters to them personally. That kind of clarity doesn’t happen by accident—it takes intentionality.
They’ve decided what “enough” looks like. This might be the most important one. Without a definition of “enough,” every milestone just becomes a launchpad for the next. You sell the company, and within six months you’re restless. You hit the number, and the number moves. The people who seem most at peace with what they have made an active decision about what they were truly after and had the discipline to recognize when they got there.
They use money to protect time, not fill it. The best use of significant wealth I’ve ever seen is time: time with family, time to be present, time to do work that feels meaningful rather than obligatory. The worst use? Spending money on things that create more obligations, more management, and more noise. More stuff that needs to be maintained, insured, staffed, and worried about.
They’re not performing: There is a version of success that is really just a long audition: They’re not trying to look successful; they’re just trying to live well, and for them, those two things stopped being the same a long time ago.
The Question to Ask
At Solidarity we work with founders, executives, and families who have built meaningful success. The financial complexity that comes with that success is real, and we spend a lot of time on it together. But some of the most valuable conversations I have don’t start with a balance sheet. They start with a question: What do you want your life to actually look like?
Not the financial plan version of that question; not “What are your retirement income needs?” The real version. What matters to you? Who do you want to be present for? What would make this all feel worth it?
Money without that answer tends to drift toward accumulation for its own sake. More property, more deals, more complexity, and somewhere underneath it, a nagging sense that none of it is quite landing the way you thought it would.
The happiest people I’ve met are the ones who figured out what they were after before the money showed up or at least asked the question seriously enough to answer it honestly. The wealth came along and amplified a life they’d already chosen. That’s a very different thing from building wealth first and hoping a life follows.
If you’re navigating significant wealth and want to think through what you’re building toward, we’d be glad to have that conversation. Reach out to our team at Solidarity Wealth at info@solidaritywealth.com or call 385-374-1665.
About Zach
Zach Whitchurch is the President and a wealth advisor at Solidarity Wealth, serving as a multi-family office for successful families, entrepreneurs, and executives in the Mountain West. Holding CFP® and CPWA® designations, he specializes in simplifying the complex and implementing creative strategies to help clients develop wealthy and healthy financial habits
Solidarity Wealth is a registered investment adviser. This material is solely for informational purposes. Advisory services are only offered to clients or prospective clients where Solidarity Wealth and its representatives are properly licensed or exempt from licensure. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. No advice may be rendered by Solidarity Wealth unless a client service agreement is in place.
