Reflections on wealth, freedom, and purpose - after reading Morgan Housel’s The Art of Spending Money.
"Is this it?"
The question arrives unexpectedly, usually during a review of another strong year. The numbers are good. Wealth has grown notably. By any objective measure, this should feel like success. And yet.
Years of late nights building the business. Stress about payroll, cash flow, making it all work. Money carefully set aside through all of it. Maybe retirement has finally arrived. The hard part is supposed to be over.
But the portfolio grows, and something still feels incomplete. The destination was supposed to feel different than this.
This moment, this quiet crisis of purpose, happens more often than anyone wants to admit. Morgan Housel's new book, The Art of Spending Money, circles around it for twenty chapters. The central tension isn't about spending versus saving, or risk versus safety. It's about something far more fundamental: What is wealth actually for?
Not in theory. In your specific, unrepeatable life.
The Unasked Question
There's a conversation that happens in every professional relationship involving wealth. Accountants discuss tax optimization. Lawyers review estate structures. Advisors present portfolio returns and risk metrics. The technical work gets done.
But there's a conversation that almost never happens, regardless of which professional is in the room: What would make you look back and think your wealth served its purpose?
Not "did it grow" or "did you save on taxes" or "is the estate plan complete." But: Did it deliver the life you actually wanted?
Housel offers what might be the most useful definition of wealth ever written: "The best measure of wealth is what you have minus what you want."
The gap between those two things, between possession and desire, is the only measurement that ultimately matters for a human life.
"If your expectations grow faster than your income, you will never be happy with your money." The mathematics are brutal. Someone could compound wealth at 10% annually for thirty years and still feel perpetually behind if what they want is compounding at 11%.
The work of building wealth is precise, measurable, benchmarkable. The work of deciding what it's for? That gets skipped. Deferred. Assumed to be obvious.
It's never obvious.
What Should Be Measured
Here's what gets tracked: returns, costs, allocation percentages, account balances, tax savings, estate structure efficiency. The technical metrics, monitored continuously, reported regularly.
Here's what should also be measured but rarely is: Whether someone spent the year becoming more or less free. Whether wealth created possibility or anxiety. Whether money served as a tool or became a master.
The latter questions matter more. They're just harder to pin down, not because people don't think about them, but because there's no common framework for making them tangible.
"Desiring less doesn't mean giving up. It's the deepest way to enjoy what you already have." Housel is describing something essential here, something that can't be captured in a quarterly report. Contentment isn't resignation. It's clarity about what matters.
The Pattern Worth Noticing
There's a pattern that emerges: wealth can grow while freedom shrinks. The portfolio compounds. The complexity compounds with it. More properties to manage. More tax strategies to navigate. More decisions to make. More things that could go wrong.
At some point, the wealth that was supposed to create freedom becomes another thing demanding attention. The tool becomes a burden.
This is what Housel means when he writes that wealth without independence is its own form of poverty. You can have substantial assets and still feel trapped by obligations you've created, expectations you're maintaining, an image you're protecting.
Independence looks different for everyone, but the specifics matter: The ability to help children during the early years of grandchildren's lives. The freedom to say no to projects they don't enjoy anymore. The ability to spend dark Canadian winters somewhere sunny and invite family to join them until they wear out their welcome. Time to volunteer at an organization they're proud of. Unrushed mornings.
Clarity about what you want your money to do, and what you're willing to say no to, makes all the difference.
The Questions That Actually Matter
Housel writes about risk in an unexpected way. The real risk, he suggests, isn't volatility or market drawdowns. It's future regret. Looking back decades from now and realizing you were optimizing for something that didn't actually matter to you.
The questions worth asking aren't about performance metrics. They're about direction:
Did I spend my time this year the way I wanted to?
Am I more or less free than I was twelve months ago?
What memories did my wealth help create?
Did money serve as a tool, or did I spend the year serving it?
These aren't questions with objective answers. They require knowing what you're actually building toward. And that's where most people get stuck, not because they're doing it wrong, but because no one ever asked them to get specific about what "right" looks like for them.
The investment world obsesses over compound interest. As an advisor, it's my responsibility to obsess over these things too. The returns matter.
But Housel points to a different kind of compounding: memory.
Money spent on experiences with people you care about doesn't just create a moment. It creates something you'll revisit for years. The story that gets retold. The shared reference point that becomes part of your family's language. The thing that makes someone say, decades later, "Remember when we..."
For many people, this represents the highest-returning investment they'll ever make.
The Other Performance Review
Markets have a tendency to double roughly every decade. Assuming reasonable returns and consistent investment, most people's portfolios follow a similar trajectory. Ten years ago, your wealth was likely around half of what it is today.
Here's the question that matters: Has your satisfaction doubled?
Not your net worth. Your actual satisfaction with how you're living. The freedom you experience day to day. The sense that your wealth is serving its purpose.
For many people, the honest answer is no. Wealth grew, but satisfaction didn't track with it. Sometimes it barely moved at all. In some cases, complexity and anxiety grew faster than the portfolio did.
This isn't a failure. It's just what happens when all the attention goes to one set of metrics and almost none goes to the other.
Housel frames it this way: "Good memories are the closest thing to living for today while compounding for tomorrow." The real work isn't just generating returns over the next decade. It's ensuring that the experiences, the freedom, the memories compound at the same rate your wealth does.
That ten years from now, when your material wealth has doubled again, you can honestly say the life attached to it improved proportionally.
That requires knowing what you're measuring for. And it requires actually measuring it.
Close: The Conversation Worth Having
Housel's book doesn't provide a formula. There isn't one. What constitutes a life well-lived is too personal, too specific to individual circumstances and values, to be reduced to a universal framework.
But it does provide the questions worth sitting with:
What is your wealth actually supposed to accomplish?
What would make you look back from your final chapters and feel it served its purpose?
How will you know if it's working?
These aren't questions to answer once and move on. They're questions that evolve as life evolves, as priorities shift, as what matters becomes clearer or changes entirely.
The work of wealth management will continue to be precise and technical. Returns will be monitored. Risk will be managed. Portfolios will be optimized.
But perhaps it's time to apply the same rigor to the question underneath all of it: Is this delivering the life you actually want?
Because that's the only benchmark that ultimately matters.