Especially in the US, many of us are trained from an early age to think of money as the ultimate scorecard. More is better. Higher numbers win. A bigger salary, a more valuable portfolio, a pricier house: these are the metrics of success we're conditioned to chase.
But what if that's fundamentally misguided?
As my colleague recently wrote (Scarcity and Abundance: Money vs. Wealth), money and "net worth" are not worthy goals; money is merely a proxy for what we actually value ("wealth"). When we strip away the dollar signs, we often discover that our true priorities have little to do with raw numbers and everything to do with freedom, security, time, flexibility, and enjoyment.
The following "Would You Rather" thought experiments may help illustrate that more is not always better.
As with many thought experiments, they begin with the borderline absurd and obvious, which is helpful in determining what you definitely believe before advancing to deciding what you might believe that's less obvious.
Where You Live, and What It's Worth
Let's start with an easy one: Would you rather live in a home purchased in 2021 with a $3,000 monthly mortgage payment at a low interest rate, or the exact same house in the same location, bought three years later with a $5,000 monthly payment due to higher interest rates?
Obviously, most people would prefer to pay less every month to live in what is otherwise exactly the same situation. So, what's the point of the question? If anything, it may seem only to reinforce the typical belief, that saving money (and having more leftover) would be better. But the example demonstrates more than it first appears.
What if you could have retained a level of control over the interest rates to which you are exposed? How much would you give up in advance of this scenario, in order to obtain the positioning required for you to make Scenario 1 happen, instead of Scenario 2? How much value does that difference have to you? In this case, the house, its value, and your life within it are not what changes. All that matters are the circumstances surrounding the house, and what factors remain external vs internal to your decision making. Many real-world environments are complex and/or complicated. Decisions that would make sense "if all else remained equal" rarely matter - all else is typically not equal.
To add a challenge, what if the house is worth $100,000 more in the second example? Does that change your calculation? What if it's worth $200,000 more? Are you inclined to believe having a house that is worth more changes your opinion about it?
For starters, what is it about a higher value house that you actually want? Remember, in this case, the house and location haven't changed. If you plan to stay in the home for the next 20-30 years, what good does it really do you for it to be worth more? In the meantime, your life is exactly the same, except your monthly cash flow is weaker. The person with the 2021 purchase is keeping an extra $2,000 in their pocket every single month. Over just five years, that's $120,000 in actual cash flow – money that can be invested, used for experiences, or simply provide breathing room in the monthly budget.
The increased home value is merely potential money, locked away until you sell or refinance. Meanwhile, the higher mortgage payment creates real constraints on your daily life.
Key Takeaway: The definition of "more", "same", or "better" is almost always multi-faceted.
Higher Incomes
Would you rather earn $300,000 annually with a $275,000 cost of living, or $100,000 with everything paid for (let's say by a magic genie)?
Most people default to assuming that a higher paycheck is better. After all, $300,000 is the more impressive salary to report between the two, and who doesn't wish they made more money?
Of course, the second example is better mathematically; the recipient would be netting/saving an additional $100,000 per year, compared to just $25,000 in the first example. But the second scenario offers something potentially more valuable than an extra $75,000 - it offers simplicity, predictability, and freedom from financial stress. No rent or mortgage payments. No utility bills. No unexpected home repairs or car maintenance. Just discretionary income to use as you please. How would it feel to have that version, compared to the feelings involved in the first example, even if we changed the "cost of living" figure to just $200,000 and made it apples-to-apples?
Which creates more actual value in your life? The prestige of a high income that largely flows right back out, or the emotional consequences that would come from having your basic needs met automatically?
What if we made the example less mathematically obvious by changing other variables. What if your cost of living was the same, but your lifestyle was different? What if in exchange for the extra money, you added two hours of commuting and saw far less of your family and friends? What if your commute and working hours stayed the same, but you woke up every day angry instead of happy?
As above, you can't determine if "more is better" until you consider all of the factors involved. In real life, Scenario's 1 and 2 may be more realistic than they initially sound, when you consider different forms of compensation and areas with drastically different cost of living. And they're incredibly realistic when you consider quality-of-life factors above cost-of-living factors.
Key Takeaway: Non-monetary values like "lack of worry" matter. And as above, "more pay" isn't enough information to make a decision; you have to consider everything that comes along with "more money" to know if you're better or worse off.
Access vs. Amount
Would you rather have $1,000,000 locked in a trust that only allows you to access 2% annually ($20,000), or $750,000 from which you can draw 6% per year ($45,000)?
The first option looks better on a net worth statement. You're a millionaire! But the second hypothetical option would provide more than twice the actual usable income. Unless you're primarily concerned with leaving a large inheritance, the smaller sum with greater access likely creates substantially more value in your life.
A slight adjustment with similar results:
- Scenario 1: You have an investment account full of stocks valued at $1,000,000, but it has a high built-in tax liability (due to growth over time) should you ever need to sell for liquidity. As a result, you're considering obtaining access to this account's value by borrowing against it instead of selling to access it directly. Because it's full of stocks, let's say the bank agrees you can borrow up to 60% ($600,000).
- Scenario 2: You have a different account, and it's full of relatively safer assets. It hasn't grown as much, since you've taken a conservative approach, so it's only worth $750,000. Since it's full of assets the bank believes to be less volatile and more secure, they will offer you up to 95% of the value in available borrowing ($712,500).
Now we're getting much closer to the kinds of tough decisions people actually face. If you're like many, it may be deeply difficult for you, upon reading this, to accept that you'd rather have less money. Everything about growing your assets more and having a higher net worth feels like it has to be better.
But now that you have to consider what to do after that, it's not so simple. The only way to access the larger pool is to sell it, and because you'll owe so much in taxes, you can't effectively access all of it. Taking the other road - borrowing - yields a smaller bucket of assets you can actually use than if you hadn't invested it for maximum growth in the first place. This seems almost impossible to believe, but it happens all the time. How you're set up affects what you can do next. More is not always better.
Key Takeaway: Top line asset values do not tell the whole story. Decumulation is as important as, if not more important than, accumulation.
Breaking Free from the Money-First Mindset
These examples highlight a crucial truth: monetary values are imperfect proxies for what truly matters to us. When we focus exclusively on maximizing dollar amounts, we often miss the forest for the trees.
What we actually value tends to be things like:
- Freedom to make choices without financial constraint
- Security and predictability in our essential needs
- Time to spend as we wish
- Relationships that enrich our lives
- Experiences that create meaning and memories
- Mental well-being and reduced stress
None of these are directly measured by a bank balance or net worth calculation.
The Better Question
Instead of asking "How can I maximize my money?" perhaps the more valuable question is "How can I optimize for what I truly value?"
Sometimes that could mean accepting a lower salary for a shorter commute. Sometimes it could mean choosing the smaller house with the more manageable payment - or the opposite. It could mean sacrificing apparent wins in the short term in exchange for better optionality and positioning when it will matter for a bigger decision, later. Sometimes it means prioritizing liquid assets over impressive but inaccessible numbers.
When we recognize that money is merely a tool for creating the life we want, and not the goal itself, we may open up new possibilities for measuring success and making decisions that reflect our values.
Next time you're faced with a financial choice, look beyond the raw numbers. Ask yourself: Which option gives me more of what I actually value? The answer might surprise you.
2025-8246880.1 Exp 08/2025