The basic problem is that both of you are equating the lack of stress over money issues with happiness and the same stress with unhappiness.
The Buddha, who was the heir to great wealth, threw it all away in his search for nirvana. Jesus died penniless on the cross. Mother Theresa, Ghandi, the Dahli Lama, all poor...and happy.
There are also many examples of men and women with great wealth who are/were decidedly unhappy, including Howard Hughes and William Randolph Hurst.
So clearly, happiness is not directly connected to wealth.
When we examine those who have wealth and ARE happy, the relationship becomes clear.
Those who maintain perspective and who use their money in ways that benefit people are those that are happy.
Bill Gates donates billions of dollars to charity, does not live in the biggest house off of Lake Washington, and who has said that his children will have to work for their living is apparently happy.
This is of course why the saying "money can't buy you happiness" is often misconstrued, because to some it seems that these wealthy people MUST be happy and it MUST come from their money.
Likewise why some do not understand the corallary, that the love of money is the root of all evil, thinking that it is money itself that is evil, because people commit great evils while pursuing money.
In short, money is a tool, being external to ourselves.
Happiness, which is a state of being, must come from within.
At best, money can influence the environment in which we pursue happiness (i.e. provide an environment without the stress of "how will I feed my children" and "how will I afford shelter for my family?")
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"Of all tyrannies, a tyranny exercised for the good of its victims may be the most oppressive. It may be better to live under robber barons than under omnipotent moral busybodies. The robber baron's cruelty may sometimes sleep, his cupidity may at some point be satiated; but those who torment us for our own good will torment us without end, for they do so with the approval of their own conscience." – C. S. Lewis
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