"Spending like a drunken sailor" is not just about being loose with one's money ... it's about being completely open to follow the opportunity of the moment ... regardless of whether or not it costs you anything or takes you away from they way you planned to use your resources. But I totally agree that the downside of spending this way all the time is that whether we are Bill Gates or a budget traveler we all have some limit to our available finances. The freedom to follow the moment will eventually give way to the tyranny of poverty. It's like a dictatorial country that you automatically become a citizen of when you have no money ... because then you have no choices.
Mabuhay from Boracay! Living a SIMPLE thrifty lifestyle keeping active and entertaining oneself withOUT constantly spending money, shopping or seeking human contact through consumerism is a sure way of reaching control and financial freedom over one's life. But my wife and I do indeed KNOW EXACTLY what you are talking about, when one lives their life like this those around him make the type of remarks and maintain the same attitudes you are talking about above. I find this attitude or cultural group mentality the WORST in the States but it's very common here in the Philippines also where the "millionaire for a DAY" attitude is also a widespread Filipino cultural trait. How else would SO MANY PAWN SHOPS all over the Philippines stay in business and prosper? But again as I've mentioned before this spendthrift critical attitude toward "Cheap Charlies" seems MOST common in catholic cultures.
My wife and I don't let it bother us much as we have ALWAYS KNOWN, "it's LONELY at the TOP" so prefer our OWN COMPANIONSHIP ( and our cash savings, bank deposits and land titles ) to maintaining a "posse" eager for us to offer them "FREEBIES" each and everyday they wake up looking for others to support their consumer junky habits.
A Word to the WISE read Benjamin Franklin's "Poor Richard's Almanac" , Henry David Thoreau's "Walden" and "Thoughts of Thoreau" for such universal tips like "never a borrower nor a lender be", "early to bed early to rise makes a man healthy wealthy and wise" . WALKING and READING and spending lots of quality intimatecy time are FREE and for those who want to travel REMIND YOURSELVES working that 2nd and 3rd job even at less salaries than hoped for allows you to SAVE MONEY and "SEE the LIGHT AT THE END OF THE TUNNEL" as when working you are NOT spending.
I agree 100 with your statement: "I am encouraged by the world to spend money like a Drunken Sailor, and when I do not, they call me Cheap."
I live in the US and deal with this implicit guilt trip often. Maybe I sit at a table and order a drink and an appetizer, then ask for the check without getting an actual meal. Or maybe I go to lunch and get just a sandwich with a cup for some tap water. Maybe the server cares, maybe they don't, but often I feel as though I am implicitly being called "cheap", especially because here in the States by me not ordering more it actually does reduce their earnings via the tipping process. But the worst is how all the sandwich shops and delis, even places like Subway now put up a jar next to the register for tips. For doing nothing but their job... And you wouldn't believe how many people throw a dollar in. Why? The person didn't even make my sandwich, they are just standing at the register taking my money.