
The following is a guest post. Alden Tan is a rock star blogger who quit his job to follow his dream to be a writer. He blogs about inspiration, and has the uncanny ability to not care about what others think.
You have tons of money, and without a care in the world, you’re always ready to spend a bucket load on your friends.
I mean, who doesn’t like free stuff? Surely you’re making them happy.
Then you feel all high and great about yourself, thinking that you’re the cool, rich friend who’s super generous.
That must be a pretty awesome life right?
No, not really.
I’ve seen it and felt it with my own eyes.
I used to party a lot and hung out with rich folks, who were all too ready to always buy people drinks.
That’s cool.
But I got envious. I actually thought it would make me a big man if I did the same.
And with a new credit card, I did just that.
It was a trap.
The idea of being generous with money just because you have it. The enticing lure of wanting to be rich and feeling like you’d be elevated to such financial freedom is a short-lived farce.
Many people typically want to be rich, but having tons of money actually require a certain control in your finances.
Now, people say it’s about making sure you don’t spend too much on yourself…
… I say it’s about making sure you don’t be too generous.
Generosity can mess with your sense of logic
Picture this:
I felt good and “rich” buying drinks for my friends. I justified that it was all good because everyone was happy, drinks in hand anyway.
It didn’t exactly bother me that I had a lot of expensive weekends. I just got used to it. What’s wrong with getting used to fun and being happy with your friends?
It was only when I started feeling the pinch of spending too much, and I talked to a friend about it. And he said something so sensible I just wondered why the hell I didn’t catch it from the start.
He said, “You don’t need a million dollars to be financially free. You like drinks? Just get a few good friends, and split the bill“.
Now think about it: What does financially free mean to you?
And does it necessarily mean you got to be a millionaire to be free?
Let me tell you the answer: No.
Being financially free can come in so many different ways. I say, it’s about knowing the true value of a dollar and not being held by its societal value.
It’s true when they said there are many things in life money cannot buy. So do you want to take part in the paper chase that goes one full circle back to paper?
Or, would you rather be free from the grasp of money, and realize there’s more to life than just money in this world?
My revelation was simple, but it was a profound one that showed me simplicity and making sensible choices can bring you a long way in life.
You think you are giving happiness, when you’re really not
Let me just put it straight and clean: Buying things for people doesn’t automatically mean you’re delivering happiness.
Money can’t buy happiness, that’s the cliché, but it’s true.
Just like how the intoxication from alcohol wears off, so do the “happiness”.
How much respect, trust or rapport can you really build with someone with mere money?
That comes with an obvious answer: Not much.
But because you think you ought to be generous, your sense of judgement may be clouded with your supposed elevation from wanting to be or feel rich.
Think that you did a “good one” by buying everyone drinks? Think again. They’re probably just thinking when the next drink will come.
There’s nothing wrong with being generous
But do it sparingly.
Having a lot of money doesn’t mean you need to buy stuff for people.
Evaluate why you buying something for someone first before you fork out the cash. If it’s just to feel good about yourself, then you ought to reflect upon that.
You worked hard for your own money, so why spend it on others?


No matter how much money I have I will always be frugal with it. I am the type of person who will never think what I have is enough and I will always want to work towards more.
Hey,
Hmm perhaps you ought to free yourself and be happy with what you have already?
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
That is a great attitude to have as long as you don’t go overboard. I personally live the same way. In my budget, FUN is listed as a need. I fund my fun money or as I like to call it “Mad Money”, with a generous amount and enjoy life. However, I don’t blow that money, I enjoy saving and being frugal so I still price shop… why not get the most for your money right?
Jeremiah Brown recently posted..How To Make QUICK MONEY – Part 4 – WRITE FOR MONEY
For sure…some fun money is pretty important. If we deprive ourselves too much, what’s the point of even having money? Some people just get so caught up in the idea of money that they don’t stop to enjoy it.
I think I get what you’re really trying to say here, but for what you’ve written here I, um, completely disagree.
Most people who identify as being truly happy spend most of their time focused on helping others, using whatever resources (including their ‘wealth’ to do it).
They typically favour experiential (doing things) purchases over material purchases (having things) and unless they are doing things by themselves, this inherently means spending their money on doing things with other people.
The point of wealth is to be generous, studies talk about an inflection point of around $60k per year where anything you earn above this doesnt really seem to make you any happier, so .. if not, why not be generous with anything over this.
And not only to the people around you, but those who aren’t (around you).
I could go on here, but I think thats probably enough to make my point. Always happy to discuss further, feel free to get in touch
Vincent Turner recently posted..SF New Tech
Great reply Vincent!
Hmmm well I feel that money goes hand-in-hand with generosity, so much so it somehow becomes “automatic” for you.
That means to say, you stop thinking, and your judgement is impaired.
At least to me it happened.
Yes being generous is all good, without a doubt. But perhaps a little self-control should be be in place.
Alright! I’ll definitely email you!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I get the point of this post, but the use of “generosity” to mean “buying someone else’s drinks” and particularly the last sentence is jarring. I believe in generosity, but toward people who can’t reciprocate.
Hey Emily,
Yeah maybe I came across as that. Indeed “drinks” being the tangible good in question may be too subjective on its own.
I was just using it as medium for the article. The alcohol did not impair my judgement, but as I mostly hung out with friends who partied together, drinks somehow became the medium, and it sort of went hand-in-hand with generosity.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
oh and I love how you said, ” I believe in generosity, but toward people who can’t reciprocate.”
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I have an uncle/aunt who are richy rich rich. They dont’ buy lots of stuff for people all the time or anything, but every once in awhile they do treat everyone to ice cream or something. It’s a nice compromise — I feel happy because they’re not gloaty about their money, I’m not always wondering when they’ll treat again, and I’m reminded that if I”m careful with my money that I can rich too… and it seems like they’re happy becuase no one expects them to pay all the time or are taking advantage of them.
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Hey,
Your uncle and aunt are cool people!
Thanks for dropping by.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I used to be similar. I would buy my friends drinks and other things, but I stopped doing that. It ended up being too expensive!
Michelle recently posted..Our Updated Budget
I know what you mean. I totally stopped partying and ironically, I work in a club now lol.
The main purpose of it being to occupy my time so I won’t go out to spend otherwise.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Generosity and buying drinks don’t go hand in hand. When I’m out at a bar for a friends birthday or any other random occasion, I buy a drink out of respect. Either that person has already purchased me a drink, and I’m returning the favor, or simply because I respect them as a good friend, co-worker etc.
Personally I don’t ever get into awkward scenarios at bars. I go in with “X” amount and that’s it. When that allocated and budgeted money goes – that’s it for the night.
Hey Eddie,
Yeah drinks being the exchange is subjective for sure. The bar being a place of its own culture definitely has its value too.
I used to buy out of respect too, mostly to return favours. I didn’t want to come across as a leech.
But as I wrote in my article, it just feels like (or least those I’ve seen), that buying a round brings you “up there”.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Yeah you’re right that buying rounds gets you up there. Walk into any club any night, and you’ll see a lot of “tail” gawking, mooching and men being glorified because they are….how can I say this…”popin bottles”.
It’s a show thing. Much like a guy who pulls up in his BMW in front of the line of the car, and uses the clubs valet parking. Coincidence? I think not.
But what our eyes see at times is very deceiving. A lot of these bottles are purchased illegally, which I won’t get into here. Club game is dirty, and you’re either “rollin” or you’re going to be rolled over.
Yeah, I’m not really into buying people stuff to feel rich. I tend to believe that the reason people buy stuff for others is because it’s the way most people show and receive love these days.
We play value and happiness in material possessions, so by giving them to people we can therefore display how much we care about them.
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That is true. Perhaps it is also very convenient and the easiest thing to think of.
And what more, in a bar, you can be judged by simply the number of drinks you buy, making you the leech or the rich.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Great post. In my younger days I really did try to buy friends. I had very low self esteem and I thought that by buying things I would show my worth and why they should be friends with me. Not an effective plan at all. In fact I ended up in debt because of it. I have since learned my lesson.
Great that you learnt!
I certainly learnt mine too. I just left with an empty wallet and I did not think my friends looked up to me then.
And yeah, girls don’t stick to you too right after they finish up

Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I know the feeling too well of buying a round of shots for everyone. I’m a very selfless person when it comes to generosity. I like to give and give, but it is definitely harder when the people you are giving to are either unappreciative or do not reciprocate. It’s nice to get a thank you once in awhile but it works really well if you are trying to build relationships or network.
Also, my BF will always offer to pay for the bill if he is eating out with my family. When it comes to family, I think there is really no limit for generosity – especially if you can afford it. There just has to be a limit. It can’t be all the time and it can’t be never.
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Hey,
Yeah I know what you mean. Drinks at a bar work this way I guess. It can be about networking, or it’s a way of showing you “stand for something”.
That’s cool about your boyfriend!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Generosity is very often misinterpreted by so many people. They think that you have to give away what you don’t have and also at your own expense. This is faulty and dangerous thinking. Generosity can go a long way, but it;s potentially harmful if we use it as a way to gain acceptance and receive admiration from others.
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Great insight Anthony.
Indeed it is! I don’t really see a point in “sacrificing” all the time. Why be generous to someone who’s obviously a leech?
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
“Having a lot of money doesn’t mean you need to buy stuff for people.”
This rings true for me. My husband and I are more well off than his family members because we are responsible with our money and make sensible decisions while they do not. They are always in a jam and look to us to bail them out because we have money. Just the other day my husband sent his 34 year old sister $300 because she was fired from her restaurant job and told him she was “scraping together change to put gas in her car.” I’m not against helping people out but his sister chose to live this lifestyle rather than put her Master’s degree to work and get a regular, steady paying job. It’s always bugged me a little that we are like the family bank and pay for other people’s bad choices. But then I would feel guilty for feeling that way.
Your post made me feel a little bit better about that!
No prob Kasi. Glad it helped!
True that! I’d never lend money to anyone if I know it wouldn’t help them positively. Sure, showering them with gifts is one thing, but if it just leads to negative results? Why bother then.
I’ve a friend who borrows profusely to clear his gambling debts. We all pretty much avoid him now.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Thank you for this guest post Alden. And thank you for taking the time to respond to the comments. There were plenty of interesting comments so far. While buying drinks was the example used in the post, this kind of thinking does apply to all kinds of scenarios. You don’t have to always be buying people stuff just because you think you have the funds to do so. People did mention some good exceptions such as dinners with family or a drink for the birthday boy/girl.
No prob Jeremy!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I’m pretty frugal and don’t party very often. When I do, I tend to be pretty generous with friends who I know don’t have a lot. It probably only costs me a couple hundred bucks a year, which isn’t bed. But its get to be a vicious circle for me, though, especially when I see people wasting money by smoking or something. I still can’t resist letting that get to me for some reason… So I guess I’m pretty generous but judgmental?
Nick recently posted..2012 Goals Update
Hmm how are you judgemental?
Perhaps you’re too nice? I would never give much to friends, even if they don’t have much when I know they’re just going to waste it away.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
I’m not entirely sure but I often look for bad habits and the use for the money before giving someone money. For example, if someone had a crazy emergency (baby sick, car accident, etc.) I would not look as hard. But if a smoker who is just getting back from a cruise with three bags of duty free vodka and asks for a few bucks to make their mortgage payment it gets to me.
But I agree with you. I think I’m doing them a favor. But they don’t often take it that way. (It doesn’t happen THAT often, but it happens). The way I see it, some people’s problems are that “they don’t have enough problems.” So if someone is wasting money, they need to really feel they don’t have a backstop in order to change, IMO. That’s my philosophy anyhow.
Good point though. I agree with you, but it’s tough love, which (by definition) is “tough” sometimes.
Nick recently posted..Saving Money On a Wedding (Even If You Don’t Pay For It)
I’m really hoping that you are not as selfish as this post makes you sound. There’s foolish generosity and then there’s caring generosity. One reason I work hard to live a frugal life is so that I can give a portion of my money and time to helping people in need. There’s little point in amassing wealth if it makes us uncaring and uninvolved in our communities. I would never spend my money buying people drinks in a bar but I will always contribute a part of my income to the food bank and to other community organizations and charities I support.
Beth @ Aunt B’s Kitchen recently posted..Stewed Steak
Nah I am not selfish.
But what I am trying to say is, perhaps check carefully what or who you’re giving your money away to.
Case in point, drinks aren’t the way to go.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
The problem with being too generous and buying your friends drinks is that they come to expect it. It sets you up to be in a bad situation when you stop being too generous. But I guess when you stop you can see who you’re true friends are.
I believe in helping people in need, but not just giving away money to people who can do well for themselves.
True enough!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Although I see you have taken a beating for your opinion, Alden, watch the early film The Freshman with Harold Lloyd (1925) for confirmation of your point of view. Harold’s character squanders his funds to lavish gifts and parties on his new college “friends” who laugh at him behind his back. It’s silent but hilarious.
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Thanks Astro!
Nah I don’t see it as a beating. It’s good to discuss!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
This is timely because I just came back from a bachelor party with work colleagues and the boss only bought one round of drinks (after winning $200 at the casino). He makes around 200k so he could easily afford it, but he must have gotten the advance copy of your article!
I always respect contrarian points of view – great defense of greed, though I would advocate just doing what you want to do in the moment and not conveniently scheduling bathroom breaks when it’s your turn to buy a round.
John | Married (with Debt) recently posted..Debt Payoff Progress April 2012
Haha did he now?
Well I’m trying to advocate some self-control, EVEN when it comes to being generous (however you want to see it).
The bathroom bit sounds funny, but so true in many people.
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
Time is the most valuable thing a person has to offer. If I give my time to hang out with people, I don’t feel I should have to spend money to make them happy.
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Nicely said!
Alden recently posted..Your greatest foe is yourself. Your best ally is failure
There are certainly ways to be generous without the use of cash money. You can be generous with your time, helping a buddy move or just listening when someone has a problem. You can be generous and offer to host a potluck, all the effort and cleaning, and keeping people happy when they’re over certainly isn’t expensive, but it is a lot of work. Similar in the blog land, you can comment, send link love and whatnot even if you don’t buy someone’s ebook.
That’s very true. There is a lot of ways you can just be generous with your time. People are often too worried about trying to impress others though and try to buy their friendship. They just see blowing some money as a shortcut.
I completely agree that, money cannot buy happiness. Though, I do think that money can buy freedom.
What do I mean by this? Well, if I have no money I need to get a job, any job, to give me some money. If I have money, I have a little bit more breathing time to find a job that aligns with what I want.
As I gain financial freedom it gives me more breathing room to pursue those potential opportunities in my life that I am truly excited about.
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In other words, money indirectly buys happiness. It may not be the direct source of that happiness, but that flexibility that it provides gives you greater ability to create happiness.