Generous People Have More To Give


A few weeks ago in Miami I only had a $5 bill when it came time to get out of the airport shuttle.

I’d love to tell you I gave the driver five bucks instead of the usual $1-2, but I kept it in my pocket and just said “Thanks.” Generosity fail.

When it comes to generosity, the general rule with me is: Win some, lose some. It’s funny how I don’t often regret being generous, but when I choose to be stingy, it comes back to me later.

It’s like dropping keys: some days I drop keys, some days I build cages. The goal is to keep tipping the balance toward key-dropping… more empowerment, less selfishness.

I really like the idea that “Generous people have more to give.” I’m not sure it’s always true, but it’s one of those things where it’s probably better to act like it’s true. Then if it turns out to be wrong once in a while, well, at least you were generous.

Another thing I’ve learned through numerous failed attempts at generosity: it’s easy to get hung up on why not to do something helpful. Self-justification has been around for a long-time, so if you’re looking for a reason to avoid generosity, you’ll probably find it. Thus it can be an uphill battle, but hopefully one worth fighting.

Freely receive, freely give. How can you try out that idea today?


Inspiration: Danielle
Image: D1109

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  • John Sifferman says:

    Something else I try to keep in mind… if it doesn’t cost me anything (or much), am I really being generous at all?

  • rob white says:

    Hi Chris
    That’s a great example, Chris. Its true, one will never regret being generous. You cannot receive value unless you give value. Sowing and Reaping is an intricate part of this ever expanding cosmos in which we live. It is important to notice that the word ‘SOWING’ primes the pump. It’s not reaping and sowing… it is sowing and reaping. The small tips we give (or don’t give) determine our relationship to money. We must make friends with money so it doesn’t avoid us. Have a great feeling about money. Love money for all the good it can do for us, our loved ones, and the planet… and it will return in multiples.

  • Annie Stith says:

    Well, now you’ve gone and done it. I have a new favorite phrase to toss out there in the midst of conversation: “Generosity Fail” 😉 (You knocked off the phrase, “That’s their part; what’s yours?” (my best friend and my best girlfriend and I are all codependent.)

    I so enjoy the way you write, in subject matter, attitude and your casual tone. Way to go!

  • Mel says:

    I think I am generous by nature, however, my downfall is that my ego often expects “thanks” or qualifies “how deserving” something/someone is. Pretty bad thing to admit about oneself but hey, admitting you have a problem is a step in the right direction.

  • Norbert says:

    For me it’s really easy to find a reason not to be generous. Like you said, self-justification is always there. But lately I’ve been trying to be more open about “generosity” by trying to look it from the perspective of the “receiver”, not the “giver”. This often helps me soften my heart, pocket, or whatever I’m being generous with.

    And it’s so true. You never regret being generous. In fact, I feel really good when I am. But when I’m not in the “generous mood”, it haunts me for a while.

  • Charlotte K says:

    I have had times in my life where $5 made all the difference in the world to my financial state. I am far, far beyond that point now, but it’s useful to remember it when I am in a position to give someone $5 (like the one you describe) when custom might dictate less. If you have it, and can spare it, give it, at least once in a while. You may never know the good it did the recipient.

  • Dwight ???? says:

    I find that especially when you have spent a lot of your time giving yourself, this attitude settles in where you don’t have to give more. I feel that way often. But shouldn’t it be the opposite? Doesn’t help that the general attitude about giving is, “Give and you will RECIEVE”… when we give a let go of our desire for gratification/recognition, I believe it’s the most rewarding.


  • Jessica says:

    My parents decided last Christmas that they were going to give everyone who assisted them a generous tip. They did this for the two weeks prior up to Christmas Day. They not only gave to waitresses and other standard tipped personnel, but also to those who don’t generally receive tips. The most memorable is when their flight attendant (on Christmas Eve) was having a very rough day and at the end of the flight my mom handed her $100, smiled, and said “Merry Christmas, I hope your day gets better.” The flight attendant started to cry, it had made her day. It was inspiring. While I don’t have the funds to do this, I do try more little gestures such as paying $5 toward the persons coffee behind me in the coffee drivethru.

  • Phil - Less Ordinary Living says:

    You made my day that you were stingy over a few bucks. It’s good to know that no-one is perfect out there. Generosity is such a wonderful thing, yet very difficult to put into practice. There’s always that question over where to draw the line. For me, I try to give generously with my time as much as my treasure – that can be the biggest gift of all. Thanks for the post.

  • Hugh says:

    It’s my belief that I have a lot to give BECAUSE I am generous. When you give, whatever you give comes back to you and then some. Now, this isn’t the reason I give at all. However, generosity is strangely powerful and it feels great.

    Regarding tips…When I’m on the fence about whether to give someone – a waiter, bell hop, delivery guy – either a good tip or a great tip, I always give the extra couple of bucks. 99% of the time those extra $3-4 means a lot more to the other person than to me. You can make a waiter’s entire night with a 30% tip.

  • Carl Harvey says:

    Yeah dude.

    I went out for a £30 dinner last night, and tipped only the coins I had on me (£1.50) rather than the £5 note I had in my pocket.

    I felt like a tight bastard. So I left the restaurant, and immediately the heavens opened, and I got soaked.

    Lesson learned. Someone up there is keeping tabs!

    PS – Nice wisdom with the line “It’s funny how I don’t often regret being generous, but when I choose to be stingy, it comes back to me later.” I NEVER regret being generous. Well reminded.

  • Livingstone says:

    I guess that’s a constant question, right? When to give, how much and how often. Good question for bloggers too. The more you give, the more you get… But, as you mentioned, it might not always work that way. Ultimately, I think we must find the gift in the giving itself. I’ve got a lot of value in my experience that may be able to help one person or a billion people. Either way, it’s got more value in being given than me keeping it. Now, ‘scuse me while I go write and post some value!

    Thanks bro!

  • Border Explorer says:

    This is a beautiful post. As a person who works at various homeless shelters and housing programs, I’d like to add that very often I am struck by the realization that those who have the least are the most generous.

  • Chris says:

    I’ve done that before, and felt lousy about it. Since then, I always keep about a dozen $1.00 bills with my travel docs (not in my pocket or wallet where I’m likely to spend them) just for the shuttle.

  • Amanda says:

    I love the term “generosity fail.” Been through the same thing. Such a great example of the idea that giving and receiving are opposite sides of the same coin. When we aren’t generous we rob ourselves of receiving the good feeling that comes with a generous act.

  • Hannah says:

    There are material and energetic ways of being generous.

    Forgiving others or apologizing — even when you’re right — is generous. Giving a big tip on a small bill when the waiter/ waitress really busted it out is generous. Helping friends pack for a move (or unpack) is generous. Even smiling can make someone’s whole day.

    Ignoring other people’s generosity, or taking it for granted, is a fast ticket to losing friends, influence, and personal power. Once you start to feel like you’re owed you’d better get out the shovel.

  • Christy Z. says:

    It’s true that we never regret generosity. I think we’re never more alive than when we give.

    I just returned from Zambia, and I will never forget meeting one particularly destitute family. The little boy received a bag of goodies from his child sponsor. After struggling to get the top of a candy container open, he passed it to his little brother to take the first one. Then he passed it to his baby sister. There was more than enough for each one of them, but they all wanted the other to have the first piece. That act of pure generosity has stayed with me.

  • SusanE says:

    Poor people are generous. Rich people are generous. However, they are generous in different ways. The poor will leave a big cash tip at a restaurant or perhaps the beauty parlor. The rich will donate if there is a record and it is deemed charitable.

    My poor friends, and my rich friends, are a whole different species of animal. The rich give to well endowed charities, the poor give to each other. I am sure both benefit from their generosity.

  • Tricia says:

    So true.I felt really bad for not tipping the hairdresser yesterday. I rationalized that ‘I cant afford it,’ since the service she had given me was very expensive anyway. So when I saw your post I felt especially crummy about it. Thanks for the lesson. As the Good Book says, ‘Practice giving, and people will give to YOU. They will pour into YOUR laps a fine measure, pressed down, shaken together and overflowing. For with the measure that YOU are measuring out, they will measure out to YOU in return.’ I guess in this respects practise makes perfect…gotta keep working on it! Thanks for the reminder Chris!

  • MutantSupermodel says:

    I can’t get past the line “A few weeks ago in Miami…”

    You were here?! And I missed you? So sad! 🙁

  • Hermann Delorme says:

    So you didn’t tip…so what? This has nothing to do with generosity or stinginess. You respected your limits and there’s nothing wrong with that. We’re socially conditioned to tip everyone and if we don’t, we’re going to feel guilty?? If so, we’re in bad shape, people…as if not tipping on a rare occasion was going to lead us straight to hell.
    Has it come to the point that if we don’t live up to all expectations, not only are we going to be judged, but will will cause even more damage by judging ourselves? Come on Chris, I hope you’re not serious and just fueling a discussion

  • linda says:

    I love your blog, and decided to comment for the first time today because I am SO glad you wrote about this. I’m a big tipper and get told off by everyone for being way too generous, especially with money (I’m a student). But then I also get comments like “What a lucky coincidence” etc. about certain events in my life.
    It ain’t luck.
    It’s karma I tell you.

    Thank you Chris!

  • STEPHEN says:

    I follow some advise that was given to me a few years back and that is to never turn down an offer to help someone who asks for help. It doesn’t matter what kind of help they are asking for. If it is within my power to help…. in any way…. I go for it. For me, personally, these are opportunities to lighten my own karma baggage…. a little at a time. so… have a self interest in giving time, money, resources.

  • Wendy says:

    One of my favourite quotes: “Real generosity is doing something for someone who will never find out”

  • Joel says:

    Freely receive, freely give.

    I’m always amazed at how much I get back when I choose to give. It’s so lopsided in my favor that it’s not even funny.

  • Del says:

    Hey Chris, great post. My husband and I were just talking about generosity this morning. We try be generous in a variety of ways so that we show our kids that there are many ways to be generous. For example, we lend neighbors our lawnmower, we often have famished students over our house for dinner, we share vegetables from our garden, we give extra gear away to friends. Our family is on a tight budget and this is helpful for us because we can’t always give money. I think that the trick with generosity is to be creative; our favorite ways to do so: time, food, and respect.

  • Del says:

    Forgot to finish my thought…The upside of being generous is that we never lack anything. Seriously. Our friends have lent us really nice cars to take trips away from our town. They’ve given us full use of beautiful NYC apartments. They’ve donated bunk beds. Watched our kids for free. The list could go on…

  • Jason Olshefsky says:

    Long story short, a few years ago I was inspired to set aside money and give it away. It comes with malleable rules, but some core things seem to be to take it out first (i.e. when I draw from my business account) before everything else, once it is set aside I may not use it, and when I give it away, I cannot derive a direct or circuitous benefit (i.e. I can’t use it for gifts for my friends, but I can put it in the tip jar for bands). Each circumstance is different and I find that I must do a spiritual inventory to assess what to do at any time — these rules are just what I’ve observed reasonably consistently.

    I carry a couple $20’s almost all the time. Just last night I was approached by a person on the street. (I live in a mid-sized northern city, so I get approached maybe 3 times a year). He had some story about needing to get bus fare to a nearby town. I asked him to be plain with me. I asked him why he was doing this. But he was kind of stuck in a rut. I hope that I helped by talking with him for a minute. And I gave him $20; his eyes bugged out and he almost literally ran away.

    I was on my way to a familiar bar. The door guy inquired and said I shouldn’t give money that way. That has become the default: that when someone asks, you should never give money away. I think it’s interesting that I can give it away indiscriminately without weight on my conscience, but there are innumerable excuses when one did not. Generosity wins.

    The funny part is when I tell people a tale like this, they often will ask, “can I have some money then?” I offer it to them, but they somehow know it’s wrong to take it. Only once in a while does someone I know personally actually take the money they asked for. Weird, huh?

  • kerri twigg says:

    I do more planned generosity, than random. I give away a lot of stuff on freecycle. But, really it’s to have less crap in my house. I do love when someone actually needs what I want to get rid of.

    On the streets, if I have change I’ll give it to whoever asks first, but I am sure to awknowledge whoever asks. I heard that is the worst part of street begging — feeling invisible.

  • mary lemmenes says:

    Inspiring article, Chris, and certainly true in my experience. I’m am delighted to have found your blog through an Empty Easel article and review of your Art and Money ebook.

    Also am fascinated by the coincidence that you are listed as currently in Minsk, since I had an amazing conversation with a brilliant young man from Minsk at a party here in Jacksonville, FL just last night. It enabled me to relive my time there in communist days in 1984 and to learn a bunch about his experiences and views of his home. Expanding one’s world understanding is priceless.

  • Colleen Clifford says:

    I try to be generous when I can, but I admit that most of my generosity is actually selfish in nature. It makes *me* feel good to do something nice for someone (give an extra-large tip, pay for the person behind me in line, etc). The fact that it helps someone else is important to me, but secondary if I’m really honest with myself about it.

    OK, before you judge the previous statement, think about this: If someone asks you why you would go out of your way to do something kind or generous, what do you say? Most likely “Because I want to help.” Note the words *I WANT* in there? You did it for you first.

    I think there’s no such thing as true altruism in humans — we’re inherently selfish creatures. The trick is to find ways to put our selfish nature to work in ways that do provide benefit for others as well.

    What has so much (or so little) meaning for you that you’ll happily give lots of it away to others who could use it? Go do that.

  • Marc Winitz says:

    Although I understand your point I wouldn’t crucify myself over this Chris. Like you, I travel a lot and tip when I can. I actually go out of my way to do it. But sometimes you need to hang on to whatever you have for some other short term reason. That doesn’t make you stingy as long as you are in the cycle of giving (which you are through this blog for example).

  • Erica says:

    “Generous people have more to give.” I believe that to be true. And when it comes to giving it’s preferable to come from a state of not expecting anything in return.

  • Jason Wright says:

    When it comes to giving, time and effort are the ultimate measurements. Nothing is harder to give up, and nothing makes a bigger difference to the one who receives it. Challenge yourself by looking for opportunities to spend your time and energy in ways that benefit someone else; you will be amazed.

  • Brooke says:

    Christy Z says we’re never more alive than when we give. I’m with ya, 10,000%. I end up giving more of my time than anything else (husband and I both unemployed short of my small business) but… boy, it makes me feel good, even when I don’t see the results.

    I’m glad there are still some like-minded folks out there who will still give and not expect (or, worse… demand) reciprocity. It’s nice if it happens, but not a requirement for me to do a good deed. 🙂

  • kat says:

    Funny… this was the message given to us in church, today!

  • Linda Gabriel says:

    As some others have noted, this is not the first time I’ve heard this message today. In fact it was the theme of the whole afternoon! Thanks for the synchronicity Chris!

  • ami | 40daystochange says:

    Thanks for sharing Chris. It’s good to know that other people are imperfect 🙂

    I believe that being generous opens you up to incoming generosity. Seems like when I’m generous, the pie magically expands, and there’s more pie for everyone. When I’m not generous, I feel guilty, stingy and small. When am I not generous? When I’m scared. I’m scared that I’ll need the extra $5 for toll, gas or something else, I’m scared that the thing I’m thinking about giving is the last one, and I won’t have anything left for myself. Yet these fears usually turn out to be untrue – or even irrelevant. It feels good to be generous and bad to be ungenerous – so why is it hard to be generous all the time (at least for me)?

  • Annabel Candy says:

    Had to comment on this because I’ve come to the same realisation recently. Why hoard stuff, links, love, ideas, hugs, money? Better to pass it on, there’s always plenty more to go around. I’ve started buying ebooks and courses online. Seems like I should invest in the type of products I hope to sell myself one day. If I don’t buy things online why should I expect my clients to?

    I smiled when I got here and saw Rob White was the 2nd person to comment. He inspired me to be more generous recently by generously sending me a signed copy of his fabulous book all the way from Boston to Australia. What a wonderful role model:) Thanks Rob and Chris:)

  • Tessa says:

    Love this post, though I also agree with Colleen, above. I don’t think empowerment and selfishness are by any means mutually exclusive! We’ve all given the term “selfish” such a bad rap. I think when it comes to generosity, the people with their own best interests at heart are the ones who likewise have compassion for others. That’s genuine selfishness at work, whether we embrace the term or not! I’ve never met a selfless person in my life. But I’ve seen (and experienced) plenty of amazing generosity!

    (My intuitive 2 cents: What do “freely receive” and “freely give” have in common? Freedom. Freely live with your mind and heart & things will generally work out.)

  • Deborah Wall says:

    I was walking on the beach this morning thinking about how I could create more generosity towards others, especially the people who work for us. When I got home I found your post in my inbox.

    Thank you, thank you. The words are wise and the discussion that it has created is generous in itself.

    I know personally that I could be far more generous and that it is only fear of not having enough for myself and family that holds me back.

    The weird thing is that in my heart of hearts I know the act of generosity never leaves you without. That giving with the right intention fills you up beyond any dollar value. The payoff is it enriches your human value.

    Thanks for the reminder, Chris. Love your work.

  • Nancy B. says:

    I completely agree. Just today I was faced with my own demons. One of the girls I work with asked me to sponser her in a corporate event by donating to the local Heart and Stroke Foundation. This is a charity that is definitely on my radar most of the time, and I give when I can. Lately this person has really been rubbing me the wrong way and I just wasn’t feeling entirely cooperative, but I had to remind myself that this event isn’t about her, it’s about the foundation. I put in my $20, and felt good knowing that I gave her enough to be able to participate in the event and a little extra just because.

  • Susanne Williams says:


  • Jean Burman says:

    Great topic Chris… thanks for posting it 🙂

    For the best example of giving without thought for what’s in it for them.. you need look no further than your mom. Mothers give of themselves without a second thought. It’s instinctive. And self denial becomes such a way of life that they sometimes have to be reminded [much later when the kids are all grown up and gone] that they too deserve to receive. It’s a slippery slope. But the not insignificant joys along the way are [of course] their own reward! [Grin]

  • Peter says:

    Well Chris… I’ve actually learned that the “bigger picture” makes it better! Because with being generous you ultimately are the winning party. So you should say: Generous people have more to receive!

  • Deanna McNeil says:

    I am often generous, maybe too much. You know what I do though that takes away from the good of giving and that is expecting (or even just hoping) for things to come back when I imagine they should. I have received serendipitously enough to realize there is no need to have expectations but…alas, at times I do. How much we need one another to remind ourselves of what things are good and true to keep on doing those things. I really appreciated this post.

  • Daisy says:

    One of my favorite random acts of generosity is filling the parking meter – as we leave. Finding a meter with time on it is such a pleasure, and it costs me next to nothing to give someone else that privilege.

    Another simple pleasure of living in a small city: cheap parking.

  • Victoria says:

    Although some people might give to receive later on, I really think that it’s bad to set that expectation for acts of kindness.

    When I am generous and I do something for others, it’s not for me – it never has been. It’s for them, to put a smile on their face, to make them happy… and in the the end, to make the world a better place.

  • Melissa Dinwiddie says:

    Wow, I so resonate with this, Chris. With money tight in my life, I find myself feeling stingy a lot, which I really hate! I try to stay in generosity, knowing that I’ll feel better, and that (as Ami says above) the pie magically expands. But it’s not always so easy when resources feel strapped…

    Definitely something to work on!

  • Natalie says:

    Chris, I appreciate your example as the same thing’s happened to me before and I walked away feeling lousy.

    I once took a class and they had us fast for a day, then spend half of the next day wandering downtown Phoenix. We weren’t aloud to take any money, no cell phones. And we were only permitted to say three things to people. One was, “May I sit with you.” That one was easy for me.

    But the one I remember best is, “I’m hungry. Will you feed me.”

    It was so scary to say those words to a stranger. My hunger and my desire to overcome my fear urged me on. I said those words, shaking, to an older couple I thought looked friendly and kind. The wife ignored me and the husband shook his head.

    But a mother with a young child overheard me. She approached and invited me to come into the deli with her and order anything I wanted. She encouraged me to get desert too.

    I was so touched to tears by her generosity. She clearly had a lot to give.

  • Rebecca H says:

    You can never do a kindness too soon, as you never know how soon it will be too late….Amish Proverb.

    Just a wise tidbit to temper discrection in the moment with!

  • Leila Anasazi says:

    Yesterday the agent at the airport check-in counter was upbeat and helpful and our waiter at the coffee shop engaged with us in a genuine way. They were “just doing their jobs” but in a generous way which was true balm to our very weary selves.

    Generosity takes many forms, and the “pay-offs” are unpredictable and often invisible–but so valuable.

    I’ve always been a giving kind of person; I’m currently refining my understanding that being generous does not require putting myself last … the happier and healthier I am, the more I can give.

    It was a gift of freedom when my rabbi explained to me that it is not up to me to determine the validity of someone’s expressed need–there are higher powers which contend with weighing people’s lives. So now I can give with an open heart when asked by strangers on the street.

  • Anne says:

    I work in development for a non-profit, and one thing learned on the job is that philanthropy is greatly influenced by generational generosity. If your grandparents and parents were/are generous people, you are more likely to be too. Similarly, if Mom and Dad were/are stingy, you are more likely to hoard your wealth (however much it may be worth) rather than share it with others.

  • Su says:

    I still feel guilt and disappointed with myself – when I saw a guy sitting in a doorway, cold and soaked from the rain with his head bowed in his hands. I ‘almost’ stopped and got a shawl out of my backpack to give to him. Something stopped me.

  • michele says:

    that… and compassion. also easy to fail at but so simple to create.

  • Joan Campion says:

    Absolutely, I have found that if I give what little I may have without worrying about it, it will turn out that I have nothing to worry about–I will end up having my own needs met, very often with bonuses I never even dreamed of. So my advice is, “When in doubt, give with an open heart.”

  • David says:

    Keep up the interesting posts. The old saying “you get what you give” comes to mind….

  • Nancy says:

    Thanks for the inspiring post! Reminds me when I was just 19 and hitchhiking to work at 5:30 in California, in the rain- some nice person stopped, gave me an umbrella and a ride to work-that made me a true believer in generosity!!

  • Sean M Kelly says:

    Sometimes its a great idea to be generous with someone even though they’ll never find out it was you! For example you can send someone some money, or buy them a ticket to a movie or concert and send it to them without revealing who you are. It’s great if you hear them talk about it later and the difference it made to them.

    Carpe Diem!

  • Andrea says:

    Love this … what a testament to perseverance!

  • Tessha says:

    I feel like I’ve been “taken care of” during hard times; sometimes, just because God cares but also as a cause and effect from having served someone else at one point. Besides, there is so much joy that comes from serving / giving. Nice uplifting topic Chris.

  • Jon W. says:

    I thought it was too much of a coincidence to pass by…just this morning I read a proverb written 3000 years ago that said the same thing:

    Prov 11:24 One gives freely, yet grows all the richer;
    another withholds what he should give, and only suffers want.

    Chris, thanks for reminding us of a time-tested principle!!

  • Marilyn Oliva says:

    I think generous people are just like that regardless of how much money they have. I remember many times when I have given my last dollar. I think we may be always looking for the feeling we get from being generous (i.e. feeling good about yourself, thinking it will come back to you somehow) and avoiding the guilty feeling we get when we don’t act with generosity.
    I have even given when I know better just to avoid the guilty feeling. For example on a trip to Vegas, a well dressed man asked me to help him with cab far to the airport. He gave me some story about his wallet being stolen and took my business card saying he would send me a check. I gave him $40 and you know I never saw a penny. Even though his story seemed fishy to me it was better to lose $40 than to be left with the guilt of not helping someone who may have really needed it.

  • Brandon Yanofsky says:

    “Generous people have more to give.”

    Love that. I know when I’m more generous, I definitely feel much richer. Not necessarily with money, but with friends, experiences, etc. All the fun parts of life. And being generous doesn’t have to be money. It could be time, or even just befriending someone.

  • Sherry Ott says:

    Chris – I hope to God you are going to write a book about how you obtained visas for all of these countries…I absolutely LOVE reading about it and appreciate all of the little oddities you share! I’m doing the Mongol Rally next year (drive from London to Mongolia) and am already anticipating the hassle of getting visas to drive through all of those countries!

  • Alexis says:

    I love this experience. I was having breakfast in an hotel in Nagita, Japan. I was in between flights and flying out later that morning. At the next table a Nigerian couple were talking about their bill. The husband was saying, he was not going to change a $100US travellers cheque for a few cents. They were short for their bill and the waiter insisted they pay what was about 40 cents.
    I leant over and gave the woman, (beautiful, in National Costume) a few dollars and she brought me back my change. This is what makes the world go round.

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