To Pay or Not to Pay

One of the more challenging aspects of wealth is how to share it. This time I don’t mean charity, but instead with friends and family. Life is a great journey and we are lucky when our loved ones have our backs in bad times, but just as important when we can share the good parts.

While generosity is a noble quality, there can be a thing as too much. Throwing money around can allow people to take advantage, fuel other’s misperceptions of you or themselves, and cause imbalances in relationships. On the other side, most wealthy people I know want to share some of the cool things wealth offers, help others when able, and just have a good time with those they love.

So how do people find that balance? One friend of mine plans and throws destination weekends, often footing the bill for many aspects, while requiring others to “do their part” by arranging and paying for their own transportation and incidentals. Another takes a different approach and just pays for everyone, forcing him and his friends to get over any weirdness. Some I know spend their money less on parties or travel, but things that are more acceptable to share, like vacation homes.

It’s something I constantly struggle with. I do have a few rules that I try to follow:

  • I never fight over a bill. If someone wants to pay or really doesn’t want me to, I don’t force it
  • I will often try to pick up the tab, but not always, and almost never with people who I don’t know
  • I try to pay for little things (like a round of drinks after dinner), in non-obvious ways
  • A gift, once given, is no longer mine and comes with no unspoken obligations
  • I always graciously accept other people’s gifts in return
  • I work hard at being inviting and open to everyone equally
Most importantly:
  • I try to focus my friendships around time and energy – money and things are secondary

I’m not perfect at it. I’m sure there are some in my life who feel embittered about my paying for something, and those who feel I don’t do my part. While I don’t necessarily worry what other people think about me, I would prefer those around me to know the authentic John, and would like my interactions to be based on authenticity and intimacy, not money or power.


    • Kevin Ward
    • April 9th, 2012

    I think it’s important to Give for yourself.

    I moved a friend of mine to Vegas and supported him in getting started here. Was completely outside of what anyone would expect from a friend, but it’s something I had on my bucketlist, that I wanted to do. I could of expected a lot from him in return, but I realized that helping a friend make a real change takes energy, time and caring, not money.

    I feel that 90% + of the time if someone is broke and you give them just money. Next month they’ll be broke again.

    It’s hard when friends start to see you as money bags. I think when you realize that you paying or not, isn’t going to make a big difference in their life, it helps you choose from a place of what you want to do. Authentic.

  1. I’m pretty sure you had those rules before you had money.

    • Quite possibly! Now I don’t bounce as many checks.

      I remember one day awhile ago where I bought Brian Fiete (cofounder) lunch and had him drop me off to pick up my car from the bodyshop. My card bounced and I had to have him may my autobill.

    • Lindsay
    • April 9th, 2012

    With great money comes great responsibility. I think you do a great job since you genuinely just want everyone to be able to have fun, money or not.

    • True. I need to make sure we’re not just having fun, but genuinely able to build deeper and better relationships, while having fun!

    • Maggie Tai Tucker
    • April 10th, 2012

    Our kids’ friendship with you is based on your and their shared love of potty humor, never fear. You are raising some good issues here. I have a financially well-off friend for whom it’s an issue if anyone pays for anything for her. I personally prefer to take turns treating for small things like coffee and used to bring little gifts to her children. But then she felt like she needed to pay me back or to give back gifts of exactly equal value. I came to realize that for her receiving a gift carries some type of emotional cost — meaning that I wasn’t really being a thoughtful friend when I gave her something. So now we split the gifts down the middle and if I really want to get something special for one of her kids I barter or trade with her for it.

    • Poop is great power, never let your children forget that.

      It feels like your friend is allowing her wealth to cause a barrier between herself and others. Reciprocity is a pretty important part of human interactions. Part of writing about wealth is to help people deal with it better as I doubt she means to make things more stressful for herself and others.

      It is great that you saw what was happening though, and as a friend, came up with a solution that allows your friendship to be more authentic.

    • Maggie Tai Tucker
    • April 10th, 2012

    Oops, I meant to say “we split bills down the middle”.

    • Meriem (djazzy supafly)
    • April 10th, 2012

    I personally keep giving (and paying) as long as I don’t expect anything in return. As soon as I expect something in return, I know I am not doing it for the right reason 🙂 And I’m blessed to be surrounded with good people who never make me expect anything in return 🙂
    I guess the key is spirituality… being true to yourself and not caring about anything else but your relation to the universe and your impact on it, is the only way to keep you sane and happy 🙂

      • Maggie Tai Tucker
      • April 10th, 2012

      John, I think Meriem is onto something there. My dad, who basically lived off other people his entire adult life (as an itinerant poet, naturalist, and artist, he was basically a year-round roving houseguest), was also the most generous person I have ever known. It was a little exasperating to people who splurged to buy him something like a really good pair of binoculars when he would turn around and give the binoculars away the next week. But he would have found someone who could make even better use of them and would give them freely and without regret. He thought of himself as a conduit for positive happenings. He was never owned by any of his possessions or by his money even when he had some.

    • That’s a good rule of thumb. Stop paying when you expect something in return. I will add it to my unofficial list.

      I think the spiritual side is important, but it’s easy, with money, to have false compassion. Sometimes we may want to pay for everything, expect nothing in return, but it still cause more problems than benefits.

      So even while we may not expect something in return, if others feel an unnecessary obligation, that’s just as bad.

    • Mark Carlson
    • April 10th, 2012

    John, You had once said you wish you could be as tough as me. I have to laugh a little at that since the rewards for those actions are not shall we say “good”. I read this blog often and i am amazed at just what a good person you are. If i could wish for something, i wish i could be half a cool, and half as good, then i would finally know what being a true man is! I am so proud of you in every way. Oh and by the way, when you come to visit and feel like paying for dinner, you gotta beat me in arm wrestling!

    • In all my days of living uncle Mark, I doubt I will ever be able to beat you in arm wrestling!

      Love you so much and appreciate your post!

    • Dave Del Principe
    • April 10th, 2012


    You are well aware that there is no right or perfect answer. I personally dislike having people pick up the bill I have created. I always feel as if I owe them until I can return the favor.

    If it is a good friend or family member, it is easier to accept a gift because I know I will return the favor in a short amount of time.

    I always worry about being taken advantage of because I see it in a lot of family inheritance and legacy issues at work. It seems that my fear of being taken advantage of would be my primary concern.

    Good questions you pose, keep up the good work

    • Terry
    • April 15th, 2012

    Care to take the idea a little farther? Looking beyond generosity where material wealth is concerned leads to the question of generosity with other personal assets, such as talent and time. That last one, time, has fascinated me for quite a while.

    Some people have more money or talent than others, but everyone has exactly the same amount of time; it is impossible to put it into the bank to spend later. It is a true equalizer. Look around you and see who is generous with their time. It can be a humbling exercise.

    • Maggie Tai Tucker
    • April 17th, 2012

    I recently read a quote by Johnny Depp that said, “Money can’t buy you happiness, but it can buy you a big enough yacht to sail right up to it.” (Depp owns a big boat that he takes his family sailing on.) There are a lot of things missing from that statement — for example some people sail the yacht in the totally opposite direction from happiness. But this discussion is also making me think that you have to be careful not to run over, cut off, or swamp other people’s boats.

  2. I have thought a lot about this perhaps too much. I found your blog via looking through reddit. Much of your blog seems to deal with how to deal with wealth and how to give.

    I am not wealthy. I am still trying to find and figure out ways to become wealthy. But I often find myself thinking what I would do if I were wealthy. I would help teach other people how to amass money for their goals. The teach a person to fish philosophy. In my search for wealth I have come across many, many ways a person can create wealth for themselves. Grants, crowdfunding, businesses, investments, etc. I have also come across on ways to become frugal. This knowledge seems to be the things people actually lack. So I would compile all of this knowledge and hopefully I’ll teach people how to achieve their goals. Try to give hope to people who feel hopeless. If a person is too stressed out about living life so they cannot create wealth for themselves, then take on the burden of some of those stresses. An example would be if a person need education or training to get a certain job, but cannot afford to live day to day. Then offer them meals and a a nice place to live while they are learning, teach them how to be frugal and how to manage money as well, also offer the necessary tools or place so they can learn.

    This is an old wordpress, but I found it and thought I would share my thoughts in hopes you see it.

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