Buddy can you spare $20?

My generosity experiment from last December began on the NYC subway.  A homeless man asked passengers for money, I thought about giving, but then I rationalized and stalled just long enough to let myself off the hook.  When I walked out of the train I knew I had done the wrong thing.

People who run ultramarathons –100 mile runs – say that in order to finish, they have to decide and commit before the race how they’re going to react to duress.  If they don’t have a plan, they will make decisions in the moment, based on fear or pain, that will keep them from finishing.  There’s power in the decision you make beforehand to act a certain way in a situation you’ve deemed important (and stressful).

Last week I was on that same NYC subway train when another homeless man asked the riders for money.  He had, he said, just been let out of the hospital – he had discharge papers and unfilled prescriptions in his hand – and was asking for money to fill the prescriptions.  His swollen legs were enough to show his diabetes.  I stood up between stations and – impulsively, but armed with my prior decision – gave him $20.  A few others in the car then stood up and gave him a few dollars each.

Reading about giving $20 to a guy on the subway doesn’t seem like much.  Handing someone a $20 bill in that situation – where social norms say that you maybe give a dollar – felt like a big deal.

How do I go about changing what I do – which, over time, leads to the evolution who I am?  What works for me is making a decision to make a change and then starting to act differently – sometimes in small, safer ways before making the big leap.

$20 is very little money, but it’s way outside the norm for that particular situation.  So I got an incredible deal.  I got to experience the feeling of being absurdly generous when compared to what the world expected of me (and I expected of myself) at that exact moment.

It felt great.  It was exhilarating.  And once I had given away the $20, it was no longer mine.  And that was just fine.

Lots of people have told me over the last two months that they thought a lot about the generosity experiment.  For those of you who liked the idea, even if (maybe especially if) you don’t have a lot of money to give away, why not invest $20 to see how it feels?

Why not give a $20 tip on your next cup of coffee, or to a person who asks for money on the street, or to the person you buy the paper from or the full service gas station attendant or to a street vendor where you love to buy lunch?

Why not give $20, once, in a situation where it’s an unexpected thing to do?  Why not break the norm and see what happens and see how it feels?

I promise, you’re the one getting the great deal.

(comments welcome on how it felt)

P.S. If you do any sort of fundraising, you really shouldn’t take a pass on this.  I promise it’s a worthwhile investment in you and your ability to do what you do better.

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3 thoughts on “Buddy can you spare $20?

  1. We as a society have made soliciting in the subway illegal.


    I understand your larger point is to break through whatever convenient excuses we make for ourselves not to help someone in need, but continually asking people to break the law just to make themselves feel good about their generosity is perhaps not the outcome you mean to be promoting.

    There are arguments whether this is a just law, but there are certainly reasonable arguments on both sides. If you feel it is an unjust law perhaps you should push your elected representatives to change the law to allow soliciting and panhandling. But I suspect you would run into resistance not only from those who simply don’t want to give, but also from those who don’t want to encourage more volume, more aggression, and higher fraud from the panhandling community. (There was a time, twenty years ago or so, when aggressive panhandling was considered such a problem many felt the subway was unsafe.)

    As to your larger point of breaking through all the excuses not to be generous; perhaps we could ask more of ourselves than reaching into our pockets for some cash and walking away.

    Inspired by your story, I looked up a few links, donated a few bucks, made a few calls, and asked about the best way to help people I come across in the subway.


    Now that I’ve donated, I’ll point the next person who asks me for money in the subway to one of these organizations which should be able to help with their specific needs.

    In the spirit of full disclosure and to give some context and background, Sasha and I go way back and some have said we can be competitive. In that spirit, I’ll venture that while perhaps I don’t feel as exhilarated as Sasha did, I’d argue I’ll do more good. And is the point for readers of this blog to feel good, or to do good?

  2. Jamie, thank you for your thoughtful comments, and thank you more still for your own generosity. If this post has inspired just these thoughts and actions, then I’m glad to have written it.

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