How to win friends and give away your money

Reflections on a year of giving loudly

Act I: The Setup

Last year, I made a promise to my friends:

Like most real stories, it didn’t happen in a particularly linear sequence of events. The idea started with my parents, who always gave money to charity. “Oh, yeah, we already gave to you guys this year” and “Did we donate to _____ yet?” were phrases I heard constantly as a child. When I landed a full-time job out of grad school, I started to think about my own giving.

I spent months mulling over what charities I would support once I was working (as a university hire, I signed my offer about 8 months before actually setting foot on Microsoft’s campus). During that time, I visited several friends on a whirlwind this-might-be-my-last-true-summer-break-ever trip. While sitting in our friend Michelle’s kitchen with Ellen, I told them about the list of charities I was thinking of giving to and asked for suggestions to round out the list. They both jumped in with several great suggestions, and inadvertently planted the seed of an idea in my head.

My friends knew about great charities. Why not ask them directly where I should give?

I wasn’t sure how many of my friends actually gave money to charity, but I assumed that enough of them would have good suggestions to support a year of giving. After all, I only needed 12 organizations to donate to. If worst came to worst I would just fill them in on my own.

As I thought about it more, I realized that I had no idea where my friends donated. Or how much they donated. Or whether they donated at all. We’d talked about scholarships and curricular innovation and robots and deep dark family secrets and embarrassing high school moments, but never about this.

Giving money to charity had become another conversational land mine, alongside religion and politics. It makes some sense: donating to charity is linked to income, and nobody discusses money in polite (American) company. At the same time, giving doesn’t have to be about quantity. Giving $5 and $50,000 a year both count as donating.

I decided that I was going to be public about my donations — because I didn’t know anybody who talked at all about their giving habits.

At the same time, I didn’t actually want it to be about me. I wanted it to be about the organizations I was giving to, and the people who advocated for them.

I picked a simple formula: I asked my friends where to give, then asked them to describe the organization and explain why it mattered to them. I topped it off with a challenge to do something unique and interesting to persuade me to donate. I was about to promise away $12,000 — why not make it fun for myself?

Then I blasted it out to my friends on Facebook and Twitter.

People from all over my social network (including quite a few friends-of-friends) chimed in. One of the first things I learned is that a lot people default to baked goods as a bribe. My friends offered me enough cookies, breads, and scones to sabotage a moderately sized paleo commune.

Some people are slightly offended when you ask them to bribe you, and offer you things like “appealing to your sense of reason” and “maximum return on investment”. Most of my friends were enthusiastic, though, and answered cheerfully.

Some of my favorite offers:

Satisfied with the number of good responses, I threw together a simple webpage and picked my first donation target.

Act II: Lessons learned

My friends are generally a lot more charitable than I thought.

I learned that quite a few people put away significant amounts of money for their own giving. None of them had ever talked about giving before, so I suppose I can consider my attempts at starting a dialogue somewhat successful.

Some told me quietly, working it into their suggestions: “I always give to this organization”, “I try to donate every month”. A few reached out to me privately over email and social media. Others just talked about it casually when I was around, just another conversational topic between friends.

Almost everyone suggested small local nonprofits, not well-established organizations.

I expected to get suggestions like UNICEF and the Red Cross. Although some people did recommend that I give to those places, most steered me towards organizations that I’d never heard of. I’m not sure where my friends found all of these hyperlocal nonprofits, but it was exciting to learn about them. In general, the smaller and quieter an organization, the harder my friends worked to bribe me to donate to them. It was nice confirmation of the Millennial tendency to get emotionally involved in organizations, instead of just sending a check and calling it a day.

People think that $1000 is a really big deal.

The organizations I supported were excited to get a donation of $1000 (plus $1000 of matching from Microsoft); for a small charity that can be more than 10% of their operating budget.

People in my social group were quick to tell people about my project in front of me, using it as an easy introduction. I half-jokingly told them that I mostly tried not to think about how many dollars it was. I was flattered, and glad that they thought it was interesting, but figured it was largely social niceties.

I was hanging out in Boston with my friend Tom, and he told me that when he talked to others about my project, they were astonished at how much money I was donating. He said that even though they were tech industry workers making at least as much as me (probably more, since I’m pretty junior), their automatic assumption was that I “must be really rich” to give so much.

I was surprised, because I had done some simple algebra to come up with $1000/month:

MSFT paycheck - (taxes etc*) = (grad school paycheck - taxes etc**) + $1000

In other words, if I did not change my standard of living, I could afford to donate $1000 a month (while still saving for retirement). I went for it.

To be fair, I had 2 very important things going for me:

  1. Most of my hobbies are very cheap, especially to maintain.
  2. Because I had a generous college scholarship (thanks, Olin!) and a graduate TA appointment at UW, I graduated without debt.

Regardless, you don’t need to be a one-percenter to be able to give at this level. A standard tech company salary and a willingness to plan for it are enough.

Most charities have no idea how to create a great donor experience. In other words, giving often sucks.

For example, in the third month of the project, I donated to the Humane Society. My experience was initially awesome — the director of donor relations called me personally to thank me for my donation and ask what had inspired it!

However, it wasn’t long before they were hitting me up for more money at every possible opportunity. I still get junk mail from them several times a week, and there was a week they called me every day to ask me to join a conference call about… something. I’m not sure what. I hate conference calls, and I’m not ready to invest that kind of energy in their organization (especially given how large they are!).

A lot of the traditional nonprofits that I gave to, especially the larger ones, have maxed out this harassment-as-engagement strategy. People are quick to argue numbers, but quite frankly I think we’ve reached a local maximum.

In contrast, here a few organizations that were amazing to give to:

  • Seattle Young People’s Project sent me a handwritten thank you card, and hasn’t sent me any mail-merged asks or generic mailer postcards.
  • The Seattle Public Library Foundation does send me a lot of mass emails — but instead of asking me for more money, they’re inviting me to special events with authors, speakers, and photographers. They also contacted me personally to ask about my project and asked for my input on engaging young donors.
  • Haiti Babi sent me a code for a free ticket to their annual gala because “you’ve already donated, so you shouldn’t have to pay to attend”. They also sent me a card, handwritten by one of the women in Haiti supported by my donation. I promised them I would donate again if they contacted me again in a year with a reminder, and didn’t bug me before then (I think they’ll do it).

Act III: Where do we go from here?

We need to question the nonprofit status quo. Giving should feel good.

Donors should be driven by positive emotions: humor, awe, a desire to do something. We shouldn’t be giving out of guilt or discomfort (for example: charity muggers). Even if you can turn that into a sustainable revenue model, it’s at odds with the ideal of making the world a better place — the whole point of nonprofit organizations is to codify prioritizing humanitarian good over income!

There are so many simple things that charities can do to engage donors, on their terms. Nonprofits should take a look at how their for-profit neighbors engage customers. Simple things, like “don’t make your customers annoyed” and “provide a clear value proposition for spending money”. And then more complicated stuff, that nonprofits in particular can really tap into: creating a brand that feeds into an identity. What if people had the same feelings about the charity they support as they do about their iPhone?

It’s not just charities that need to step up. Everyone should be part of this conversation.

It doesn’t matter if you give $50,000 or $5. You are a philanthropist. How do you want to be treated when you donate? What problems do you want to see solved? How do you want to contribute? You should be comfortable speaking up.

Philanthropy is about society, and you are part of society. You’re part of this conversation. If you don’t give, think about why. If it’s because you honestly do not care, then fine. That’s actually a really good reason. If you don’t have money, that’s also a good reason. There aren’t many other good reasons.

How can we create our own positive giving experiences?

I had a blast doing 12 Months of Giving, and now I’m trying to share that experience with my friends. I’m almost halfway through curating a 6 month long giving experience for my friends and acquaintances, and I’m going to launch another round when this one finishes. My goal is simple: make it fun, engaging, and meaningful for people to give regularly (just $10 a month).

If you want me to do the work of making donating fun for you, shoot an email to and I’ll poke you when I’m about to start the next round.

If you’re up to the challenge, strike out on your own. Find a way to make donating fun for yourself, and share it with your friends. It’s worth it.

*Microsoft “taxes etc”: taxes, 401k contribution, and a bit of employee stock options

**Grad School “taxes etc”: taxes, graduate student union fees