By now, I imagine, we are all familiar with Wikipedia's Appeals for donations. I am an avid fan of Wikipedia, I use it all the time, and I want the appeal to be successful.
I find the text above interesting because the implicit messaging is in direct conflict with the explicit goal of getting people to donate money. For example, if boiled down to a sentence, the logic of the text goes: Nearly 100% of people do not donate to Wikipedia, Wikipedia is a non-profit that depends on donations, therefore you should donate.
Though this argument may make internal sense to the Wikimedia Foundation, and though it likely the result of a lot of tweaking, unfortunately, it runs counter to basic psychological principles, including a) how communication works, b) persuasive-rhetorical techniques like social proof.
The main thing Wikipedia's appeal ignores is that people implicitly communicate assumptions and presuppositions alongside what they are explicitly communicating.  For example, the one-sentence logical summary communicates the following:
99% of other rational people don’t donate to Wikipedia. Maybe there is a reason. Why do it if other people don’t?
Generally speaking, this is not something you want to be communicating to people right before you ask them for money. It also seems disingenuous. The English Wikipedia gets 3 Billion page views per month from the United States alone, and at that scale, human intuition about percentages isn’t great: it would be surprising if slightly less than 30 million (1% of 3 Billion, which also happens to be 1 out of every 10 people in the US) donated to Wikipedia each month.
This being said, a friend pointed me to this twitter conversation, wherein Wikimedia staff find that this messaging is more effective than their previous attempts. It makes me think that the original copy works by preventing the bystander effect and making the reader feel uniquely responsible for “saving Wikipedia.”
While the message works for some, it does not work for me. One danger of A/B testing text is that if you have 15 places in a piece of text where 1 of 3 possible words can appear, you are now testing out 14,348,907 variations of a paragraph which will, by and large, carry the same semantic content. Though the paragraph can be optimized, the end result can still represent a local minimum.
With all of that in mind, here’s a translation of the appeal in the photograph at the top of this piece:
We are trying not to be very or a little awkward about asking for money. Be scared that Wikipedia will mysteriously become vaguely not independent. Be awed that we don’t tell you why we are asking for money. Be amazed that we don’t tell you what we will spend it on.
We depend on a range of donation amounts, the average of which is $16.33. Also: ALMOST NO ONE DONATES, especially if you don’t think about it. But if this weren’t true and reality were completely flipped on its head, wherein everyone donated $2.75, we’d be just fine. It’s like imagining what you would do if you woke up tomorrow and were a multi-millionaire. An organization can dream, okay? That’s why we underlined that sentence. Look, $2.75 is the price of a non-bougie coffee. Shouldn’t that amount be easy for you to part with? Shouldn’t you donate? We know enough to avoid explicitly shaming you into donating, but we want you to come to that conclusion yourself.
People told us we’d regret our decision. Sometimes, we think they are right. Woe is us. You too can regret our decision to tell you this if you imagine the specter of us becoming a crass commercial entity that runs advertisements. We won’t mention the B-Corp option, because that might not scare you enough to donate. We also want to blame you: don’t make us regret our decision.
Now that we’ve asked you for money and implied what you should do, we are going to list some of Wikipedia’s positive benefits: it’s a great place to learn, it unites contributors, (which you probably aren’t), readers like you, and donors (which you have a 99% chance or greater of not being.) Also, the heart and soul of Wikipedia is a community you probably don’t care about, have never interacted with, but which you can intellectually recognize as vitally important. Please take a minute to donate some of your hard-earned cash out of pity. Thanks.
In addition, avid readers and fans —i.e. those likely to donate money — are also likely to appreciate more precision and transparency. When Wikipedia uses the phrase “if everyone reading were to donate…”, how do they define everyone? Or how about the phrase “Thriving for years to come” — what does that really mean? 
Personally, I’d like to see a link to another web-page that outlines the budget in terms of cost per user. And don’t tell me that 99% of users don’t give! That’s the opposite of social proof! Give me a little form where I can input my zip code and see how many people from my surrounding area have donated. (If no one from zipcode has donated, invite me to be the first, and show me how many people from my state have already donated, etc.) I believe that this can be incorporated into messaging that also overcomes the bystander effect, as professional copywriters do this all of the time.
The appeal is also an attempt to create a relationship between a donor and an organization. In general, relationships built on pity and shame are neither healthy nor sustainable in the long run.
With all of this in mind, here’s a revised version:
It’s time for our perennial appeal. We do this because we are a proudly reader-backed, non-profit institution. While being non-commercial important to the integrity of our platforms, it does make funding our operations tricky from time to time. We serve ___ Billions of web-pages per month, and doing so costs ______.
Your donation is an investment in knowledge, and some of the best the internet has to offer. Our operating costs are $____ per user, and today we are raising money to cover the cost of <internet servers | I.T. support | backups | personnel| etc.> . <Here’s how the noun at the end of the previous sentence positively benefits you>.
In the name of full transparency, here is a link to a page with a breakdown of our budget, and some information regarding what we will do with the money we raise. How much should you donate? We’d hate for it to be a hardship for you, and thus we recommend choosing one of the following three ways of thinking about your investment:
a) If you buy coffee, you can donate the price of one Latte.
b) The median donation is ______.
c) Consider donating the equivalent of half of what you make in an hour.
Feel free to come up with your own amount! When you donate, you’ll have the option to be added to a donor-only newsletter that outlines what we are doing, and what our future plans are. This way, if you opt-in, you’ll know that you’ve made a good investment (in addition to your future use of Wikipedia.)
Lastly, X people in your [zip-code|state] helped underwrite Wikipedia in the last year. We hope you will join them.”
Two of the main differences between this version and the original one are that a) “a donation” is reframed to be “an investment”, and b) there is no internal conflict between what is implied and what is stated. While any version would need to be edited and A/B tested, people respond well to the congruence between what’s implicit and explicit, whether in a person, work of art, or piece of communication. 
The larger moral of the story is that what is communicated just beneath the surface of the words is as important as the words themselves.
 The idea that people implicit communicate premises has been researched academically in linguistics (see George Lakoff’s work on metaphor or Suzette Elgin’s work on presuppositions, for example) and in cognitive science (see Robert Cialdini’s work); it can be found in books on marketing (e.g. Dan Kennedy’s); law students are taught to pay attention to what a question assumes about the state of the world, etc.
 The Appeal text also uses the word “thriving” twice, and never defines the term. The editor in me is sad.
 For another example of textual incongruence, Vita Coco’s new advertising campaign for coconut water utilizes the tagline “Impossible to Hate.” Sadly, this implies that people have considered hating the product, or have hated other versions of coconut water in the past. And if people have hated prior coconut waters, maybe there’s a good reason to dislike this new one, too.
Thanks for reading. If you work for Wikipedia / the Wikimedia Foundation and are interested in talking with me, or if know someone who does, I’d love to chat.