Whimwords:
A Radical Experiment in Friendliness

About this essay

[ author ] My name is Rudi Seitz. Rudi Seitz I'm a writer, guitarist, and software builder based in Boston, MA.

[ history ] I wrote this essay in August 2008, as I was founding a project called Whimwords to help people start conversations. The project is alive as of 2010; I am looking for help. Some of the details of the project have changed since I wrote this, but my motivation is the same.

[ writing goals ] My goals in writing the essay were to:

[ format ] In August 2010, I formatted the essay in Reprose Reprose, a system I'm building for making prose easier to read, write, edit, and discuss.

[ comments ] I welcome comments on anything I say here. Write me

Problem: Boston social climate
[ contrast: views of Boston social climate ] I moved to Boston in 1998, fresh out of college and ready to explore a new place. Since then, I've met many Bostonians who love their city. But I've also met many who are unhappy with its social scene.
[ point ]
My Boston is a city of stimulation, filled with beautiful architecture, amazing music, varied neighborhoods, buzzing campuses, history, food, art, and most importantly, friends. In fact, I think Boston is a great place to meet people.
[ counterpoint ]
But I sometimes hear people say that others in this town are unfriendly and stand-offish: our city is provincial, stuck-up, Puritan, cold. No one talks to you. If you’re not in an established social circle, it’s impossible to make new friends.

[ question: who's right? ] These two views of Boston have clashed in my mind for a decade. Are the complainers ignoring the virtues of the place? Or are my good experiences making me blind to the problems?

[ hypothesis ] I think there is a real problem in Boston’s social climate. Our problem is that we give each other the wrong signals. It’s not that we’re unfriendly, but that we’re caught in a cycle of misinterpretation. This bookish city must learn to read itself better.

[ viewpoint: optimistic ] I think Boston’s social climate is poised to improve, but it needs a push. My optimism rests on this point: most people who think the city is unfriendly are contradictions to that very stereotype. And, Boston has lots of these contradictions, all living in a few-mile radius. What’s needed is a way for the contradictions to become more aware of each other.

[ typical case: a Bostonian ] Unlike the provincial and stand-offish stereotype, most Bostonians are looking for social opportunities, making an effort to reach out — but sometimes finding the horizons narrow. I've seen this pattern over and over again: a person who's friendly and open to new connections decides they can't meet anyone else like them in the city.

[ restatement: Boston problem ] The climate of the city is at odds with our potential; the stereotype that Bostonians hold of themselves as a group doesn’t match who they are as individuals. The friendly majority in Boston has come to think of itself as a minority.

[ problem aspect: self-reinforcement ] This “Boston conundrum” can also be self-reinforcing: we are, after all, less apt to be friendly if we perceive an unfriendly environment. It takes a courageous person to break the cycle; most people end up participating in it and the stereotype becomes further entrenched.

Exploration: Possible solutions

[ question: exploiting technology ] As a software engineer, I've often wondered whether the connective power of the web could be applied to this problem. Could a social networking site for Bostonians help change the way we all think of our city?

[ viewpoint: skepticism ] I’m skeptical. There are already plenty of opportunities for Bostonians to meet online, and once you get online its easy to forget about the city you’re in. What shapes people’s attitudes to a city is their real-world experience of the place, not the time they spend interacting with devices.

[ solution requirement ] What we need isn’t another reason to stare at our laptops or mobile phones, but a way that the ease and comfort of meeting people online can be brought to the offline world, into the streets, parks, cafes, and other public places in the city.

[ introduction : whimwords ] My work towards this goal is a project that I call Whimwords.

Brainstorming: How I came up with Whimwords

[ whimwords: original question ] My project started with an audacious question: What if all the friendly people in Boston had a way of identifying themselves as friendly?

[ brainstorm: initial idea ] I was thinking of something simple and low-tech. What if there were a badge or sticker you could wear that said “I’m friendly”? The preponderance of friendly people could then look around and discover its true status as a majority. “Oh, you’re friendly too? I would never have guessed…”

[ brainstorm: snag ] It's a well-intentioned idea, but Bostonians wouldn't go for it. One could think of an “I'm friendly” badge as a radical statement, but many people would consider it an act of conformance, a cheesy gimmick, a fashion faux pas. If enough people did wear it, the badge might lose its significance.

[ brainstorm: follow-up question ] These gotchas led to my second question: What if the act of displaying membership in the “community of friendly Bostonians” could be framed as an expression of creativity, individuality, and style?

[ brainstorm: refinement ] I stuck to the idea of wearing a visual symbol of friendliness, but imagined that people could pick their own word or phrase to display, as a personalized conversation starter.

[ elaboration: wearable words as conversation starters ] You could say “I’m hungry,” or “I like coffee.” You could say “Gondola” or “octothorpe” or “hot.” You could display this word or phrase however you liked, in your preferred colors and style, making it as bold or quiet as you wanted. You could put it on a T shirt, pin, or sticker. You could write it yourself or commission a design from a local artist. When someone noticed your word on display as you walked through the streets of Boston, they’d have an excuse to come up and talk to you. If there was no other conversation topic at hand, they could ask you about the word and how you chose it.

[ brainstorm: snag ] People already wear words and phrases on their T shirts and other garments. So, if you were walking down Boylston Street and you saw someone wearing text, how would you know whether it was a friendly person—someone open to conversation—or a stand-offish neo-Puritan who just happened to have a T shirt with lettering on it?

[ solution: logo ] [ name origin: whimwords ] [ inception: whimwords as a company ] I thought we could use a logo to identify this “friendly text” as such. Because I imagined that people could choose this text in a whimsical way, and could use it to start conversations “on a whim,” I decided to call these words whimwords, and a friend of mine suggested a logo based on the W shape (an @ sign with a w inside instead of an a). If you saw this logo next to a word, you’d know it was a whimword, an invitation to conversation, not just any old word. Ideally, it would signal your membership in a local community of creative and open-minded people. I hatched plans for a company that would distribute Whimwords shirts and other items.

Details: Whimwords system design

[ brainstorm: question ] As I began this process, I came to a third question: What if whimwords could go beyond helping people start conversations, and actually help them stay in touch? Specifically, could whimwords help people swap contact information? Working through this question took a couple of tries and led to the technical meat of the project.

[ design: first attempt ] First, I imagined that you could register your whimword on a website that I’d build, and you could associate your contact information with the word. Someone who encountered you in person and noticed your whimword could look it up later on the website and find out how to get in touch with you.

[ design: elaboration ] I went on to imagine that the whimword could be used not as a keyword for finding your contact information, but as a virtual address or alias where someone could send you a message. The whimword would be like an email address that you wear. This way, anyone you met would have a way of getting in touch with you and continuing the conversation, but it would be your choice whether to reply and keep the connection going.

[ design: snag ] I saw one problem with using whimwords as virtual addresses: the potential for spam. Like most people, I'm swamped with online communication and don't want more of it. The whole idea of Whimwords was to promote real world interaction, inviting Bostonians to go out and meet others face-to-face. I hoped it would trigger an exodus off the web, back to live venues. With this online component, however, it was turning into a system that would flood participants with more electronic chatter.

[ solution: background ] My approach to tackling this problem deals with a larger, general issue in today’s world: information overload. While I am hoping to promote worthwhile interaction, not all communication equals connection. To focus on creating mutually desired connections, I decided to set up the Whimwords messaging system in a novel way. In this system, messages are only delivered between mutually interested parties.

[ solution: mechanics: mutuality condition ] Here’s how it works: if I send a message to your whimword, the message doesn’t reach you immediately; in fact, you don’t even learn that I sent it. However, if you then send a message to my whimword, the system now knows that we’re both interested in talking to each other. At this time, it delivers both of the messages – I get yours and you get mine.

[ solution: benefits ] Why impose a mutuality condition on message exchange? There are two benefits to this approach:

[ contrast: whimwords messaging vs. conventional systems ] [ terminology: sending to vs. sending towards ]
In conventional messaging systems like email, instant messaging, texting, and postal mail, we're used to sending messages directly to their destinations. We send the message and expect it to be delivered as soon as possible.
In the Whimwords messaging system, messages obey a different logic. We send messages towards and not to their destinations. Just because you send something doesn't mean it will arrive — it only arrives if the other person also sends something towards you. Two people reaching out towards each other get connected; if the interest is one-way, nothing happens.

[ analogy: whimwords messaging and speed dating ] The Whimwords messaging system is kind of like speed dating, except it's decentralized: you can use it anywhere, anytime, to convey any kind of message.

Recap & Future

[ summary: what whimwords is] To sum it up, Whimwords is two systems that work together:

[ summary: why I started whimwords ] This project is my personal response to the Boston Conundrum: the fact that there are so many friendly, fascinating people in this city who believe that others like them aren’t around. Whimwords is one tool that might increase their chances of meeting.

[ summary: my hopes for the project ] My dream is that Whimwords will get Boston talking, and ultimately that it might help Bostonians shed their own stereotype of themselves. If you live in Boston, whether you participate in Whimwords or not, I hope you’ll do what you see fit to combat that stereotype.

[ concrete step: whimwords as a company ] As for the future of Whimwords: I started a company in 2008 to turn the vision into a reality.

[ clarification: whimwords scope ] We’re based in Boston, but the scope of Whimwords isn’t limited to any particular place: it can be used in any city or town. It works just as well in public places as at private events: it’s a great way to get guests mingling.

[ conclusion: invitation ] There’s no telling where a conversation will lead, but the Whimwords philosophy is that conversation is a positive force for all. If you agree, I invite you to pick a whimword!

Postscript: 2010

[ project history: events ] I conceived Whimwords as a social initiative, an experiment. but I believed that for the project to grow, it would need to support itself as an actual business. After founding Whimwords in 2008 I gathered a group of friends to work with me on the project as a startup. We wrote a business plan, formed a corporation and all of that. More importantly, we built the system and brought Whimwords to events around town: art gallery soirees, singles' mixers, private parties, and even volleyball tournament. We also took a step outside Boston, in fact outside the US: we ran a Whimwords event at a large college campus in Goa, India.

[ project shift: seeking focus ] In late 2009, I came to believe that for Whimwords to work as a venture, we'd need to focus our effort. What did our product do best and who really needed it? Having seen how Whimwords worked in different settings, we noticed that singles' events were a particularly natural fit. In that context, the need for icebreakers is clear, and the idea of discreet message exchange is familiar to attendees — the system needs very little explaining. So we simplified our pitch and rebranded the project, for the time being, as a single's service.

[ project shift: retrospect ] I still think Whimwords is great for singles events, and I still think focus is good. But in retrospect, I think the plan to focusing exclusively on singles events was too narrow. As I wrote in the original essay, the Whimwords concept works well at any event where people are trying to meet each other. Recently I've been excited to introduce Whimwords at entrepreneurial networking events like Boston's Venture Cafe. Venture Cafe

[ revisit: personal intentions ] What I really want to do is help people start conversations. I care about that goal more than I care about the specific technology I've developed.
[ technology ]
Earlier in the project, I sometimes got caught up in explaining and defending the technical design of the system: how our website and texting system worked, what's powerful about mutual-only message delivery, and so on. In some cases, the technology was a distraction from the simple goal of getting people to talk.
[ essence ]
In fact I've seen that Whimwords can work well apart from the technology: just scribble an interesting word on your nametag, and that's it. The simple gesture of displaying a word is powerful in itself: I encourage people to do that whether they use our technology or not.

[ addition: personal intention ] A motivation that I didn't explore in the original essay is my unabashed love of words. QuadrivialQuandary
(my site for
word lovers)
In addition to helping people meet, I want to help people enjoy words: learn new words, discover the power of words they already know. And, I want to help words themselves — unusual, fascinating, neglected words — escape the confines of the dictionary and get out into the world, into our conversations and onto our nametags!