• Çingleton. October 14-15. Montreal, Québec. My friends Guy English, Scott Morrison, and Luc Vandal teamed up to put on a very small, very focused “symposium.” I love the small scale and single-tracked nature, but it comes with one huge drawback: low capacity. Just as the similarly formatted C4 conferences sold out quickly every year, I expect Çingleton will do the same.
• MacTech. November 2-4, Los Angeles, California. This year’s show features a keynote from Guy Kawasaki, which will be exciting for me, since I’ve corresponded with Guy over the years: he’s provided a ton of valuable feedback about MarsEdit. Also exciting is the addition to the organization team of Scotty from iDeveloperTV, who will be running the developer side of the conference.
• Voices That Matter. November 12-13. Boston, Massachusetts. The floating conference moves back to Boston, the site of its first show, at which I also had the pleasure of speaking. They have just posted the schedule, revealing that Aaron Hillegass will be delivering the opening keynote. Definitely wake up for this!

The Voices That Matter folks are offering a coupon code with a twist: $150 off for the purchaser, with a $50 bonus for me as the speaker. I am not paid for the speaking itself, so if you are looking for a discount, consider using “BSTSPK5“. When combined with the early-bird pricing, it brings the cost of the conference down to $395.

With such a busy speaking lineup, I have once again had to pass on some other conferences where I would have enjoyed the less demanding experience of simply attending. In particular, I am bummed to be missing:

• 360iDev. September 11-14. Denver, Colorado. Another show I haven’t had the pleasure of attending yet, but that is celebrated by many of my peers. The schedule a more conventional, multi-track affair, which is great for those who prefer to pick a favorite topic from a variety of choices. The keynote address will be delivered by my friend Matt Drance, whose work you may also know from his past life as an Apple evangelist.
• SecondConf. September 23-25. Chicago, Illinois. Seen by many as the organic successor to C4, I have been hoping to attend for the past two years. This year’s roster of speakers is outstanding, featuring some well-known developers and … Andy Ihnatko! But it’s also notable for featuring some folks who don’t do as much public speaking, including Mike Rohde, the designer of Red Sweater’s logo!

Suffice to say, there is a lot going on this fall. If you are looking  for something to do, take a click-through to some of these great shows and see if any of them sounds like the right place for you.

Consider the work that went into the first word processors and web browsers, whose work can now be mimicked by a Mac developer who knows how to embed NSTextView or or WebView. Imagine the time that early game developers invested in rudimentary sprite drawing, animation, and collision, which is now achieved easily in iOS games with open source packages such as cocos2d.

Still, building truly great software continues to elude most developers. It’s easy to assume that a large amount of time invested in a project, combined with an impressive outcome, is the key to a successful product. But it’s not so simple.

The ninety-ninety rule is often cited when describing the challenge of finessing a product after most of the hard work has seemingly been done:

“The first 90 percent of the code accounts for the first 90 percent of the development time. The remaining 10 percent of the code accounts for the other 90 percent of the development time.” — Tom Cargill

I agree with this perspective, and I cite it often when discussing software with others. The rule as stated is in terms of “code” but is also applicable to all the visual design, user experience, marketing, and positioning of a product. I think the rule is also recursive: whatever is missing can always be split up such that an “easy” 90% of the job can be done, leaving an elusive 10% of finesse work.

Many developers mistakenly assume that after they’ve put a ton of work into a project, and it achieves some impressive feat, that their work is done. When you focus on the enormity of work completed thus far, it’s tempting to pat yourself on the back and call it a day.

But customers don’t care about the hard work that went into the 90%. They only notice the flaws or omissions in the 10%. Imagine if Michelangelo’s statue of David was perfect in every detail, except that where David’s face should be, a clump of ragged, unfinished marble lay crudely in its place. Instead of marveling at the exquisite details of David’s feet, torso, and arms, viewers would reject it as unfinished and clumsy.

An important takeaway for software developers is that the missing 10%, or the missing one-tenth of 10%, may be something that will take a great deal of work to get right, but it may be something you simply overlooked the importance of.

You might build an impressive skyscraper projecting 40 stories into the sky. The architecture, interior design, plumbing, and electrical work may all be superior to that of your peers. But if some blindness in your product vision prevents you from adding windows, the product will never sell. It doesn’t matter how much time or effort went into this masterpiece: nobody will live in a windowless skyscraper.

I learned about the news via Lessien on Twitter, a woman about whom I know little, except that she offers reliably intelligent opinion about the tech world, and the mobile industry in particular. She shared the news with some curiosity about Facebook’s role in the deal:

Wow, although I’m a bit surprised by the buyer. Congrats to the @pushpoppress team.

It does seem a little unusual for Facebook to acquire a publishing company. But Facebook has made at least one similar acquisition recently: Sofa, the Dutch Mac developer and design firm. What interest did Facebook have in a company that sells Mac-only point of sale and developer software tools? They didn’t.

Facebook bought Sofa for their world-class design team. I expect the situation is similar when it comes to Push Pop Press. I can imagine Facebook putting Push Pop’s publishing software to some good use, but that’s just the icing on the Mike Matas cake.

Who will Facebook acquire next? Don’t let product scope cloud your crystal ball. Look for the most consistently polished user experiences in the software you use in any industry, on any platform. If it’s on Facebook’s radar, don’t be surprised to see them acquired next.

This speaks well to Facebook’s product priorities, especially as they are increasingly framed as a competitor to Google, whose design is famously underwhelming. For Facebook, setting themselves apart as purveyors of finely crafted interfaces will become a huge competitive advantage.

Downloads used to be shown in a completely separate window, which could be toggled using the keyboard shortcut Cmd-Opt-L. In Lion, they appear in a popover panel attached to the toolbar of whatever browser window you happen to be using. Unfortunately, there is no keyboard shortcut to toggle the appearance of this popover.

Using FastScripts and a simple UI Scripting script, I was able to restore this functionality, so that Safari on Lion toggles the panel using the familiar Cmd-Opt-L shortcut.

Download the “Toggle Downloads Popover” script

Download the script, and copy it to:

[Home] -> Library -> Scripts -> Applications -> Safari

Here it will show up in FastScripts (or Apple’s script menu) only when Safari is the front-most app. You can also assign it a keyboard shortcut, like Cmd-Opt-L, that will only be active when Safari is active.

Important: If your Mac is not configured to run with English as the primary language, the script will not work without a minor adjustment. You will need to open up the script and change the text string “Downloads” to the language-specific description for the downloads panel in your language. For example, to make it work with Safari running in Spanish, you would change the string to “Descargas”.

I find it very useful to be able to popup the panel when I am checking on the status of a long download, or when I want to check quickly whether I already downloaded something I had intended to. Hope this script works well for you as well!

Let me break the announcements today into three policy change assertions, and how I react to them.

1. Access to Twitter direct messages will require a new level of user-granted permission. This is a great thing! I recently tweeted that exactly something like this was necessary, because I’ve grown tired of giving every damn service that I wish to connect to Twitter, access to all my confidential direct messages. The new permission allows developers of client apps to state their desired permissions, and those permissions will be listed prominently on your list of approved applications.

   Verdict: Kudos, Twitter.

2. Developers of Twitter clients will be required to use OAuth in order to gain this new permission. In laymen terms, this means client apps can’t log you in with just your username and password. You will need to be redirected to the web. This requirement is ostensibly because Twitter wants to increase the likelihood that end-users will be made aware of exactly which permissions a client application is requesting. Without this requirement, a native application could claim to seek read-only access, but behind the scenes be using your username and password, by way of Twitter’s xAuth solution, to request a higher level of permission than you intended to allow.

   I concede that this requirement is, on the face of it, an added protection for customers who are wary of providing Twitter credentials to an untrusted app. But here’s the catch with native software: you better trust it, because there is no shortage of ways in which it could screw you. It’s running with some degree of elevated permission on your own device. Twitter putting shackles on native app developers in the name of security is laughable. For example, it would be easy for an untrustworthy native app to provide a custom, compromised browser view that purports to drive a user through the Twitter OAuth permission flow with a given permission, but is actually requesting a different level of permission in a second, undisplayed web flow.

   This is not to say that we shouldn’t bother reining in native software that may be flawed or whose permission we may want to revoke. This is what is so clever about the xAuth workflow, the compromise that allows native apps to authenticate as if by way of an OAuth flow, but using a user’s username and password to facilitate the process. If an end-user or Twitter itself loses confidence in an xAuth based application, they can still revoke access to the application in the same way they would for any other OAuth managed client.

   Verdict: Nice try, but if you don’t trust your native software, Twitter can’t do much to keep you from getting screwed.

3. These requirements apply unilaterally to all native clients. Except Twitter’s. I grant you, it makes sense for a company to exempt itself from security restrictions that are imposed to prevent “bad guys” from taking control of a user’s credentials and doing damage to the user or to Twitter itself. But this story is complicated by the fact that Twitter entered a competitive market of native clients of its own system, where for years it was not a player, and then proceeded to adopt increasingly developer-hostile attitudes. In particular towards developers of software that aims to fill that coveted role of a “general purpose read/write Twitter client.”

   Is it illegal to do what Twitter has done? Absolutely not, nor should it be. But in my opinion these 3rd party developers were a valuable asset that was pivotal in building passion for Twitter in the earliest years of its existence. Many of the features that we take for granted in Twitter itself were prototyped in 3rd party native applications. Hell, even Twitter’s own native Mac app was itself a 3rd party application (Tweetie) until not too long ago.

   Twitter’s attitude towards these developers seems to be: thanks for all the help, but we’re done with you. The fact that Twitter is willing to “whitelist” their own apps further suggests that this may not be a pure security play. Only legitimate developers of trustworthy apps would be interested in seeking an API key to connect to Twitter. If your aim is to write malevolent software that abuses Twitter or its users, you should be content to take an app like Twitter’s own Mac client, extract the portions that communicate “securely” with Twitter, and build your own app that only the savviest user will notice is actually posting to Twitter as “Twitter for Mac.”

   Twitter’s willingness to exempt any apps from the OAuth procedure is a concession that they don’t view xAuth authentication as inherently insecure. But they want to limit which API keys get the privilege of continuing to use it. So, expand that list of API keys. At the very least, add long-time supporters such as Iconfactory’s Twitterrific. Better? Provide some kind of approval process through which any qualified developer can seek first-class status. Best of all? Stick to what OAuth and xAuth are best for: providing the power to revoke access for bad actors after bad intentions are discovered. Forcing applications through OAuth is not going to prevent offensive, buggy, or intentionally malevolent code from being authorized by users, but it is going to degrade the user experience for all native clients except, oh, how about that? Twitter’s own.

   Verdict: Dick move, Twitter.

I think this is a useful way of thinking about it, but it’s insufficient for describing the way that information actually travels. Even taking to heart Minar’s reminder that information can’t strictly “want” to do anything, the suggestion that it even tends toward or prefers freedom is not accurate.

Information is like water: it wants to be everywhere. Unlike say, a person, who will almost universally want to be free. Information in a cage will not rattle the bars, or scramble frantically to reach a just-too-distant key. On the contrary, information is happy to occupy every corner of the cage, and yes, given an opening, to seep out of the cage as well.

This is truer than ever in the digital age. As individuals we have more capacity than ever to stash away information for our own private use. And we relish it. Consider your private computer archives with their thousands of photographs, unfinished stories, poems that nobody will ever read, and bookmarks that nobody will ever visit. Information is as content to live on the front page of the New York Times as it is to occupy several square millimeters of hard disk surface in a Backblaze server farm.

For every person who wants to shout information from the rooftops, there are probably twenty who want to keep a nice private stash of it for their own enjoyment. The presumed motivation for information to be either public, private, or undiscovered is imbued by the people who care most deeply for it. Perhaps in this light the truly earth-shattering, profound information does want to be free. But by default, information wants to be everywhere.

Update: I originally cited the content of a customer’s email in this post, and although I didn’t reveal her identity, I don’t think this was appropriate or particularly constructive.

Mea culpa.

In the future I will never cite the contents of a customer’s private email, no matter how anonymously, unless they have expressly permitted me to do so.

I have edited the post to remove the contents of our correspondence with each other. I am leaving the post because I still think it expresses some interesting ideas.

Continuing the recent trend of posts about, essentially, “just doing it,” the purpose of this post is to underscore the wisdom of staying in touch with customers, while acknowledging that doing so brings its own challenges.

Since I established my own web store a few years ago, I have collected the emails of customers who buy my software and, for those who leave the pre-checked option selected, subscribe them to a company newsletter for infrequent announcements:

Infrequently is the operative word here. In more than three years I’ve neglected to send even one email to these folks. This is a problem, because permitting me to contact them set up the expectation that I would. When major releases such as MarsEdit 3 have come out, some people don’t find out until months later, and tend to be annoyed that they haven’t heard about it directly from me.

Yesterday, I finally got around to setting up a mailing list with Campaign Monitor, drafting a simple plain-text letter, and pressing the send button. I finally broke the ice.

For those of you who are not on the mailing list, here’s what I said:

News From Red Sweater Software

Hello from Red Sweater! This is Daniel Jalkut, its founder and, for now, its only employee.

When you purchased one of my products, you agreed to receive infrequent email updates that keep you up to do date with my latest products. Since that time you have received approximately zero emails! I sort of dropped the ball on direct communication, but I’m working to rectify that now.

Messages will still be infrequent and hopefully pertinent, but if you are no longer interested in receiving updates about Red Sweater, just visit this link to unsubscribe:

(unsubscribe link)

On to the news: what’s happening at Red Sweater?

1. MarsEdit 3 Released

Earlier this year I released a major update to MarsEdit, our desktop blog editing application. MarsEdit now sports a rich text “WYSIWYG” editor, support for WordPress pages, and a media browser that integrates with iPhoto, Aperture, and Lightroom. Read more about MarsEdit 3 on the web:

http://www.red-sweater.com/marsedit/new3.html

If you don’t already own MarsEdit 3 you can purchase it for $39.95, or update from a previous version for $14.95:

https://www.red-sweater.com/store/

2. iPhone and iPad Releases?

People often ask about my plans to release applications for the iPhone, iPad and iPod touch. It’s easy enough to convey my intentions, but a bit harder to make specific promises. I am very excited about building iPhone and iPad versions of my apps, especially MarsEdit and Black Ink. I have made significant progress on these apps but there is still fine-tuning that needs to be done before I’ll be prepared to release them publicly.

3. The Mac App Store

You may have heard the news that Apple is planning to launch a Mac version of the App Store, which will give Mac users the ability to easily browse, purchase, and install applications in a similar manner to the way it works for iPhones and iPads. I’m hoping to get most or all of my apps into the catalog so I can reach an even wider audience of users. The good news for you, my existing customers? More customers will hopefully lead to more revenue, which means more resources and impetus to continue adding great features to the applications you already love.

4. Keeping In Touch

As I said earlier, I am resolving to do a better job keeping in touch. Next time a major update like MarsEdit 3 is released, you’ll hear about it before 6 months have passed! But if you want to proactively stay tuned in on an even finer level, there are some resources available to help you monitor our progress:

Email support. You can contact Red Sweater with whatever’s on your mind, be it a bug report, feature request, or just to say hi.
Address: support@red-sweater.com

Red Sweater Blog. The official company blog is my platform for providing a combination of company news and business-related thoughts and analysis.
Link: http://www.red-sweater.com/blog

Twitter accounts. For short, conversational style updates I maintain a personal account, a company account, and a special account just for MarsEdit:
Link: http://twitter.com/danielpunkass
Link: http://twitter.com/redsweater
Link: http://twitter.com/marsedit

5. Thank You

I want to close by thanking you for your business. I have been working on Red Sweater for over 10 years now, and in the past few years it has reached a level of success that supports myself, my wife, and my son. This is so unfathomable to me that I can only assume the sky is the limit! Let’s keep working together: your feedback and support combined with my desire to build great products should lead to many more years of successful results.

Daniel Jalkut
Founder, Red Sweater Software

To unsubscribe from this email list, just visit this link:

(unsubscribe link)

Delivery Confirmation

Campaign Monitor made the mass delivery painless for me. Thanks to their sophisticated tools, I know a day later that the vast majority of recipients received the letter, and only a small percentage have unsubscribed. Out of the thousands (wow!) of messages that were sent:

97.1% appear to be delivered
2.9% bounced
1.48% unsubscribed after receiving
1 reported it as spam (1 person, not percent – can’t win them all!)

This kind of feedback is great, but nothing compared to the direct responses I got from customers. The semi-personal tone of my letter inspired customers to respond in kind with heartfelt support and encouragement.

I received dozens of responses, ranging from the brief, enthusiastic “Word!” to longer, philosophical letters about small business, following one’s dreams, and the meaning of work in life.

Then, early this morning, I received this:

[EDITED: In retrospect, I do not believe it was appropriate for me to share the content of a customer's email here, even if information about her identity was removed.]

An upset or merely irritated customer always calls for a cautious response. The last thing I want is to escalate the situation. But this response is particular challenging, due to the number of provocative facets:

1. The customer is not pleased by the email I sent.
2. The customer is using a sarcastic, admonishing tone.
3. The customer projects a lack of respect by omitting proper punctuation and sentence structure.
4. The customer’s core criticisms are vague and subjective, making it hard for me to evaluate whether an apology or correction is called for.

These facets sort of multiply with each other and make it difficult not to respond defensively. My first reaction is to shout something into my email client like “What the hell?! Most people like a little humanity in a company, and furthermore, I did enumerate benefits where appropriate, and the content of this letter addresses the most common questions I have received over the past few months. And … and … who pissed in your Wheaties, anyway?”

Instead I take a deep breath, vent a little to my friends on IRC, and respond:

[EDITED: As with the content of the email from the customer, I don't believe it is appropriate for me to include the content of my response.]

I then proceeded to vent on Twitter about the response. I wasn’t particularly looking for comfort, but was glad to receive supportive responses from people who agreed there was cause to feel irritated by the customer’s tone. A sample of the dozens of reactions:

“That’s the kind of thing, when said in person, earns someone a kick in the teeth.” — @dssstrkl

“That guy is a jerk. Keep your personality in your work. if he doesn’t like it, let him use products from huge faceless corps” — @scottaw

“Personally, I couldn’t live with myself without adding a note about their tone. Why encourage an asshole.” — @mrgan

“Screw that guy. He’s just jealous that your Indie endeavors are successful enough to support you and your family. Good on ya!” — @fonix

“He presumes to speak for all your customers, co-opting “us.” He does not. Bravo on your measured and thoughtful response.” — @artgillespie

“That guy replied as if you were trying to sell him something. Your letter was more like a ‘state of the union’ communication.” — @morrick

Many of the responses refer to the customer as “him,” while none of them refer to “her.” In fact, this customer is either a woman, or a man with a very feminine name. Apropos of not much, but it’s interesting that we tend to assume somebody who is “being a jerk” is a man. I would have made the same assumption.

Do I feel a little disingenuous about responding to the customer politely and without indication of my annoyance, while essentially glorifying her message behind her back on Twitter and now here? Yes. This is not really my style, and I don’t think it’s very classy of me to share the private message of a customer, even if I am preserving her anonymity.

But, I think this experience is instructive both to customers and other small-business owners. And since I already vented on Twitter and essentially let the cat out of the bag, I thought I might as well go all the way.

Staying In Touch

What does it mean to stay in touch? It means building and preserving a relationship with customers. The stronger the relationship, the greater the empathy for the other’s circumstance. But as with other relationships, the increase in communication and contact leads to an increased risk of misunderstanding and offense.

My letter served a valuable purpose. It let my customers know that I’m thinking about them, that the checkbox they vaguely remember leaving selected wasn’t pointless. That I do have plans for the company and for the products they purchased, and that I am interested in turning a new leaf with regard to communicating directly with them.

The challenging customer and my reaction to her has also been helpful. It reminds me of the related importance of “staying in touch” with my own values and priorities. Over the course of Red Sweater’s growth, I have used a very rules-based approach to how I handle just about everything. Running my own business means biting my tongue and doing “the right thing” even when the instinct in my animal brain wants to do the opposite. This is true for coding habits, fiscal responsibility, and yes, customer support habits. A variety of informal rules help to keep me in line.

As I have gained confidence in my own decisions, I find myself more prepared to break these rules. I suppose that pragmatism slowly takes over. When I first started out, I informed my decisions by asking “what would a good business do?” Then I learned to admire other Mac software companies such as Bare Bones, Rogue Amoeba, Panic, and Omni, and asked myself “what would they do?” I still defer often to the wisdom of others, but sometimes I have the distinct pleasure of asking myself “What would I do?” and acting on it. Staying in touch with myself is as important as staying in touch with my customers.

While I don’t think C4 can be replaced, there are other conferences of a similar scale that can help to fill the void. This Fall offers a full calendar of options for folks who are looking for an opportunity to socialize with peers and learn a few new tricks of the trade:

VTM iPhone Developer’s Conference: October 16-17, Philadelphia, PA.
Voices That Matter has been on a run with iPhone-targeted conferences, putting on a show every 6 months or so at different locations around the country. I spoke at the Boston event a year or so ago, and had a great time.

I am attending the Philadelphia event as a speaker alumni guest, and they have also passed along a discount code to share with you: PHBLOGS. If you use this code before September 10th, it combines with early bird pricing for a total savings of $300.

MacTech Conference: November 3-5, Los Angeles, CA.
For all you hardcore Mac and IT nerds who have had enough of the iPhone-only conferences, this is the place for you. This is the inaugural event and seems to have come at least in part as a reaction to Apple’s substantial omission of Mac and IT content from the WWDC event this year.

I’m speaking at this conference and although I won’t say exactly what my topic is, it just might set me up for a world class showdown with my illustrious friend Wil Shipley, who is also scheduled to appear.

360 iDev: November 7-10, Austin, TX.
Hot on the heels of MacTech, 360 iDev is another iPhone-oriented conference that has been skipping around the country. The Austin, TX location is a big draw for me, but I think with so much other activity and the speaking gig just prior in Los Angeles, I will have to sit this one out.

Apple Developer Tech Talks: November-December? Worldwide.
If you haven’t been lucky enough to live near enough and apply quickly enough for these stellar events, you’ve missed out. For the past several years Apple has sent some of its best communicators to put on what amounts to a micro-WWDC: a day of intensive sessions on the latest and greatest Apple technologies.

I attended last year’s New York event and wrote up the experience for TUAW. Assuming Apple puts this tour on again this year, and I’m eligible to attend, I’ll be scampering to sign up. You should, too!

What else is going on in the Apple-sphere this Fall? If I am overlooking something big, please share with us in the comments below. I’ll update the post later with a more “definitive” list of options to choose from.

I participate extensively on Twitter with my personal account: @danielpunkass, and my company account: @redsweater. One of my applications, @marsedit, also tweets with a mind of its own.

I have strong opinions about what works well on Twitter, and what doesn’t. I decided I would start writing down these opinions so that I can easily reference them in the future. This advice is as much a memorandum to myself as to any readers who might feel that I am preaching to them. I violate most of these recommendations on a regular basis, but I hope that writing this guide helps me to do so less often.

Tweet Anatomy

For such a simple format, there is an incredible complexity to the variety of tweets, and the metadata that go along with them. In this section I will identify all of the standard tweet forms and many conventional metadata forms, and how they should be used.

Mentions

When referring to any person, product, or company that has an official presence on Twitter, include their @username organically in the content of your tweet. By including their @username, you provide a canonical link to their presence on Twitter, and make it easy for them to take notice of your comments, if they choose to. If it’s important to include the proper name as well, then include the Twitter name in parentheses:

Never start a tweet with a @username, unless that Tweet is a reply to the user. Placing the @username at the beginning of the tweet will mark it as a reply, preventing it from being seen by members of your audience who don’t also follow the user:

@danielpunkass was at the meeting last night, and he told me some juicy gossip about @marsedit.

Twitter claims that this should not show up as a reply, but in practice it seems to happen more often than not. Perhaps it is because Twitter clients set the “reply” flag on tweets that are written this way, even if they shouldn’t. To be safe, edit the format of your tweet so that the @username shows up elsewhere in the content:

I met Daniel Jalkut (@danielpunkass) last night. He told me some juicy gossip about the next release of @marsedit!

Because @username mentions will draw the attention of the user you are tweeting about, don’t overuse a particular user’s name in your tweets. You will irritate them and they may choose to block you.

Replies

Replies are a special form of mention that indicates your tweet is addressed specifically to the attention of another user. Reply directly to another tweet by using the reply feature of the web site or your Twitter client. This will ensure that the reply intent, and conversation flow is tracked appropriately inside Twitter.

In general you should not edit the standard formatting for replies, which include the @username of the user you are replying to at the beginning of the tweet. Deviating from this format will cause your reply to be visible to all of your followers, instead of just the ones who follow both you and your recipient.

Some users abuse this fact by adding an arbitrary character before the username, so that all of their followers see the reply:

.@danielpunkass I think you’re full of crap, and everybody knows it.

If it’s imperative to share a reply with your entire audience, be respectful and edit your tweet to adopt the format of a mention, so your audience knows you are not abusing the reply format:

I think @danielpunkass is full of crap, and everybody knows it.

You can address a tweet to more than one person by including multiple space-separated @usernames at the beginning of the tweet. Always list the primary target as the first name in the list.

Acknowledgements

Acknowledgement is a special form of mention where the @username does not show up organically in the content of the tweet. Use acknowledgements to credit other users as the source of content. Add acknowledgements to the end of your tweet, in parentheses if possible, and include shorthand citation language such as “via” or “thx” to clarify the kind of acknowledgement. Sometimes it is appropriate to use the shorthand “/cc” to indicate that you only mean to ensure these users are aware of the content of your Tweet:

Oops. Turns out I was totally wrong about Macworld’s editorial policy. Check this out: http://example.com/ (thx @danielpunkass, /cc @jsnell)

When you share information with your audience, always acknowledge the source of that information unless the source has explicitly requested to remain anonymous.

Tagging

Add tags to a tweet by adding a space-separated list of words at the end of the tweet, with a hash character before each word. These units are referred to as hashtags:

I don’t even like hashtags, but I guess I’ll use them just to make a point. #hashtags #twitterstyle #uglytweets

Use tags when you want your tweet, regardless of content, to be locatable as part of a larger trend or standardized category of tweet. For example, some people use the #fb tag to tag tweets that should automatically be copied to Facebook, or #ff to indicate that the tweet is a list of @usernames somebody recommends you follow as part of the “Follow Friday” meme.

Retweets

When you want to share another user’s tweet with all of your followers, use the retweet feature of the web site or your Twitter client. If your client does not include a retweet feature, adopt standard “organic” retweeting notation:

RT @danielpunkass Everybody should download MarsEdit today.

It’s highly preferable to use standard retweet features where available, because they store intent about the retweet into Twitter, and allow for more advanced filtering and searching by your audience. Using the standard retweet feature also eliminates the need to edit the original tweet to make room for the “RT @username” notation.

If you copy the contents of another user’s tweet without using the retweet feature or standard RT notation, you must put that content into quotation marks, and clearly cite the original author:

“Everybody should download MarsEdit today.” — Whoo hoo, @danielpunkass is right about that.

Failure to do this leads to confusion about whether you, or the person you are citing, is the original author of the content.

Direct Messages

When you wish to communicate privately with another Twitter user who follows you, use the direct message feature of the web site or your Twitter client. If your client does not support a direct message feature, or the user in question does not follow you, there is no way to communicate privately with them via Twitter.

You should never use replies to highlight the fact that you can’t direct message a user. This is a rude implication that the other user should be following you, when it’s every user’s prerogative to manage their following list as they see fit.

If you need to get in touch with somebody privately, and you can’t find contact information for them on their personal blog, web site or by other means, request their attention tastefully with a reply tweet:

@danielpunkass I’m trying to get in touch with you privately about something. It’s important. Can you direct-message me your contact info?

Before writing such a tweet, make sure you are following the person so that their gracious attempt to contact you with a direct message will succeed.

Write For The Medium

Twitter’s 140 character limitation beguiles and infuriates its users. At its best, it forces users to come up with the most concise, purest of language expressions for their thoughts. At its worst, it leaves users “just a few characters shy” of pure genius. The advice in this section is intended to clarify how you can best embrace these constraints: work with them and not against them, and your audience will thank you.

Avoid Abbreviation

Brevity is an art, and Twitter’s 140 character limit encourages it. Don’t compress more than 140 characters worth of thought by using abbreviations, or worse, non-grammatical fragments. If u try 2 hard to fit yr thoughts, it duz not work. You just sound like a moron.

Exceptions: some shorthand notation has become so commonplace on Twitter that you should use it in favor of longer-form words. For example, never spell out “RETWEET” in your efforts to retweet another user. Also, abbreviations are acceptable inside acknowledgements, because this language is not considered part of the language of your tweet.

One Tweet Per Thought

When an expression doesn’t fit in 140 characters, don’t spread it out over multiple tweets. Instead, switch to a longer form medium such as a blog and write as extensively as you wish on the subject. Then, summarize your long-form post in a single tweet and link to the longer-form content.

Never “Tweet-longer.”

Using services such as Twitlonger achieves the goal of limiting yourself to one tweet per thought, but it does so in a sloppy way that does not inspire confidence among your audience. They want to hear your thoughts, carefully edited for consumption, not vomited out onto the table.

Identify Linked Content

A tweet should stand on its own, and should not require outside resources to be understood. This problem is exacerbated on Twitter, where the destination of a link is often masked by the use of a URL shortening service.

Never post bare URLs, or URLs with a meaningless description. It’s insulting to your audience and doesn’t fulfill the value of Twitter as a content vehicle:

This is hilarious! http://bit.ly/4Wm7cs

Instead, include a meaningful comment that makes it clear what your audience will find when they click the link, and helps them decide whether they want to or not:

It’s going to be hilarious when you click this link and find out it’s Rick Astley: http://bit.ly/4Wm7cs

Write For Your Audience

Because there are few explicit rules to what you may use Twitter for, there are a variety of interesting uses that don’t map directly to “a person’s identity.” For example, companies, products, even news sources and aggregators use Twitter as a means of publicizing information in short bursts of text.

In any case, every Twitter account publishes content that is directed towards an intended audience. This audience may include your close circle of friends, your customers, professional peers, or a combination of all these and more.

You know your audience best, so speak to them in ways that make sense. The more diverse your audience is, the harder it is to refine content to their taste. The advice in this section is intended to help you limit widely-offensive behavior in your tweets.

Write Every Tweet By Hand

Never let a service automate tweets on your behalf. Unless your audience expects the content of your tweets to be machine-made, make the effort to editorialize everything you share. Users who follow you expect to see original content, not the mechanized ramblings of location-aware services, or the spam-like news of your progress in an online game. Even the seemingly innocuous plugins that tweet about updates to your blog are transparently automated, and take away from the human aspect of your account. Write those tweets by hand, as well.

Avoid Ideological Hotspots

Unless your audience shares you political or religious views, resist the temptation to rant about your ideological beliefs. As satisfying as this can be, it alienates many of your readers and gives the impression that you lack the discipline to avoid obviously provocative topics.

Complain Constructively

Nobody cares to hear about the subtle inequities of your daily life:

Grr, I wish that newspaper boy would FREAKING learn how to get the paper onto the porch!

It may feel good to get it off your chest, but it’s boring to the rest of us. Even if we happen to commiserate with you, it’s a useless tweet. Instead, channel your frustration into valuable content:

I wrote a blog post: 10 tips for getting the newspaper boy to do his job better.

While it may be meaningless to some of your audience, at least it offers constructive content for those who are interested.

Be Yourself, Only Better

Twitter is your opportunity to show off your best attributes. Some people will defend rude or tactless behavior on Twitter by quipping, “I’m just being myself.” It’s true, but you’re also just being yourself when you’re using the toilet. Don’t share every little facet of your life, only the charming parts.

Don’t Pick Fights

If you disagree with something another user has said, offer thoughtful evidence that they may be wrong, without resorting to snide or sarcastic language. Don’t assume that the only way to attract the attention of another user is to provoke them to angry debate. This kind of personality defect is easy to detect, and if you persist in picking fights, your targets will block you, and your followers will abandon you.

Take It Outside

When Twitter replies start to resemble chat, the interchange can be joyous for the people taking part, but tedious for those followers who are forced to watch. Unless the content of a discussion is of particular interest to a wide audience, it should be taken to a private medium such as direct messages, chat, or email. This is doubly true for any discussion that has the hallmark tones of argument.

In Summary

Twitter is a powerful vehicle for sharing our thoughts with the world. Used appropriately, we maximize this power and encourage others to respect and applaud us. Used carelessly or with sinister motivations, we simply beg to be ignored.

I hope this collection of advice helps you maximize the power of your tweets. Those of you who also have strong opinions, what did I leave out? What did I get completely wrong? Let me know in the comments so I can consider revising this as a living reference for using Twitter correctly.

Be gracious. Be thoughtful of other peoples’ interests. Don’t be a whiner. Be generous. Be inclusive. Pay it forward… you get the picture.

Have you ever noticed this phenomenon of the internet? As the ultimate reference archive, it reveals the most arcane and lesser-known facts of science, art, and trivia. It teaches us about the world. But as the ultimate social connector, it teaches us about people, how we do or don’t, and how we should or shouldn’t get along with each other.

I experienced this the other day when I was tweeting enthusiastically about Tweetie for the Mac and how I might be interested in taking the product over if it doesn’t fit into Twitter’s plans for the app. In the excitement, I not only violated one of the social rules of politeness by filling my followers’ Twitter screens to the brim, but I made the mistake of taking a stab at a company called Brizzly.

See, my friends Buzz and Neven built a wonderful iPhone Twitter app called Birdfeed. A few months ago, Brizzly acquired Birdfeed from my friends, and revamped the user interface a bit to match their style. I’m not a fan of these revisions, and I have stuck with the original Birdfeed app on my phone. But I used this distaste for the UI changes to fuel a less constructive tweet that I would characterize as a “low blow” against Brizzly. I have since deleted the original tweet, but it prompted a response from Brizzly’s CEO:

@phopkins He may be hella cool but does he realize that smacking Brizzly isn’t going to get him anywhere?

I immediately had one of those wake-up-call feelings where you realize that what was just mindless banter at “somebody else’s” expense was actually at the expense of somebody very particular. Yes, I reminded myself, there are actually people on the internet:

I should know this by now: there are people behind products. Ashamed of my tasteless treatment of Brizzly, and by extension, @shellen.

Some people who don’t know me very well assume that because my Twitter name, @danielpunkass, is a bit crass, that I must be a provocative and thoughtless person. They are surprised to meet me in person and find out that I’m actually pretty nice.

What my Twitter name represents to me is my willingness to be the cheeky one. To defy the standards and be a bit of a jerk when it’s called for, but only when it’s called for. Sometimes, the most unexpected, uncalled for, provocative, defiant move you can make is to be nicer than people expected you to be.