Dopp Juice

As luck would have it, the two books I contributed to this year are being launched in the same week.  This is actually quite lucky because it means I can confuse everyone with it, and distract them from looking at one book with the other.

Here they are…

1) Gender Outlaws: The Next Generation

Edited by Kate Bornstein and S. Bear Bergman. (Get it.)

This is a very powerful and important book, and you should buy it.  I say this not as a contributor, but as someone who’s been holding space in the gender-variance advocacy world, who knows that most of you are craving more exposure and information, and don’t know how to get it without coming across as clumsy.  THIS IS A GOOD BOOK.  It’s a patchwork collage of 52 voices, many of whom are hidden in daily life, but all of whom are well-spoken and have something powerful to say.

I’m honored to add that my piece is the End Note. It’s a brief meditation at the back of the book about where I see us, and where I think we’re going.  An excerpt:

We are five years old. Eighteen. Thirty-seven. Sixty. We are starting grad school, starting companies, starting families, and starting trends. We are serving coffee and signing paychecks, nursing the sick and teaching children, building technology, growing food, producing masterpieces, and changing laws. We are woven into this culture and we are finding each other. We are sharing our notes, strengthening our stories, reaching out for one another, and welcoming everyone in.

And when we wake up in five, ten, twenty-five years, we’ll find that the queer issues we’re fighting so hard for today have been trumped by an understanding of the fluidity of gender. We’ll have learned that masculinity and femininity are not mutually exclusive, and how satisfying it can feel to represent both at once, or neither…

Buy the book to read the rest, and the REST! ALL of the incredible essays, stories, poems, naked pictures (yes, naked pictures), cartoons, and conversations. I’m serious. You want this one. Go get it.

2) Coming & Crying

Edited by Melissa Gira Grant and Meaghan O’Connell. (Don’t get it.)

This is the other book I’m in. You don’t need to read it.

The project itself, from a purely observational standpoint, is fascinating. Melissa Gira Grant and Meaghan O’Connell decided they wanted to have an intervention into publishing — especially published sex writing — and to bring more of the rich, raw, honest writing style that was surfacing on the internet (about sex) to the printed page. They used a service called Kickstarter to raise some money from the community before they gathered the writing, so they could self-publish it properly. Their goal was to raise $3,000. They raised $17,000. And now they’re starting their own media label.

(But just because the project is fascinating does not mean you have to buy the book.)

The book is erotica-meets-drama. It’s a book of sex stories with all the messy awkwardness and overanalysis left in. I wrote a story for it. It’s under my real name. It’s a very personal story. Let’s just accept right now that I’m never going to run for Senate.

If you are a member of my family, I strongly recommend that you (please) do not buy this book. If you have a purely professional relationship with me and would rather not feel weird the next time you see me, I also really don’t think you should buy it.

And if you’re anyone else, you know what? We’re in a recession. You need to buy groceries. Look! Shiny things! I think your grandmother is on fire. Don’t look at the book.

Also? It was a limited print run. They’re gonna sell out soon anyway. And who knows — they might not print any more. So you probably can’t get the book anyway. It wasn’t meant to be. No, you can’t see an excerpt. You never heard about this. Enjoy your day.

(Don’t get it.)

Love,
Sarah

Two different people just asked me about this in the last five minutes, so it seems worth writing out.  And then I can link to this post in my GChat status message! Shortcut!

Here’s the scenario: Through the luck of the emailing, you’ve scored my secret gmail address, and I’m showing up in your chat list.  You’ve already noticed two things:

1. I seem to be there all the time. Like, 24/7. Like, why the heck doesn’t this Dopp ever sleep?
2. I am always, always, without exception marked Busy. Red. Unavailable. “Warning warning, saying hi is rude right now!”  Etc. Never green.

There are good explanations for this.

Why are you always there?

I have a Google Android-based cell phone that gets Gtalk.  So as long as my cellphone is on, I’m pokeable.  (Note that if you send me a chat message when my computer is off, I’ll get it on my phone, it will feel like a text message to me. Our communication paradigm will have shifted, and you won’t have any way of knowing. *cue scary music*)

Why are you always busy?

BECAUSE I’M ALWAYS BUSY!  I usually have at least 10 projects going at once, and if I’m at my computer, I’m probably working on one of them. The Internet is my office, and my business hours are Whenever I’m Awake. If you want to hang out with me when I’m taking a break, you need to come meet me at Dolores Park in San Francisco. I’ll be the one stretching, wandering around, enjoying the sun, and not looking at my phone or computer.

So… can I gchat with you?

Sure!  (Maybe.)  Here’s what I’d love:

If you’re working with me on something, you can always send me a message. It’s a good way to get a quick answer from me. If I’m there, I’ll respond.  If I don’t respond, please send me an email.  (Gchat messages are known for getting lost.)

If you’re not working with me on something, please don’t open with “hi” or “hey” or “what’s up?” and wait for me to respond. I probably won’t. Just start with the thing you want to talk about. (And if I don’t respond, follow up over email.)

If you don’t have anything in particular you want to talk about, but you want to talk to me, please ask me if we can get coffee sometime.  Don’t try to catch up with me over gchat.

If you have something funny or interesting you want to send me, go ahead and just gchat me the link.  I may or may not be able to look at it, and I probably won’t have much time to talk about it, but I’ll appreciate the thought.

I know, I know, this is me being weird again.  First I don’t answer my phone, and now this.

But think of it this way: at least I’m reachable.  Remember when I shut down IM completely for four years?  You hated that.  This is my compromise.

Love you,
Sarah

It’s here — the holiday of all holidays — Geek New Year.  The intersection of the end of SXSW Interactive and St. Patrick’s Day, when everyone who made the annual pilgrimage to Austin, TX is wandering home, rubbing their eyes and thinking a thousand new thoughts about how the coming year will be. And drinking.

I skipped SXSW this year, and didn’t miss it much.  But apparently, 2009 Me took some steps to keep 2010 Me in the loop just so I wouldn’t feel left out.  I woke up this morning to an email I’d sent myself a year ago using FutureMe.org. The subject line read, “listenupmotherfucker.” (And I’m such a nice person to everyone else…)

If you’ve watched me twitter on New Years, you know I make a grandiose attempt to discourage everyone in the world from making resolutions.  Resolutions are often about picking something really hard that you feel guilty about, and throwing yourself at it drunkenly with all your might, only to fail in about a month. What does that really do, besides pull a few muscles and prove your incompetence?  We need better traditions.

Mine is writing a letter to myself a year in the future.  I include reminders, predictions, ideas, requests, and stories I want to carry forward.  It’s me having an ongoing, ritualized conversation between the past, the present, and the future, and I love it. I love watching my own story unfold in a correspondence with myself over time.

Except last year I fucked it up.

Last year I forgot to write myself a letter on New Years, and it bugged me for months.  So on March 17th, St. Patrick’s Day and the end of SXSWi, after two weeks of traveling, I decided that despite being too wrecked to move, I could see the whole timeline of my life Very Clearly and had a LOT to say about it.

Here’s the letter I received this morning (with a few light revisions to make it more bloggable):

From: Sarah Dopp
To: Sarah Dopp
Date: March 17, 2010
Subj: From me to me, listenupmotherfucker.

Dear FutureMe,

It’s the last night of SXSW and I’m a fucking zombie. I’ve been traveling for two weeks — first a week in Portland and now this. Roomed with Melissa, Boffery’s a madman of vision, and Genderfork is exploding with passion. I want my Dopp Juice voice back. Queer Open Mic is getting its sea legs again, and occasionally I think about book deals and self-publishing. I’m speaking soon on gender and sexuality ambiguities, and in general, my life’s pretty fucking cool.

So why am I so stoned on exhaustion that I can’t even pack my fucking suitcase?

Okay, listen up. I skipped the letter from New Years so this one’s a few months late. Here’s the deal. You’re reading this in 2010, right? Shut up and keep talking. That’s my brilliant plan. Just do that, and you’ll be fine.

No, seriously, though. Here’s what you need to know:

1) Stop calling yourself an entrepreneur. It’s bullshit.

2) Don’t go back to school, even if you know you can. It’s bullshit, and you have better ways to spend your time.

3) If you forget the different between following your heart and doing what seems right, go read XKCD’s Fuck That Shit again.

4) If you get stuck, go read the Cult of Done Manifesto again.

5) Genderfork Book. Build the community. Meetups, volunteers, whatever.

6) Go talk to [redacted] about representing a community that you don’t see yourself as a complete representative of.

7) You can do this. You have to. You don’t know how not to.

Stay alive. I love you.

Sarah

p.s. I really like The Squeeze right now.

I must have been very tired, because I have absolutely no recollection of writing this.

I’m particularly fond of the line, “Shut up and keep talking. That’s my brilliant plan. Just do that, and you’ll be fine.”

And aside from that… yeah… this is how I talk to myself.

Go write your letter now.  It’s a new New Year.

Sometimes I email people.

Like, a lot of people at once. I do the “bcc” thing, and I hand pick the people who I think want to hear about something, and then I remember after I sent the email that I forgot a bunch of people. But it works well enough.  Sometimes an email to a lot of people is the right medium for what we’re doing.

Then again, sometimes blog posts are the right medium. Or tweets. Or personal emails. Or facebook wall posts. Or text messages. Or (gasp!) a phone call (but let’s not talk about that). I try to stick to whatever medium is right (except when it’s a phone call, and then I’ll try to come up with something else, anything else, that will substitute. But again, let’s not talk about that).

When I send out a big email, it’s usually because:

• Someone sent me a really cool job or gig that doesn’t fit me very well, and I want to pass it on to other good people.
• I want to hire assistance for something, but I don’t really want the whole world to know about it.
• I want to tell people what’s changed recently in my consulting work, so they know what I’m a good fit for and what I’m not interested in.
• I want to tell the story of my consulting work — what I’m learning and doing and accomplishing and messing up along the way — without feeling totally public and naked about it.
• I want to talk about a new personal project I’m working on (usually relating to gender or sexuality or queer culture, or maybe creative writing) and see what people think before I make it public.
• I want to announce something I’m doing or hosting or organizing or traveling to (or whatever) to people I care about.
• I want to pass on information about something amazing that I care a lot about.

And… as you can probably tell from that list, these emails are starting to feel a little bit like having a newsletter… just, minus the “consent” part.

So let’s get consensual about this.

If you would like to be part of my inner circle of advisors, or if you want to hang out within catching range of the job/gig leads that I pass on, or if you find the neurotic journey of a consultant interesting, or if you think the stuff I do for the queer world is making a difference and you want to know about my next big thing before it happens, or if you’re just my friend who never gets to spend time with me and is looking for some insight into why I won’t answer my phone…

You can sign up to get emails from me here:

Subscribe to Sarah Dopp’s Brain

Email:

Visit this group

After you hit “Submit” above, Google will probably email you to make sure you really meant to do that. Just tell Google, “Yeah, I did,” and then you’ll be done with it. (And if you have any problems, tell me.)

In exchange for your consent, interest, and trust, I vow to:

• …not send you things that feel impersonal or spammy.  If I’m sending you something, it’s because I think it really, really matters, and I will tell you exactly why.
• …never ever ever sell/trade/share your email with others, or let anyone else hijack my list to use it for their own agenda.
• …not email you more often than I think is respectful. That’s subjective, I know. In reality, it will probably only once a month or so — maybe less.  I’m not setting a schedule.  If it starts getting more frequent than that, I’ll be extra careful.
• …keep it a one-way announcement list.  This isn’t a big huge discussion group. If you respond, you’ll be writing directly to me, not to everybody.
• …never take it personally if you want to unsubscribe.  In fact, I probably won’t even know.  I don’t keep track of that stuff.

Past and current clients, friends, family members, genderfork fans, queer open mic regulars, conference acquaintances, former lovers, co-conspirators, and total strangers are all welcome.  Just remember: this is me talking about what I care about.  If you don’t share the same interests, you might not find this very exciting.

But if you do, you probably already think this is awesome.

(Sweet. Me too.)

Love,
Sarah

I think I’m ready to consider my next large contract, but only if it’s exactly right.  And I mean that: I’m perfectly happy right now hanging out in Small Contract Land, and I won’t let anything big into my life unless it’s absolutely the right match for both of us.  But maybe that perfect match is out there somewhere, just waiting for me to wink in the right direction. Let’s find out…*

Passionate Multi-Talented Consultant Seeks Online Community that has Lost its Way

Me? I’m a smart, tech-savvy online community organizer who gets really excited about making good stuff happen in the world.

You? You’re the extended online community of a company that appreciates you and wants you to be happy, but that doesn’t quite know how to take good care of you yet. You have a lot to offer and you can tell this organization wants you to shine, but for some reason, somehow, the pieces just aren’t lining up.

At your core, you’re a real catch (and you know it, too). You enjoy lively, informed discussions and you sincerely care about helping people. (In fact, you often have so many ideas about how the world could be better that you can hardly contain yourself! It’s okay, I understand that.) You’re creative and multi-faceted with lots of hobbies and interests, and you bring what seems like lifetimes of experience to the table. Anyone would consider themselves lucky to have you, but it’s disappointingly rare for you to be with someone who grasps exactly how precious and invaluable you really are.

If you let me in, I will be that someone. I will listen to you, find out what you need, and do whatever I can to provide for you.  I will ease your internal conflicts and nurture the parts of you that want to make the world a better place.  I will help bridge that gap between your needs and your organization’s needs, and I will empower you to make a meaningful difference in the way they approach their work.  Under my care, you will grow stronger and healthier, making it possible for you to also grow bigger.

But I need to tell you up front: I’m not interested in a traditional relationship. If you’re looking for the perfect partner who will meet all of your needs for the rest of your life, you’ll have to keep looking — that’s not me.  I have a rich and varied lifestyle with room only for hot, life-changing affairs, and I want us to live in the moment on this one. I’ll come in to your life, strengthen you, heal your wounds, and make the connections you’re craving. I’ll show your organization exactly how valuable you can be to them, and I’ll teach both of you to take care of each other directly, so you won’t need to rely on me. And then I’ll let you stand up on your own.

Are you okay with that?  I know the goodbye will be hard, but I think you’ll agree with me that it will have all been worth it.

A little more about me… I’ve founded and nurtured several online communities that grew in size and scope over time by natural interest. I’m fascinated with what drives people to contribute to things, and obsessed with helping them find ways to do it. I’m excited, engaging, optimistic, and interesting. And I also work my butt off.

I’ve been blogging and building websites for over ten years, and have expert skills in HTML and CSS, as well as strong social media savvy. I’m also a formally trained technical writer with a knack for making complex things easy to understand.  I’ve been making a living as a technology consultant for over five years, and I work well in lots of different environments, including from my home. I’m in San Francisco, but you can be based anywhere.

The arrangement I’m looking for would involve a contract (I’m not an employee) at respectable business rates.  My ideal commitment would be about 20 hours a week over a period of 6 – 12 months, but I want to make sure all your needs are being met, too.

If you know the matchmaker who can arrange this affair, please send this to them, and I will owe you a hundred hugs.

And if that matchmaker is you, I look forward to your reply. Please email me here:

info at sarahdopp dot com

…and we can further explore our compatibility.

With great appreciation,
Sarah

* a hat tip to Havi for this format. (Have you read her stuff yet? She’s wonderful.)

I had a timeline all worked out, and it involved me being unemployed right now. I was going to take a few weeks off to sit down, reorganize how I want to approach my work, identify the kinds of contracts I’m looking for, redo my web presence, and then begin The Search for New Clients.

Instead, I’m not even done with my old contract yet, I haven’t asked anyone for new work, and I already have seven clients. Hi. Okay.

Here’s the thing.  The kinds of clients I’m interested in (and, magically, the ones that I’m attracting) are creative individuals and organizations who are doing cool and meaningful things in the world, and who need a stronger web presence to reflect that.  That may sound like “everyone,” but it’s not.  It’s a very specific type.  Clients of this sort tend to already have an interesting public personality, or an established “voice” that they want to make more public. They come equipped with the professional motivation to update their web content without my help.  They learn quickly. They need periodic guidance and technical assistance to setup, rejuvenate, and maintain certain things.  And as a general rule, they don’t have a lot of money to burn, but they can afford to spend some here and there because this help is very important to them.

The challenge, apparently, is not finding these clients.

The challenge, already, is keeping track of them all and coming up with the right agreements.  Let’s be honest: having a dozen small contracts is not the work equivalent of having one large contract, even if they add up to the same number of billable hours.  And when every hour is carefully budgeted, “what I think we should spend time on” is much less important than “what they need to move forward on.”

I’m waist-deep in reorganizing.

If you’re working with a similar client base, now’s a good time to get in touch with me. We have notes and resources to share…

On the continuing subject of my pending-but-not-really-cuz-it’s-way-more-complicated-and-a-lot-less-scary-than-that unemployment, I’ve come up with a few more “Aha!”s.

Remember me blogging recently about noticing that the answers show up when I stop thinking — that when I relax my thoughts and let go of distractions, I gain access to the clear mind that lets me see what’s next?

Well, I sat with that for awhile… chilled out and took a vacation from some of my distraction habits, hoping to gain access to that nice clear mind that would help me aim my income-hunting efforts in the Right Direction. And you know what happened?

I realized I was mixing up my “clear serene reflection pond mind” with my “crazy idea-generating waterfall mind.” I had lost touch with both and, though I didn’t know it, I was actually more interested in the latter. I love that waterfall. I missed it.

It’s back now.

Sort of.

A hard truth confronted me as soon as I went swimming, and I haven’t quite finished wrestling with it yet: This part of me that revels in constantly generating new, creative ideas is often in conflict with (what I would call) my more conservative side — the side of me that wants to make a stable living, that doesn’t want my friends and family to worry about me, and that wants to be reliable.

It’s a pretty serious conflict — the kind that takes no prisoners. And somehow, whenever this conflict goes to blows, the conservative side wins and the creative side shuts down.

This is because the conservative side has a secret weapon. All it has to do is call my creative side “crazy,” and the battle is over.

Crazy.

Naive.

Stupid.

Freak.

Those are labels we put on things we don’t take seriously — things we want to diminish and push out of the way. They’re words we use to describe people we don’t want to get to know, who are different from us in ways that make us uncomfortable. They’re some of the words I grew up applying to myself to account for my differences. Apparently I still use them. Affectionately, sometimes. But often.

Screw it. It’s time to feed the freak.

I think what I’m looking at is an internal power balance. My conservative side is necessary for survival. My creative side, technically, isn’t (although my quality of life standards would beg to differ with that). Somehow, now, my conservative side has gotten all up on a high horse about its Status of Necessity, and my creative side doesn’t stand a chance against that kind of arrogance.

I want to submit an alternate structure.

What if my powerful conservative side considered honoring my creative side as a source of wisdom and inspiration? What if my creative side took up a post of leadership and offered to gently (and probably slowly) guide the rest of me into more experimental directions?

This might seem like a counter-intuitive comparison to make, but what I’m describing feels a lot like trying to get powerful income-earning adults and high-energy invincible youth to honor retirees and seniors.

Am I making any sense?

Maybe I’m just crazy.

But I think there are answers here.

When I realized it was becoming time for me to leave Cerado, I gave them three months notice. I spent the first month second-guessing that decision and trying to figure out how I could rearrange my contract and stay. When I finally confirmed the choice, I promised myself that I’d spend the second month freely exploring what matters to me and what I might be looking for next, without biasing that thinking with actual “real world” opportunities and limitations. And then I’d get practical in the third month.

Yesterday was the last day of the Month Two, and I wasn’t feeling very confident that I had unlocked enough answers. I was getting stuck on the tension between “How can I be happy?” and “How can I be productive?”, and mostly just tried to pass the time by sleeping a lot.

Magically, though, sometime around 1am last night, I gave up on sleeping and started writing. And a month’s worth of half-answered questions and quickly-scribbled post-it notes of wisdom finally clicked into place.

The answer is that I already have all the answers. I know exactly what’s right for me and what’s not, what I should be doing next and what I shouldn’t, what matters to me and what doesn’t. I just can’t hear those answer while I’m thinking, while I’m distracted, or while I’m trying to numb myself. And it just so happens that I spend most of my day thinking, distracted, or numb — habitually. Intentionally, in a way, to avoid those answers. Because accessing them is actually scary as hell.

I can thank Hugh MacLeod, Kate Bornstein, John T Unger, and a few other key smart folks for giving me enough post-it notes of wisdom to finally piece together why it’s so scary: I’m still very dependent on receiving approval from the people I care about. Or rather, I’m terrified of their negative judgments.

Sort of.

This narrative’s admittedly a little old for me — I’ve had to smash through the “who I’m supposed to be” walls a number of times already for the sake of my own survival, and miraculously I didn’t lose anyone I cared about in the process. Some relationships did end up shifting, but it was usually to a place of greater respect. And yet somehow, the fear of becoming an embarrassment, a burden, or someone unworthy of love and respect as the result of doing what feels most right for me still creeps in and changes my behavior — enough to give me plenty of excuses to avoid-like-hell the activities that clear my head and let me see what’s next for me. I’m talking about little acts like having my coffee before I check my email, more intentional things like meditation or exercise, and gestures as basic as letting myself fall asleep without aid or a movie in front of me.

I don’t need to think my way through this transitional period. I need to stop thinking, clear my head, and hold onto the wisdom that doing what feels right is worthwhile, even when it takes me further away from what’s safe.

(Easy…. right? *snort*)

So… yes. The subtle references and whispered insanities are true: I’ll be leaving Cerado in September.

This means I’m voluntarily entering the worst job market ever to happen in my lifetime — a market in which heartwrenching handfuls of talented peers and friends have been unemployed for over a year now — as a free agent.

There. It’s acknowledged. And that is the last we ever speak of the Impossible Economy in association with me looking for work again. If I can get my mother to stop reminding me of this dismal fact (and I have), surely you can play along with my game, too. Do it as a favor to a friend.

The other seemingly ludicrous point to note is that I’m leaving on very good terms with a high regard for the company, and I’ve sincerely enjoyed working with them. Chris Carfi is an impressive hybrid of creative genius and brilliant storyteller — when it comes to social media marketing, he gets it on both a theoretical and a social level. I’ve learned a lot from working with him, and from working alongside fellow mad genius Mark Resch as well. The clients (hi, BlogHer) and developers (George the PHP guru, Eric the King of iPhone dev, …) I’ve been paired with have also been top notch. I will be sad to let them go.

So why am I leaving?  Because it stopped fitting me.  What the Job Needed From Me and What I Wanted to Do crept further and further apart over time, and it finally became evident that something had to change.  It wasn’t anyone’s fault; it was just growth. And it has a hidden upside for Cerado: being able to let go of the role means I can now help them restructure their management process without my interests in the equation. The result is shaping up to be something that’s much more tailored to their changing needs, with a more efficient use of resources.

I kind of enjoy working myself out of a job.  It has a certain satisfaction to it.

It just leaves one question: What’s next?

I don’t know.  And call me crazy (I’m used to it by now), but I’m not really interested in job leads just yet.  I’d like to give a little more thought first to what I’m looking for.

When I was in Chicago for BlogHer recently, I ran my situation past a childhood friend, Jim Conti.  He gave me a useful way of approaching the “what should I do next?” question:

Ask yourself…

What am I good at?
What brings me joy?
What does the world need me to do?

…and find the intersection of all three of those.

In other words…

When the grownups asked us what we wanted to be when we grew up, they forgot to explain that this was what they meant. Most of us probably answered based on how we wanted to be seen, realizing that “astronaut” and “veterinarian” sounded worthy enough of praise.  So do “rich” and “famous.”

A psychologist friend of mine made an interesting comment to me recently.  She said, “This is going to sound terrible, but I strongly prefer working with wealthy clients. It’s not because they pay me better. It’s because they already know that money’s not going to fix their problems.”

Neither is doing what they’re good at even if they don’t like it. Or doing what they enjoy when it’s useless to the rest of the world. Or being a miserable martyr for the sake of humanity. We have more work to do than this.

And I still haven’t answered the question.

I know some of the things I’m good at…

- XHTML/CSS development
- Product and project management
- Social media consulting
- Technical and promotional writing
- Public speaking
- Building community spaces

I’m feeling the tugs of what the world wants me to do in terms of social media marketing, community development, and LGBT activism.

I just… might need to get back into the groove of what brings me joy for a bit.

Then maybe I’ll know what I want to be when I grow up.

I want to believe in micropayments.

It’s like Santa Claus, the tooth fairy, the economic stimulus package, predefined timelines for large projects, nonfat lattes, and God. I want to believe in micropayments because it gives me hope…

I’m talking about hope that we’re on the right track. Hope that we have a viable, sustainable alternate plan for the business models we’re turning upside down with our new technology. Hope that we can decentralize power without losing it altogether. Hope that we can survive without the monopolies. Hope that artists will be able make a living just by inspiring people. Hope that the average Internet user will soon derive as much satisfaction from giving financial props to someone they find valuable as they’d get from buying them a beer.

I naively believed we were close to this reality because someone — iTunes — is actually finally doing it well. I believed the biggest barrier was form of payment: if you have to enter your credit card number or go to a separate payment website or do anything that takes more than a click or a few keystrokes, the method won’t catch on.  iTunes broke that barrier for iPhone users when they required us to sign up for an iTunes account (and enter our credit card number in advance) just to download those nifty free apps. We didn’t like entering our credit card number, but it was Apple, so we knew everything was gonna be okay. Now that we’ve done it, whenever we get a song stuck in our heads at 3 AM and decide we need to listen to it right then, all we have to do is enter a password and it’s ours for 99 cents. A password. Just a password!  Anywhere we are.  It’s brilliant.

It was so easy to take it a step further: if Apple can do it, other industries can’t be too far behind.  Heck, we could even let Apple become the new PayPal and run all of our micropayments throught them, since they already have our trust.  Why not?  Let independent artists have their own merchant accounts.  Expand the system to cover writers, filmmakers, painters, and photographers.  Let high school kids make 50 cents each time one of the cool screen savers they create is downloaded.  Let me pay for shareware incrementally based on the number of times I use it.  Let me donate to a nonprofit in small chunks whenever they inspire or move me.  Empower the bloggers to fund each other.  Make it easy for us to put our money where our hearts are.  

I was this close to swallowing the whole story of technological utopia when Clay Shirky — in his infinite clarity — shot it down this morning.

“The essential thing to understand about small payments is that users don’t like being nickel-and-dimed. We have the phrase ‘nickel-and-dimed’ because this dislike is both general and strong.”

So… people don’t like micropayments.  Oh. Right.  (And… now that I think about it, yeah okay, I kinda hate them, too.)

And…

“The lesson of iTunes et al (indeed, the only real lesson of small payment systems generally) is that if you want something that doesn’t survive contact with the market, you can’t let it have contact with the market.  …small payments survive in the absence of a market for other legal options.”

So… iTunes is an aberration that only works because the music industry is kinda screwed up at the moment.

He ends with:

“We should be talking about new models for employing reporters rather than resuscitating old models for employing publishers; the longer we waste fantasizing about magic solutions for the latter problem, the less time we have to figure out real solutions to the former one.”

But Clay!  I wasn’t talking about employing publishers! I want the micropayments to go directly to the reporters!

But okay… fine… you win.  It won’t work for that, either.

So what’s our Plan B?