Of course, there reaches a point where the amount of time spent executing a process outweighs the time gained by it. This has happened to me recently in how I manage site templates.

The old way

Some time back in my old job, when we were building out new sites at a pretty aggressive clip, I thought it’d be useful to develop a starter kit—a directory of files, folders, useful styles and Javascript functions that would serve as a foundation from which to build out a new site. When I left the job, I took the kit with me, and continued to update it with new techniques and standards as I developed them.

Except this wasn’t as easy as it sounds. When in the process of developing a site do I decide that a piece of code is suddenly a new standard and needs to be added back to the foundation? Standards don’t come about immediately, they are sussed out over time. Only after a technique has been tried and tested is it ready to be put into the vault, and by that time, I’ve moved onto other parts of the project.

Even if I do decide some particular solution is vault-worthy, the last thing I want to do is stop the flow of my work and figure out a way to abstract what I’ve just done and fit into a generic template. It was becoming more trouble than it was worth.

The new hotness

I’ve come up with a plan. Instead of committing to a master template that contains all my best code, along with the burden that comes with its upkeep, I’m designing something much lighter. It’s a simple table: a list of techniques in one column, and the site where they’re used in another. It’s an abstracted, distributed solution, which, taking the cues from wikis and the like, holds much more promise for long-term usefulness.

With a list like this, the template still exists, but in a bare-bones form. There will always be pieces of a site that are universal, like the DOCTYPE, a basic directory structure, and certain CSS files. Beyond that, the template is a clean slate. All those tricks and tools that get used only occasionally—mostly CSS and Javascript techniques—are getting removed and abstracted into this new list.

I see a couple benefits. There’s the relief of the frustration I mention above, with the constant wondering if what I’m doing needs to be abstracted for vault-keeping. Now, if I recognize that something I’ve coded or designed deserves to be memorialized, I simply have to list a reference to it. Then, later, if I want to expand its scope to include references to solutions I see out in the wild, I can.

I’ve only started putting this idea to use, so I can’t yet say if it’s the right solution. The key here, as with any system, will be remembering to use it. Both on the input end and the output. It’s no good having a list of tips to refer to if the list doesn’t mature and stay relevant.

I know this is an over-glorified bookmarking system. You can forgive me if I treat it like a bit of a breakthrough. Anytime I can increase my ratio of productivity : time, it’s cause for a minor party in my brain.

Do we expect a more exciting, interactive worklife because it’s necessary, or because that’s what we’re conditioned to expect from the nine-to-five jobs we all take after college? The article cites examples of people who can’t deal with the lack of structure in the work-at-home model, including someone who “enjoys the reassuring cadences of the nine-to-five world.” I get this, as I like to rely heavily on structure, but I also find it a little disappointing.

I got an office for many of the reasons mentioned in the article. I needed separation between work life and home life, and I wanted the comraderie that comes with sharing an office with nine others. But then a funny thing happened. I find that the most productive times of my week are when I leave both venues and take my laptop to a coffeeshop. Comraderie—either live or over IM —is a nice short term pleasure, but as a constant presence, it can seriously cut into productivity.

So, on the one hand, you’ve got the working-at-home life, which leads to boredom and ennui. On the other, you’ve got office life, which leads to distraction. The key, at least as far as I’ve found, is embracing the flexibility of choosing between the two on a daily basis. Being my own boss means being able to decide when I go into the office, when I stay at home to work, and when it’s time to break out of the routine and hit a coffeeshop. It seems obvious, but it took me several months to realize that just because I was paying for space, I didn’t have to use it for eight hours a day. Indeed, I should be used for exactly as many hours as are needed to be most efficient. No less, and certainly no more.

It’s easy to believe that we have to choose between one model or the other—work at home or work at the office. Yet going independent is supposed to allow us to break the shackles of the nine-to-five world. Sometimes it’s easy to forget how many shackles that really entails.

What I do find interesting, though, is when that kind of status is bestowed on others out of respect, or as an accident of timing. Take, for instance, the URL syntax for an actor on IMDB. Here’s the one for Philip Baker Hall:

http://www.imdb.com/name/nm0001311/

Apparently Philip was the 1,311th actor entered into their database. Who do you think would pop up if you replaced those last four digits with ‘0001’? Take a minute to guess, then click to find the answer:

http://www.imdb.com/name/nm0000001/

Not too big of a surprise, I guess. Dig a little deeper and you’ll see that his #1 status may only partially be due to favoritism, and partially to alphabetical priority. Number 1 through 82 (composer Victor Young) are all members of Hollywood’s elite, in alpha order. So, okay, Fred’s not necessarily their favorite, just in an 82-way tie for first. Still respectable.

How about movies? Movies on IMDB have their own ID category. Here’s the link for Hudson Hawk:

http://www.imdb.com/title/tt0102070/

Replace those digits with 000001, and you get…

http://www.imdb.com/title/tt0000001/

That’s Carmencita, a one-minute movie made in 1894. The description takes longer to read than the movie does to watch: “Performing on what looks like a small wooden stage, wearing a dress with a hoop skirt and white high-heeled pumps, Carmencita does a dance with kicks and twirls, a smile always on her face.” Okay, one of the first movies ever made. Makes sense it’d be #0000001.

So now I’m hooked, and beginning to reconsider my snotty attitude on the hyper-coolness of being #1. I couldn’t help but dig around my bookmarks and frequently visited sites, and come up with a bunch of sites that use a similar ID-based syntax for their URLs. The interestingness of the following list of number ones will vary based on your tolerance of the mundane and trivial. (Mine = off the charts.)

Board Game Geek
Entry #1 on BGG is a game I’ve never heard of called Die Macher, released in 1986. It seems plenty favored by the Board Game Geekers, with a 8.1 rating out of 10. It’s not the highest-rated game on there, but it’s pre-Settlers of Catan, so maybe it was the highest when the database was set up.

Fun meta-game for BGG-surfing: try to find the oldest game on there. The earliest date I’ve found is 200 A.D., the supposed release date of Backgammon.

Metafilter
No revelation here, since Matt links to it every July 14, but the #1 post on MeFi is a link to cat-scan.com, “one of the strangest sites [mathowie’s] ever seen.” It’s heartening to consider what passed for strange in our halcyon pre-Goatse days.

Cooking.com
If you’re setting up a cooking database and had to pick a recipe to enter first, you’d probably go with your favorite breakfast dish, too. In this case it’s Classic Omelets with Fines Herbes and Toato Concass. Being the first entry, its fame was quickly eclipsed by newer, trendier dishes, and as such it’s never gotten a single rating. Perhaps no one has access to chervil. Fear not, little dish, give me a weekend, and I’ll rescue you from the dark caverns of the unrated.

Twitter
It’s not possible to search just on twitter ID, so I couldn’t find #1. I was able to find the first tweets of Twitter founders Biz and Ev (posts #21 and #28, repsectively), both of whom sum up the early twitter gestalt perfectly, as their first messages are exactly the same: “just setting up my twttr”.

TinyURL
The URL-shrinking service TinyURL has been around since 2002, so I was a little surprised to find that the site first shortened by it was still online. Type in tinyurl.com/1, and you’ll end up at gilby.com, the “home of Gilby Productions,” a site dedicated to unicycling and the promotion thereof. Amusingly, the TinyURL address—a URL meant to be a shortcut to the final destination—is actually longer than “gilby.com”.

Bonus TinyURL nerdery
A generated TinyURL is constructed of a seemingly random assortment of numbers and letters. Which means that on occasion, the URL ID is going to spell out a word. It took me a number of tries to land on something that didn’t redirect to a 404, but I’m happy to report that if you’re ever looking for the Microsoft Exchange Server Mailbox Merge Wizard, your life just got a lot easier. All you need to remember is this: http://tinyurl.com/poop.

I went into the building Wednesday morning with a notecard in my back pocket. This is more or less—more more than less—what it said:

• When I was in high school, the web had just been invented, and there was no such thing as a web developer. No one could have told me what I was going to do. New jobs are invented all the time. There’s a good chance you’ll end up doing something you can’t even dream of yet.
• It’s okay to change your mind about what you want to do, as many times as you want to. Don’t worry about picking the right major the first time around. Or the first job. Or second, or fifth.
• The story of my rise from immigrant bean picker to CEO of a multi-thousand-dollar organization.
• College is about trying new things and finding what fits. When I was in college I spent half my time in my major and half the time at the newspaper with J-school dorks. Explore.
• Endearing story about living in CRC, the best dorm ever. I went with Illumi-Hinman.
• What they don’t tell you is that college is about making connections, building a network. Seems like cheating, but it’s true. Real, honest, human connections is what propels you along in life and allows you to have the confidence to do risky, scary things. It’s what’s helped me.
• You guys are smart. You know what’s right. Be skeptical. Don’t be distrustful, but skeptical. Make sure the things people are telling you (including what I’m saying here) make sense to you before buying it. Trust yourself.

Which took me to the five minute mark, because really, shut the boring adult up already. At this point, I’d ask for questions, which would usually come slowly, so I’d turn it around and ask the kids a few things, like who knows what they want to do? Or who has parents who are insisting they do something in particular? One of those got us going, and then we’d riff for the next fifteen minutes until it was time for the next speaker.

Fortunately, it was wasn’t my intention to recruit them into web design or computer programming, because I would have been deflated to learn LPHS doesn’t offer programming or web design classes. Instead I probed them about what they really wanted to do. It was uplifting to find that a lot of kids had really specific ideas. Nurse anesthesiologist. Computer animator. Stock trader. Musician. I made my pitch for web design anyway, and told them to use their resourcefulness to research it online and try it out on their own time.

The kids were genuinely engaged and interested. It wasn’t hard to have a conversation with them for fifteen minutes. They had relevant follow-ups to the points I made. One girl really latched onto the point about networking, saying she found it so frustrating that she’s having to compete against kids her age who are unfairly ahead due to the networks their parents built for them. I tried to encourage her to go out and make her own connections right now; she was a sophomore, after all. If you start now, I told her, you’ll be ahead of most of your peers in no time.

As good as it all went, I’d change some tactics for next time:

• Lean heavily on the personal anecdotes, and less on the fortune cookie wisdom. No one likes to have someone preach to them. Much more effective is first-hand accounts of the benefits of all these lessons.

• Come prepared to drop names… Every class asked about two things. The first was “Have you worked with anyone famous?” I didn’t have a good answer.

• And numbers. The second: money, money, money, just like Lilli predicted. When I told them I charged $5000 to make a website, their eyes lit up and I swear for a few seconds they all wanted to be web designers. But then they asked the gynecological oncologist how much she made, and they immediately forgot who I was.

• Offer a way to stay in touch. I brought my business cards with me, but forgot about them until the last period. When I offered them out, at least 12 kids came up after the class to take one. I was floored. I don’t expect to hear from most of them, but if even one writes me, I’ll be thrilled.

• Collect addresses. Knowing how short their attention spans are, I would love to have a collection of their emails, so I could follow up with an invitation to talk more about web design or programming as a career, if they were interested.

• Have an answer prepared for the inevitable “what good is all this?” question. As in, why do I give a shit about how to calculate the derivative of a quadratic? I was caught off-guard by this one, especially when it was asked by the math teacher, and didn’t have an answer ready, so I kind of stumbled through a riff on how college teaches you about how fun it is just to learn for learning’s sake. It’s an important question, one that I remember wondering when I was in high school. Next time I’ll come with something prepared.

Recently, I registered with the Alumni for Public Schools, an organization that connects Chicago Public Schools with the volunteer arms of local college alumni clubs. I signed up on behalf of the Northwestern Alumni Club, a group that’s been hooked up with local heavyweight Lincoln Park High School. A couple weeks ago, they sent me my first mission: speak to the high school students as part of their career day. Or, as they’re calling it, “Meet Your Future—Career Motivation Morning.”

If I was in high school, and saw “Meet Your Future Day” on my calendar, and couldn’t find a way to fall down a flight of stairs or contract a 24-hour cold the night before, I’d use that morning’s commute to steel myself against the onslaught of irrelevance and banality that was about to fill my day. Which means that even if, as an invited presenter, you come with good intentions and possibly even a message chock full of meaning, you’re going to start off against the ropes and down a few points.

Despite all that, I said sure, I’d be happy to show up and play the part of the kids’ future. That was a couple weeks ago. Now it’s three days before C-Day, and I’m still stuck figuring out what to say. The invitation email encouraged a sort of theme: “The content of your twenty-minute informative/motivational/inspirational message should incorporate the value of post-secondary education and how a career unfolds.”

I’m assuming a few things:

• Dressing up as a Wal-Mart employee, prisoner, or cadaver will be looked upon unkindly.
• When they say “value,” they actually mean “positive value.”
• The bar for what stands for inspirational to high schoolers climbs ever higher, and a twenty-minute soliloquy by a computer nerd talking about his stirring rise from post-collegiate ASP programmer to 31-year-old PHP programmer isn’t likely to drive anyone to break out the SAT study guide over lunch.
• When they say “twenty minutes,” they don’t mean “four minutes on your job and sixteen minutes debating who’s the best ottoman humper.”

Right. So of course, college is valuable. Happy to preach it. And for most high school kids, especially those at the 47th-best high school in the country as rated by Newsweek, absolutely I’d recommend going to college if you’re the slightest bit interested. I’m just wondering how to make that message interesting to a class of high school seniors without talking down to them or telling them things they already know.

So I’m soliciting advice. What do you wish someone would have told you about college and careers when you were a senior?

Which is why I about cried for joy when I learned about Jumpchart, an online tool that does, well, pretty much exactly that. It takes the elemental concepts of a wiki—communal editing—and adds the ability to organize things hierarchically. It allows you to trim down your site to its basic components, pages and the way they’re ordered, and then open the floor up for content management until you’re ready to port it to the real site.

Jumpchart feels a lot like 37signals’ Writeboard tool, and it one crucial way, Writeboard is better—it tracks changes. For a certain type of client, like one who needs a collaborative tool to hash out internal disagreements about mood and style,
Writeboards’ are the way to go. Jumpchart hasn’t implemented anything like this, though I suspect someday it’ll come. But what Writeboards lack—hierarchy—is, to me, much more crucial. As one-off collaborative editing tools, Writeboards excel. Jumpcharts are meant for full-site content collection, and for that, they may be salvation.

Enough for hype; how’s it play out in practice? I’ve tested out Jumpchart with one project, a small one with just a few pages. It took a little prodding to get the client to sign up for yet another tool (they were already on Basecamp), but as soon as they were on board, I think they immediately saw the benefit. I know from my point of view, it saved me hours of collecting and managing ownership and reminding the client to send me their owed copy. Instead I simply opened up the Jumpchart floor to them, and pulled the content down in one final swoop shortly before the final site testing began.

For that small project, It worked really well. Yet, there are a few crucial missing features that prevent me from jumping on with both feet for all my projects, big or small. The most important:

• Control over export. They’re kind enough to let you export your file as XHTML, but they peculiarly wrap everything in a full page’s worth of code. I’ve got my own headers and footers; all I need is the code for the headers and paragraphs I’ve typed up. Bonus points for adding the option to export in Textile or Markdown.

• Versioning. Mentioned above. Not a deal-breaker, but it would be so helpful in those inevitable times the client changes something after I’ve moved the text over to the site.

• Mass entry. If my site is thirty pages long, I’d rather not have to use the interface to add page after page. Let me upload an OPML file, or simply type in the outline in a textbox according to a predetermined syntax.

• Quick formatting. It’s nice that I’, able to click a formatting rule and have it appear at the bottom of the editing textarea. What’d be even nicer is if I could select some text, click the rule, and have that rule apply to the selected text. I hate WYSIWYG as much as the next hand-coder, but this small concession would go a long way.

• Sitemap and overview. In thinking how I’d use this with clients, I’m realizing it’d be hella useful to have a description for each page. The more direction I can give my clients, the better, and a list of what’s needed would allow clients to simply surf through the outline and add whatever it said.

Bottom line: Anytime a company can tap into my brain and build something that so exactly meets my wishes, I’m impressed. A little frightened, but mostly impressed. Jumpchart is strong enough a product that I’m confident using it on small projects and recommending it others. Another version or two, and I’m sure it’ll be going into my core toolbox for site development.

The system is centered on a tool called Kinkless GTD. This is my master vault, where I keep all my to-dos, organized by project. On the surface, it is simply an outline written in the excellent OmniOutliner. Underneath the surface, however, are scads of scripting and formatting rules developed by one Ethan Schoonover, using OmniOutliner’s support for third-party scripting. He calls the package Kinkless GTD, or kGTD.

This system is not for everyone. It can be clunky at times. For me, it works, because it embodies the principal of GTD I value most, which is to Get Things Out of My Brain. Everytime I have a thought about a project, I write it down in my kGTD document, filing it under the proper project. Everytime I get an email from a client, saying she’s going to delivery something by X date, I write it down in kGTD, tag it as “Waiting on” and list the date it’s supposed to arrive. Everything anything happens, it goes down in my kGTD outline.

The benefit being, if all my to-dos are one place, they’re easy to retrieve. The first thing I do everyday is open up my kGTD file, sync (which removes done items and changes the formatting of due items so they stand out more), and then scan the document for items to do today. I write those down on a separate list—usually a notepad next to my keboard—then work exclusively off that list for the rest of the day. If I’m feeling really energetic, I’ll even mark down time slots for each task, so I know, realistically, what I’ll be getting done today for sure.

What was revelatory for me about GTD was not the specific systems it describes, but the philosophies behind them. Get stuff off your brain and onto paper. If you’re frustrated, fix the process. Put stuff where it belongs. I’ve tried lots of other tools, and I keep coming back to kGTD, because it’s the easiest tool that allows me to accomplish those goals.

Nevertheless, it’s always really tough to take a vacation as a full-time freelancer. As much as I try to plan them, project schedules are a beast of their own desires. I got lucky this time; the week could have just as easily been one of hectic deadlines, forcing me to bust out my laptop at inopportune times, like on the subway, or at my sister’s wedding.

On the flip side, of course, is that a freelancer’s life gives one the chance to take vacations whenever they mood, and pocketbook, pleases. We are a highly mobile class; it’s just as easy for me to respond to email in, say, New Delhi, as it is from my desk. For this, I feel very fortunate. I have the kind of mind that requires consistently fresh stimuli in order to avoid boredom. That I can take my work with me to the porch, or a coffeeshop, or to Boston, and get just as much done—or quite likely more—makes me a very happy worker bee.

The tricky part is avoiding the guilt. (Oh, but isn’t that always the case for sons of Jewish mothers?) It comes from both sides. If it’s not the guilt of waking up in a foreign city with all sorts of lovely stuff to do and finding myself working instead, then it’s the guilt of having fun while my to-do list remains untended. The solution I’ve found is to set some short-term, project-based goals, work until I meet them, then feel free to spend the rest of the day galavanting, guilt-free.

It’s easy to think, as a independent worker, that without constant attention, your whole business will fall apart. I’m finding this to be less and less true. There were days on this trip when circumstances prevented me from working or getting online until late at night. And yet, nothing caught fire or broke down. Instead, I was able to check out and enjoy my vacation. In the long run, this makes me feel healthier and more creative and, in turn, more excited to get back and do my job.

But, as with every challenge I encounter these days as a self-employed web wonk, I decided to turn this problem into a teachable moment. As in, Let’s Learn about Captchas!

Here’s what I already knew:

• Captchas are those elements on comment forms that you to interpret a few characters of scribbled text.
• They often look like they were written by a serial killer.
• They are tedious.
• They are often unnecessary, as there are simpler, less cryptic ways to tell if you are a spambot.

After some research, here’s what I learned:

• Captcha is actually CAPTCHA, an acronym.
• What CAPTCHA stands for isn’t important, as the words were clearly defined after the acronym, and the fit is less than snug. The important point is that the T stands for Turing.
• Actually, the T stands for Turing Test, which goes to show you what I mean.
• The folks at Carnegie Mellon’s School of Computer Science, who devised CAPTCHAs in the first place, have come up with reCAPTCHA, something so ingeniously cool I found myself thanking the spammers for giving me reason to use it.

In a nutshell, reCAPTCHA tests your humanness by asking you to retype two words. One of the words is computer-generated, and it’s against this word that the system tests your entry to see if you’ve got a brain. The second word looks exactly the same, but it comes from a different place: a repository of text scanned in via OCR, as part of a massive book digitization project. OCR technology is not perfect, and for very old books, the text is often illegible. By harnessing human brainpower in very small, distributed chunks, reCAPTCHA has random blog users interpret the words for them, adding value to the project without requiring massive amounts of extra resources.

The thing that makes reCAPTCHA so brilliant is the very same concept behind the water-pumping playground and SETI@Home—100% recycled energy. Capture some energy that’s already being used, and funnel it into the powers of good.

I’ve installed the reCAPTCHA Wordpress plugin on this here blog; I don’t have much to contribute, traffic-wise, but hopefully those numbers will increase over time. Big kudos to Carnegie Mellon for designing and developing this project. I’m embarrassed to admit I had a chance to attend your school for undergraduate studies, but passed you up for a sexier campus with a evener boy-girl ratio. Clearly you’re much cooler than I realized back then. I hope we can still be friends.