When you're a freelance software developer and the relatives come calling, you learn quickly - if you want to keep your business afloat - how to let them down easy. When friends of relatives come calling, however, it gets tougher, especially when they're as enthusiastic as Jane.

Dick's second cousin (once removed) had pitched Jane's idea as "similar to Khan Academy or MIT's online college", which didn't really float Dick's boat: it sounded either extremely boring or impossible. But Dick sat down for coffee with Jane anyway, and found himself confronted with the following business plan:

The goal of the Math Institute is to use modern web internet technology like XHTML, HTML5, CSS, Adobe Flash, WordPress, Microsoft .NET, and Rubies and Pearls to create a fun and interactive program for students struggling with math.

After politely declining to point out that whoever wrote that plan seemed to be struggling with "modern web internet technology", Dick found Jane's actual requirements simple and reasonable enough that he signed a contract - after all, she only needed him to leverage just enough new technology to qualify the program for some obscure form of government funding.

Two weeks into the project, Dick had his first whiff of trouble. It wasn't that the requirements they'd discussed weren't simple and reasonable - they just turned out to not be Jane's actual requirements. On the phone, Jane demanded to see a minute-by-minute breakdown of the first invoice. Dick hardly had time to explain that he could only summarize each week before Jane shifted gears:

"Is the videoconferencing done yet?"

Dick pressed for details, though he was by now afraid to hear them: the original requirements hadn't made any mention of videoconferencing.

"I want parents to be able to videoconference with their kids while they're working on the program," she explained. With a silent communion between his forehead and his desk, Dick reiterated the original requirements. The rest of the call was a blur, but when he hung up the phone, Dick had got Jane to agree to what she'd agreed to.

That agreement lasted three blissful, productive days. Then Jane sent an email requesting additional features, unrelated where they weren't incomprehensible. Against his better judgement, Dick agreed to implement some of the changes, if Jane would extend their contract accordingly. Once this pact was sealed, the project - and Dick along with it - entered a spiral of weekly changes and invoices from which they would not emerge for four months.

When Dick finally dusted off his hands at the end of that interminable summer, the fun and interactive program using modern web internet technology had been reduced by Jane's budget constraints and increasingly unhelpful demands to a set of downloadable zip files containing math problems - not a Ruby nor a Pearl was to be found on the web server. Nonetheless, Dick had done his job, maintained his sanity, and sent Jane a final invoice with instructions for using the administration interface he'd developed. All was well for all of a week, when Jane called, frantic, unable to edit the website. Dick imagined Jane had been confronted by a PHP error on the admin interface and cursed himself, mentally preparing to dive back into the spiral to debug. But Jane wasn't able to describe the problems she was having, and urged Dick to meet her in a week, in person.

A week passed, and Dick found himself sitting at the coffee shop where an unbelievably enthusiastic Jane had pitched him on her bold vision. As he waited for her to arrive, Dick was thoroughly confused: he had tested the admin interface in his development environment, logged onto the production server, and all was as it should be. When Jane arrived, as unenthusiastic as he had ever seen her, she showed Dick how she had copy/pasted the website into Photoshop and "improved the layout" (by removing all visual niceties and changing the font to Comic Sans), but she couldn't figure out why the site itself didn't change on the Internet when she hit Save.

Dick's hands trembled - no doubt due to his double Americano - as he explained that if she wanted to edit the website's layout instead of its content, he would either need to develop a WYSIWYG editor or make the changes himself. As reluctant as he was to continue a business relationship with Jane, Dick was just about to suggest a new contract when she slammed her fist on the table.


The conversation did not go uphill after Jane's outburst, and Dick would always remember that Starbucks as being the place where he fired his very first client. He told Jane that he expected to be paid according to their contract with all its addenda, and that she should find someone else to do further work on the site.

Two weeks after firing his first client, however, upon receipt of a check for $1.00 whose memo field read "site doesn't work", Dick found himself hiring his very first lawyer. Though his first cousin (twice removed) had recommended her, she was not as enthusiastic as Jane had been.

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