
In 2008, I spoke at a ton of conferences.

I had read Purple Cow and Chad Fowler's India book, and I created a hybrid strategy based on those books (and a few others) which I detail in the Handcuffs video. The short version: market myself as a programmer to a large number of people by building something remarkable and telling people about it. The strategy worked perfectly, but what it got me turned out to have some unsatisfying side effects.
The biggest problem: being expected to be constantly hacking. I actually pretty much am constantly hacking anyway, so this wasn't a killer, but it was a roadblock. If that confuses you, you're missing a key piece of information. My goal was not career security or even career success; my goal was leverage. I wanted superstar programmer status because I thought it would help me achieve something else.
In 2001 I used the excuse of the dot-com downturn to move away from San Francisco to rural New Mexico and make a hard break with technology. I began living broke while studying hypnosis, art, and music, and writing screenplays. While this experience rocked in some ways, the living broke part sucked, and since I hadn't had the presence of mind to study business or marketing, I inevitably made my way back into technology, and the Bay Area, in around 2004, to start making money again.
When I was back in the Bay Area, I began studying acting on the weekends, for two reasons. First, I missed studying art, and it seemed the easiest art form to study on the weekends without losing any time during the week. Second, I wanted to be in classes every weekend, all day, both days, because the Bay Area is filled with excellent parties, and I knew if I didn't have obligations busying me, I might get bogged down in partying too much.

This was basically me in 1997.
In 1997-2001, I lived in San Francisco; 2004, I was in Silicon Valley. By 2005, I was sick to death of the Valley. I bailed, returning to New Mexico, and set about finding a way to both work in technology and develop as an artist. I took a part-time job at a local web dev shop, but that fell apart due to an astounding story I tell in the Handcuffs blog post. I set up my own consulting business doing Rails, which was awesome but required much too much committment. Through this business I visited Los Angeles, fell in love with it, and moved out here to work for a company that promised me the ability to work part-time while making a decent income. That promise went unfulfilled, and I got fired when a manager told me to do something and I refused, literally telling the guy, "No, I won't do that, it's boring."
Those might even be exactly the words I said; to his credit, the manager in question was surprisingly cool about it, and I became friends with him later on, although the friendship's always had some rocky elements to it (as you might imagine). The real reason for my refusal, of course, was resentment at working a full-time schedule while expecting a part-time one. Anyway, all of this occurred before my sprint of speaking at nearly every conference in 2008. The point here is that I had tried, and failed, several different approaches to working part-time in tech while focusing my other time on my artistic interests, and I concluded that to do it successfully, I would need to be very in-demand. This led to the Handcuffs strategy, which succeeded at its immediate target - so-called "Ruby ninja" status, and the job offers and consulting rate to match - but faltered in its ultimate goal, namely, obtaining the leverage to guarantee stable part-time work.
The details of why it failed don't really matter. Essentially, I was expected to be in Campfire like all the freaking time, even though I signed up for 20 hours a week and was very explicit about it. What I've noticed is that these attempts often fail, for one reason or another. So, in 2010, I abandoned the whole idea of working for other people and engaged in a variety of entrepreneurial experiments. I had no savings, and no credit cards; I paid the rent with information products, affiliate marketing, and career coaching for programmers. I made it at least six months without problems, and indeed enjoyed some nice prosperity, but my money management skills were terrible, and I continued living paycheck-to-paycheck, as I had for many years, even though I was no longer even receiving paychecks from anyone in any meaningful sense.
This meant I was very vulnerable when an information product inevitably flopped. If you're creating products to sell, you can't count on every single one of them succeeding, and unfortunately, I was in exactly that position. So I ran out of cash, had to make money in a hurry, and didn't have the option of failing. So I went on Dice, announced my availability, and very quickly had a JavaScript contract in Downtown LA, a daily commute of around fifteen minutes max, even in rush hour traffic. It pays the bills.

What comes next? I don't know. At the start of 2009, I announced a project to launch a new miniapp every month; this only succeeded halfway in its immediate target, as I frequently skipped months, but in its ultimate goal - making me somebody who implements and launches simple apps quickly - it succeeded wildly. At the start of 2010, I announced a project to launch a new side business every month; this only succeeded halfway in its immediate target, as during several months I just launched new products instead of new mini-businesses, but in its ultimate goal - making me an entrepreneur - I think it's succeeded very well. It's very likely that I'll be formulating a similar "something every month" plan for 2011 in the next month or two; what that plan will be, I haven't decided yet.
By the way, just for the record, this company that uses Windows, they also use PHP, but I had written a Ruby code generator for them within a week or two of working there, and we've discussed how I might solve some of their other problems with a Node.js miniapp. Where a lot of people might have complained about the limitations of the dev environment, or judged the company for their decisions, I looked for ways to solve their problems and make them happy. When you use that as your guiding principle, it's pretty easy to get free reign with your choice of tools. A few weeks ago, I started work on a video about how to master corporate politics, but never got around to creating it and selling it; if I do, one of its main points will be that you can pretty much do anything you want, anywhere you want, as long as you focus on what other people need. That's a story for another post, though. It's probably also the answer to my part-time dilemma, come to think of it, but that's a story for another post, too.
I don't know if I'll get to write that one, but I sure hope so.





































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