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Quitting Jobs, Part 3

Sunday, March 18th, 2012: Jobs, Stories.

(The carefree Dotcom Boom: Partying like there's no tomorrow!)

After years of poverty, debt, and frustration, I entered the Web industry at the point when the swell begins rising and you realize it’s going to be a big wave. It was such a heady time that I temporarily lost touch with who I was. Many people in the industry believed that the Web was their generation’s revolution that would solve the world’s problems through technology. There was an internet collective called Cyborganic that courted me from the beginning. They were all young, arty and over-educated and trying to use the new technology to spread knowledge democratically. Amazingly, they got venture capital and leased a flashy building in the heart of downtown San Francisco where they threw massive parties and exhibited Web art.

After a full-day interview, including a presentation to staff that I had cobbled together the night before out of photos of my old art work, I was shortlisted for the position of director of IDEO Product Design’s new interactive division. For years, IDEO had been the most celebrated design firm in the world. But at the same time, the hippest web agency in the industry, vivid studios, offered me a job as information designer. I took the latter because although IDEO was more prestigious, vivid seemed to represent the future, and their culture seemed more idealistic and less corporate.

I excelled in this new field, learning by trial and error and helping invent a new profession that would rapidly become a foundation of the Web industry. The first project I was given leadership of was a big hit, with rave reviews in the national press. But a few months later, I was fired under mysterious circumstances which I attributed once again to the hothouse environment, excessive ambition and insecurity. Ironically, a few weeks after firing me, management begged me to come back to lead a project that I’d pitched before being fired. My pitch had won the contract and now they needed me after all!

After finishing this project, which won an international award, I quit again and started my own business. The Fortune 500 clients I had worked for at vivid now brought their design projects directly to me. I opened an office in North Beach, hired an assistant and recruited hot young designers and coders for the challenging, high-profile projects that kept flowing my way. All of downtown San Francisco hummed with energy; dotcommers met for cocktails in trendy bars then went back to the office to work all night. Twenty-somethings were paying cash for hot city property and becoming slumlords. I worked on one project with a kid who had his own NASCAR team.

On warm evenings in my neighborhood, you could hear laughter and the tinkle of drinks at rooftop industry parties overhead. I was flying all over the country, advising billionaire investors and CEOs. Again and again, powerful companies offered me prestigious positions which I turned down. I had so much work I was blowing off new contracts, and I believed that I had finally found a solution to life’s financial rollercoaster. I would grow my business, meet my soulmate, get married and have a family, sell the business for a fortune and retire early, and figure out what to do about all my frustrated dreams and passions.

But of course the wave had to break, the boom had to end. Everyone knew that, but we were all going to ride the wave as long as we could. Instead of a soulmate, I met an idealistic neo-hippie girl who cared nothing for the Web industry lifestyle and had no respect for what I was doing. And as the dotcom crash unfolded, a strange thing happened. Although the girl and I were traumatically incompatible, she shocked me out of the megalomaniacal Web industry delusion and back onto my own true idealistic life path.

What little I had saved ran out quickly, and more years of struggle followed, with even longer periods of unemployment and deeper credit card debt, living in dramatically reduced circumstances. I started a new art project, looked into organic farming and other idealistic careers, did backbreaking habitat restoration as a community volunteer, chopping acres of invasive plants out of nature preserves. I fell into depression and my health began to deteriorate. But eventually, after three years, the Web industry revived, and the few old colleagues who had survived the crash started calling me with new projects, bless their hearts.

This time, I had a more realistic long-term plan. Instead of using my profits to live the dotcom lifestyle, I would continue to live cheaply, save money, and look for a place far from the rat race, with low cost of living, which would allow me to work less on the Web and more on my dreams.

That brought me to where I am today.

And yes, I quit again!

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