I took a self-funded sabbatical in 1995, and I’m taking another one now. I think they’re great.

In 1991, I graduated from college and set off on my first cross country journey, by Ryder van, to Redmond, Washington. My first job was at Microsoft. This was, I would like to point out, before everybody hated Microsoft. In those days, only college kids and UNIX weenies hated Microsoft because it made “toy” products and boring office software for suits. One of the kids in my class was offered a job to work on OS/2. “No way I’m going down with that ship,” he said, and went to law school instead.

I was, to say the least, unhappy at the prospect of being out of school. I thrived on the social atmosphere of dorm life and was dreading the prospect of living in a dull apartment in a grey city where I didn’t know anybody. Of course, that’s the trick at Microsoft: most new hires are recent graduates from around the country who arrive in the waterlogged suburbia of Redmond without too many friends or social life. For the average geek, this formula means that you spend all your time at work. A typical day consisted of: wake up, walk to work (try not to step on any slugs), work until late at night, go home, watch TV, go to sleep, repeat.

My version was a little bit different, because I’m not a totally hopeless geek; I went to the gym in the evening instead of watching TV, and spent my weekends biking around Lake Washington to the U. District where I hung out at bookstores, libraries, and coffee houses and felt grumpy about not being in college anymore. But after a couple of years of this, I noticed that I wasn’t developing much of a social life; I didn’t have a boyfriend; everybody I knew was from Microsoft. Drabsville.

Needing a change, I moved to New York to work for Microsoft Consulting Services. At some point, I want to write a book-length treatment about that horrible hellmouth of incompetence. For now, suffice it to say that I didn’t last for long. A quick calculation of my stock options showed that I had accumulated about $120,000 in 2 1/2 years at “the soft”, and, by my calculations, I thought I could afford the risk of working at a startup.

I got a job offer from Pipeline, an early ISP in the New York area, and quit Microsoft. But talking to the founder and owner of Pipeline gave me some bad feelings, and thus began my first sabbatical.

Over the next 9 months or so, I did a couple of things. First, I learned. It was 1994, the Internet was starting to happen, and I had some catching up to do after living in the insular waters of Microsoft Before The Memo when it was assumed that MSN was going to compete with, and subsume, the Internet totally.

I also went through the exercise of thinking about my own startup – twice. Both exercises fell apart after a few weeks work because I didn’t have the right partner, and I didn’t know what I was doing, but I would like to compliment myself with the thoughts that the first startup could have become Yahoo! and the second startup could have become Vermeer (the company that became Microsoft Front Page.) I have specs somewhere on my hard drive for products that, if we had actually created them, really could have been huge Internet companies. But it’s not the idea that matters, it’s the execution — an idea I will return to many times in this weblog.

Another idea that had been itching in the back of my mind was to take a cross-country bicycle trip. When these startup ideas fell through, I started planning to take a trip in the spring, as soon as the weather was warm enough. (This was before I knew that it rains a lot in the spring.) The trip was great, you can read my web log (from way back in 1995!) here.

Somewhere in Idaho, riding through an empty road, my mood changed; I felt totally rested and eager to get back to work. Sitting in the library at Boise State, I read all the computer industry trade rags enthusiastically, and was excited to see how much was changing and how many new things there were to learn. When I got home and checked my bank account, I was happy to discover that the $7000 dollars it took for the 10 week bike trip had been magically replaced through the mystical power of Microsoft stock; being out of work for eight or nine months had barely depleted my savings.

So that was sabbatical one. It took about 2 days to find another, interesting job, and I spent the next four years working: first at Viacom, then at Juno.

Last November, some of the really bad management over at Juno had just worn me down. I found it impossible to be excited any more. It was increasingly difficult to ignore the subtle and unsubtle ways that Juno managers at all levels were screwing up. Worse, the intense politicalness and arrogance of management there convinced me that I had almost no chance of changing things. I joined the flow of talented, frustrated people streaming for the doors.

I really like the formula of working for four years, and then taking one year off. This time I’m pretty convinced that when I go back to work I want to work in a real startup, as a founder. I’ve learned a lot about this over the years, and I’ve gradually come to realize that there is nothing really risky about starting a company these days. There are billions of not-very-smart venture dollars out there looking for somebody to spend; even startups pay good salaries (they have to); and the chance of having a “liquidity event” – IPO or selling the company — is high enough that over the average career, say, working at 4 startups over a 10 year period, there is a fantanstic chance that you will make a big buttload of moolah.