There are other worlds than these

sixth and final in a series of major life event/direction choices...

Many little choices and some major ones characterized my life in Silicon Valley, but all of the decisions were made under a certain common mindset that had begun with my change in perspective in 1995-96, when I saw the internet, and my role in it, being more important than the sorts of causes and political action that had been a central part of my life up until then. The point of the last essay was to understand how that choice evolved from an inability to find work in policy areas, and a sense of the new opportunities on the internet--not just to find a job and work, but also to contribute something good to society in a more creative way than I felt I could do in the legal/policy arena.

Similarly, the change that is occurring now in my perspective was set up by the decisions and choices described in great detail below, culminating in a major event and a major choice that I now realize set the wheels in motion for a significant realignment of perspective that goes far beyond a choice of career.

I worked at Smart Valley for a year and a half. That is not a long time, but it was somewhat expected that people working there would "move on" to bigger and better things. The organization itself was only chartered to exist for 5 years. Also, this was really the "boom time" for the Internet and dotcoms. Every day, I could see page after page of job postings on www.craigslist.org. Everyone was getting into some new startup that was going to be the next big thing. Smart Valley hosted a monthly series of events called "Smart Talks" where speakers from start up companies would come and talk about what they were doing and how they were going to change the world.

My initial role at Smart Valley was simply to edit the website. But, when our systems administrator left for glory and riches, I eagerly took on a more technical role and took a couple of classes in systems administration so I could manage their webserver, an HP9000 that lived in a facility at Stanford where it was attached to one of the main BBN backbone networks. I started writing more dynamic pages and code to create simple web applications. Over time, I crafted my role into that of a technical project manager as well as systems and programming person. I became the web guy. But there were limits to the position. We were never going to hire developers, except on a project by project basis. When we did take on more technical projects, we hired a project manager with more experience and he ended up taking over my most exciting project, Smart Voter, hiring an expert programmer to do all the hard work. I felt somewhat jealous, but I also knew that I did not have all the skills to do it myself, and I actually viewed hiring him as a way to implement my vision. We collaborated on several projects of this nature, but to some extent, I felt redundant. Once he had a real programmer to work with, I was just getting in the way.

We tried to hire a person for me to manage and that did not work out well. The guy just did not do the work and I spent a lot of time trying to get my bosses to let me fire him. My hope was that I could move him into the role of running the internal website while I became more of a project director, with the opportunity to plan and manage projects like Smart Voter. But this turned out to be a big management problem for me and ultimately, I found it easier to move on to another job than replace this person.

My first move from Smart Valley was to a company where I was the first web developer, writing perl scripts and database routines to make a web-based version of their software product. Decisive Technology had developed an application that enabled people to run email-based surveys. A user could create a survey in the software tool, then deploy emails and/or have the software generate a web page version of the survey. Then, the responses could be imported/parsed out of email and via the web for analysis in the software. Many customers did not want to go to the trouble of doing it all themselves and they lacked the marketing expertise to design the surveys effectively or interpret the results scientifically. So Decisive created a Professional Services group to use the product and conduct the surveys for clients directly.

I was the first technical person on the services team. It was an exciting job because, over the course of the next year, our group expanded and became the main focus of the company. For me, it was a rapid rise to power and responsibility as I built a team of 6 web developers and took over all the technology for the company. There was some tension (repeated in so many other companies during this time) between the "engineers"--the software guys with years of experience, CS degrees and high 5-figure or more salaries and the "web developers"--guys who could crank out a solution in a day instead of weeks. I was typical of the web developer of that time; no computer science degree, self-taught, and impatient as hell. I would see resumes from senior software engineers and my reaction was always, "I want somebody who can write a perl script and have a site up and running in a couple days, not develop a software application."

My manager went through a similar growth spiral. He was originally VP of Professional Services. But then, as the company failed to sell the software product and our group was generating all the revenue, the Board of Directors sacked our CEO and put my boss in charge. They also directed we reduce staff by some 20 people to buy time to grow. So, I got put into the position of helping decide who stayed and who was layed off. Our group was safe, but the rest of the company was gutted. This was a small company; maybe 60 employees, some of whom had been there for 5 years. I would not be surprised if many of them did not remember me fondly.

To a certain extent, I overreached. I took on the role of something like a Chief Technology Officer. I had my team of web developers, but I was also responsible for "operations"--keeping the web site running, etc. I was also the principal technical sales contact--I would go out with the Sales VP to pitch our technology to customers and figure out how we could do what they needed.

One of my most memorable trips was up to Washington State to help close a deal with Microsoft. A previous vendor had conducted an employee satisfaction survey within Microsoft. The project had failed miserably when the web server could not handle the load generated by all the employees taking the survey at the same time. They wanted us to guarantee that a similar fiasco would not happen.

Our sales VP, along with the director of research (e.g. survey design/analysis), and I flew up to Microsoft and met with the heads of Microsoft's software QA departments. They grilled me on how the technology worked...which involved revealing that our web server was actually a Sun Solaris unix server--not Microsoft software! It was a grueling experience, but I convinced them we were at least competent to take on the task.

That was the kind of thing I enjoyed most about my job--meeting directly with customers and solving their problems, then going back to the office to lead the implementation of it. I did a little of everything in this job. Technology-wise, it was light years behind the infrastructure I manage today for a company that is 10 times less complex. My wife and I bought our first home, a townhouse in the East Bay--actually, Pleasanton--a 40-mile commute. I would leave before 5am to beat the traffic and get to the office before 6am, then be there until 7pm or later. Sometimes I would get home at midnight, sleep 4 hours and go back again.

I was only at this company for year and a half, but it seemed a lot longer. When it was good, it was great--I felt important and valuable. But over time, things began to fall apart. As the company was reorganized, the novelty of what we were doing became the primary focus of the business, and my "best efforts" were not adequate to meet the kind of 100% uptime we really needed. My biggest mistake was keeping ownership of the IT function--I should have insisted on having that delegated out and separated from me. Instead, I created 3 teams below me: development, delivery, and operations. Operations is what killed me. Delivery is where I was meant to be.

However, in a story I have seen repeated in my technical life, operational failures are always perceived as delivery failures. So the first nail in my coffin was the hiring of a "client services manager" to project manage my delivery team. Operations first collapsed when the former IT manager quit while I was on vacation. Then, we hired a replacement who was a great guy, but none of us really had the expertise to set up a real data center at this point. Interestingly, this is the area that I have been drawn to most following this experience, so that today, I know 100 times more than I did then. But it is still a tough challenge to keep the systems running smoothly. To be effective at delivering services, the manager must be able to assume the systems just work. When he is constantly drawn into troubleshooting problems there, he neglects the business priorities, and what's worse, his efforts are seldom understood by anyone else. Every problem solved is often a problem people are shocked to know existed. So it is a lose-lose kind of world.

Another phenomena about systems is that experienced technical people often think they know more about systems than they really do. The CTO, the VP of Engineering, the Board Member who hacks together databases at 3am on the weekends--they all think that systems work is something they could easily do, but they are smarter and have moved beyond it. However, they freely offer their own solutions to what they think the problem is, ignoring the fact that the systems people have actually been working on the problem for much longer. The point is that for me, systems issues have been very interesting for me to tackle, but they have also been very dangerous because when I run into problems I can't solve, I am responsible as an individual technical person. It's kind of like "you broke it, you bought it." As a manager, I can help craft a solution and I can understand the issues and what resources my people need. But when it is just me trying to solve the problem...I run into problems.

My friend and I left the company as it was imploding and trying to be acquired. We had a couple of problems where our website was down or we lost some data and I got blamed for it. I was spread too thin, workwise, and emotionally, so I was ripe for a reactionary move. Nobody wanted me to go--they offered me a huge raise to stay and would have put me in more of a technical sales role. But that was kind of an insult to what I thought I was good at and I had no faith in the people anymore. My friend, whom I had brought in as technical person #2, was even more angry and upset than I was. We all spent a lot of time walking around the building or sitting in the divey sports bar nearby, bitching and complaining about work. It was a very unpleasant dynamic.

My friend and I started our own company when we left. The idea was to set up a website that would host online stores. E.g. yahoo store. That was a mistake for me. Originally, we had a third person we thought was going to be our sales person, but he did not materialize. I really regret doing the startup company thing, mainly because I feel like I let my friend down because I did not have the same entrepreneurial passion he did. It was a half-assed effort on my part--not because I did not work at it, but because I did not have enough commitment to it. I was setting up web servers from scratch and doing all sorts of IT things. We had sort of a plan, but not really. I felt isolated and alone and didn't see how it was ever going to work out. I did it for 6 months, then said I needed a real job.

In retrospect, we were very naive about how to really launch a business. But we did not know that; we read a lot of books and wrote a business plan, etc., but so much of it was in our heads and not the reality of what was out there. People did not want to pay us $1000 to set up a website for them. We did not really understand how online selling was going to work--we had a lot of good ideas, but we were not small business experienced. I was experienced at going to a meeting and closing the deal by wowing a few people with my creative problem solving. But those people had budgets and were ready to spend thousands of dollars. There were not small business owners who did not know what they would do with a website.

The main frustration was that I did not really know what to do. We kind of jumped into it and spent a lot of time making our website, but what I needed to be doing was meeting and talking to people and getting a feel for whether or not the business was even there. My friend was a lot more motivated in this direction and initially, I guess I hoped he would find our first client and get us going while I focused on setting up the servers. But after six months, I realized this was an expensive adventure for me and I was not even enjoying it. My wife was the only one working and her job was far from a dream job either. So I decided to quit the startup and find a job.

The first job I took was terrible. A former co-worker (the VP of Sales) got me into a new company (Decisive did in fact get acquired and implode soon after we left) where she was working. I was like a project manager for a dysfunctional dot com company. I accomplished some things there, but as soon as I could find something else, I jumped ship.

The next company was a true startup. I was the 2nd technical person, in charge of setting up the systems stuff. This was not unlike my role in the 2-person company, but this company had some funding and a plan. We grew rapidly and I carved out a good role for myself where I was generally respected and contributed a lot to the team. But I was not satisfied--I wanted to be figuring out the solution, not just implementing the technology. I was bored with my role and frustrated at times that all the product decisions were beyond my control.

In May 2000, I learned of another opportunity (my Sales friend had changed jobs again, to another survey-oriented company). This company looked like a functional version of the chaotic company I had left a couple of years earlier. I interviewed to be their Director of Operations and was offered the job. I accepted and gave my notice.

However, at this time, a major event happened in my personal life. My father, living alone 3000 miles away, suffered a massive stroke. I flew back and forth to manage his medical care and was planning to move him to California, but the stroke proved to have caused too much damage and he died several months later.

As this was going on, I re-evaluated my career and decided that it was not the right time to be starting a new job. My main reason for leaving was to seek new challenges, and I felt I would have my hands full with my father and would not be able to get fully into starting a new job and major leadership position. I rescinded my acceptance and withdrew my resignation.

The story of my father's stroke and medical care would fill many pages. I did everything I could and planned for the worst. We had made an offer to buy a second house that we would put in his name and then move him to a nursing home in San Jose, then eventually to the house. But he did not live to see that.

I continued to work at the same company through the summer of 2000 and my father died at the end of July. By September, I was thinking of moving on again.

In November, I accepted a position as a Product Manager at a dot com in Sunnyvale. For several weeks, it was frustrating, as I did not really understand what my role was supposed to be. So I created a role. I determined that they needed to migrate their websites from their old architecture--running 18 separate webservers--to a common codebase. I teamed up with the Director of Engineering to lead an effort to migrate everything to Microsoft .NET.

Over the course of the next 18 months, many things changed in the company. My boss decided to become a photographer. The Director of Engineering got sick for 3 weeks, then never came back (he found another job). Half the company was layed off. When the dust settled, I was leading the technical team as their new Director of Engineering, leading a team of almost a dozen people.

However, no matter how successful we were, the economy was killing us all. Every quarter, more spreadsheet projections were made and the decision to cut more people was made. In the first round of cuts, I was fortunate to be merely consulted, but after that, I made the decisions. On of the more unpleasant moments in my professional life was laying off a woman who had just come back from maternity leave because she was the highest paid person and truly, the other people were more productive, given how the nature of our work had changed. But it got ridiculous. The company had been 60 people at one point. Now we were 20. And even that was not enough.

My team was 2 web developers and a network engineer. Then the CEO came to me and said we needed to lay off one more...and he thought it should be the network guy because we didn't want to be left with only one programmer. I said, "well, you know, I can make this easier...I have accepted another job offer..."

I had seen the writing on the wall and the writing was not "you are going to lose your job," but "you are going to have to take over the systems job when the network engineer gets layed off." That, to me, was an even greater nightmare than being layed off.

But I have gotten ahead of the story here; opportunities don't just materialize out of thin air. I had been looking around for a few months already...

The event that changed my life, especially following my father's death in 2000, was September 11, 2001. My wife and I had actually been on the East Coast the weekend before and and flown back from Washington, DC to San Francisco on United--like the plane that went down in Pennsylvania. On our flight, I read a fictional book about Osama Bin Laden planning to set off a nuclear bomb. So when we turned on the television and watched the twin towers burn, my first thought was, "Bin Laden."

There were two main types of thoughts I had about 9/11. One was a feeling that maybe I was in the wrong place. We had been busy with the Internet and trying to climb the success ladder, after leaving the political scene behind, trusting that things would be taken care of. Then Bush won in 2000. Maybe if I had stayed true to the course of activism and involvement it could have made a difference in the direction the country went. It seems very tenuous, I know; I was not interested in terrorism, and certainly many people smarter than me and with more experience were warning Bush about Bin Laden to no avail. But maybe there was some role for me to play, however small, that in the larger scheme of things might have made a difference. Instead, I was sitting on my back porch in California smoking pot and trying to figure out how to become VP of Engineering and make $100K/year.

The second feeling was geographic. I like California, but our family was in the East. My Dad had been alone for so long and I saw him only a few times a year. I don't know if I could have done anything to help him avoid his stroke, but it was a lot easier for me to be 3000 miles away than it was for him. In December, a college friend sent me a wedding invitation and I decided to attend, spending the weekend in Boston.

Returning to Boston felt right. It felt like coming home again. I also signed up for a class--one of those executive training things that MIT Sloan School does for product managers. The only thing that accomplished was to convince me not to waste any money on an MBA. While I was here, I walked all over the city and remembered what it had been like to live here in the 80s when I was at MIT. The trip gave me a sense of coming home that germinated an idea in my head, leading me to start looking at job postings in the Boston area.

In April 2002, I saw a job posting for a Boston job that was 1) a perfect match to my skills and 2) involved working for a company that's mission was to help people quit smoking. When I read the description, I could immediately see a whole path before me and I asked my wife, should I send an email on this? If I do, I think we might be living in Boston within 3 months. Would you like that? Yes, yes, yes. So I did and it all worked out perfectly. Phone interviews, a cheap redeye flight, an offer at my desired salary level. Then we sold our house at the peak of the market in California, came to Boston and bought a house in one weekend, my wife transferred from her job to a branch office in Boston, and we were SET!. It was a huge, exciting change--the moment was right and all the pieces fell together to make it possible. We started our new life here in July 2002.

We changed our life by moving and it was the greatest change in our lifes. Career-wise, it did not work out exactly as I had hoped, but I do not regret the move at all. This is the last essay in major choices because the next choice is not yet made--how to deal with my job situation--but it important to see that choice as being a consequence of a larger life choice, a change in values and perspective that necessarily impacts my objective in a career. From this point on, the essays are in the present tense, it is about who I am and what I want to do, because the choice is not complete yet.

That morning of 9/11, I stood out on my back porch in San Jose, smoking a cigarette (I quit in March 2002), I could imagine I heard the sound of a distant horn, the wailing siren, a calling to come back and DO SOMETHING THAT MATTERS. It was at that moment that the passion for engineering web solutions and managing teams to build cool stuff died. It evaporated in the pointless inconsequence of the set of values that had shaped my career in the Internet world became apparent. I'm not saying it was all that bad--it's not that the dotcoms were a rat-race or that I was just a money-grubbing materialist or something. But it was not enough for me to be a part of that world anymore, on the belief that our efforts were really improving the world in some tangential way. At the time, I did not perceive that some passion in me had "died," it was more like I suddenly felt something new starting up. I did not know what it was, but I could see that I was no longer "in the right place." That feeling I had had in 1995 about being in the right place at the right time was gone and I knew I needed to move to find it again.

The job I identified here enabled me to move, but just because the company did stuff that mattered and helped the world, etc. it has not been enough for me. I have been working here now for over 2 1/2 years. I could write a lot of garbage about what frustrates me about my job, but what's the point? It all stems from the fact that I don't have the passion for this business anymore. I need to find what my new calling really is. I have described who I was and I must define who I am and who I will be.