A certain level of burnout with my job at Microsoft made me loath, or at least unmotivated, to seriously consider moving around within the company as my situation became more frustrating. It just wasn’t what I wanted.

I did spend some time looking around at similar jobs both inside and outside the company, and I tried to keep my mind open to staying, because, as I had long realized, I would need more money to realize most of my other ambitions, and it was a very lucrative way to collect savings toward that end. An alternately charming and sleazy career consultant told me the same when I confided in him that I was looking for something very different than I was doing.

Four of my long vacation trips to Japan during my Microsoft career coincided with professional crises. The first one, my first actual vacation as a Microsoft employee, wasn’t really planned to occur under such circumstances; a power struggle between two managers placed me in a frustrating position, and I had a long-planned vacation that my manager didn’t tell my new manager about, departing only a few days before I was being acquired by the new team in some sort of deal between them.

It was an awkward position to be in, but my new manager considered the information omission an error on the part of of my old manager and asked me to take my vacation as planned. During that trip, I was full of torn loyalties, feelings of disappointment, and apprehension. But my vacation, which was an incredible first experience in Japan, and my first trip outside of North America after my exchange program to Germany, gave me a lot of time to think about my future. It actually was the catalyst for a fledgling addiction to collecting contemporary Japanese ceramics, and expanded my culinary consciousness incalculably.

Over the next 6 years, my other three long vacations were very similar, although both of those vacations I took because I was frustrated at work, and wanted a distraction. It turned out that vacations were quite therapeutic, and even my short few extra days here and there that I got on business trips to Japan or elsewhere were extraordinarily refreshing.

I had the time to stop and take pleasures in basic human needs… good food, interaction with people, conscious moments of relative tranquility.

Strangely, it took me over a year to go on such a vacation again after my career frustrations began to mount. Before that, I spent more time than was probably healthy essentially fantasizing about alternative careers.

I felt really frustrated, and I had some self-destructive impulses… I thought about just walking off from my job without notice and burning some bridges, much like one of my employees did (the same forces that led me to consider leaving hit him harder, since I was deflecting some of them until he was moved under a different lead, and was used to certain kinds of irritation that were less tolerable for him). I had a few short-lived relationships where I was essentially completely emotionally unavailable and surely a source of other kinds of frustration for the women I was seeing.

I took refuge in my obsessions… I cooked a lot of elaborate meals for friends and acquaintances, refining some of my cooking skills. I spent a lot of time in pottery classes, considering early on the possibility that I might import some ceramics, and I thought it would be smart to have some first-hand understanding. Those pottery classes were also suitably humbling, as I did not have a natural talent and I sent a lot of clay flying. I also spent some taking Korean classes, remembering a college-era ambition of learning at least seven languages in my lifetime.

Early on, I started thinking about projects that I could indulge in with great passion, with some prospect for financial reward. I considered some restaurant projects, a small retail shop, and a more wholesale-focused import business.

In Part III, I’ll talk about how I evaluated the potential of these projects.