My Microsoft Years: Fortune and Misfortune


I was hired by Microsoft in 1990. When some people hear that, they assume I have millions from all the stock options given out at that time. I wish I did.

The atmosphere at Microsoft was inspiring. I felt like I was part of the personal computer revolution. When I left the company for the first time, Windows 95 was just released, and Microsoft was flush and famous.

They expected a lot from us, but team spirit was high. We had access to the latest technology. There was a real sense of camaraderie.

We had meetings in places like the Jacuzzi at Microsoft’s sports club or while hiking in the nearby mountains. Beer, wine, and catered food flowed down the halls for almost any reason, all to keep us going and making our deadlines. Many a Softie (not me) slept on an office futon or under their desk.

There were small kitchens located around the halls. They were stocked with drinks, all free. There was also plenty of good and inexpensive food in each building cafeteria. We never had to leave the Microsoft campus. That was the point.

The abundance of money included impressive bonuses as well as stock options. The vesting time for the options was four and a half years. After this time you could exercise the options or let them grow in value (as they did continuously back then).

Along with the money, there were extravagant presents handed out at company meetings, such as engraved stadium blankets, a kit of expensive emergency car tools, nice camping supplies, and lots of product t-shirts and coffee mugs.

The Christmas parties were lavish. I remember going to one just a month after I started working at Microsoft. The company had taken over a huge convention center and there were white balloons everywhere, a huge ice sculpture, a canoe filled with shrimp, and stations of free food and alcohol. During my second Christmas party, there was even a dedicated children’s room with carnival rides. In other rooms, different bands played. I could barely take it all in.

Of course, there were also the down sides. The work could be so demanding and expectations so high that at times it was hard to keep up. But we did, in part because of the “golden handcuffs.” This was a term used to describe the practice of keeping employees from leaving the company, due to the millions in stock we might lose if we did.

Some of my co-workers who vested their stock options and realized their millions left to retire at an early age or start a new venture. It was a stunning example of what I could do as well. To me it felt like magic.

Shortly after I left Microsoft as an employee in 1995, the lure of the company pulled me back and I returned as a contractor until 2008. There weren’t the same perks, but I still had the stock money I made during those early years. I thought it would never end, and had a blast spending almost all of it. It’s by far one of my biggest regrets.

Still, I know how fortunate I was to have lived through that special time and have had all the money to lose. Unfortunately, I don’t think I will ever experience that kind of excess again.

1 Comment

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One Response to My Microsoft Years: Fortune and Misfortune

  1. joNo Gravatar

    ALL so true! Nice summary.

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