Walking Away From the Money at Microsoft

Eleven years ago, I made a list of the happiest periods in my life, and I realized that none of them involved money. I realized that building stuff and being creative and inventive made me happy.
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From Delivering Happiness: A Path to Passion, Profits and Purpose by Tony Hsieh.

A bet is a bet. If I lose a bet, I always pay up.

On graduation day in college, my friends made a bet with me. They bet that I would become a millionaire within 10 years, and if it happened, then we would all go on a cruise together, and I would pay for everyone's trip. If it didn't happen, then we would still go on a cruise together, but they would pool together and pay for my trip. To me, it seemed like a win-win situation: either I would be a millionaire or I would get a free cruise. Either way, I would be happy, so agreed to the bet.

It was early 1999, and we all flew to Florida to take a three-day cruise to the Bahamas. I decided to invite some of my other friends as well, so we ended up with a group of about 15 people. I had never been on a cruise before, so I was pretty amazed at how big the ship was. There was a nightclub, ten bars, swimming pools, and five all-you-can-eat restaurants. We had a great time drinking, eating, partying, and then drinking, eating, and partying some more. It was like a mini college reunion, without all the boring parts.

We all decided to go to the nightclub on the final night of the cruise to drink and dance the night away. In the eyes of all my friends on the cruise, I was everything that they thought defined success and happiness. My friends commented that I seemed more self-confident and congratulated me on selling the company to Microsoft. [I sold LinkExchange, a web-based advertising company, to Microsoft in 1998 for a $265M.]

At 1:00 AM, the DJ announced that it was last call, and that the bar and club would be shutting down soon. As everyone headed to the bar to get one last drink before the night was over, I stood by myself for a moment to avoid the rush and to take in the moment. If someone had told me four years ago that I would be a millionaire and on a cruise ship celebrating, I would not have believed it.

Yet, as the drinks flowed, the music pulsated, and friends cheered and toasted one another, a nagging voice in the back of my mind repeatedly brought up the same questions that had been there ever since the silent walk with Sanjay back to the office the day the Microsoft deal closed: Now what? What's next? And then there were the follow-up questions: What is success? What is happiness? What am I working toward?

I still didn't have the answers. So I went to the bar, ordered a shot of vodka, and clinked glasses with Sanjay. Figuring out the answers could wait until later.

After the cruise, I felt like I was on autopilot: waking up late, making an appearance at the office for a few hours and checking my e-mail, then heading home early. Every once in a while, I'd skip going to the office altogether. I had a lot of free time and I didn't know what to do with it. So I had a lot of time to think. I'd already bought all the things I wanted: a place to live, a big-screen TV, a computer, and a home theater system. I started going to Vegas every other weekend to play poker. I wasn't playing for the money. It was about the challenge of figuring out how to beat the game. Poker is the only casino game where you're playing against other players instead of the house, so as long as you're better than the average player at your table, you actually can win in the long run.

But most of my free time was spent just being introspective and thinking. I didn't need more money, so what was it good for? I wasn't spending the money I already had. So why was I
staying at Microsoft, vesting in peace, trying to get more of it?

I made a list of the happiest periods in my life, and I realized that none of them involved money. I realized that building stuff and being creative and inventive made me happy. Connecting with a friend and talking through the entire night until the sun rose made me happy. Trick-or-treating in middle school with a group of my closest friends made me happy. Eating a baked potato after a swim meet made me happy. Pickles made me happy. (Although for that one, I'm still unclear why. I think it's just because they are obviously delicious and I enjoy saying "pickles.")

I thought about how easily we are all brainwashed by our society and culture to stop thinking and just assume by default that more money equals more success and more happiness, when ultimately happiness is really just about enjoying life.

I thought about how I enjoyed creating, building, and doing stuff that I was passionate about. And there was so much opportunity to create and build stuff, especially with the Internet still exploding, and not enough time to pursue every idea out there. And yet here I was, wasting my time, wasting my life, so that I could make more money even though I had all the money I ever needed for the rest of my life.

A lot was going to change about the world. We were on the eve of not only a new century, but a new millennium. The world was about to change in a dramatic way, and I was about to miss out on it so that I could make even more money when I already had all the money I would ever need.

And then I stopped thinking to myself and started talking to myself: "There will never be another 1999. What are you going to do about it?" I already knew the answer. In that moment, I had chosen to be true to myself and walk away from the all the money that was keeping me at Microsoft.

A few days later, I went to the office, sent my good-bye e-mail to the company, and walked out the door. I didn't know exactly what I was going to do, but I knew what I wasn't going to do. I wasn't going to sit around letting my life and the world pass me by. People thought I was crazy for giving up all that money. And yes, making that decision was scary, but in a good

I didn't realize it at the time, but it was a turning point for me in my life. I had decided to stop chasing the money, and start chasing the passion. I was ready for the next chapter in my life.

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