The last couple of days I’ve read some very wise blog posts. My Google Reader is filled with tech entrepreneur and VC blogs. These people are very smart, but I wouldn’t call them “wise”. On Monday Mark Suster did an incredible post on happiness, “Life is 10% How You Make it and 90% How You Take it.” The next day Jamie Siminoff followed up with another awesome post, “The Lottery of Statups.”

Both of these guys are incredibly successful entrepreneur’s from my perspective. They’ve built and sold companies for millions. But neither of them is a grandslam entrepreneur who has taken a company public or sold it off to become a billionaire. Reading their posts it’s clear that that is of no significance at all. Both of them are incredibly happy. They lead fulfilled lives. At the end of the day would you rather be a millionaire with a great family, awesome job, and content existence or a billionaire with an estranged family, stressful job and miserable daily life?

This is an important lesson for young entrepreneurs like myself. Talking with a mentor recently I said, “I was supposed to be running the world by now!” Starting your first business right out of college or after a few years working (as I did) can yield sky high expectations. As a first time founder you have yet to be weathered by reality. This is a good thing in someways because it keeps you going where others would quit. But it can also lead to disappointment, as it did for me. Looking back on the projections for TaskUs I was supposed to be a millionaire by now.

So why am I happier now than I have ever been? I choose freedom over glory. My life is no longer about becoming a multi-billionaire. Instead I want happiness. This isn’t an esoteric take on happiness. Happiness for me is freedom. That includes financial freedom, having enough money to never have to think about money. But it also includes psychological freedom, having enough perspective to never obsess over the irrelevant (while realizing its all irrelevant).

Last week I tweeted the trailer for the new film The Social Network (the story of the founding of Facebook). In the tweet I called Zuckerberg the most successful entrepreneur of our generation. I’ve wrestled with this since. If measured in terms of dollars and cents he is without a doubt the most successful. But if you measure based on happiness and freedom, I think I’d give him a run for his money.

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