After university, I had interviews with both Forbes and Variety. Of course, more people want to write for Variety and I got the job at Forbes. So you could ask: what if I had got a job at Variety? There was someone in my class at Harvard called Frank Rich. He's now a New York Times columnist and wrote theatre reviews for years. In a sense, I wanted to be him. Interestingly, he is now writing about politics and the role of the internet. So had I got the Variety job, I'd have become very involved in the entertainment business and the internet. I might well have ended up exactly where I am now, but I'd have come to it through the business of entertainment rather than the business of business.
There are certainly investments I could have made but didn't, and some I did make that I shouldn't have. None where I think: 'God, that changed my life.' I've invested in companies that have failed, but with one exception I still like the people, so I don't feel it was a complete waste. The money was wasted perhaps, but the friendships and learning were real. My e-mail signature file says: 'Always make new mistakes.' In some sense, I've never made a decision – the path has always presented itself clearly, but I flatter myself that it presents itself earlier to me than to most people. I have a good feel for what is interesting and important.
If I had to start again, maybe I'd spend a little more time on the beach, but I'm pretty happy. My advice is: do something where you can learn, that excites you, and don't worry about it too much because you can always change. Measure success by your own criteria. Do something that makes you happy that is also worthwhile. I'm lucky – not everybody is made happy by something that is worthwhile and also pays well. If you're lucky, enjoy it. If you're unlucky, figure out how to change it.
Esther Dyson is chairman of EDventure Holdings, which publishes the tech industry newsletter Release 1.0. She was chairman of the ICANN board 1998-2000