1. Go in to the Internet space
I was doing Office installations at an insurance company when I read that the Heaven Gate Cult had all killed themselves. What struck me was the massive mansion they owned, all earned by web development. That month I started my own Internet company.
2. Staying in the Internet
It seems odd now but in 2003 I had to clean up my CV to remove references to web and Internet. Against the market trends I kept my faith in the long term potential of this technology, and didn't go in to real estate or banking.
3. Staying out of finance
4. Going in the SharePoint
The 2003 product was a bit, well bad. At my job at the time no one wanted to have anything to do with it, so the roll-out of a multi-million pound SharePoint deployment just landed in my lap. As long as I billed time on other work I could promote, train and support SharePoint. Best technology bet of my life.
5. Going with Microsoft
In 1999 most people working in the web were Unix Apache people. Good technology, with Java even better. Easy to deploy and maintain? No. Microsoft stack has had great success in that area.
I have been "singing" my praises for this amazing piece of technology.
7. Tiny Linux Laptops
You can confirm this with my wife if you like, I have been converting old and small laptop to Linux for a couple years now seeing the future in a small light laptop. I know have built about 3 and own one very small one. They are going to play a big role in the futue. If only Microsoft had read my blogs.
I knew it was a dog first time I saw it.
9. Jorn Barger
Just because I agreed with everyone that he was something of a nut case was no reason not to religiously read his blog.
And when I was wrong
1. Telling someone who knew the facebook founders the field was too crowded and had no potential.
2. Dismissing .NET 1.0 as a fad and not training up before it came out.
3. Not understanding how .NET is kind of a fad, and how companies and public sector agencies still depend on ASP sites written in VB6.
4. Not getting a Second Life account in 2003. My first avatar was in 2005. I have gotten to see everything important but not the founding days.
5. Building a small Pearl "blogging" tool in 1998, using if for myself and my friends, and then forgetting about it. SUPER DOH.
6. Userland Frontier, not sure about this one. I learned a lot in the late '90s about web content management but I was sort to wasting my time on a tool.