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I've written a bit about how I started as Guy In A Cubicle and eventually transitioned to Dotcom Thousandaire, running S3stat and Twiddla: http://www.expatsoft

I've written a bit about how I started as Guy In A Cubicle and eventually transitioned to Dotcom Thousandaire, running S3stat and Twiddla: http://www.expatsoftware.com/articles/guy-on-the-beach-with-a-laptop.html http://www.expatsoftware.com/articles/guy-on-the-beach-with-... The short version is moving to Contracting, then Consulting Remotely, then Building Products while doing same, then learning how to Market them. With a good helping of Living Cheaply thrown in to keep the burn rate down. It's a nice way to go about it, since you never need to worry about running out of money, and you can move at whatever speed you like since there's always a "day job" supplementing the product revenue. Even better, since the business is built to run in the background while working elsewhere, once you turn off the "working elsewhere" part, you're effectively retired.

pinchharmonic 9y ago
How did you deal with seeing family? Also, at what age/technical ability did you take the jump? I feel a bit of "impostor syndrome" when I think about going off and trying to do contracting work (I'm age 25 with a little experience making CRUD web apps and some standard backend work for a bank). Thanks!
- jasonkester 9y ago
  I think I was around 30 when I started doing the travel, contract, repeat cycle. By then I had established a reputation for being good at building things and a handful of good contacts at places that needed work done from time to time. Job hopping helps with the impostor syndrome thing, which everybody has to a degree. After half a dozen stints at different companies each telling you that you're good at what you do, it eventually starts to sink in. It also helps prove to you that you can in fact pick up work quickly when you need it in this industry (usually including a nice rate bump). And of course, the more people you work for, the bigger the list of "ex-bosses friends building a team" becomes, and with it the pool of options for future gigs. Good luck!

pinchharmonic 9y ago

How did you deal with seeing family? Also, at what age/technical ability did you take the jump? I feel a bit of "impostor syndrome" when I think about going off and trying to do contracting work (I'm age 25 with a little experience making CRUD web apps and some standard backend work for a bank). Thanks!

jasonkester 9y ago
I think I was around 30 when I started doing the travel, contract, repeat cycle. By then I had established a reputation for being good at building things and a handful of good contacts at places that needed work done from time to time. Job hopping helps with the impostor syndrome thing, which everybody has to a degree. After half a dozen stints at different companies each telling you that you're good at what you do, it eventually starts to sink in. It also helps prove to you that you can in fact pick up work quickly when you need it in this industry (usually including a nice rate bump). And of course, the more people you work for, the bigger the list of "ex-bosses friends building a team" becomes, and with it the pool of options for future gigs. Good luck!