Getting from there to here
Given my risk averse nature, most people find it amazing that I live my life as a freelance consultant.  I guess, when I sit back and think about it, I do too.  I was thinking about this in detail as I prepared to give a talk for a class at the University of Michigan, to a group of computer science students.

When I finished college (in 1986), I took a job with a medium sized company and worked there for a year or so.  I wanted to be closer to my family and friends, so I found a new job in the metro Detroit area, and moved back.  This job was with a small company but it had a larger, successful sister company.  I left the company when I found out that it was using the sister company to make payroll and was struggling in a time when the rest of the industry was going gangbusters.  Did I mention that I was risk averse?

In any case, I worked for a few years for a larger company, ultimately bought by a huge German company.  I liked my job, but I was trying to go to graduate school at the same time and found that working during the day and taking classes as night was very difficult for me.  I decided to pursue my graduate degree part-time.  This risk averse person quit her job and went back to grad school for two years!  Perhaps that was the first part of the transformation?