It's been a great time for job advice in the geospatial community. Many of the recent posts at GeoHipster focus on career care and feeding. One interviewee, Thierry Gregorius, went so far as to offer even more details about the GIS career path. James Fee tells techies what languages are hot. Nathan Heazlewood explains how to Plan your GIS Career on LinkedIn. And, over on Reddit/GIS there are career and education questions patiently answered nearly every day. I've written and podcasted about job skills and job hunting over the years (1, 2).
What we tend to talk about less is being happy with the jobs we ultimately select. The luckiest among us are happy during most of our working lives. I consider myself one of those people. I wish I could say that was by design, but it's not. It's a bit of luck and bit of learning along the way.