Ignoring the 4-5 years I had a paper route, I started working in retail during the summer of 1987 when I got a job with Bradlees Department Store. I worked there as a cashier/supervisor through 1990, and then quit so I could attend the sophomore semester in Rome with my college, Thomas More. So that's 3.5 years. After I got back, I got a job at Market Basket in June 1991 and worked in the deli through October 1995. That's about 4.5 years, so that's 8 years in retail. Starting in June 1995, I worked for the U.S. Postal Service as a temporary employee doing data entry, working both that job and the supermarket deli until more hours became available for the data entry job. That job wasn't retail work as such, but it wasn't a professional "office" job either (and because the data entry center was always planned to be a temporary facility, it wasn't going to lead to permanent jobs either), so I'm counting it with the retail work. I worked there until June 1998, so that's 3 years, but because of the overlap with the supermarket job it adds only 2.5 years to the non-professional total, now 10.5 years. I knew I was getting nowhere with my job search so I finally quit the postal service and started working through temp agencies. Although the temp assignments were office work, I still wasn't employed full-time on my own as a professional, so I'll count that into the non-professional total too. I worked as a temp for about 8 months before being hired full-time by one of the clients. I'll just round it off and say that's a grand total of 11 years working retail/non-professional jobs.
So, my professional career began in March 1999, working for a construction and engineering management/legal consulting group essentially as a para-consultant. I stayed with them through February 2002, then moved to Seattle and began working in the software industry as a technical writer and editor. My first job ran from March 2002 to February 2003, and my second from February 2003 until March 2007. That's 8 years actually working in offices as a professional. Now that I'm freelance, I no longer work in offices, but it's still professional work, so at the end of this month I will have finished the ninth year of my professional career.
The answer, then, to the dream question is "no, not yet." I've still got another couple years to match. But overall I'm happy with the direction of my professional career, and I'm fairly confident in March 2010 I'll be looking forward to my next 11 years as a working professional.