Dropped out of college at age 19, bounced around from job to job, knocked up a girl when I was 22 and she was 18. Went back to school and got an Associate's Degree in Network Administration. Knocked up same girl (now my wife) again while I was still in college. Oops. Graduated at age 27 and got a job as a Jr. Linux System Admin. Worked for 4 years in various Admin roles as a shy nerd. Got my VMware cert in 2010 and was laid off later that year. Decided to move from South Dakota to the Twin Cities, found work at a VAR as an implementation engineer, then moved into some pre-sales, and eventually went 100% pre-sales. Now work as a sales engineer at a storage company.
Today I'm 37 and my pay has grown by over 5x since my first job. Pushing for it to exceed 7x this year after getting a small promotion this month. Escaping the cubicle and leaving my comfort zone has been the best thing ever for me personally and professionally.