I’ve gotten a lot of questions from TechRepublic members about the best ways to direct their careers. There is the inevitable certification vs. degree debate as well as questions about experience vs. education.

Since each situation is unique, there is no clear answer across the board. What I’ve decided to do in the coming weeks, however, is feature personal stories from top IT pros as to how they got into IT and succeeded at it. I hope you’ll find these stories useful in making your own career moves.

First up is Jay Rollins. Jay has served as VP of IT/CIO of several mid-sized companies and technology start ups. He has varied industry experience including gaming, media and entertainment, healthcare and ecommerce. I first met Jay a couple of years ago when he was the CIO of Churchill Downs, the thoroughbred racetrack here in Kentucky most famous for hosting the Kentucky Derby annually. Here’s the story of his path into IT:I went to college out of high school but could not afford to continue after my Freshman year so I joined the Navy. I did television and radio broadcasting. I was a news anchor, director, technical director and radio DJ in Alaska and Japan. When I got out, I used the GI Bill to pay for my under grad. I worked full time with the Navy as a civilian public affairs officer responsible for TV operations and went to school full time.

When I was working for the Navy as a civilian I started learning how to build a database in Paradox so we could be more efficient in generating press releases and archiving news stories. During this time I owned my first PC. While trying to make more room on my hard drive so I could play a video game I deleted two files that I thought were unimportant (AUTOEXEC.BAT and CONFIG.SYS). Obviously that was a bad thing to do. I re-built those files over the phone with my father who was a software developer. Once I understood what the various lines in these files were and how they controlled everything about the computer, I realized how straight forward computers seemed. From there, I became the office IT guy as well. That was when they asked me to create the website.

Once I started to learn HTML, I knew that this was the future and quickly changed careers. Upon graduation with a BS in management from UMASS and a couple of websites under my belt, I landed my first IT job as a webmaster. I read a ton of books to teach myself Javascript, ASP, and VB. Basically I went through all the tutorials I could get my hands on and then applied what I learned in what I was developing. The company paid for some training later on where I learned Lotus Notes, Power Builder and Oracle PL SQL. The Oracle training was probably the most valuable for me. Once I understood databases, everything fell into place. About 2 years into my new IT career, I started my MBA and Bentley College in Waltham, MA.

The broadcasting career helped a lot with communication. We were taught to write at the sixth grade level to make it easier for our audience to absorb what we were saying. That carried over into my IT career to help keep the technical jargon down to a minimum and explain technology to non-technical managers in a way that was easier for them to understand.