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Denny Cherry's SQL Server career -- Is freelancing for you?

Conventional wisdom holds that, to be successful, you have to be a clean-cut, super-competitive, Ivy-league educated power player. Denny Cherry has thrived as one of the best-respected experts in SQL Server by being the opposite of this description. With his trademark waist-length hair, easy-going nature and infectious passion for SQL Server technologies, Cherry is a very familiar sight on the SQL Server conference circuit, delivering talks at TechEd, TechEd Europe and PASS this last year. It can be said with no doubt that Denny Cherry has a very successful SQL Server career.

Cherry's father was an executive at the now defunct tech company Wordplex, so computers were a part of the Cherry household. Cherry says he was probably five or six when he got his first computer.

"I played a lot of games, and we had Prodigy and Compuserve," he remembers. When he was eight or nine, his dad gave him Visual Basic 1, which came with games on it. "It had source code for the games," he remembers, "I spent way more time messing with the source code than I did with the games. That's when I knew I'd end up in technology someday."

No, he did not grow up wearing a pocket protector

Despite his early interest and aptitude for technology, Cherry was not exactly a teacher's pet.

"I was a horrible student," he remembers with a laugh. "If it weren't for band and theater, I probably would have had a two- or one-point-something GPA."

School did influence him in some ways, though. His district had a required typing class where he fondly remembers using the Apple IIE, and he took an advanced computer skills class twice in high school because, as he remembers, "it was fun." Both teachers who taught the class were very encouraging of those who wanted to go into any computer-related field. However, "I didn’t go to college at all," says Cherry. Instead, he began working right out of high school.

His first job in the technical field was for Earthlink, taking tech support calls from customers. Eventually, he began calling back customers who had requested assistance with escalated issues and problems. He noted that his team used a paper-based system for scheduling call backs rather than an automated one. Cherry saw room for a process improvement. "I built something in Access that would let supervisors figure out if a slot was available for a callback," he recalls. The new system was a success for his team, and got management's attention.

At the time, Earthlink was forming a new reporting group, which they asked him to join. Literally overnight, he went from call center staff to database engineer. "I knew data, and I knew how to program," he says. He built an automated call-center staff monitoring and reporting application, first based in Access, then in SQL Server. What sparked the love affair between Cherry and SQL Server? "I got into it because it was easy. I tried other options, and it just was not happening with them. SQL Server just worked."

Cherry's last corporate job prior to freelancing was with Awareness Technologies, which makes employee monitoring software. "Very 'Big Brother,'" laughs Cherry. After being laid off, he decided to strike out on his own. Networking helped keep himself afloat. "Like, half my friends are consultants. They were able to feed me some work when it was extremely important, and I just kept doing it." He never looked back. 

Ahhhh, the freelance life...not

Cherry says the greatest challenge of being a full-time freelancer is finding clients. "There are lots of consultants out there," he says, "but fortunately, there's also lots of work.... It's just a matter of getting the right two people talking to each other." His other major challenge? "The whole life-work balance thing -- that sometimes gets a little screwed up."

What's a typical day in the life of Denny Cherry? "It's surprisingly boring. I check my email, see what's coming in from clients. Check the website for new requests for consulting. I then check on projects in the works, see what needs to be done on them. It's a lot like being a DBA [database administrator], really."

For more on SQL Server careers

Why you should consider a BI SQL Server career path

What Kilt Day at PASS says about SQL Server careers

Freelancing has been good to Cherry, but would he recommend it to others? "Some people. It takes the right kind of person to want to be a freelancer and deal with all the stuff that comes along with it. As a freelancer, you're also a lawyer, an accountant, a negotiator and probably a bunch of other things."

What other advice does he have for young geeks looking to follow in his footsteps? Make sure you're in the right field.

"I hear all the time 'I want to go into IT and make a lot of money.' What part of IT are you interested in? 'I'm not ...' Don't do it. You won't enjoy your career; you won't enjoy what you do you; you won't enjoy your life. You won't be one of the guys at the conferences who's having a good time."

Would Mr. Denny ever go back to a corporate 9-to-5 job? The very suggestion brings a loud groan from Cherry. "God I hope not … I had to drive in rush hour the other day and just wanted to die." What would it take to coerce him back into a suit, tie and cube? After a pause, he responds, "The appropriate size Brinks truck full of money." Denny Cherry, though, seems content to enjoy his professional life as a solo artist.


This was first published in December 2012

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