This article originally appeared in the November 2015 issue of 425 Business.

Greg Jackson’s musical happy hour

Greg Jackson always has wanted to be among the stars. Growing up in Chicago, he dreamed of becoming an astronaut and soaring into space. These days, his dreams are slightly more down-to-earth: Jackson wants to be a rock star.

The software engineer started singing formally (beyond belting it out in the shower or along with the car radio) about nine years ago, when a pal at Indiana’s Rose-Hulman Institute of Technology asked him to join a choir because there was a shortage of male voices. After graduation, Jackson relocated to Kirkland for an internship at Microsoft. When he got to the Eastside, Jackson learned the shortage of male choir members seemed to be a nationwide crisis — his manager asked him to join the Redmond Chorale for the same reason.

“There definitely seems to be a theme, because Redmond Chorale was in need of more guys to join the group,” Jackson said. “It was great, because I was looking for a way to get involved and be part of the community.”

The Redmond Chorale is a semi-auditioned performance group that partners with local charities to raise money for a variety of causes. This holiday season, the chorale is partnering with Cancer Lifeline.

“We sing everything from traditional to pop. Each season is pretty different,” Jackson said. “We’ll start practicing Christmas songs in August, so those can get old pretty fast, but our director does a good job at picking songs, so we don’t have to be stuck singing ‘Rudolph the Red-Nosed Reindeer’ all the time.”


Greg Jackson regularly performs solo acoustic shows at Caffé Rococo in Kirkland.

Being a part of the choir has helped Jackson ease his stage fright. “I think it’s all performers’ dirty little secret,” Jackson said. “It’s not about getting rid of that feeling, but turning it into energy and being solid enough in what you’re doing. You have to learn how to make a mistake and still be able to keep going.”

Jackson was hired by Microsoft after his internship ended. Two years ago, he decided to make the daily commute across the lake to work at Amazon. He enjoys his job, and said work-life balance is easier to achieve at Amazon than most people believe. “It’s easy to move my schedule around if I have performances I need to get to,” Jackson said. “The flexibility of having a tech job is great to support my hobbies.” Since his foray into the choir world, Jackson has added a few more musical projects. He previously played in a ukulele band that covered Christmas and pop songs. He recently formed a four-member alternative rock group called Side of 9, which is working on a mix of covers and original music.

“The process of bringing a song to the band has every member contributing his own personal flavor to the song,” Jackson said. “So everyone’s hand is definitely in everything we do.” Jackson’s strength is writing lyrics.

Jackson also has a solo act with a folk-rock vibe. His favorite songs to sing are classics like “Blackbird” and “Hallelujah,” or his original composition, “Blessings.” Another of his original songs harkens back to his astronomical childhood dream — it is about an astronaut floating alone in space.

“Practicing and performing lets me do something very different from how I spend the rest of my day,” Jackson said. “It’s nice to have something productive to do that doesn’t make me feel like I’m back at work.”

Jackson says he performs his solo act about once or twice month. His favorite venue is Kirkland’s Caffé Rococo. “It’s nice and cozy, kind of like performing in someone’s living room with a bunch of friends,” he said.

Jackson has worked hard to hone his musical craft and encourages everyone to get in on the act.

“I am a firm believer that everyone who isn’t tone deaf can sing. It’s a matter of technique and a skill set,” Jackson said. “I’ve seen so many people who have gone from only being able to hold pitch to a good singer. Effort is the most important thing.”