Sara Jackson-Holman Thursday, June 3

You think playing pop music is scary? Try classical piano competitions.

IMAGE: Christa Taylor

[SINGER-SONGWRITER] Sara Jackson-Holman tenses up when she thinks about her musical past. Although she is now a singer-songwriter, for years her onstage experience was limited to classical piano competitions. So she recalls the crushing silence between performances, hearing critical whispers in the audience and the sound of judges scribbling on notepads.

"It's not an unfriendly atmosphere, but it's very cold," says the 21-year-old Portland-born chanteuse over the phone from her current hometown of Bend.

Things are a bit different today. When You Dream, Jackson-Holman's debut, is certainly the work of an accomplished musician, but it's a long way away from the rigid artistic environment she grew up in. The disc's jazzy compositions—alternately whimsical and swooning—have a warm, playful quality not far removed from that of Feist, for whom the singer's gentle wisp of a voice is a dead ringer. Suffice to say, it's hard to imagine a crowd sitting in quiet judgment after hearing these songs.

As an instrumentalist, Jackson-Holman started young. She was only 6 years old when she first tinkered on her great-grandmother's piano; she later joined a choir, where she discovered her voice. When it comes to writing songs, however, Jackson-Holman was a bit of a late bloomer. "My mom had told me previously that she thought I should write music, and I said, 'No way, that's not my thing,'" she says. It wasn't until she went away to college in Spokane and got exposed to a heap of new music—as well as the romantic busker drama Once—that she finally decided to try creating her own material. Combining her talents as a pianist and singer with her love of self-described "English nerd things," Jackson-Holman soon found herself evolving into a legitimate artist. "I just had to build confidence, and be at the right place and hear the right music," she says.

Still, even as she began to play out at coffee shops and upload recordings of her songs to the Internet, Jackson-Holman didn't seriously consider doing music as anything more than a hobby. Then last June, she posted a comment on Blind Pilot's MySpace page—just "a typical fan post," she says—that caught the attention of Portland's Anthony McNamer, president of the band's label Expunged Records. He listened to her demos online and offered to put out her album. Jackson-Holman spent the summer writing, then went into the studio with producer Skyler Norwood of Team Evil and Point Juncture, WA (who has also worked extensively with Blind Pilot). Now, on the eve of her record release show, where she will be supported by an all-star backing band featuring Norwood and members of Blind Pilot, Horse Feathers and the Decemberists, and a small summer tour, she is preparing to enter a new phase of her musical life—one where she's not simply being judged, but encouraged.

"At first, it was really scary to write things and put it out there. But audiences in general really want you to do well as a performer," she says. "They're really forgiving."

SEE IT: Sara Jackson-Holman releases When You Dream at the Woods on Thursday, June 3, with On the Stairs and Team Evil. 9 pm. $7. 21+.

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