"The thing is—and this might sound Oprah-esque—but if you don't ask, you don't know," says William Bernhard. "And if you don't try, you don't know."

The 39-year-old Bernhard, who spent his early Seattle years struggling as a barista and aspiring singer-songwriter, is the kind of guy more likely to ask why not than why.

That approach made him persist in getting former Best Kissers in the World frontman Gerald Collier to audition his old group the Superstitions as a backing band—a move that uncovered some undeniable musical chemistry. It also led him to suggest releasing an album's worth of hidden gems from that band's heyday (Collier's recently released How Can There Be Another Day?) and to pull off the impossible—getting Collier, bassist Jeff Wood, and drummer John Hollis back together for a couple of shows last year after an acrimonious parting almost a decade ago.

Bernhard's persistence also rubbed off on his other musical project, Sky Cries Mary—another beloved Seattle band from the '90s that ended prematurely. What started two years ago as a couple of live reunion shows to celebrate getting the rights to the band's material back turned into the release of a live album. "We'll see what happens after that" turned into a new album, Small Town, which comes out in mid-June.

Like many musicians, during his younger years, Bernhard had a dream of making it in music. Now, as he stares down 40, that vision has altered substantially. He's resigned to no longer making a living as a musician, but music is still an essential—if not primary—element.

"For me, things kind of moved along," he explains. "I have this wonderful person in my life who I've been with for 10 years and she's always wanted to be a doctor. And you start to realize it's not all about me and being in bands and playing these shows. I have to accommodate this other person—not under duress but because I want to. So that changed my focus on music. And music for me is far more enjoyable now than it was 10 or 12 years ago because I don't care," he laughs.

That's not apathy, it's freedom—and it's allowed Bernhard to delve into another passion: writing. Prompting from his wife led him to take a class while the couple was living in Portland. The teacher was David Biespiel, a noted poet and editor of Poetry Northwest, one of the preeminent poetry magazines in the United States. Bernhard, who's been a web designer for the past 10 years, volunteered to create a website for the publication. In typical fashion, one thing led to another—in this case, returning to school to pursue a Master of Fine Arts in poetry.

"It's kind of one of those things that was 'if not now, when?'" he says. "It's weird to be like, 'Okay, I'm going to change everything in my life in a few months and I have no idea what that looks like, but I have to do it.'"

It was a near-death experience that provided the impetus for Bernhard's life-grabbing philosophy. In 1990, he was involved in a serious car crash—fatal to the driver—and has seen the world quite differently ever since.

"I'd just read Camus's The Myth of Sisyphus, and it was one of those books where you're going, 'This guy is saying everything I've always thought and I've never been able to articulate,'" he says. "This whole idea that it's your life and maybe it makes no sense, but it's yours. Maybe it has a terrible ending, but it's yours."

Bernhard laughingly acknowledges that he's going to be "really fucking broke" when he returns to school in the fall. And while he'd love to see the Sky Cries Mary album do well here and finally get a fighting chance in Europe, he relies on nothing and no one but himself for happiness.

"You have this one life, as far as I know, to do the things you want to do," he says. "I don't want to be lying on my deathbed going, 'I wish I had gone to graduate school.' Because I'm not going to be lying there going, 'I'm sure glad I didn't miss that meeting at work.'"