In the spring of 2007, I moved to Seattle along with the other three devastatingly good-looking members of my band. A year and a half later, after endless months of cripplingly horrible shows, desperate attempts to cobble together part-time jobs, and Oasis-worthy internecine squabbling, one of us finally broke.

"Guys," our guitarist said one night at a band meeting, "I'm gonna play out the shows we have booked, and then I'm done. I can't keep going on like this."

We had thought that moving to a bigger city might help actualize our dream, never mind the fact that we knew exactly one person in Seattle. Emboldened by a blissfully naive confidence, laughing off the idea of vitamin D deficiency with quips about Flintstone vitamins, we had disentangled ourselves from our sleepy California town, packed our minivan, and driven north into the leprous arms of impending doom.

We played our Seattle debut the week we arrived, a show I'd booked from out of state. Our ignorance as to which clubs (not) to play was profound. On that first night, we found ourselves unloading a trailer full of gear into the friendly confines of the Central Saloon in the teeth of a driving rain. An hour and a half later, we'd performed a full set of contemplative indie rock for the bartender and our single friend, been blasted with jock metal for every second of the experience we weren't actually playing, and seen our group morale sink to previously unimaginable depths.

You'd think this holocaust of a coming-out party would have led to a tempering of my freewheeling booking strategy. Fool me once, and all that. Instead, I continued to engage in shameless, ill-fated MySpace binges, hitting up reputable bands (Thao with the Get Down Stay Down, the Cave Singers, even—oh, good grief—Fleet Foxes), none of which I ever heard back from. I imagined them lazily scrolling through their inboxes while eating oysters purchased with the sort of royalty checks I would never see, skimming my pleas while thinking, Who're these assholes? They only have two plays today.

So it went. Playing a community center in Kirkland for a crowd with an average age of 12? Check. Agreeing to play a "festival" that turned out to be a Mennonite farmers market in Central Washington at 11 in the morning? Double check. Having the bartender at the Comet Tavern put on an extreme grind record in the middle of our final song because he didn't even realize we were still playing? If it hadn't happened to me, I wouldn't believe the story.

Ours were trials robust enough to shake the faith of even the most committed troubadours. Which we weren't.

After a while, I had to wonder: Was this the dream for which I'd given up my job, the comfort of my mother's green-bean salad, a chance at making out with Genevieve Flaversham? In hindsight... I guess it was. Nobody had guaranteed us anything. True, people had told us we had a spark, a great live show, a facility for interesting arrangements. Who cares if half those people were our parents? Who were we to argue?! We believed in the pot of PBR-soaked gold at the end of the Sub Pop rainbow. We had been drunk on the idea of making it as a band.

They say that what doesn't kill you makes you stronger. If there is some fantastic mathematics through which debt, relational strain, public humiliation, and endless frustration may be transmuted into strength, then I'm Hulk Hogan. That may be. But for a long time—and I say this with real regret—I got a bitter pinch in my stomach every time I heard about the buzz springing up around local bands we'd played with or that I thought we were at least as good as, whatever that means.

I can still remember a party I attended in the fall of 2004 at my friend's Orange County ranch house. I was milling among a throng in the backyard, when a group of four young men emerged from the house and picked up some instruments leaning against the toolshed. Unbeknownst to me, I'd shown up at what turned out to be the first show ever put on by my soon-to-be-famous schoolmates Cold War Kids.

Over the next several years, I fawned over the band publicly while whining in private. Why did the Cold War Kids of the world get to strut like beautiful flamingos across David Letterman's stage while I was trying to convince the bartender at Chop Suey to let me have a bottled water? Hadn't we worked our asses off? Weren't we paying our dues? The deck was stacked against us! I mean, how could we make connections when we were locked in the basement four nights a week writing songs with hooks so dreamy Ben Gibbard could only fantasize about them? He had Zooey to comfort him. I only had bandmates I'd grown tired of seeing, a house with no central heating, and a hamper full of dirty clothes the smell of which permeated my bedroom so profoundly that I was often kept awake at night—as much by the smell of moldering long johns as by my endless second-guessing of our decision to leave Santa Cruz.

It's been almost three years since we broke up and no answer to my questions has been forthcoming, unless of course you count my growing awareness of how grotesque my sense of entitlement was. Part of me seems to have assumed that I had the right to be paid to play music. Turns out that's not how life works.

I still find myself occasionally pining for the sour-beer smell of a club before it opens, a greenroom fridge full of skunky Heinekens, and a 40-minute time slot. Alas, our bass player moved back to California, where he now works nights in the vast walk-in refrigerator of the local Safeway. Sometimes I imagine him stocking gallons of 2 percent milk in that freezing, dark cavern that smells like a mausoleum, and I wonder how big a cemetery you would need to inter the savaged hopes, burned-out dreams, and low-quality merch of all the forgotten bands that've ever played the High Dive on a Monday night.

Ben Bishop is the former pianist and singer in Caravel.