When Can I Start? How to Lose a Job and Gain a Personality, the latest memoir-in-essays by Joseph Lezza, is a darkly funny exploration of unemployment, identity, and the absurdities of the American job market. Framed as a board game, Lezza chronicles years of job applications, rejections, side gigs, and existential crises while questioning why we tie so much of who we are to what we do for a living.
Lezza is the author of I’m Never Fine: Scenes and Spasms on Loss, and his work has appeared in Slate, Longreads, The Massachusetts Review, and elsewhere. When Can I Start? will be published by Vine Leaves Press on January 27, 2027.
Debutiful is honored to reveal the cover of When Can I Start?, designed by Jessica Bell. Below, Lezza discusses transforming the chaos of unemployment into a board game, drawing inspiration from classic tabletop games, and how the cover’s playful yet sinister imagery captures the unpredictable experience of searching for work.
While writing the book, did you have any ideas for what you wanted the cover to look like?
Only a few dozen. I tried to keep them at bay, however, until I was sure the framing device (gaming device?) was one I was going to stick with. And, I’d say I wasn’t sure until about halfway through the writinng process. Actually, at first, I envisioned writing the book as a set of instructions for a nonexistent game. But, then, I recalled how instructions are seldom adhered to, if they’re even read at all. And, those are usually only a few pages. So, who the hell would want to read 300+ pages of instructions? Some deviant? Some sick freak? Not on my watch.
So, that idea was jettisoned rather quickly. Once it was, I got to have a lot of fun translating the reality of the American job market into classic game tropes; the board, the pieces, the state of play. And, it became obvious that the cover would have to reflect that, not unlike the boxes that housed our favorite tabletop games. I knew I wanted the cover to be evocative of that experience, daring the reader to snatch it off the shelf and shake it to hear the bits and bobs rattling around inside.
Can you explain what the design process was like once you started working with your publishing team?
There’s a great deal more design involved in this book than my last one, both inside and out. Inside there are board spaces, and new pieces you encounter with each new chapter, and an ever fluctuating bank tally to, hopefully, act as agents of propulsion as well as to keep the reader fully immersed in this world. With those, I started with very rudimentary graphics that I either did up myself or farmed from the web for inspiration. Once the manuscript was handed over to my folx at Vine Leaves, their design team took what I provided and created a gorgeous, original graphic suite. Human arists. Who knew, rite?
Cover-wise, VLP’s process is to send their authors a questionnaire asking them to describe how what they envision their cover looking like, having us provide a list of visual items featured in the book that best represent its subjects and themes, as well as having us share a selection of covers we’ve seen in the wild – de facto “book swatches” whose look and feel stood out to us or whose color palette we admire. They allow us to be as vague or descriptive as we want and then they run with it. Once the first draft comes in, authors are given a round of notes and, from there, it’s more or less finalized.
For me, I definitely knew I wanted the cover to be graphic vs. photorealistic. I knew I wanted it to be a visual representation of the game. Outside of that, I tried not to get too prescriptive with it as I’m not a visual artist and I find it’s best to give the experts plenty of latitude to do what they do.
What was it like seeing your finalized cover for the first time?
A blind date is a horrible analogy. But, there it is. You have a sense, more or less, as to what it’s going to look like. You, sort of concoct expectations, built on nothing but your own wild delusions. And, then, there it is. Real, and raw, and waiting to be loved. And, I’m lucky enough to say I did, rather instantly.
We tend to ask a lot of our covers. They have to draw a prospective reader in and say some combination of the exact right things to get them interested enough to take it home. They have to be, at once, sexy, enigmatic, and bold enough to throw elbows against stacks of competition. They have to be Patrick Verona in 10 Things I Hate About You. Maybe, it’s unrealistic. But, I don’t make the rules.
How does the cover work to convey what the book is all about?
Initially, I was envisioning a simpler cover, one that focused on the main character/game piece, Corporate Logo Hoodie. I thought it would be clean and striking. But, I was also aware that it would do little to actually convey what the book was about. The lived reality of unemployment & job searching is utterly chaotic. Especially today. It’s linear, then it’s not. It’s ridiculous, then serious. It’s real, then entirely surreal. And, the cover had to communicate that. The title suggests memoir, the subtitle suggest’s it’s a how-to book, meanwhile the design is evocative of classic table games.
It’s kind of perfect because so much of game play is what we make of it. Yes, maybe we read the rules but, as soon as we dive in, we start to bend them and make it our own. So, I wanted to leave space for that, for the reader to make of this book what they will. To not watch the protagonist, but play as him. If I’ve done my job right, whether someone is looking for a story, for advice, for a feverish escape or a wet nightmare, they’ll find that all in here.
When my publisher asked me to describe the cover in few words, I said “playful, but sinister.” And, I definitely think you see that here. It’s colorful, inviting, even a bit nostalgic. It suggests amusement, yes, But, then, there are ominous figures prominently featured – like the raven, the urn, and the tombstone – to indicate that some very real and unavoidable darkness awaits. There are dice to suggest chance and arrows pointing in opposite directions, nodding to the fact that any step forward can be followed by several steps back. There’s your chaos, again. And, finally, that diabolical red slash through “When,” instantly turns one question into two. Is it a matter of “when,” or is it “if”? Is this the real life, or is this fantasy? Is this a book, or is it actually cake? Only one way to find out.