How this Young Author Got His First Book Deal

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“Any situation you’re in when you are trying to sell a book or get your idea to someone, it is about leveraging whatever you have,” said Greg Dybec. “In my case, I knew working for Elite Daily, having that audience built-in, having carved a little bit of a voice for myself, I knew that would be a selling point. I didn’t want to take that out of the equation.

I first came across Dybec’s work a couple of years ago, when he republished a post at author Neil Strauss’s website. I reached out and we ended up chatting about what kept him busy and his work with Elite Daily, where he works as the managing editor.

Fast forward to a few months ago, when Dybec announced that he was writing his first book, an essay collection entitled “The Art of Living Other People's Lives,” with Running Press. We chatted about his recent book deal, how things were going for him, and how he even locked the deal down in the first place.

“But at the same time, I think opportunities come at random times, and it’s really just a matter of being brave enough or paying attention enough to be able to walk through that door when it does open. Or at least attempt to.

“For me, when WME started working with Elite Daily, I didn’t care who I annoyed. I’m not the person to send a thousand emails or call you or text you a million times, I’m usually patient with that,” Dybec continued. “But this was a case where I felt like if I wasn’t persistent, it could slip away.

“I just ended up begging some of the other employees at Elite Daily who were working closer with WME to put in a word for me, or just get me one contact in their literary department. With enough pestering, they finally gave me an email, probably to shut me up, and then I reached out and I think because of the relationship with Elite Daily they were at least willing to see what idea I had.”

Dybec’s determination reminds me of when The New Yorker staff writer and author John Seabrook said, “You have to make due with the tools you have at hand. No one starts at The New Yorker.”

Outside of his work for Elite Daily, Dybec had already written and polished his own essays in his spare time. He was prepared when he discovered the opportunity to work with WME. He said, “It’s just making sure that you are always working on the craft, making sure that you do have something ready. In my case, I just knew that if I had essays in my back pocket, things I’d been working on, work that I was proud of that when the opportunity came, I’d be ready right away with work to show.”

“I don’t know what they were expecting, but I sent some of the essays over with sort of a makeshift proposal because I didn’t really know how to put one together. Really, just the description of what my vision for the book was, and they got back to me. I don’t think that they thought someone would have something so put together or essays that were clearly worked on and crafted.

Dybec’s preparation paid off, and WME was interested in working with him to shape a proposal, refine his essays, and discuss the book publishing process with him.

I had a feeling that one of the three essays he sent over was the one I first read, about his spending a summer as a pick up artist, which he confirmed with a chuckle. While that essay made it into the final book, the other two he originally sent did not. Dybec said, “They were at least able to see the passion that I had, see the fact that writing has been a craft that I’ve been working on and that I did have an original enough of a story to tell.”

Just as Dybec was on the cusp of finalizing his proposal and relationship with WME, the two companies decided not to work together. Dybec immediately reached out to WME, urging them to keep the book proposal in play despite the disruption in their working relationship with Elite Daily. During the two weeks WME discussed the project, Dybec was wrought with nervousness. He did not sleep well.

Eventually, WME wrote back telling Dybec they believed enough in the project to keep him on regardless of their relationship with Elite Daily. Dybec said, “That was one of the many, many, bumps in the road, which I’m finding out having spoken to other authors who are in on the process of writing their book or have books out. It’s super common. But in the moment, it’s terrifying.”

With that terror behind him, Dybec got started working on his book in earnest. He said, “For me, I think with essays, especially this being my first collection, I had the entire timeline of my life to go back to. I didn’t want to write a chronological memoir, I just really wanted to pick out these moments where either I’ve learned some serious lessons in life, maybe acted stupidly, and I kind of came to this theme where working for the Internet, people expect you to be plugged in all the time.

“They expect you to be on, spewing this insight, having all this information at your fingertips, and something that I realized about myself is I created this identity where I was trying to be that Instagram version of myself. It’s just not real, it’s not how it works, everything’s not glamorous, especially for me,” he said. It’s a tension that I also struggle with.

“I’m blessed to work at Elite Daily, but most days it’s still just an office job. I just want to present something that was honest, the moments where I did make mistakes, I want to show some of my anxieties, my insecurities. It was just a matter of sitting down and watching a reel of film in my head about all the moments in my life, it was just so strange, the things that just naturally stuck out.

“Moments that I didn’t even think would be able to make a story, but just really letting them come to you. I think being open to that creative process, some of my best brainstorming wasn’t just sitting down on a page and trying to create something,” he said.

Dybec’s memories and introspection served as his writing prompts. “It was seriously sitting back and thinking, ‘What was Christmas like four years ago?’ or, ‘What was my relationship with my brother growing up?’ or, ‘What did I really feel when I got this job, or did this thing?’ It was almost like a therapy session with myself, and I think when one of the stories hit hard enough or stuck with me, or I’d wake up the next morning thinking about that one moment, that’s when I knew, ‘Hm, let me explore this a little,’ or, ‘Let me take this to the page, maybe write around it a little.’ It’s strange how stories just at that point start to develop on their own. I think it’s a weird process when you have to reflect on your own life to find those stories.”

I find it equal parts terrifying and empowering to be so honest with so many people — and strangers at that. Dybec writes in spite of the terror. “There are those few moments I wonder, ‘What are my parents going to think when they read this?’ or, ‘Ooh, my girlfriend’s dad specifically reading this line, I might lose some sleep.’

“But you just push it aside. I think for the most part, anyone’s going to appreciate honesty. I think a lot of people respect writing for that reason, because it’s someone that’s able to take time and just be honest. For me, it’s just really hoping that any of these stories — above all, it’s entertainment. I would want people to enjoy them.

“But at the same time, it’s knowing that there could be someone out there that realizes they’ve had the same thoughts, or have had the same questions, I think that’s more motivating and inspiring than worrying about what your mom’s going to think. She’ll get over it in the end. She’ll be proud enough anyway.”

Dybec’s introspective writing process is tied in with his intuition. He advised writers to follow their instincts. He also recommended that writers don’t get too caught up with the system and creative process — that people are also a very important factor.

“Agents, publishers, they’re not just robots in the system that if you have a proposal and send it to the right address that it’ll just happen. They’re people that are accessible, they’re people that have social media profiles, people that you can get to know well before you submit your proposal,” he said.

“I think sometimes people make the mistake of — instead of just taking that human approach, they try to go above and beyond too much. I think that’s when, I would say, step back and think if this strategy is getting seen or getting your work out there. Is that genuine? Is that really what you’d want to do? Or is it over the top for the sake of being over the top?”

Dybec advised younger writers to leverage their youth and write what they know. “I think we’re a generation — we’re gonna change book publishing in one way or another. I think it’s at that point where agents, publishers, they understand that and they are looking for creative ways and people to stand out in a way that shows what their voice is.

“I think that’s to be seen, how that process changes, but they’re people too. When you reach out to anyone, it’s just someone sitting on the other end of the computer, reading your email. Now I’m finding this common theme of this human approach, that was a really good way to put it, but I think that really does need to seep into every aspect of it.”

Dybec sends me an email saying he’s going to send me a proof of his upcoming book, “The Art of Living Other People's Lives,” to review. I’m not sure quite what to expect, as the only other essay collection I’ve finished was Tim Kreider’s (and I loved it).

To my delight, and probably his, I really like it. I’m no book reviewer, but I found his book to very relatable. During our conversation, Dybec and I chatted about figuring out how to make sure reading doesn’t die with our generation. As I think about it, I believe part of that means writing honest stories by us, for us. I’m confident his book will pull us in the right direction.