From Florence to Fame: The Untold Story Behind Nicolas Cole’s First Book

Scroll down for a live video of Nicolas Cole typing out a reply.

Nicolas Cole is known for being one of Quora’s most-read writers and for co-running the Ship30for30 community with Dickie Bush. He also has his own ghostwriting agency, Digital Press.

Cole is the most prolific writer I’ve interviewed so far. He’s written at least five books.

Why “at least”? I’m not sure if I should count the bundle of his best Quora answers as a book, and who knows how many books he’s ghostwritten? 

Nicolas Cole and his dog

His official bibliography is made up of Confessions of a Teenage Gamer; Slow Down, Wake Up; 19 Tiny Habits that Lead to Huge Results; Letter to my Imagination; and The Art and Business of Online Writing

To stay in line with previous interviews, we’ll focus on his first book, Confessions of a Teenage Gamer, which he published in 2016. But as his most recent book, The Art and Business of Online Writing, is something you’re probably more interested in, I’ll share some of my insights from that as well.

A teenage memoir

Nicolas Cole’s first book was a memoir about his teenage years playing World of Warcraft competitively while growing up undiagnosed with Celiac Disease. He says he had a weird childhood, was constantly sick and missed school so often during the second year of high school that he almost had to repeat the grade.

To make matters worse, he fractured his spine twice playing hockey. As a result, he spent the entire four years of high school alone, at home, playing World of Warcraft. And that’s how he ended up becoming one of the highest-ranked players in the United States.

While he was making a name for himself as a successful gamer, Cole started blogging about his games and other gamers. Before long, he earned a readership of about 10,000 other gamers. By the time he was a senior in high school, his childhood dreams of becoming a writer had solidified. 

This was the first time he had the idea of writing a memoir about his high-school years, but he wouldn’t publish it until several years later.

The tipping point

At college, he struggled to find his true purpose until he stumbled upon fiction writing. He wrote a short story about the defining moment of his gaming journey: his 2v2 team had become one of the highest-ranked teams in the country. 

The short story was about the realisation that his parents, who were against his obsession with gaming, weren’t going to understand his achievement. What was so important to him, just wouldn’t mean anything to them. 

Everyone loved the short story. 

And that was a turning point, especially since the teacher also encouraged him to “keep exploring the material.”

Writing the first draft

After that first short story, he spent three months creating an outline. It had been almost four years since he had played World of Warcraft, so it took a while to get all the details right. 

He created a master timeline of everything and made a list of the main characters. Then he just started writing.

Most of that happened In the summer of 2011 while studying abroad in Prague and Florence (Italy). In his hostel, which didn’t have any AC or internet, he wrote the first 500-page draft.

“My original idea for the book was to alternate between in-game chapters and “real life” chapters — and drive home the point that World of Warcraft had become my primary reality by writing the in-game chapters in the first person, and the “real life” chapters in the third person. It was an ambitious idea for a 20-year-old who was trying to write his first book, but I gave it a shot.”

Back at college, he showed it to one of his new professors, but it wasn’t well received. The man explained that the first person/third person thing wasn’t working and that he needed to dig deeper. At the time, Cole was upset and angry with his professor, but after sitting on it for a month or two, he realised he needed to rewrite the entire thing.

“Writing Confessions took me 4 years. And I worked on it almost every single day.”

The good news was that after writing hundreds and hundreds of stories, he had a better idea of which stories he wanted to tell. He still wrote hundreds of other stories he didn’t end up using in subsequent drafts, but they’re all saved on his computer somewhere. Who knows, someday they might see the light of day.

Writing more drafts

During his entire senior year of college, he worked on the second draft, but he still had a hard time letting go of the original first-person/third-person concept. The whole thing just felt forced. By the end of the year, he almost gave up. He put it away for a while, focused on bodybuilding, and didn’t touch the draft again until after his graduation.

He started the third draft a few months into his first job. He had been working as a copywriter at an ad agency in downtown Chicago, and he very quickly realised that real life was a lot harder than college. By the time he had finished work and a gym session, it was 9:00 pm and the day was over. Making minimum wage and not even saving $50/month, he realised that he needed to keep investing in his own writing. Otherwise, this was going to be his life.

Moving into a studio apartment, he was considering if he could even afford an internet subscription. But before even making the calculation, he decided not to get one until finishing the book. This would prevent him from coming home exhausted and just squander the rest of the night. How’s that for a commitment? 

About halfway through this third draft, he hit a wall again. The deeper he got into the material, the more Cole realised he was trying to write about things he hadn’t emotionally processed yet. Not having many friends in high school. Not attending any of the school dances or do anything most high school kids do. He didn’t have a girlfriend until senior year, and she went to another school 40 minutes away. He had many insecurities. On top of that, he had a toxic relationship with his family. He constantly felt like he would never live up to their expectations. 

To help himself with the writing process, he signed up for therapy (and has been going ever since).

As he climbed up the work ladder and started taking on more at the ad agency, he fluctuated between really productive writing periods and months where he could barely get any writing done at all. Eventually, he did finish that third draft after about three years. 

Nicolas Cole, The Quora Guy

When he started writing on Quora in 2014, everything changed. Nicolas Cole is now one of the most-read writers on Quora. At one point, he even was the most-read writer.

Quora is where he started to find his voice as a writer. It was a very different type of writing than what he was trying to execute in his first book. But the amount of feedback taught him a tremendous amount about what readers want and don’t want. The success on Quora made him realise he needed to rewrite the book again.

He threw the entire thing out and started over, one last time.

Between 2014 and 2016, he cut 80%, only keeping the emotionally intense parts. The ones that made him laugh out loud or even cry. He started to apply what he had learned on Quora, compressing each section as much as possible. 

By day, he wrote at work, and then he wrote a daily Quora answer at the Starbucks down the street. At home, he still didn’t have Internet, and so by night, he worked on his book.

In the meantime, a Quora answer had gone viral and he created two related ebooks about it. Selling those earned him his first $2.000 online and “officially” made him an author. But it wasn’t a “real” book yet.

He finally finished his first “real” book, Confessions of a Teenage Game, in August of 2016 and published it shortly after. He doesn’t regret rewriting it four times at all. he believes the final product is lightyears ahead of where the material had started.

Cole’s current writing process

His daily writing process today is very different from what it used to be.

While writing his first book, he was trying to fit writing in with everything else going on. Usually, that meant either early in the morning before class/work or late at night.

Now, he writes for a living. Some mornings he does his own writing, then transitions to ghostwriting and client work. Other mornings, he does the opposite. He now has a lot more freedom to write the things he feels like writing. 

He doesn’t track word count or even hours. “I love writing, so I basically write until I can’t anymore. Some days, I’ll write for 8+ hours. Other days I’ll write for 30 minutes, and that’s it.”

On these big writing days, mornings are his most productive hours. At night he catches his second wind from 7-9 pm.

I’m yet to meet a writer who thinks his most productive hours are in the afternoon.

Some general writing advice:

  • Schedule calls or other activities at times where your writing productivity is low.
  • Write in public to accelerate your progress.
  • Writing in the vacuum of your apartment for four years isn’t such a good idea. 

Tips from The Art and Business of Online Writing

  • The broader you are, the more confusing you are. 
  • The number of hours you spend consuming should never equal or exceed the number of hours you spend creating.
  • What you’re aiming for is the most value you can deliver without confusing the reader or wasting their time.
  • You never want to have more than three successive long paragraphs.
  • A good headline communicates three things at the same time:
    • What is it about?
    • Who is it for?
    • What problem does it solve?
    • Pro level: apply the curiosity gap. Tell this without revealing the answer. You still need people to read. 
  • Use the 1/3/1 introduction or a variation of it.
    • One strong opening sentence.
    • Three descriptive lines.
    • One conclusion.

Cole’s headline writing strategy I love:

  1. Write what you want to say in as many words as you need to.
  2. Consider your promise: is it worth reading? Can I promise more?
  3. Is it clear? Which words are too vague?
  4. Delete as many words as possible to get a concise headline. 

What does the future have in store?

Watch Cole at work replying to this question or read my edited version below.

Pardon the bad quality. I had to act quickly.

Cole says he has a lot of goals as a writer. But they all point in the same direction: to show that it’s possible to produce a legendary body of work and have a legendary career without walking the conventional path of signing with a major publishing house.

Growing up, he had a very binary definition of what it meant to be a “successful writer.” You either become the next Hemingway, or you die poor, lonely, and forgotten. It was the narrative that was fed to him by teachers, parents, and just about anyone he turned to for advice.

Later on, he learned there are hundreds of different definitions of what it means to be a successful writer.

For him it means a couple of things:

One, to build a library of books that produces millions of dollars in revenue independently. Over the long term, this is 100% doable. And yet, most writers don’t believe it is and insist they need a major publishing house to get there. Cole wants to find out for himself and prove the conventional thinkers wrong.

Another goal is to be the first writer to document his entire life in a series of memoirs, each one pulling the reader into the next chapter, and so on. Not a traditional series of memoirs, like three of them, but dozens and dozens. 

He also believes there is tremendous room for innovation in audiobooks, which many writers choose not to experiment with. With his memoirs, he plans on creating “sonic audiobooks” that are so much more than just the writer (or a paid narrator) reading the words on the page. 

Nicolas Cole spent the past 10 years practising his craft and achieving financial independence. Now that he doesn’t have to optimise for money as much, he can invest more heavily in taking creative risks and sharing more of his own work. 

Who knows what else the future holds!

First book: Confessions of a Teenage Gamer
Twitter: @nicolascole77
Newsletter: Daily Writing Habits

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2 thoughts on “From Florence to Fame: The Untold Story Behind Nicolas Cole’s First Book”

  1. Spenser Warren

    Such an insightful interview! I learned a lot about Cole and his journey that I didn’t know before. Thanks for sharing!

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