Lessons from the “Birthing” of a Bestseller

I just read a fascinating post about the litany of breakthroughs and breakdowns that go into writing a book. The piece is by Ben Casnocha, and it’s about the process of co-authoring The Start-Up of You with Reid Hoffman, chairman of LinkedIn.

Please dive into the original post. It’s long and worth your time. Following are insights that I took away, along with relevant quotes.

Think of your book project as a start-up 

“In this long, print-length article, I recount the process of conceiving and publishing a book and share the key lessons we learned throughout. It’s the story of coming up with an idea, forming a founding team, finding partners and investors, iterating on the idea, shipping a beta product, iterating some more, and marketing the product to customers. Sound familiar?!”

 Find a clear and compelling question to answer in your book

“When the economy took a turn for the worse in 2008-2009, record unemployment numbers and stories of broken careers in broken industries dominated the headlines…. There was a dearth of discussion focused on what every individual could do to survive and thrive in a more competitive economy. In other words, what could every person do to take control of his or her future in uncertain times?”

Think carefully about revealing your book project

“Starting something ambitious is impressive…. But finishing something ambitious is even more impressive. When you publicly announce that you’re starting toward a goal, you can benefit from the self-fulfilling prophecy effect, you can collect feedback from your network, and be held accountable to lots of external people tracking your progress. On the flip side, when you announce a goal, you risk tricking your mind into believing you’ve already partially accomplished it when in fact you’ve done nothing.”

Leverage the power of a book to force substance and clarity

“…the most significant benefit of starting with a book was one we didn’t fully appreciate at the outset: a book’s linear, static format, and the expectations around the length and detail and substance of what’s inside of a book, collectively force upon the creative process a rigor unmatched in other mediums.”

Prepare for trade-offs in presenting your ideas

Breadth versus depth? Books that purport to offer the secrets of “success” or “explain how the world works” are hopelessly general. Super focused books, on the other hand, like the ins and outs of resume writing, serve a purpose but rarely start a broader conversation or shape the culture….

What’s the best use of stories? Everyone seems to agree that stories rule—they’re vital ’emotional transportation’ of ideas. The problem is, stories in business books are rarely impactful…. if you can tell stories that resonate and that illustrate your point, do it, because it really does become more powerful and convincing and memorable. But if you can’t do it right, don’t waste readers’ time.

Aspirational examples vs. relatable examples. We love reading stories of astronomically successful people because they inspire us. Reid’s life story (which is still unfolding!) is aspirational, but is so unusual in terms of outcomes so far that it’s not terribly relatable to people starting out.

Should the text be narrative or how-to? Should we pack the explicit how-to’s into the body of each chapter, or sum them up at the end? You want to drive home the practical takeaways, but you also don’t want to interrupt narrative flow or make smart readers feel like they’re being spoon fed….”

Be willing to iterate

“Surely a slow, careful outline, followed by execution of said outline is an approach that works for those who know exactly what they want to say —but that’s rarer than you might think. I’m a huge believer that one of the best ways to figure out what you think is to write it out and then iterate. When you do this, you quickly discover how foggy your ideas are, and you work to clarify them.”

Think about structure as much as sentences

“Oftentimes it’s harder to figure out the right order of your paragraphs than it is to write the sentences themselves. Order is hard because order represents the logic of the point you’re trying to make.”

Set up a process for collecting “fringe thoughts”

“Ideas for how to solve certain problems came to me all hours of the day and night, and I had a sticky note on my computer always full of dozens of different notes. Each week I’d transfer each note to a chapter-specific ‘punch list’ document that served as the repository for all of our fringe thoughts related to a concept.”

Prepare for mood swings

“…the hardest part of an ambitious writing project as the writer is managing your own psychology. More specifically, in my experience, the key skill is managing the self-disappointment bordering on self-loathing that can overpower other emotions through the long, hard slog.”

Know when to go offline


Ask for useful feedback from reviewers

“Line edits are important, but relatively easy to spot and execute. What’s hard is feedback on flow, structure, overall coherence…. As Tim Harford suggested to me, if you know you have work to do on the manuscript, just ask someone for one or two tips to make it better. Focus their mind exclusively on practical, actionable specific changes you can make to improve it.”


  1. Wow, this looks great, Doug. I’m STILL slogging away through my book proposal and, I have to say, it borders on excruciating sometimes. I’m going to read the whole post when I have a bit more time. Thanks so much for sharing it!


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