Starting Up The Start-Up of You

Lessons Learned and Personal Reflections on Publishing a Bestselling Business Book

August, 2012

I’ve spent the last couple years of my life working with Reid Hoffman on The Start-Up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career.

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?!

This “behind the scenes” account is not comprehensive by any means, but I hope the lessons prove useful to other authors and entrepreneurs.

Here’s an outline of what’s to come:

1. Birthing the idea – How we intellectually arrived at the book’s ideas and why we were compelled to write it now.

2. Founding team – How Reid and I decided to work with each other, the nature of the partnership, and whether to announce to the world that you’ve started on an ambitious project.

3. Writing the business plan – Writing a book proposal and grappling with the questions that explain the differences among business books.

4. Finding investors and partners – Partnering with a publisher.

5. Coding the prototype – Hard core writing, figuring out the logic behind our ideas, choosing a title.

6. Discipline, focus, and self-disappointment – Far from solitary delight, the process of writing is about managing the emotional roller coaster and figuring out a way to focus.

7. Getting feedback and help – Collecting feedback from smart people — how to ask for it, how to incorporate it.

8. Final QA testing – Continual editorial improvement till the end, manuscripts and galleys.

9. Marketing campaign – High level lessons and things to think about when marketing a book.

10. Results to date – Since publication, what’s happened?

Birthing the idea

I’ll start by sharing my intellectual arrival to the book’s ideas. From a very young age, I’ve been excited by the process of entrepreneurship. No matter how small or silly, I love the idea of building a product or service that solves a customer’s problems. I spent my teens immersed in this pursuit, and wrote my first book about what I learned—and what others learned—through the journey of entrepreneurship.

During my 2006-2008 world travels I met people as entrepreneurial and adaptive as the best Silicon Valley tech entrepreneurs, who were not actually starting tech companies. It burst my Silicon Valley bubble a bit! They were journalists, architects, professors who were thinking entrepreneurially about all aspects of their life even while holding “normal” jobs. This got me thinking. In one of the first interviews I did about My Start-Up Life in 2007, I said, “I see entrepreneurship more as a life idea than a corporate strategy. People can adopt the executive mentality even if they’re not in the corner office–they can apply the attitudes of a successful CEO to everyday life.” It struck me as an important message because not everyone wants to (or is able to) start a business.

Reid, meanwhile, had been developing and promoting a similar thesis long before me. In fact, he started a little company called LinkedIn in 2003 based on it. With an extraordinary vision for how the world of work was changing and for how relationships and networks would drive a more fluid labor market, Reid cofounded LinkedIn to be the platform on which every individual could manage themselves amidst these changes. In 2007, Reid appeared on Charlie Rose and said that every individual is now a small business. In 2009, he also gave a commencement speech at his high school telling them to be the entrepreneurs of their own lives, to do flexible planning and take intelligent risk.

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. What surprised us both (though we weren’t in touch at the time) was that much of the ensuing national discussion focused on what Washington lawmakers should do to fix the problem of jobs. Stimulus or no stimulus. Student loan policies. National re-training programs. Education reform. 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?

The founding team

Reid and I first met at a conference in Utah in a round table discussion on citizenship. We chatted for a few minutes afterwards. After the conference, I sent him a “nice to meet you” follow-up email. He in turn invited me to connect on LinkedIn and offered to get breakfast someday in Palo Alto. I was surprised at the offer, and wasn’t going to pass it up! It was my first glimpse at Reid’s openness to meeting new people despite his already large professional network; it was him living out what we call in the book “courting selective randomness.”

About five months later (busy people’s schedules, you know), we were having breakfast at a restaurant on University Ave in Palo Alto. There wasn’t a specific business agenda for the breakfast, so its worthiness was determined by the pleasure of conversation. Fortunately, the conversation flowed especially well. We just clicked.

The first topic I brought up was something I’d wanted to ask him for long time: How does he finds intellectual stimulation in a valley dominated by technologists and entrepreneurs who tend to be single-mindedly focused on their business ventures? Laser focus, I said, no doubt contributes to successful outcomes, but does it sometimes lead to less-than-interesting people?

There was a backstory to the question: During my Asia travels in 2006, I reached a point of exhaustion in New Delhi, India. So for a day I locked myself in a hotel room and listened to podcasts. One I listened to was Venture Voice, and the guest was Reid. He was talking about his career and he commented that, coming out of grad school with a master’s in philosophy, he figured he’d be an academic or public intellectual who’d write articles for magazines like The Atlantic. But he decided he’d have more impact doing something in the technology industry. I vividly recall standing in my hotel room in Delhi and being startled at hearing this, for I myself was debating whether I wanted to do more traditional entrepreneurship or do more pointy head intellectual writing. I had never heard another Silicon Valley tech person discuss a similar career tension, let alone someone as high profile as Reid.

Another topic at the Palo Alto breakfast was about entrepreneurship as a life idea. We talked about our shared passion for the how the world of work and careers was changing.

Near the end, Reid asked me what I was going to do next. I was in transition, deciding whether to a) start another company, b) do more writing, perhaps partnering with someone really interesting on a book, or c) live in Latin America and learn Spanish.

He kind of laughed when I told him about a writing partnership. He said he’d been thinking about doing a book about how every individual needs to be the CEO of their own career, drawing on his experiences founding LinkedIn and the similarities between the great entrepreneurs he’s funded as an investor and effective professionals generally. “If we become mutually interested,” he said, “Perhaps there’s a way for us to work together.”

We did.

I was interested in him for obvious reasons—he was an iconic entrepreneur in Silicon Valley. And for perhaps non-obvious reasons: he was genuinely intellectual and broad-minded and, as it related to a possible book, was interested in forming a partnership, not dictating to a ghostwriter.

Yet why would Reid want to work with me? He could have easily found a more accomplished writer or a more accomplished entrepreneur with whom to set forth on the project.

Well, to use vocabulary from the book, I brought to bear a unique competitive advantage. There are plenty of writers and plenty of entrepreneurs, but there are few who can wear both hats. In other words, there are plenty of writers who can style prose; there are plenty of entrepreneur types who can riff informally on their work. But to do be able to do both is rare—conceive original, interesting ideas on the topic and express those ideas in clear writing. As we write in the book, competitive advantage tends to emerge when you combine different assets/skills/abilities.

There’s one other important factor for why I made a good partner, I think, though this wasn’t necessarily clear at the outset: I had the ability to take on rigorous, challenging intellectual work and the willingness to take care of mundane bullshit work. Specifically, I could do book writing, high level meetings, business negotiations; at the same time, I was willing to go to Kinkos to print out cover art and manuscripts, jockey Excel spreadsheets, transcribe notes, sit in on conference calls, and take care of thousands of other brain dead details that any new venture requires.

To be sure, much of the willingness stemmed from me having skin in the game as a credited co-author. But there is a broader point relevant to assembling teams. The more accomplished one gets, the more one’s pride and ego (and opportunity cost) can get in the way of doing “bullshit work”. Yet there’ll always be bullshit work to do, and sometimes it’s just faster to take care of the bullshit yourself (instead of passing it off to someone else). In our case, five years from now I might be unwilling to take out the trash and scrub the floors on a writing project, which wouldn’t make me unqualified to do the job but it would add layers of outsourcing complication and require additional time / money.

Our partnership evolved to be consistent with how Reid thinks about most of the projects he’s involved in: a) every idea needs a founder, b) he backs an idea + founder, c) he pays careful attention to proper alignment of interests among all involved, and d) he lets the principal (the founder and/or CEO) drive the bus forward. This approach allows him to be involved in many things at once, because with each of his projects – whether it’s LinkedIn, a Greylock portfolio company, or a for-cause entity like Kiva — there’s a CEO who’s driving the thing forward day to day, and he selectively adds value where he has a comparative advantage. In the case of The Start-up of You, we were obviously co-founders, but I had the autonomy and responsibility analogous to any of his portfolio CEOs.

When you embark on a project that’s going to take awhile, you have to decide how much to publicize the fact – on your blog, to your friends — that you’ve started. Starting something ambitious is impressive—a lot of people are scared to even start. 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 your it when in fact you’ve done nothing. Derek Sivers says: “Keep your goals to yourself.”) Plus, external accountability of the wrong kind can add unhealthy pressure.

I decided to keep it private, telling those who asked that I was working on a “writing project,” and only engaging a limited number of friends and family for their advice. It wasn’t until Tom Friedman’s column ran (which I’ll describe in a bit), 15 months after Reid and I started working together, that the book’s existence was made public.

Writing the business plan

It was December, 2009. Reid and I had to first clarify our goals. We had a set of ideas that we believed could help people survive and thrive in the new world of work. By helping people transform their own careers, it would in turn make the world a better place—the ultimate driver for us as entrepreneurs. So our goal was wasn’t to write a book per se; it was to write up and share our ideas in whichever way would result in “massive impact” (to use Reid’s favorite phrase).

We decided to start by writing a book. Doing a book strikes just about everyone in Silicon Valley as retro. Indeed, there are all sorts of limitations: Books are not easily shareable (relative to online content); traditionally published, they’re expensive for consumers to buy ($15-20 per unit); they lack interactivity and multimedia; and so on. On the flip side, books still receive good retail distribution in hundreds bookstores and airports; they attract more attention from public influencers; and they are a convenient vehicle – whether in print or e-book form – for someone to consume a focused, long-form idea.

But 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.

Want to churn out some blog posts? Easy. Shout slogans from the rooftops? Easy. Relay some stories and take-aways in bullet point form? Easy. Coherently develop, assemble, and stylize a series of ideas over a couple hundred pages in book form? Hard as hell. When we began, Reid and I had the equivalent of blog posts on the themes in question, but we did not have anything close to a book. Attempting to write a book forced us to be super precise and thoughtful about what we wanted to say. And of course, once you have precise thoughts, then it’s comparatively easy to disseminate them in various channels and formats.

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The first step in the conventional non-fiction publishing process is writing a book proposal. A book proposal is like a business plan. It’s where you tell prospective publishers what you want to say, why you want to say it, why you should be the one to say it, how you’re going to say it, and how you’re going to market / sell what you say. Just as with companies, the actual book you write will likely deviate considerably from the plan, but the planning exercise clarifies your thinking at the moment.

Our high level thesis was clear: every individual is the business of themselves and there are a set of strategies (drawn from Silicon Valley) that people need to act on this reality. But what should follow from that premise and how should those follow-on details flow in an organizing structure? That was much less clear.

There are different models for how to do a business book. From Seth Godin’s short, pithy implorations, to Malcolm Gladwell’s narrative big idea books that rely on existing academic research, to Jim Collins’ original research delivered in an authoritative voice. As we contemplated what we liked and didn’t like about each of these approaches, we discovered questions that we ended up facing over and over again during the writing process. Some of them included:

• 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. It’s an obvious balancing act, but one surprisingly few books pull off successfully.

• Who is the target reader? On a related note, a very defined, narrow envisioned readership lets you craft all your examples and advice to speak directly to their specific concerns. Yet, it limits the broader relevance of the book. At the same time, when authors envision a broad readership they risk falling back on trite generalities. We eventually decided we’d try to make a good book that could resonate with a large number of people working in many types of industries, rather than the world’s greatest book–for a handful of people.

• 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. Storytelling is hard, and it takes time to paint a rich picture. Po Bronson is a modern king of narrative non-fiction storytelling and he spends pages and pages introducing you to his subjects. Business authors, their readers obsessed with take-aways, rarely are willing to carve out the space to tell an in-depth story, so instead settle for cheesy stories that are obvious set-ups. Sure, 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. When people achieve a certain level of success, some dismiss them as fundamentally different and therefore irrelevant to their own success. Yet, natural talent is overrated–there’s much to learn from deconstructing the deliberate practice that make successful people successful. Still, we felt it important to integrate into our book the stories of lots of people, who hail from different backgrounds and who’ve achieved different types of success. We focused on Silicon Valley, which is aspirational, yet also went beyond Silicon Valley for those who assume its stories are special and an exception more than a generalizable rule. In sum, the best books about winning offer both inspirational and relatable examples to the reader.

• 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. Gladwell is the gold standard for how to let sophisticated takeaways emerge from tightly told stories, but it’s rather hard to do—which is why Gladwell is Gladwell.

• Do we coin new words (and then educate the world about the meaning of the words) or try to redefine the existing vernacular? If you want to effect social change, you have to decide whether to try to work within the system or go outside the system. (Disagreement on this has been a source of internal strife within social revolutions throughout history…) We had a similar challenge: do we use the established vernacular in the space or invent our own? A “career,” as Sean Parker once put it, “is something your father brings home in a briefcase each night, looking kind of tired.” For him, the word “career” does not come close to describing the entrepreneurial and risk-taking life he’s building. Agreed. At the same time, everyone knows what you’re generally talking about when you say “career.” If you invent a brand new word to capture a new concept you’re trying to convey – say, “EntreCareers” – you have to do the hard work of orienting people on the basic gist of what you’re talking about.

Grappling with these questions caused more than a few identity crises about what on earth were we trying to create. Yet we got to enough clarity to produce a 100 page book proposal:

Finding investors and partners

We had our book proposal. Now we needed someone to publish it.

I flew to New York and, with our agent Lisa DiMona (who I had worked with earlier in my career), met with most of the big business book publishers. Due to our platform and the timeliness of the topic, most publishers were quite interested in The Start-Up of You, and as a result we could spend energy assessing fit rather than doing a hard sell.

The following week, October 2010, we held an auction for each publisher to submit bids detailing their interest in the book.

For cash-strapped writers the size of the publisher’s offered advance – the cash that’s advanced to you and that you “earn out” via royalties over time if you’re lucky — matters most. For us, the advance offered by a publisher mattered only inasmuch as it reflected commitment to the book. A large advance is a sunk cost to the publisher that they’re in theory more motivated to earn back. Reid and I agreed that we’d go with a publisher that was best fit for the book, even if they offered less money up front. (Authors sometimes forget that if the book does well, in the end you make the same amount of money – whether it comes first in an advance or later in royalties.)

Evaluating the different publisher options made us think through another classic dilemma when you’re trying to spread ideas in the world. Namely, do you try to influence society’s elite influencers (who in turn “trickle down” influence to their networks and the world at large) or affect the masses directly – i.e., go straight to the people. In a small way, we faced this choice when evaluating Harvard Business Publishing, a terrific publisher headed by a friend of mine. But, both practically in terms of physical distribution and reputationally in terms of the types of people who buy books with a Harvard logo on it, HBS books reach a business manager elite, not a mass market audience of business book readers. We wanted more mass market appeal.

After deliberation and a few rounds at auction, we decided on Crown Business, an imprint of Random House. Crown is at the top of their game as a publisher that had published several comparable titles. The editor who bid on our book – Talia Krohn – was younger and hungrier than other editors we’d talked to and we felt like she’d give it her all at every level to help make the project a success. A classic entrepreneurial people decision is to favor hustle over experience.

When I am most stressed, my teeth ache, the muscle just above my right eyeball twitches uncontrollably, and my jaw gets sore. There were three times during the project when I got stressed in this way. The first time was when we were deciding on publishers. In hindsight, it was as important a decision as I thought it was at the time (hence the stress), and fortunately, we made the right choice!

Coding the prototype

It was November, 2010. The contract deadline for manuscript delivery was May 1, 2011. It was time to lean in on the editorial tasks in front of us.

As an opening volley, Talia sent me detailed thoughts on the sample material we had submitted as part of the proposal. There were small edits throughout, but one overarching theme ran through and through: we needed to upgrade the quality of the work in every way. It was not an issue of styling prose. We needed to deepen and better organize every part of every point.

For example, in the sample book proposal material, we had a paragraph or two on weak ties. I genuinely thought it was pretty good. By the time we turned in the final manuscript a year later, I had read the actual sociology studies on weak ties, read what other popular writers had written, talk to experts, and synthesized. Reid similarly invested much more brainpower into this and other concepts.

To go deeper on the ideas at hand, I hired two research assistants on a part time basis. Josh Mitrani and Brett Bolkowy sourced great material on companies and people relevant to our work; culled research on risk, hustle, networks; fact checked data; and supported me in other editorial tasks. They, alongside our editor and agent, were a huge help.

But Reid and I ourselves were still where the ideas had to emanate from. And the physical epicenter of this idea generation was Reid’s dining room table. I visited with him roughly two weekends out of every five at his house, for 3-6 hours on both Saturday and Sunday. Before we had a set frame for the manuscript, I’d show up with a list of concepts, and we’d riff on adaptation, pivoting, relationships and networks, the follies of career ladder thinking.

Covering those topics was the plan, anyway. We struggled a bit to stay on topic during our ideation meetings. As I was quoted in the Wired profile on Reid, “We’d have a two-and-a-half-hour meeting about the book, and we’d spend the first 45 minutes debating the Singapore model of political economics. He gave me books on the philosophy of the ancient Greeks, DVDs of Japanese anime. He wanted me to think about what anime could teach us about the philosophy of life.” While these conversational digressions hurt our book productivity, it was one of the pleasures of the project and partnership for both of us.

During the week, I wrote new bits and pieces of chapters, circulated to our editor (and sometimes our agent who was hands-on editorially), collected their feedback, and went back and forth with them on it a couple times. Our editor sent me back the doc with various Track Changes and comments and usually a higher level reaction in the cover email. Then I sent a new draft to Reid before our next meeting, and we walked through it in person, going page by page. Then I incorporated his changes, and started the process over again the next week–for the next ten months. By the project’s end, we wrote roughly 100,000 words, of which about 60,000 made it into the final manuscript.

As you might be sensing, we did not draft a detailed blueprint (outline) of the book and then put our heads down and execute. We had to figure out each point as we went. We started in the middle, then did the beginning, then the end, and then re-did everything. It was chaotic. It was like learning a language by being thrown into the target country and picking it up on the street, instead of formal classroom study of grammar. 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.

Speaking of fog, E.L. Doctorow got it right when he said: “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.”

Stylistic difference

Reid and I rarely disagreed on style. We both agreed “punchy” (another favorite word of his) language is important to grab people’s attention. Clarity over flourish. Concision. There was one stylistic difference, though, that I found interesting. It has to do with the best way to open a discussion of an idea. He preferred to state the thesis or point of a section upfront, and then follow with the examples or anecdotes or detail. My instinct was to start with a story or anecdote — to throw the reader into a scene — and then zoom out and relay the lesson or point of it the section to come.

Starting with the thesis maximizes clarity; starting with a story maximizes engagement and draws the reader in (if you do it right). However, if the scene in which you throw the reader isn’t compelling, you lose the reader and never get the opportunity to make the point. We did a bit of both, but usually I deferred to him in how we opened sections. The Opportunities chapter, for example, begins with the thesis and then segues into the Groupon and George Clooney stories.

Order = logic. Logic is hard

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. For a 60,000 word book, order and structure is one of the hardest challenges and “editing” for me was an exercise in re-ordering existing words as much as it was changing words.

On Christmas Eve in 2010, I laid out a bunch of the graphics on Reid’s desk that sought to show possible flows for the chapters. I used Omnigraffle to visually architect how I thought the ideas could flow. Here’s what one early draft looked like:

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. Reid was also king of fringe thoughts, often emailing with me with subject line “fyi” and one or two cryptic sentences about an idea punched out on one of his many smartphones. If you’re involved in a creative process, be it writing a book or starting a company, capturing your fringe thoughts as they spring to mind, day and night, is essential.

The Title, The Metaphor

Through the early stages of the writing process, we continued to debate the title of the book. “The Start-Up of You” was the default, but we worried it sounded like “Brand You” and we wanted to avoid being lumped in exclusively with the personal branding community — Brand You is an important idea but we focus more on the underlying skills and experiences (“product innovation”) that produce differentiation. We also feared a title that sounded too much like a dusty “career book.” We cycled through alternatives ranging from “Quixotic Realism” to “The New A-Player” to “In Luck’s Way.” Ultimately, none seemed better than Start-Up of You. From the current vantage point, of course, Start-Up of You seems perfect!

For the subtitle, we generated a few top choices, and ran Google AdWords against relevant keywords with the different subtitle options to see which subtitle would generate the most click-throughs.

Another point of debate had to do with metaphors. The book’s primary metaphor is that your career is like a start-up and you can manage it accordingly. But there was a second metaphor we sought to rebut: the old idea of a career ladder or escalator. And we wanted to do so with a comparable physical metaphor. Is the modern career more like an ocean voyage? A jungle gym, as Sheryl Sandberg recently termed it? A rock climbing wall? In the end, we didn’t include a prominent physical counter-metaphor.

Discipline, Focus and Self-Loathing

There is a romantic story told about writing. Wine glass to the left of the keyboard, words flowing, candlewax dripping. The writer channels creative passions onto the page, and the next day, with his feet up and pen handy, he completes a round of edits. Solitary delight!

Of course, for most who write it’s not like that. It’s considerably grittier. For me, the down and dirty process of writing this book involved some dark days. The discipline required to sit and focus and write new thoughts that cohere together – it’s the reason many people talk about writing books but never do.

Entrepreneur and VC Ben Horowitz once wrote: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology. Organizational design, process design, metrics, hiring and firing were all relatively straightforward skills to master compared to keeping my mind in check. Over the years, I’ve spoken to hundreds of CEOs all with the same experience. Nonetheless, very few people talk about it and I have never read anything on the topic.”

This theory maps to serious writing projects. While outsiders tend to be very curious about how writers tactically do their job (“Do you write in the morning or at night???”), 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.

The first round of self-loathing for me came from my inability to stay focused and disciplined.

I think of myself as a focused and disciplined person in general. But idea generation and writing for many months challenged this competency in new ways. To soothe my ego, the struggle for focus and discipline seems to be endemic among writers more accomplished than I’ll ever be.

The late great David Foster Wallace once said that he spent most of the day thinking about how he should be writing, and being annoyed that he wasn’t in fact doing it. Only a small portion of the day, he said, he spent actually writing. A guy once interviewed Michael Lewis and prefaced his first question to Lewis, “So, you’ve written a lot.” Lewis interjected that in fact he has not written a lot. Lewis said he spends most of his time doing nothing writing-wise. He says that he never suffers from writers block – lack of ideas – rather, he suffers from sloth and indolence.

Bingo.

Doing focused work for 5-6 hours a day is really hard. We forget this because much of what keeps businesspeople “busy” during the day is plowing through email or sitting in random meetings or socializing. We waste hours to this daily ho hum. Yet through it all we trick ourselves into thinking we’re being productive since we’re “at work.”

The thing with writing is if you’re not being productive, you can’t pretend you are. A Word document doesn’t lie. Either you’ve written words or you haven’t. If you haven’t, a big white screen stares back at you. And you hate yourself.

To be sure, a lot of the “writing process” involves reading and research and thinking, not actual writing. So a white screen doesn’t necessarily you’ve done no work—but that’s how it feels.

The second layer of self-hate comes from the inevitable shittyness of early drafts of your writing.

I once asked David Foster Wallace in his office at Pomona, “How do you make your descriptions and adjectives so good?” And he answered, “By slaving over draft after draft.”

In the process of trying to figure out what you want to say, you write crap. And you know it’s crap. Anne Lamott’s famous writing dictum is: Shitty first drafts. But with books, it seems to be more like “shitty 20th draft.” It’s so shitty, for so long. And this wears on you.

Shitty content was what I feared most. The nightmare scenario for me was not poor sales but reviews of the book that went something like, “Some interesting ideas, but incoherently assembled, poorly written, and shallow.” It’s one thing for me to eat that review, but with Reid on-board, it seemed considerably more traumatic!

I tried a few times to hire professional writers to help out—to supplement the team we had in place. It didn’t work out, mainly because everyone outside the two of us and our editor and agent didn’t care as much as we did—they didn’t have a stake in the outcome. Ultimately I had to trust in our creative, iterative process—I had to trust that so long as we were continually improving, we’d get to a place of true quality.

What I did to improve focus

Lifestyle-wise, I started staying up late at night and waking up late. During my core work hours – 4 PM to 2 AM – few others were at work, which cut down on random phone calls and emails. I also cut various non-essential activities out of my life, which included cooking, blogging, and random socializing.

But my primary efforts were directed at managing technology. The internet is full of wonderful things. But its temptations, left unchecked, can preclude deep sea thinking and creative “flow.” If you’re checking your email every 10 minutes (or even every hour), it’s impossible to focus on serious writing. I strongly believe: YOU ARE NOT ENGAGED IN A SERIOUS WRITING PROJECT IF YOU ARE ABLE TO ACCESS THE INTERNET DURING YOUR “WRITING” TIME.

To wit:

In Microsoft Word, I used its full screen view so I could see nothing other than the white document background and a few key menu items.
I used an app called Self-Control on my Mac, which let me list domain names to block and a time period during which to block them. E.g., I could block twitter.com, facebook.com, nytimes.com from loading on my computer for up to 12 hours – and once set, there’s no way to un-do it, even if you re-start your computer. Highly recommended if you have internet addictions.
When I refused to use Self-Control, I turned off the AirPort wireless card on my computer. When that failed, I physically unplugged the internet router from the wall.
I did not upgrade my 3 year old T-Mobile Dash to a modern smartphone to prevent me from spending too much time on my phone.
I did play non-lyrical music from Pandora at times. Sometimes this jazzed the idea flow; sometimes it was a nice change of mood. (Sitting alone in your apartment all day with MS Word open can get fucking depressing.)

I started rigorously tracking my time so I couldn’t attempt self-delusion about how hard I was really working. Even if words weren’t flowing, I wanted to be sure I was logging a certain number of hours in front of the computer trying. I used an application called Toggl — I would click in and click out on the timer. If I ever got distracted and lost hard focus, I clicked out. During the first seven months of the project, I logged about 4 hours a day of hard focus time. During the eight or nine months of intense writing, I logged 7 hours of hard focus time. During the final crunch period of writing and editing, I could go up to 10 to 13 hours a day of hard focus (definitely not sustainable). Again – these are HARD focus hours – no email, web browsing, or random reading.

Unfocus matters too

Downtime is important for creativity. As Jonah Lehrer has pointed out, we generate new ideas when we let our unconscious work on a problem while our conscious attention roves on something else. Throughout the process, I took weekend trips to LA, Las Vegas, and Santa Fe to clear my mind and let my unconscious mull. I also followed SF Giants baseball a bunch and played lots of chess.

What I definitely did not do is read books for downtime. When you’re writing a lot, the last thing you want to do is open a book. Partly because you’re overloaded with language/words all day long; partly because it can make you depressed if you read really well-written books. I did less reading for pleasure in the year of writing than ever before in my adult life. (I did read a bunch for research purposes, but that’s different. Fortunately I didn’t commit suicide after reading 50 or so career books in a row.)

Immersion, disrupted

On a memorable Sunday in July 2011, I rolled out of bed, expecting to do a quick check of email and then turn off the internet and focus on writing and editing. Except, there was an email from Reid: Tom Friedman was going to write about the book in his column on Wednesday. We had not announced the book at all; we planned to do so at a time and place most strategic. Yet, always be ready for Plan B! Plan B: The book was going to be announced in Tom Friedman’s very next New York Times column. Reid and Tom were chatting about the book’s concepts at a retreat in Sun Valley and Tom got so intrigued by the topic that he wanted to write about it right away. Hard to say no. So my Sunday was spent not in ultra editorial focus, but rather working with Reid to answer Tom’s questions and get a skeleton web site up for the book in case of a traffic surge. Having to emerge from the writing cocoon and be public about what we were working on knocked me off balance, focus-wise, for about a week, but the early buzz turned out to be a good thing for us.

We were frequently re-naming and re-organizing chapters, as this stack of old drafts shows.

Another round of handwritten edits from our editor. Ink everywhere.

Getting Feedback and Help

Life’s a team sport. Tap your network. Lean on allies.

Those are messages in the book, and ones we embraced ourselves in the actual writing process.

Reid and I were always soliciting feedback from each other, of course, and we obtained huge amounts of help and feedback from start to finish from the core team, especially our editor Talia. But we also leaned on a broader circle of friends to help us at different points. In the early stages (as early as early 2010), I had regular phone chats and meetings with guys like Chris Yeh, Cal Newport, Stephen Dodson, and Ramit Sethi. On a sticky note on my computer I kept a list of open issues – e.g. how should we write about status considerations in the context of professional relationship? – so if a smart friend called me to chat, I could consult my list and get relevant advice on the spot.

In April 2011, Reid and I distributed a three-fourths complete manuscript to a set of friends. It was the first time we showed “the book” to about a dozen outsiders. Despite our qualifications that it was a rough draft missing several chapters, we assume we’d receive people’s “overall impressions” on the quality of the work.

When Reid sent the manuscript to friends, he asked, “Do you think the book is great? And if it’s not great, what can we do to make it great?”

The feedback we got back from people from our network was unfortunate in two ways: it was mostly negative and mostly unhelpful. Or, in answer to Reid’s question, their answers were that it wasn’t great, and there weren’t many suggestions on how to actually make it great.

The content of negative feedback touched on all sorts of things, such as: sprawling chapters; jerky back and forth between high minded intellectual prose and practical self-help nuggets – in other words, tone inconsistency; too many points made without concrete examples; too many tech examples and not enough career diversity represented; among other things.

Upon reflection, Reid and I agreed these were valid critiques—even if we didn’t know exactly how to fix them.

So, we were going to miss the May, 2011 submission deadline. Thinking you’re in the home stretch and then realizing you’re not makes you feel exhausted at the time and exhausted thinking about all that’s left to do. Fortunately, I was reading Bird by Bird by Anne Lamott at the time (an oldie but goodie and a must read for anyone crazy enough to do a writing project) and I happened upon the section that described the feeling of thinking you’re almost done and asking friends for just small tweaks…and then people come back and suggest deep incisions.

I told a friend I was exhausted and demoralized. The manuscript was not good enough and Reid and I didn’t know how to make it great. My friend replied, “You can do it. Take it literally one day at a time.” And so we did, from May, 2011 through to September, 2011.

***

It’s hard to get helpful help on a book manuscript.

Deep down, most smart people want to write a book and think they can write a book. Ever overconfident, feedback-givers suggest impractical changes that are influenced in part by the book they want to write. Moreover, while everyone’s written literature essays in English class, those are analyses about a finished literary product whereas giving feedback on a book-length living manuscript requires the much trickier skill of helping revise an unfinished product.

To be specific, it’s not hard to offer sentence-level feedback on word choice or grammar. Line edits are important, but relatively easy to spot and execute. What’s hard is feedback on flow, structure, overall coherence. Professional editors are able to help on both levels—think critically about overall organization and persuasiveness and edit word-by-word, sentence by sentence. Your generic super smart friend likely won’t have this dual ability.

On top of all this, someone working on a book manuscript is relatively emotionally fragile compared to someone asking you to comment on a draft of an op/ed piece.

Here’s my big lesson on how to get helpful help. Remember when Reid asked his friends whether the manuscript was great? The value judgment great / not great is helpful to know whether you are finished. We thought we were close to finished, but in fact we were not. That was a helpful part of the feedback process.

But once we realized we had more work to do, hearing whether someone thought it was great or not great – whether they liked it or didn’t like it – was not useful. What’s helpful is how you actually make the text better regardless of whether they like the current version or not. 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.

Reid himself did this well with me. He rarely passed judgment on the material. He rarely said, “I think this is good” or “I think this is rough” – instead he really zoomed in on specific ways to improve it. Only near the end of the whole process did he say, with some conclusiveness, “I think it’s pretty good – you?”

***

We didn’t do any more massive feedback-gathering efforts, but we both kept at it informally. And I should emphasize that several friends of Reid and me gave us crucial, absolutely helpful feedback. For example, I was at a San Francisco Giants game with Cal Newport and, as Tim Lincecum was getting shelled, I tested out our insight that competitive advantage emerges from the interplay of one’s assets, aspirations, and market realities—it was an especially clarifying conversation. We beefed up several chapters, improved tone and flow throughout, and finally discovered solutions to editorial organization questions that had been annoying us for months.

Special shout outs on my end to Jessie Young, Genoveva Llosa, Steve Dodson, David Casnocha, Marci Alboher, and John Lilly for offering some of the most helpful feedback.

Final QA Testing

In late July, we shipped the final manuscript. I sent it to Talia with the subject line: “Clear eyes, full hearts, can’t lose.” We were done. DONE!

Well, not quite. A few weeks after you submit the final document the publisher returns it with copyedits. A copywriter makes mostly line edits (“there” vs. “their”), but ours also addressed ideas (“This feels repetitive from the earlier page – is it necessary?”) and checked citations (“I don’t see the referenced word in the book you cite”).

The key characteristic of the copyediting stage is that it happens in Microsoft Word. It’s the last opportunity you have to make edits to the manuscript by typing into the document you’ve gotten to know so well. After the copyedits stage, authors get additional opportunities to make edits but by that point the text is already in the publisher proprietary program so you have to hand-write changes onto printed documents (called “page proofs” or “first pass docs”).

The page proofs have the text and graphics laid out and formatted so you can see what each page of the book will actually look like. It feels more than a little antiquated to be taking a pen and writing in edits on these pages, but the consolation is that by the time you reach this stage you’re only making the smallest of tweaks. Of course, Reid and I continued to notice lots of areas for potential incremental improvement, so we submitted more than the smallest of tweaks!

One day in October, 2011, Reid and I were Skyping to go over some of these last-minute edits. He was in Paris and I was in San Francisco. It was the middle of the night his time, middle afternoon my time. In a few hours, he was flying back to San Francisco and I was flying to Athens. We spent an hour going through edits, then he wanted to take a 15 minute break to take a shower and try to wake himself up. He did so, called me back, and we continued for another hour. Then, we both headed to our respective airports.

On my flight to Munich (connecting onto Athens) I wrote up the edits we had discussed. I landed in Munich, went to the Lufthansa lounge and finished inputting the edits in a separate document that would in turn get handwritten onto the pages by our tireless editor. Once done, I wanted to discard the print page proofs so they wouldn’t weigh me down (literally) on my onward journey. Ever paranoid, I placed the pages out of order into four different trash bins in the Lufthansa Munich lounge, lest someone come upon pages in the cans and see the book in its incomplete draft state!

When I got back to San Francisco, in the mail awaiting me were a few dozen “galleys” from the publisher—early paperback versions of the book designed for long lead media (e.g. monthly magazines) and other influentials (e.g. people who can blurb your book). The galleys did not incorporate our final final edits I was making in Athens, but did incorporate our copyedits from the prior stage.

A full-color, paperback galley is the first time you see all your work packaged in book form. For so long, authors must refer to their book-in-progress as a “manuscript,” since that’s what it is. It’s not a book yet; it’s just a Word document. When you get the galley, you finally feel comfortable referring to it as a book. The shift in vocabulary represents a magical moment. The finish line is in sight.

###

Sometimes, after so many iterations and edits, you can doubt whether you’re actually improving the text–or are simply spinning your wheels. Thus, one of the most rewarding emails I got post-publication was from my friend Steve who had read many early iterations:

I read the final book cover-to-cover and finished it yesterday. It’s an outstanding accomplishment. I found myself reading it, not as a friend, but as a reader, thinking about how I could use my network to enhance my career and Bretton. Like the DFW line you always reference, there should be a place where emerging writers can read all the early versions and discarded work of great writers. It’s basically the same book as what I saw early on, but it’s so much better: cleaner, funnier, smarter, sharper, more engaging.

We edited and re-edited the final page a bunch, until figuring out the winning last sentence.

A draft manuscript, the paperback galley, and the final hardcover book.

Marketing Campaign

We believed strongly that producing a great editorial product mattered more than a grand marketing plan. A movement builds from word-of-mouth and word-of-mouth happens when the product itself is worth talking about over a long period of time—in other words, if the book ain’t good, no amount of marketing jazz will make it a movement in the long run.

As a result, we spent little time thinking about marketing when we were engrossed in the writing process. Since the writing process took longer than expected, by the time we turned our attention to the marketing plan in September, we had precious little time before the February 14, 2012 pub date.

I’m not going to do a comprehensive breakdown of our marketing strategy or efforts. There’s been a lot written generally about book marketing elsewhere. And, frankly, our situation was unique. We had a large built-in platform and more resources to bring to the effort than most authors, so we were able to do many things concurrently that most authors cannot. That said, if you want to go in-depth on all the nitty gritty tactics of advanced book marketing that I learned, feel free to ping me at [email protected].

In this article I will make just five general book marketing points:

1) No one really knows what moves books. Timing matters more than anyone admits. A culture has to be ready to receive your book. Timing (and luck) matters in business too, of course, but it seems especially relevant in determining which books take the world by storm. Beyond that, you’ll hear smart people differ on the value of video trailers, traditional PR, social media, and so on—I have my own opinion on the relative worthiness of all these ideas but no one knows for sure which precise mix of things most reliably leads to success.

2) Authors have to take responsibility for much of the marketing effort. Authors work with lots of other parties, of course—the publisher, retailer partners, consultants, etc.—but in the end they have to own the process.

Business authors like to bash publishers’ marketing abilities, but publishers have a lot of really useful expertise. The problem is, no publisher as far as I know keeps an organized knowledge base (be it a wiki, document, spreadsheet, etc.) that they share with authors that report on the hundreds of book marketing exercises they take on every year. It’s up to the authors to initiate ideas and then garner feedback, money, and help.

3) Bookstores still matter in 2012. People wander through bookstores and buy your book or see your book and buy it in Amazon. CEOs look at books at airport bookstores. Publishers can get your book in bookstores. Publishers can also get your book displayed in more prominent places within the store. This is what you get with a big publisher that you don’t get self-publishing in print or online: the relationships with brick-and-mortar retailers. So it’s important to keep feeding information to your publisher, which they in turn can relay to retailers. And it’s important to stay up to date on the bookstore placement your publisher has arranged for your book in stores.

[Side note: Unfortunately, authors are not able to talk to retailers themselves. This will change soon (disintermediation is the unstoppable force in the industry) but until then, only your publisher can talk turkey with B&N and others.]

4) The bestsellers lists are not meritocratic. They track buying activity on a weekly basis in certain bookstore outlets it decides are worth tracking. A book can be a New York Times bestseller by selling several thousand books in a single week via the stores that happen to count, and then sell no more, ever. Another book can sell tends of thousand of books total over a couple months, and never be a NYT bestseller. So we were thrilled by our extended debut on “the list” and it helped create a halo effect for the book, but I never viewed that as the pinnacle achievement for the book. Nor should any author, I think.

5) Usually when people think about “book marketing” they think about how to convince an individual consumer to buy a book. But for business books, you sell more books more quickly via bulk purchases—companies, organizations, schools, governments, or well-to-do individuals who order hundreds or thousands of books at once. If you really care about sales, during the editorial process consider any angle you can develop that would make the book relevant to organizations that could order many books at once. And then figure out how to process those bulk orders in a way that reports properly to sales databases. This was one of my top uses of time in the lead-up to launch. Every business book author should have plan for pitching, processing, and fulfilling bulk orders.

There’s so much more to write on this topic, but as I said, this is not going to be a comprehensive breakdown. Perhaps in a separate article! For now, I want to give a shoutout to Surya Yalamanchili, Tara Gilbride, Paul Lamb, Meredith McGinnis, Greg Brauner, Tom Frangione, Lisa DiMona, Saida Sapieva, and others who helped in the roll-out of Start-Up of You. Ian Alas (who joined in fall 2011) and Brett Bolkowy (who continued on after his research role) were also part of the core marketing team; they have been indispensable team members.

Results To Date

Six months after publication, I’m proud to say that on the most important barometer for Reid and me—do smart, motivated people find the book helpful?—the answer has been a strong yes.

Thousands of people have shared their stories about how the Start-Up of You changed their lives. We documented some of these stories on our web site and you can see hundreds of people’s self-introductions in our LinkedIn group. The Economist and the Financial Times and other media and blog outlets reviewed the book with acclaim.

Sales have been robust. By a few months after publication, we’d shipped over 100,000 units across print, electronic, and audio channels. We debuted at #1 on the NYT bestseller list and spent seven consecutive weeks on the list. It’s been sold into over 15 languages.

A particular pleasure has been the strong uptake among students and faculty. Several schools have adopted the book into their course reading. Today’s students are tomorrow’s leaders and we’re delighted to be able to help shape the way they think about launching their careers.

Now, have we started a movement with Start-Up of You? That’s hard to measure. We see promising signs in lots of places, but it’s too early to say whether Start-Up of You is redefining the way we talk about careers. I suspect it will be months before we have a clearer sense.

Finally, this is not a postmortem! The Start-Up of You is very much a living, breathing operation. The book is launching in 15+ languages abroad and we’re continuing to explore the book’s implications to corporations and other constituencies.

On The Charlie Rose Show with Reid, followed by the book’s launch party at Michael Bloomberg’s house, followed by dinner with the Mayor. A memorable day in February, 2012.

Thanks…

Thank you to everyone who has helped make the journey so far so rewarding, and thanks most of all to Reid. From New York to Los Angeles, London to Tokyo, and who knows how many days in the Bay Area, it’s been a non-stop growth experience with him. Thanks Reid for being a friend, mentor, partner, and co-conspirator in the wild journey of conceiving and publishing a book, and launching an intellectual movement.

If my future professional endeavors involve as much entrepreneurial verve and intellectual stimulation as The Start-Up of You project, I’ll consider myself very lucky indeed.