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7 Lessons Learned From Writing a Business Book

Wow, so it’s been a long time coming, but Collaborate: The Modern Playbook for Leading a Small Team to Create, Market, and Sell Digital Products Online is almost finished!

Today, I want to share some of my lessons learned (the good, the bad, and the ugly) from writing this book…

But first, a bit of background:

I started this project a year ago this month. I actually ran the Publishizer.com crowdfunding campaign in November and doubled my funding goal by early December, 2015. To be honest, with my small audience of about 1,500 subscribers, I wasn’t sure I’d be able to hit my goal…but somehow we made it happen (thank you to all my early adopters – couldn’t have done it without you).

The problem with crowdfunding campaigns, though…especially successful ones…is that you now have to make good on the promise.

While the campaign was hard work, writing and creating a book worth reading was the REAL hard work (young Tom would later come to find out).

And now, what started as just an idea about 360 days ago, has finally become a 352 page, beautifully designed and formatted book published by Insurgent Publishing, and is almost ready for hardcover printing and distribution.

Here’s a mockup of what the hardcover will look like when it gets into your sweet little hands in January, 2016:

Collaborate Hardcover

To say I’m thrilled to see this come together is an understatement.

And I couldn’t have done it without you, the reader (nor would I have wanted to).

As a way to say thanks, here are 7 of my biggest “lessons learned” from writing a business book:

7 Lessons Learned From Writing a Business Book

Lesson #1: If it’s worthwhile, it will be hard to write

To be clear, Collaborate is not my first book and not my first business book, but it is the biggest, most bold book project I’ve undertaken , and dwarfs the other books I’ve written in terms of raw content and scope.

The idea for Collaborate has been incubating in my brain for the past 3 to 5 years. I wasn’t ready to write this book for the longest time. Ironically, even after finishing it, I still don’t feel ready to write it in a lot of ways…


Because I’m writing something that hasn’t been written before…not in this way, not in this style, not for this purpose.

It’s (generally) easy to regurgitate what others have said – it’s much more difficult to develop a new framework by collecting, analyzing, and synthesizing hundreds of seemingly disparate ideas, perspectives, case studies, research, and more…and do so in a way that is easy to follow, to understand, to use, and to embrace.

Harder still to make sure that the majority of readers will actually benefit from the book (in other words, to avoid writing fluffy drivel…I HATE fluffy drivel…).

I pulled my hair out for the past twelve months writing and rewriting Collaborate.

I seriously felt like this:

I think I went through at least 5 unique drafts, totally different from one another. The current iteration, the one you will see in your hands in a few weeks, went through over a hundred iterations as the writing progressed.

Writing is hard.

Writing something worthwhile is even harder.

The pain of creation can seem insurmountable at times.

If you’re not up to the task, scrap the idea before you start; it will save you a lot of time, money, and pain.

Alternatively, if you’re committed to your idea – if you know you have to turn this thing into reality….and you have the grit and hustle to make sure it comes to fruition, then make sure you finish and ship. Anything else is half-stepping (and nobody likes a half-stepper).

Learning Lesson: doing anything worthwhile is hard; don’t run from the discomfort, embrace it.

Lesson #2: Whatever your estimated timeline, quadruple it

Humans are terrible planners.

I know this from heuristics, but academic studies have confirmed it. From Wikipedia:

“The planning fallacy, first proposed by Daniel Kahneman and Amos Tversky in 1979, is a phenomenon in which predictions about how much time will be needed to complete a future task display an optimism bias (underestimate the time needed). This phenomenon occurs regardless of the individual’s knowledge that past tasks of a similar nature have taken longer to complete than generally planned.”

The funny thing is, no matter how well I “know” myself, I still make huge timeline mistakes on just about any project that will take more than a week to create and ship.

I expected to finish Collaborate in 3 months.

I was all like:

But then I started writing…

And the project became much more complex than I expected…

And I had to do a lot more research, analysis, and work than I anticipated…

And I ended up not finishing Collaborate until November 2016, one year later, or 4x longer than expected.

At this point I’m all like:

…and I’m just happy, that, somehow magically, Collaborate is finished.

Why, knowing we are bad at planning, can we not mitigate this reality?

I honestly have no idea.

Neither does science.

Learning Lesson: The only thing I can say is that if you’re starting a new project, use this rule of wrist:

Whatever your estimated time to complete a project, quadruple it.

Lesson #3: Nobody will write your book for you

I write, although I don’t consider myself a writer.

And I’m certainly not one of those people who wears the word “writer” proudly like a piece of Chotchkie’s flair.

That said, I recognize that writing is an important part of what I do – and an important part of what any notable entrepreneur, creator, or politician does.

I also learned pretty quick that, regardless of how much you might hate the writing process at times, nobody can write your book for you.

I learned this the hard way. Here are just a few of my missteps:

Mistake 1. I tried using old blog posts as the foundation for my new book. I really liked the idea of re-purposing useful, old (but still relevant) content. However, blog posts are blog posts and are not chapters in a book; they are written a different way with a different purpose. I ended up scrapping everything I pulled from my own blog and rewriting everything from scratch…this set me back several weeks.

Mistake 2. I looked for a co-author. I actually found a great one, a good friend of mine, actually, but after a few sessions, we parted ways because we realized the vision for the book didn’t quite align. I could have looked for another, but after spending a couple weeks trying to make this work, I decided that the particular vision I have for this project is probably only one I can bring to light (no one else will see the things the way you do). While I love the idea of co-authoring a book, for something like this that had been incubating in my brain ball for so long, it was hard to work with anyone else on it (my mistake for not recognizing this from the start). In the end, I was left writing the book by myself.

Mistake 3. I hired someone to transcribe my interviews into working pieces of content. In other words, I didn’t just want the pieces transcribed (well, I wanted that to begin with), I wanted them edited into a book-like style (with intros, properly quoting the interviewee in the context of the topic, etc.) so I could more easily place them into the context of the book. I put a lot of money toward this and what I got back were “articles” that were so incoherent with so many spelling and grammar mistakes that I literally laughed out loud. This was from a professional ghost writer, mind you. I tried to rectify the situation by asking for a rewrite…which I got, but the articles were still terrible…so I asked for a rewrite, and got back another terrible article, just with less spelling and grammar mistakes…

When I got back the third iteration of terrible, expensive articles, I was all like:

But regardless of how upset I was, there was still work to be done…and I was still forced to write everything myself.

Learning Lesson: If you’re a picky writer (and you should be if you’re writing something worthwhile…see Lesson #1 above), nobody can write your words for you. Suck it up and get to work.

Lesson #4: Create in the proper sequence

After my crowdfunding campaign I spent a lot of time organizing design notes, prepping my live webinars, outlining my course…

Which is all great, and still stuff I need to do, but these weren’t CRITICAL PATH items, which means working on them in the beginning slowed my progress.

I would explain the critical path, but Seth Godin is much smarter than me:

“The longest string of dependent, non-compressible tasks is the critical path.

Every complicated project is the same. Many people working on many elements, some of which are dependent on others. I want a garden, which means I need grading, a bulldozer, a permit, seeds, fertilizer, irrigation, weeding, planting, maintenance and time for everything to grow. Do those steps in the wrong order, nothing happens. Try to grow corn in a week by giving it a bonus or threatening to fire it, nothing happens…

Critical path analysis works backward, looking at the calendar and success and at each step from the end to the start, determining what you’ll be waiting on.

For example, in your mind’s eye, the garden has a nice sign in front. The nice sign takes about a week to get made by the sign guy, and it depends on nothing. You can order the sign any time until a week before you need it. On the other hand, you can’t plant until you grade and you can’t grade until you get the delivery of soil and you can’t get the delivery until you’ve got a permit from the local town.

Which means that if you’re the person in charge of both the sign and the permit, do the permit first.” – Seth Godin, Understanding critical path

Bottom line, whatever you are creating needs to be created in a particular sequence. That particular sequence should be developed by creating a critical path plan. That critical path plan should be developed at the start of your project by working backward from the ship date.


If you’re writing a book, stop looking at interior design inspiration before the book is written…

If you’re building a startup, stop analyzing competitor logos before you have an MVP…

If you’re building a membership site, stop reading about “scaling” until you have at least 10 customers…

I know all this,  but I broke my own rules (for the first couple months at least).

Eventually, though, I defined the critical path and stuck to it. And finally, I was all like:

Learning Lesson: the hardest work you can do as a leader (solo or collaboratively) is defining the critical path and sticking to it. It’s the hardest because it’s the most important. Don’t skip it.

Lesson #5: The Enemy will try to make you fail

Seth Godin calls it the lizard brain; Steven Pressfield calls it resistance; Winnie the Pooh calls it Heffalumps…

I like to refer to those things that keep us from doing our great work as the Enemy.

The Enemy takes many shapes:

All the ups and downs of writing Collaborate came from the Enemy; it was never any external forces that kept me from writing faster or better – it was the Enemy trying to stop me from reaching, expanding, and stretching my boundaries.

Luckily, I took care of the Enemy every time I saw it rear its ugly head:

Lesson learned: if you’re trying to do something new, different, outside your current status-quo or paradigm, the Enemy will sabatoge, prevent, and slow your progress every step of the way. Accept this. Keep moving anyway.

Lesson #6: Every book is a collaboration

I mentioned earlier that nobody will write your book for you. That’s still true. But, if you’re a writer (and if you’re the author, that’s what you are), then stick to writing. Get experts to edit, design, market, and sell.

I leveraged an amazing team of experts to bring Collaborate to life.

I had multiple editors, a great designer, and have a team that’s ready to market and sell the book when I pull the trigger. I would not attempt any of this alone.

Lesson learned: make sure you’re not going it alone. No matter how small your project, it could benefit from creative collaborators. If you aren’t sure how that works or where to start…hey, look at that! A new book on the subject:

In Collaborate, you will learn:

  • How to take personal inventory of your business and life to make better choices
  • How to define, identify, and connect with experts in your niche
  • How to assemble and organize a small team to create faster, better, and more enjoyably
  • How to rapidly prototype your idea, presell it, and then collaboratively crowdsource to build the final product
  • How to leverage the best free and inexpensive software to make remote, collaborative work a breeze
  • And much, much more…

Learn how to assemble, organize, and lead a small team of creative collaborators by signing up for the Collaborate early notification list here.

Lesson #7: I’m never writing a book again…until the next one

And my final lesson learned is that I don’t want to ever write a book again because it’s hard. Really hard. So hard I think I started to go a bit crazy:

But it’s also crazy rewarding…

Which is why I’m already working on my next book: The Tao of Nicolas Cage: A memoir of my time thinking about Nicolas Cage losing his s***

Lesson learned: once you finish your first book (or 50th), start on the next one; momentum is on your side – take advantage.

In Summary

Writing Collaborate has been an adventure with a bunch of ups and downs, but the book is finally (almost) ready to print and ship (finalizing the design right now).

My hope is that you’ve enjoyed this article, and found it useful enough to:

  1. Sign up to be notified when Collaborate launches
  2. Share with you friends, family, and social network.

I’ve made some clicktotweets to make this easy (they may or may not be appropriate, I’ll leave that to you to decide).

Thanks in advance for your support:

What Nicolas Cage epic freak-outs can teach us about writing: http://bit.ly/1Ran0Zj [CLICK TO TWEET]

What do Nicolas Cage epic freak-outs and writing a business book have in common? http://bit.ly/1Ran0Zj [CLICK TO TWEET]

7 lessons learned from writing a business books (hat tip: Nicolas Cage): http://bit.ly/1Ran0Zj [CLICK TO TWEET]

Hat tip: Nicolas Cage for the inspiration and giphy.com for all the amazing Nicolas Cage gifs


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