Writing UNSECURITY Journey –Planning

A series of posts dedicated to the journey of writing my first book, Unsecurity: Information security is failing. Breaches are epidemic. How can we fix this broken industry?. This is the fourth post in the series.

The others…

Once I had the idea for the book and found the courage to write one, I started planning. Honestly, I had no idea what I was planning at the time, but I think I was pretty good at faking it.


If you’re going to write a book, you need to have a plan. You could do what I did. I thought I had a plan, but I later found out that I had no clue. One word sums up my plan, naïve. I was naïve to think that writing a book would be simple, and I was too proud to ask someone for guidance.

Here’s the deal. I had zero experience writing books. What would make me think that I knew what it takes to write a book? The answer is pride. I got this! So, I planned like any cavalier neophyte would. I didn’t.

Well, that’s not entirely true. I did plan one thing. I planned time off to write. I set aside two full weeks to write the book. I would take two weeks, write the book, and life would be grand. After that, I’ll just give the book to our marketing team, and they’ll come back with a finished, published book. Simple, right?

Except that’s not how it works.

First off, you don’t write a book in two weeks. Not this kind of book anyway. Maybe it’s been done somewhere before by someone with super special powers, but normal people don’t write books in two weeks. Normal people take months, and even years to write a book.

Second, there’s a helluva lot more to writing a book than writing. It’s a pipe dream to think that I could write a book, go away for some period of time, and voila, a published book.

I sort of had a plan, but my planned sucked.

If would have taken the time to stop, ask questions of other authors, and listened to what they had to say, I would have known to plan much better than I did. The lack of planning led to unrealistic expectations of myself and others. It made the journey less pleasurable than it could have been. Don’t get me wrong, writing this book was an amazing experience, it just could have been amazinger.

Some of the things I didn’t know, and I wish I would have asked a fellow author about:

  1. How long it takes to write a book?
  2. How long should a book like mine be?
  3. What comes after writing a book draft?
  4. How much fighting with myself that I’d have to endure?
  5. How to overcome the times of despair?

There’s probably more, but you get the gist.

My (naïve) Plan

Get this. I was dumb enough to think I could write a book in two weeks! The notion started with a discussion I had with a colleague who suggested that I take two weeks off, get away, and write the book. He said that I’d probably knock most of it out if I was able to get in a quiet place and focus. There’s a problem with this advice, it was given by someone who’d never written a book before. If only I had known.

So, I booked two weeks away in Cancun to write. The first week, I would be completely by myself. I would be in isolation so I could write. The second week, I would be joined by my wife and my 13-year-old daughter. In the second week, I would write all day and spend the late afternoons and evenings with my family. Sounds like a helluva plan!

My goal was to have my draft completed before I was going to leave on vacation in March. This means the plan was to start writing the book on January 6th, 2018 and complete the first draft 76 days later on March 23rd, 2018. Piece of cake.

I would later learn, sometime in April, after the draft was completed, that writing a book like this in 76 days was insane! Why did I learn this later? Pride kept me from asking anyone.

Your Planning

I learned some things about planning and book writing (now), and I hope you learn from my mistakes. Here’s a shortlist of tips for you as you begin planning your first book (or even latter ones):

Ask for advice. Don’t think you know how to do something that you’ve never done before. An experienced author would have told me what to expect, would have helped me plan better, and quite frankly would have helped me create a better book.

Planning to write is only one part of planning a book. Set aside time each day. The time you set aside is sacred writing time. Writing only. Even if you don’t feel like it some days, fight through it. Even if you just sit there staring at the screen, it’s still set aside writing time.

Other planning that I didn’t do, that I most certainly will do next time:

  • Marketing the book. I think book marketing should start before you start writing. Think about who’s going to find value in your book, who’s going to read your book, and how you’re going to reach them with a message that will get them to buy your book. This a bigger plan than you think, and you’re probably going to need some help.
  • Publishing. Who’s going to publish the book? If you’re going to self-publish, you might want to read up on what this all entails. If you’re going to engage a publisher, it probably makes sense to identify potential publishers now. Publishers will cost you money, so a budget should be created. Identifying and engaging a publisher can be a project by itself. Once engaged, they will help with other parts of your plan.
  • Other help. What other help might I need, how will I find them, how much will it cost, and when will I need them? Will I need a ghost writer, one or more editors (yes), one or more proofreaders (yes), a book designer, etc.? How about endorsements? If your planning to work with a publisher, they can help you with most of these things. If your self-publishing, you’ve got more research to do.

Establish a rough timeline. I don’t suggest that you try to write a book in 76 days, or less. I suggest you find someone who can coach you and help you set appropriate expectations. Deadlines are good for some people and sticking to a timeline works. For others, deadlines and timelines only add unnecessary stress. Turns out, it’s not necessarily how much I write each day that matters as much as that I write each day.

WARNING: Don’t use planning as an excuse for writing. At some point, it’s time to write.


Don’t make the same mistake I did. If you’ve never written a book before, ask someone for advice, preferably someone who has written a book before. My failure to seek advice led to a very unhealthy 76 days, and it also led me to write twice as much content than I needed. The stress in writing a book in such a short period of time is grueling, and writing twice as much as I needed was just wasted effort.

I didn’t discover that my timeline was unrealistic or about the wasted effort until I finally asked someone who knew. My original 500+ pages in the draft wound up being 288 pages in the published book. Ugh!


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