How to Spend 10 years to write One ^@#$ Book

Why imposter syndrome and starting and stopping a project slow everything down

How to Spend 10 years to write One ^@#$ Book

Just punch yourself in the face every day instead

I wrote a blog post years ago, when I had been working from home just long enough to hate it fiercely, but not long enough to have it figured out. There were enough people that saw it and nodded their head that I thought "hey I should write more about this". I put up a landing page and said that I was writing a book about remote work. This was back when it had just stopped being called telecommuting and was called working from home. Before distributed or remote were the right terms.

Then I didn't publish the book until last week, which is ten full years later. Why did it take so long? Many reasons:

  • Although the blog post might have gotten a lot of views, it didn't contain any real solutions. I didn't have any solutions. So I felt unqualified to write more about it. I wrote up an outline and then did nothing for a few years.
  • I didn't at the time have any experience with working from home outside of my own limited experience at the time (1 spouse, 1 toddler, with an office door that shut).
  • I hadn't managed anybody who worked remotely, or started a company remotely. I had met in person every single person I was working with and ate lunch with them once a week, so it didn't feel like real remote work.
  • I didn't have the time; I had more important things to do, like rewatching The Wire, having three more kids, starting a company, and writing other stuff to figure out what I thought about what worked and what didn't.
  • I hadn't followed the advice of Scott Berkun, who said that in order to write a book about something, you need to read at least 10 other books in that style, and many more on that subject. Also, I couldn't find many books about remote work. Then Scott published his, and then Wade Foster published a guide, and many other companies told you how to run a remote team.
  • But there was still a gap, but it felt a bit too personal to talk about. Nobody seemed to write about how it takes to work remotely personally. Nobody was spitting the truth about what it is like for the worker in the negative. There was only talk of going to recitals and school events and hiking in the woods; there wasn't any discussion of how lonely and disconnected it felt, and how hard it was to get stuff done alone.
  • But by this point I had figured out some things that worked for me, and had met a lot of other remote workers that knew you have to do it just right. You also have to establish boundaries to keep yourself from going too lonely, or stir-crazy, or feeling like work and home are the same thing.
  • So I sat down and worked on it, and writing a book is harder than reading a lot of books, much harder. Writing a book is like cutting all the letters out of your favorite book, then re-assembling them using loose staples. You have to write 10 words to keep one. I remember as a child my father telling me that he had run into an author and asked him how his day was going and his reply was "Great, I've already written 3 pages today". I thought that sounded good, but my father said it meant that the book was going to be bad; that three sentences a day is more like it. I didn't understand that at the time, but I do now. You write 3 pages and cut 2.5.
  • I picked at the book for years, writing down unpolished ideas as I became more experienced with remote work. I took months away from it, and did things like watching Mad Men, The Wire in full again, and sleeping and having a career and being a father. If you don't work on it nearly every day, writing a book is even harder.
  • Then the pandemic hit, and I saw so many people struggling with sudden remote work done in an emergency. This motivated me to finish and hit publish, maybe it would help somebody, and there were suddenly many somebodies out there.

If you are looking for true advice from someone who understands the struggle of remote work and has actual useful advice, check out  Navigating Remote Work.