Lessons learned from my bad habits

Since leaving WordPress.com to return to writing full time, a surprise has been the decline in my writing habits. It has taken taken months to get them back.

As an exercise in sharing what I learn with you here on the blog, here’s my recap:

  • Writing of any kind is harder than other work. A secret benefit active writers have is they write all the time. That’s most of what they do. They forget that doing other kinds of work is so much easier (and pays so much better). In a regular job, you show up, there are piles of things that need to be done and people to do them with, and off you go. But returning to writing after having a conventional job allowed me to remake a discovery: writing is hard. It’s harder than doing most other kinds of work because you have to make everything up: the page is blank every time you start.
  • When writing feels hard it probably means you’re doing something right. I stayed at WordPress.com for 6 extra months, in part, because leading, designing, and managing, as challenging as those things can be, are easier than filling blank pages. I worked with great people, which made every day fun and gratifying. And I knew returning to writing had less immediate, and more isolated, rewards. As obvious as this all sounds, it has taken weeks to fully internalize these lessons. There is no way around it: writing is challenging. I’ve had to remind myself that when it feels hard it doesn’t mean I’m doing anything wrong, it probably means I’m doing something right.
  • The fundamental rule of making things happen in any kind of work is simple: 1) If progress is slow, reduce your scope. 2) Repeat as necessary. That’s it. If you persist, eventually you have a small enough unit of work that progress is clear and easy. This sounds obvious, but it took me months to relearn it in practice. For weeks I was working on the new book without daily goals or a clear outline or any reasonable structure at all. It was like wandering around in a half-finished maze, in the dark, with one eye open. When blogging you don’t need much structure: you can’t get lost in writing a single blog post. But for bigger writing projects you need some scaffolding to make progress.
  • The next book is always the hardest. I’ve never worked on a book based on a journal before, and I expected it’d be easier than my previous book projects. WRONG. The current book is always the hard one. Writers are good at lying to themselves about this. It’s the only way to trick ourselves into big new projects. But past projects will always seem easier than current ones. Why? Because they’re DONE.
  • Blogging is snack sized writing: I love blogging, but writing 300-1000 word pieces requires different skills and discipline than writing 2000, 5000 or 50,000 word pieces. Skill at any craft is only as good as your frequency of practice.  I hadn’t written a book in a couple of years, and all the blogging had let those writing for long reading muscles fade. Like sprinting daily for a year and then suddenly trying to run a marathon, you’re confronted with how inadequate your habits are to the task. It takes time to relearn all the little things you have to do, including changing your habits, when the goals are larger.
  • Blogging is not a diary. Some bloggers confuse publishing with keeping a diary. It’s not the same. No matter how open a blogger is about what they will share, they will write about those things differently if they are writing for other people (blog) vs. writing just for themselves (diary). I’ve kept a diary for over 20 years. It’s where I go to safely explore my own thoughts and feelings free from judgement by anyone else. If I wrote those entries knowing other eyes would see them I’d I’d write differently, and lose some of my intimacy with myself.  While working at WordPress.com I was writing so much in so many different places, including keeping a separate journal with notes for the next book, that I didn’t write in my diary often. I missed the power I got from just writing for myself.

Looking back I see how I could have been more disciplined. But working two jobs was tough, and I don’t know if I could have done it all to some imagined standard and still have been a happy guy when I wasn’t working. There’s only so much willpower and discipline any of us have.

Looking forward, the new book is coming along nicely now. And I’ll be sharing more about the book itself as well as involving you in the process as it comes together. Stay tuned. A good summary of what is in the works is here.

Have questions about my writing habits? Ask away in the comments.

7 Responses to “Lessons learned from my bad habits”

  1. Phil Simon

    Funny…I have found that writing has become easier with each book. But you’re right: you’re righting a very different book now. Perhaps it’s the type of book that’s most challenging–not the fact that it’s the most recent.

  2. Greg Linster

    Scott: Since you opened it up, I have a few questions for you.

    1) How do you initially tackle a book project once you’ve developed the overarching idea for what the book will be about?

    2) Do you map out each and every chapter in an outline or do you start with a concept, write an introductory chapter, and then go from there creating chapters as you see fit?

    3) How do you organize your references, and how do you make sure you’ve covered all the relevant literature on specific topics within the book?

    1. Scott Berkun

      Hi Greg:

      Sure. I don’t think there’s any magic way to do these things. There are many different ways to do this stuff and as long as it works for you, that’s all you need.

      1 & 2:

      I start out with a long list of ideas, topics, questions, thoughts and links, and let it grow over time. Whenever I have a thought for the project, I just add it to the list.

      Eventually I sit down and organize it roughly into chapters, and shift all the items to fit. Some don’t, but I keep them around anyway as they might fit somewhere I don’t expect later on. I might write a few sentences to explain each chapter to help myself understand what it is, what it isn’t, and how fits with the other chapters.

      At some point I’ll pick one chapter and write a draft. Writing that first draft usually makes me realize the outline needs to change, and I’ll go and do that as needed.

      3. How do you organize references?

      While I’m doing research I take notes on every book I read. I mark the page numbers for any quotes or specific points so they’re easy to refer to later. The notes aren’t fancy – just enough detail so I can remind myself what the fact/quote/point was and where in the book to find it.

      For some of my books, I’d total up my notes per book and include it in the book as an indicator of which books were more influential. You can see it here:


      If you work with a publisher, they typically expect a complete outline, a sample and a few other things, before they’d even consider your project.

  3. Kate Matsudaira

    This is a great list! I do have question I’d love your perspective on, though. When it comes to longer writing I find that I get very excited initially and then about half way through can lose my steam. At the point working on the project becomes a chore and sometimes dreadful. How do you keep yourself motivated?


  4. Bella Mahaya Carter

    Thanks, Scott, I enjoyed reading this. One thing it’s taken me 25+ years to realize is that writing doesn’t have to be hard. It’s a lot harder when I’m NOT writing than when I am. Writing is hard when I’m not trusting myself, when I’m judging my work, and worrying. When I’m able to release limiting and debilitating thoughts and behaviors writing is an absolute pleasure—not hard at all!



Leave a Reply

* Required