How To Write 50,000 Words

It was 11:30pm on a Sunday and I squinted at my to-do list. Among the first things I had planned for Sunday was to do some writing. I had deliberately not made any plans with friends to save a 3 hour block to write starting in the morning. During this Sunday I had purviewed at least 30 websites, consumed 3 cups of coffee to get in the zone, ordered two books from Amazon, called a friend, multi-tasked over 15 tabs, cooked food, and cleaned my apartment. I had done a remarkably long list of things, except write a word of anything. Slouched in front of my laptop I knew that I needed to go to bed soon in order to make my early morning meeting at work the next day. Demoralized, I called it a night, with hopes of trying better next week.

The above scenario would recur for years. I had high standards for my writing. Every paragraph had to be perfect, which would then make the perfect essay or chapter which would then lead to the perfect book. Having such high standards was paralyzing and instead of writing the perfect paragraph, I wrote no paragraphs. Then, over a two-year period, I wrote 50,000 words for a personal project.

I did this by transforming my relationship with perfectionism. The first required some inner work, and the second involved changing my habits.

One of the coolest ideas I picked up from Robert Johnson’s work was that the unconscious forces that drive your behavior can be negotiated with. The unconscious loves deals. Think of your perfectionism as a legitimate stakeholder in your psyche. You can try to ignore it, but doing so only makes it feel unheard and it lobbies for more and more attention and forces your hand. It will make sure its presence is felt by making you procrastinate.

What does your perfectionism want? Simply pick up a journal, and ask yourself this question. Wait, and eventually you will hear an answer back. In my case, it wanted my work to be really really good. It wants what I make to be legendary, perhaps to be in the pantheon of great work. It critiques every word to see if it is up to its standards. The drive to create a great body of work is a noble one, despite it being counter-productive. This is the deal I struck. You can have as much say as you want in my second, third, or fourth drafts. But you don’t get a say in my first draft. And I don’t commit to publishing anything I write. Notice the 50,000-word project appears nowhere on this blog. It may in the future or it may not. This is very liberating. I can write whatever comes to mind on my first draft without censoring myself.

Don’t hold back in the first draft! Even if you are using filthy language for something that will eventually be seen for a professional audience put it all in, and don’t go into editing mode. Writing uncensored will also transfer your energy and feeling into your writing, and then onto your future reader. You can always make it more presentable in the second or third draft.

If you are still struggling so hard to write, chances are that you are writing about the wrong thing. Your perfectionism is preventing you from writing about the right thing, because in your mind you think the right thing is too ordinary, too small and not interesting enough. There is wisdom in following the path of least resistance when it comes to writing. If something feels challenging to write, or if you are hitting a writer’s block it is often a sign that you don’t have enough life experience or information about the thing you want to write about. It means you need to do more research and spend more time on the subject, and let it brew in your subconscious before you can write about it.

For example a couple of months back, I wanted to write a long-form piece on negotiations in diplomacy. I’ve started to really focus on the theme of negotiation over the past year and thought I could write something around negotiation skills and diplomacy which is also an interest of mine. But I could barely get anything on paper. I had to really force myself to write even a couple of lines.

I stepped back to analyze my situation. I’m still new to learning about negotiation. And I hadn’t really gone deep on diplomacy for a very long time, and no case studies really appealed to me. I had stories from newspaper articles and world events that I wanted to write about. But I didn’t know the material in a very solid way. I asked myself, where in my life is negotiation coming up a lot? I work in sales at a SAAS company and I encounter situations every day where I have to negotiate. I decided to instead focus on writing about negotiation in SAAS companies. All of a sudden I wasn’t running out of material to write about any more. This goes against some advice I see online that says you should write to learn. This is good advice if your goal is to learn something. But it is bad advice if you are trying to increase the output of your writing and fight your perfectionism.

Ever go to a Starbucks and forget to tell the barista to leave enough room for cream in your coffee? You walk over to the cream station and deduce that you might be able to add enough cream without it spilling over even though the black coffee line is dangerously close to the top of the cup. You fill the cream to the very rim and congratulate yourself on getting the exact light brown color of coffee you like to drink. Then you close the lid, but as soon as you do so, the cup overflows and coffee just spills right out. Well, that’s how the subjects you want to write about should feel like. You should be picking topics where you are overflowing with ideas and perspectives.

Along with changing my relationship with perfectionism, I also built a simple habit based on the idea of chunking. That is if you have a really big task, the complexity of the task can lead to procrastination. And one way to overcome this is to chunk it down into little parts. This is useful in learning new skills and subjects.

[Read my review of Joshua Watzkin’s the Art of Learning to learn more about chunking]

I began applying this to my writing. Instead of having goals to write 1000s of words over one uninterrupted stretch of time, I’ve realized that’s really not how my brain operates. Some people are not like this. They can crank out 1000s of words in one sitting. Maybe with more practice I shall get there. However, what worked for me was learning about making a very small achievable goal: write for 15 mins a day during the weekdays. Now you might scoff at this. But 15 minutes a day paired with my earlier practice allows you to write approximately 200 words a day. Which if you write 5 days a week, you’d end up with about a 1,000 words a week. Well, 1,000 words a week is an essay a week. And if you stick to this for a year, you get to 50,000 words in a year which adds up to the first draft of a book. However, it is important to note that even if you write 5 words in those 15 minutes it is a success. I recommend even using a timer when you are first starting and then commit to ending in 15 minutes as well. This takes the pressure off, makes it easy to schedule, and then gives a sense of accomplishment at the end.