Working on Writing

I started writing publicly and regularly a few years ago with the explicit goal of improving the clarity of my thinking and sharing this thinking with others. I’ve now published over 100 blog posts and through practice, I’ve made good progress in communicating more clearly but still have a long way to go to become a better writer.

As our work becomes even more distributed (and asynchronous), the ability to communicate with both clarity AND personality can be an important addition to all of our toolkits. So I decided to take more systematic steps to improve my writing beyond just churning out a bunch more blog posts.

In general, I write about a few types of things:

  • Documenting Knowledge: Documenting a practice or a topic where I have deep experience and hopefully an interesting perspective. Examples include Product Rituals, Angel Investing.
  • Learning in Public: I’m always trying to learn new things, and by writing things down and sharing them, I can use these posts to refine my point of view from smart(er), or more knowledgeable people out there. Examples include Models for Giving, Open World.
  • Personal Reflections and/or Growth: Sharing my own lessons and learnings, books I’ve read, etc. These are some of the best opportunities to practice communicating with more personality and authenticity. Examples include Being 40, A Purposeful Career.

In all these cases, I want to present a well-structured perspective communicated in a way that showcases not only my knowledge or thinking but also my personality. On reflection and feedback from friends, I think I’ve improved at structure and clarity but made less progress on communicating with humor and personality.

To further improve, I read books from great writers (on writing) and hired an editor to read a selection of my previous posts/writing and help with specific, actionable feedback.

The three books I read were:

  • On Writing, Stephen King: Excellent and easy read by one of the greats. It was personal, yet practical, and I strongly recommend it.
  • The Hero’s Journey, Joseph Campbell: Breaks stories into three phases: Departure, Initiation, and Return. This translates to me into the “why”, “the what/how and the struggle”, and the “lessons learned”.
  • Draft #4, John McFee: I found this less useful but the main takeaway for me was to write liberally without over-constraining yourself upfront, but to edit very aggressively – only keep the best bits.
  • Daily Rituals, Mason Currey: It’s all about creating the right rituals, mindset, and environment to be productive. This book is mostly geared toward people who have writer’s block or struggle to write consistently.

I found the editor by asking for some recommendations through friends, and ultimately, it came through a friend who worked at Random House for a long time. We had a few coaching sessions where she reviewed and edited a number of my prior blog posts, including the about section of my blog where we specifically worked on adding a bit more personality to that section and having a little more fun with it.

Here are the specific learnings and actions from all the books and working with an editor:

  • “Writing is Refined Thinking” is my favorite quote from Stephen King and captures succinctly much of why I enjoy writing – it helps me think more clearly and plug the holes in my logic.
  • Write more like I would speak, and avoid words that sound too clever. It’s ok to start sentences with “I”. Avoid jargon when it’s not necessary.
  • Summarize the main idea in the first paragraph, then set up the structure for the post, and then follow this structure in the writing.
  • Do a full read-through for the “voice” and make sure I’m using a consistent voice/verb tense (mixing “I”s and “you”s can be jarring, and I have a bad habit of doing this).
  • Include more personal stories and specific examples as it makes tougher concepts more easy to understand and humanizes the writing, making it more tangible.
  • Make sure I keep writing consistently. I’ve barely posted anything new this year, and it’s easy to make excuses when I have a busy job, am angel investing, and have a young family, but it’s all about creating the time and space for writing.

What’s been great about re-learning how to write is that at each milestone, I realize there is so much more to learn and improve. It feels good to see progression even in the middle of my life, and makes me believe that I can still learn new crafts at any phase of my life, and I can’t help but be optimistic for the future.

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