#51: 7 Lessons From 1 Year Of Writing

Intro

I started writing on Substack a year ago because I realized that I needed to develop my ability to articulate myself. I set a goal to write one blog post per week, and didn't have too many constraints on what that had to look like. No word count limit, no subject limit, just had to write something. My hope was that I wrote more, I would advance my ability to articulate myself.

I posted my first blog on October 9th, 2023, but for the sake of transparency, I did actually miss 2 weeks of posting a blog throughout the year, so I can't say I completely achieved the goal of posting every single week. 

Writing has turned out to have much more of an impact than I had expected, to the point where it's led me to try to convince many of friends to do the same. So I figured I'd make a video covering a few lessons I've learned along the way. So, let’s dive in. 

Lesson 1: Writing is formalized thinking

When I'm about to write, I tend to think I have a clear understanding of the idea or story I want to convey, and when I sit down to write it out, it's going to be clear on the page immediately because I feel like I have such a fundamental understanding of it.

Then I sit down, and that is not what happens at all. As I begin to write, the words on the page do not articulate what I'm thinking at all. 

• The idea is incomplete. 

• There are significant gaps in my thoughts. 

• The paragraphs, sentences, and words lack meaning and are completely out of order. 

And I don't know how to fix it. I sit there struggling, and it hurts to see how poorly the words on the page reflect the idea I am striving to convey. 

Through this writing process, I can literally see, on the page, how bad my communication is on this particular idea or subject. Even as I wrote down this lesson, I experienced this same process. 

And there's a term for this, your first stab at writing something. It's called a rough draft. And if you're anything like me, version 0 of your rough draft is always terrible. It's just incoherent words vomited on the page. 

And what I learned is that this is the process of thinking. When you're thinking, you're not sure where you're going. You're trying to move your understanding forward, trying to get from point A to point B, but you're not exactly sure what or where point B is. And you certainly don't know the straightest path to get there. 

So that process of 

• vomiting everything onto the page, 

• trying to understand where these thoughts are taking you 

• and nailing down that destination

• and trying to delete all the unnecessary fluff and just go straight from A to B

• is the process of thinking. 

The catch is that I, and most people, often think by talking. And when we think by talking, we are speaking out loud our roughest of drafts onto the world. We're dragging people through that windy path because we don't even know where we're headed. And we tend not to notice it because, unlike when it's written, we can't literally see how poor our articulation is like we can when it is written down. I call this process of thinking by talking Rough Draft Speaking.

So, I try to do a whole lot less Rough Draft Speaking now. It's much better to vomit those words onto a page first instead of onto someone else.

One last thing I'll mention here, since it was a bit of a revelation for me, is that when articulate people take long pauses before answering a question, the process they are going through in their heads is exactly this process of thinking. They're trying to identify point B and think of a way to articulate the straightest line between A and B before they open their mouth. I'm trying to do more of that. 

Lesson 2: Tell a story

There is an old proverb that reads: "Tell me the facts and I'll learn. Tell me the truth and I'll believe. But tell me a story and it will live in my heart forever."

Of the first 50 blog posts that I wrote, 7 of them were stories from my own life. I found that the posts that were stories from my own life were by far the most interesting and engaging for those people reading them. 

This is important to know because if you're trying to articulate a lesson or concept that you want to stick with an individual or a group of people, you want to understand what makes a lesson stick. This year I read this book titled "Storyworthy" by Matthew Dicks where he breaks down how to be an effective storyteller, and I can't recommend the book enough. One thing that really stuck with me from the book is the idea that he coins "Cinema of the Mind", which is a concept that, as the storyteller, your job is to create a movie in the mind of your audience. They should be able to see and experience the story as you lead them through it. If you can do that effectively, your story and lesson have a much better chance at landing and sticking with your audience. 

Lesson 3: Writing pinpoints misalignments and disagreements

Writing makes it much easier for someone to tell you exactly where they disagree with you or think you may be off track. It does this by: 

• Allowing the reader to move through your thoughts at their own pace

• Removing the burden of the listener worrying about whether or not they should interrupt you in the middle of your rant. 

As they read, they can circle or highlight specific words or sentences on the page and show you the exact point they disagree with. They don't have to try to memorize a point you made while you continue to talk. 

I genuinely feel like this can make a conversation more productive by a factor of 10x. 

An example of when I do this is with a mentor of mine named Alem. Alem sits on the board and is invested in Sway, the company I lead, so obviously, the effectiveness of our conversations is extremely important. Frequently when we meet, I'll come to the meeting with one or multiple pages of content for him to read at the very beginning. When I do this effectively, he can digest in under 5 minutes what would have taken us an entire hour or more to talk through. As he reads what I've written, he can pinpoint on the page exactly where he 

• thinks I'm off track, or 

• needs clarification, or, 

• needs to challenge my assumptions or logic. (which, quick sidenote, is the primary thing I'm asking him to do). 

This process gives me invaluable insight into where my articulation of certain ideas is strong and where it is weak, which allows me to dial in my messaging going forward. 

Now, you've obviously got to balance the amount of time you put into the writing itself. You don't want to spend 10 hours writing to prepare for a 30-minute conversation every single time. But when you consider that you will understand your own thoughts with an order of magnitude more clarity after just writing for 15 or 30 minutes, and the benefit the reader gets from moving through your written thoughts, that 30-minute investment pays enormous dividends.

Lesson 4: Writing ensures that the story communicated up, down, and across the chain of command is consistent

Within organizations, many different conversations happen. 

And if you're a leader, which you are, you need to make sure that the narrative and details that you are sharing are consistent across all of those conversations. 

This is easier said than done. By writing down your thoughts and sharing them, you greatly increase the odds that your story is the same across all conversations. Because anyone can reference your written word, it allows people in the organization to ask clarifying questions in a very specific manner and see where they may have misinterpreted something you said or disagreed with something you said.

Lesson 5: Writing creates transparency

If you write something and share that, even if people don't know if you've shared it up the chain of command, they know that they can hold you to your word. That in itself creates the feeling of transparency, and that feeling is not false, because you can be held to those words. If you've ever worked for someone who you suspect says different things to different people, this should resonate with you. If someone writes out their thoughts and emails them to everyone or posts them in a place where everyone can see them, you know for certain what is being communicated.

Lesson 6: Writing lasts through time, aligning us on what happened in the past

During the Korean War, Chesty Puller, a legend in the Marine Corps, writes to his wife:

Everything is quiet and I now have little to do except get my reports prepared and submitted. I wish I had a flair for writing, as then I am certain this regiment would get the credit due them when the history of this operation is finally written. Now everyone knows, but in a few years what is written will govern. Rest assured that I will do a better job of getting the facts in my reports than I did in the past war. I will also claim everything due the regiment.

Many times I have regretted that my English education was cut short during the first war. Please do your best to impress on our children the necessity of taking advantage of every opportunity... in this hard old world of ours."

That line, "In a few years, what is written will govern" really stuck with me. As our memory fades with time, if we write down what has happened and how things transpired as they do in real-time, we allow ourselves the ability to reflect on that and learn the lessons of our own history. If we aren’t aligned on our history, we won’t be aligned on the lessons learned from history.

Lesson 7: My audience is my future self

A while back I stumbled upon this journal I had briefly started back in October 2016. The journal started out with a letter from me to my future self and had a few entries as well. When I opened that journal and read those entries from 2016, it felt as though I was going back in time, sitting across the table and having a discussion with that kid. And I have so many questions for that young man:

• What was he thinking?

• How did he look at the world? 

• What was that kid's hope for where he'd be in 5 years and 10 years? 

• What would he think about where he ended up so far today? 

• What would he be proud that he did?

• What would he be ashamed of?

• What were his values? And how have they changed? 

Going through this journal showed me very clearly that my target audience for my writing is me. It's me 1, 5, 10, and 50 years from now. 

• What do I want that guy to remember? 

• What lessons do I need him to take to heart? 

• What are his weak points that he needs to remain aware of?

• How can I convey to him what I'm feeling in this moment? So that 30 years from now, he can sit down at a table with me and explore the current texture of my mind and thoughts.

So yeah, when I write, that's what I'm trying to focus on. What am I trying to convey to that guy in the future? What are the lessons I'm learning right now that I don't want to lose? That I don't want to relearn over and over again by making the same mistakes. And if others can benefit from bits of the writing along the way, that's great as well. 

Closing 

So, that wraps up the 7 lessons from my first year of writing. When I started on this journey, I didn't know where it would take me or if it would stick, and I certainly couldn't have imagined it having the impact on me that it's had. 

If I had to try to quantify it, I'd say the perspective shift from not writing to writing is just as impactful, if not more impactful, than the shift from not reading to reading. 

It's completely changed the texture of my mind, how I understand my thoughts and thought process, and how I look at the world. 

So, if you're thinking about writing I'd highly recommend you take a stab at it. I'm certainly glad I did. 

I'll be doing more of these types of videos in the future, so if you've made it this far and enjoyed it give it a like and subscribe. You can also subscribe to my substack, I'll put the link in the description below.

I appreciate you all, keep getting after it.