Lessons learned from writing 100 newsletter issues

July 9, 2022

This month, I hit an unexpected milestone—100 issues of my newsletter, Proof of Concept, celebrating with 100 - The 100th issue. Like many things in my life, it was serendipitous and unplanned.

How it started

I started my newsletter in December of 2019, and after eight months, I only wrote three issues. I did not have the discipline to be consistent. I was frustrated with myself not following through with all the projects I’ve wanted to do. Serendipitously, a friend of mine shared with me a writing fellowship called On Deck.

I enrolled in On Deck's Writing fellowship, a spark that led me to become a program partner several months later. On Deck Writing (ODW) was exactly what I needed. There are a lot of great writing courses out there (some very expensive) and what I was seeking—community accountability and a place to learn and grow. In addition to peer group writing sessions, some of the best writers joined for fireside chats to share their wisdom. One of the guests was Polina Marinova, author and founder of The Profile—one of my favorite newsletters.

Marinova dropped some knowledge bombs in her fireside chat. She said these words that I'll never forget: "consistency builds trust." Those three words were exactly what I needed to hear with my writing habits. The main piece I wrote during the 8-week fellowship at ODW was Jodorowsky's product roadmap, I wrote issues of my newsletter weekly as a way to practice. Fast forward to today, and I have not missed a Sunday writing the newsletter. I'm not sure if I'm planning to have a Cal Ripken-type iron man streak. If  the streak breaks, it breaks. However, writing has become a passion accompanied by discipline. 100 issues celebrates consistency.

Why a newsletter? To focus on community. The word “community” is used as a catch-all these days. I don’t see writing a newsletter as a replacement for blogging, and I plan to blog more frequently now that I have a rhythm with the newsletter. The newsletter isn’t a replacement for Twitter or other channels. When I started building Proof of Concept, I wanted something unique delivered to people’s inbox or RSS. I was looking for a smaller connection.

Sharing lessons learned

I've learned a lot throughout the past three years maintaining the newsletter. It's not only writing. You have to think about content generation, making visuals, and running it like a product. There are hundreds of lessons and I'll focus on the first five that come to mind.

1. Write drafts, lots of them

When creating a newsletter, you're on the hook with a certain cadence, so that means deadlines. There is no worst feeling for me to sit in front of a computer and have no idea what to write about. Art school taught me to fill the canvas quickly to allow refinement. In the beginning of Proof of Concept, I was frantically spending nearly an entire day going through the entire content creation process: ideation, writing, editing, creative, and publishing.

The most helpful tool I added was writing Morning Pages and using as a morning practice. Instead of waiting until Saturday, I spend every morning during my morning coffee to write. To be honest, most of what I write is horrible, but that's the point. The idea is to get a high volume of writing done so you can be and editor and curate. There are certainly some days when I'm writing on Saturday, though those are rare. My Saturday mornings is more focused on editing, refining, and publishing from a backlog of ideas. Don't get stuck in front of a blank screen.

2. Ship it,  avoid perfectionism

On Saturdays, I schedule the newsletter regardless if I'm finished with it or not. It's a forcing function for me to have a sense of urgency to get it done and out there. Yes, it's backfired, and there have been a few instances where I sent a newsletter with grammatical errors. Would I prefer catching that? Of course. Is it the end of the world? No.

I stumbled upon this tweet and it's too real.

One of the main reasons that prevent people from writing is not because nobody will read it. It's because you made something tangible to the world for people to see and react to. It's a scary thing to do, and takes a lot of courage to put yourself out there. The fortunate part is digital work has the luxury of making quick fixes and improvements.

3. Solicit feedback early and often

Early readers have been my largest source of inspiration. Get feedback and ideas from them. The earlier you receive feedback, the faster you can refine the trajectory of your desired outcomes. In the first 10 issues, I renamed the newsletter to, "The Creative Odyssey." People hated it, and honestly, I realized I did too. Proof of Concept resonated more and was relevant to the theme of the content. I'm thick-skinned when it comes to feedback. I studied studio art and built mobile apps for the App Store—you're used to criticism.

Share the early drafts with people who will be critical. I recommend avoiding sharing with friends and family because most of them will tell you its great. Naturally, they want to support you, and people broader in your network will give more critical feedback.

4. Storytelling with words and visuals is my preference

Don't expect to smash that like button or support me on Patreon any time soon. I have no desire to become a creator and want to focus on building tools for creators. This newsletter is a way for me to dog food the workflow. I've learned writing and making visuals is my preferred way of storytelling. I have heaps of respect for YouTubers, Podcasters, and various creators. However, I don't have the time to spend on high production content like that. The production cycle in writing is more rapid.

5. Keep a physical notebook

I love software and truly believe it can change the world. I also believe in making computation humane and using it as a tool. The irony of a digital publication is I spend 80% of my time writing and drawing on pen and paper.

The computer is my assembly line. When I sit down in front of my purple iMac, it's processing. Pen and paper is the ultimate tools for thought. My LEUCHTTURM1917 dot grid A5 notebook has been my notebook of choice for the past decade.

What's next

It's been a wild ride, and I'm going to keep it going. I am a huge advocate of side projects as the learnings are applied to your daily work. Proof of Concept has been a tiny corner of the internet I get to spend to express ideas, thoughts, and strive to improve. I enjoy the intimacy of a newsletter instead of blasting threads on Twitter. I'm excited to see what the next hundred issues might look like. But first, I'll focus on issue 101.

Proof of Concept: The 000 Series

Get the digital download for $13.00
Buy the zine