5 Insights From Writing Every Single Day

30 hard days and 100,000 views later…

Conor Dewey
Jul 10, 2018 · 9 min read


This post isn’t original. It certainly isn’t the first of it’s kind. I would need a scientific calculator to come up with the actual number of What I Learned from Writing posts on Medium.

I’m still publishing this regardless. Why? Because I recently finished writing every morning for the last 30 days. For many established writers out there, this is child’s play. Many speak to the importance of writing every day and blocking off time to be creative.

That’s not me though.

I had never written for 5 days straight before this. Let alone for a whole month. I’ll go through stints where I publish a lot and then it’s radio silence for several weeks or even months. I was the type of person that wrote when inspiration hit or when a project came to fruition. No more, no less.

I wanted to change this. I knew the benefits of writing but I hadn’t given myself a chance to experience them on any significant scale.

“Whether you’re keeping a journal or writing as a meditation, it’s the same thing. What’s important is you’re having a relationship with your mind.“ — Natalie Goldberg

I knew where I wanted to be. I also knew that, like most things worthwhile, the only way to get there was to lean in and practice each and every day.

With this in mind, I began.

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Source: Unsplash

The Process

I knew that if I was going to write every day, it had to be first thing in the morning. I’m a huge believer in doing the most important things right away. For me, this involved blocking off an hour every weekday morning starting at 7am before I left for work. When it came to weekends, it was a free-for-all sometimes, but I made sure it happened. I couldn’t let myself break the streak.

With enough deliberate practice, you’re going to get better. It’s that simple.

As the days went on, and I began to develop a rhythm. I saw some changes begin to take place. My writing improved. I got better at connecting with my audience, sharing thoughts, and communicating complex ideas in simple terms.

In turn, my work began to reach more people. I saw my follower base on grow by 1,000+ users and my weekly newsletter subscriptions more than double in size. On the very last day of the month, I hit the 100,000 views milestone for the previous 30 days.

As this experience came to a close, I decided to sit down and reflect on things. I grabbed a notepad and pen and wrote down everything that I learned throughout the process. Here’s the 5 most impactful insights and observations that I walked away with.

Writing Is a Black Box

Something is referred to as a black box when the device, process, or system has known inputs and outputs, but unknown internal workings. The more that I wrote and shipped my work, the more I came to see writing as a black box. Let me elaborate.

You have an idea that you want to develop or share so you sit down and fire up Medium or your text editor of choice. Once you’ve finally written and revised your work, it’s time to ship.

You send your thoughts and ideas out into the world without any concrete idea of how they will be perceived. Even after some time, feedback is given in the form of super high-level metrics such as views, claps, or fans.

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What happens in between the publish button and those feedback statistics?

The truth is that we don’t know. The closest we get to true feedback is from responses that are few and far between. The current feedback loop between readers and writers is far from perfect.

We are forced to rely on vanity metrics to interpret the reception of our work. I refuse to believe that sheer number of claps is the strongest possible indicator of a story and it’s impact. For now though, it’s the best we have.

Overcoming Hesitation

Shipping isn’t always quite as glamorous as some other articles and quotes make it seem. Sometimes it can be difficult to click publish. This was especially true for me early on in my writing journey, and it still affects me to this day.

This is the harsh reality of publishing your work. We fear that it won’t resonate or that others will judge the work and the writer by association, so we hesitate. Whether this hesitation lasts for a second or a month, we put off the act of shipping out of fear and insecurity.

“It takes courage to publish when no-one is listening, but you must”

This is further compounded by the black box nature of the process outlined earlier. If your driving motivation is number of views and other vanity metrics, you will burn out when they let you down — and they will.

Instead, focus on how sharing your thoughts and ideas with others can positively influence your growth. This simple shift in mindset can make shipping that much easier, particularly when practiced daily.

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With time, you’ll get more and more comfortable clicking Publish. It’s not always going to be easy, sometimes it’s still going to be difficult. But we must.

Building Momentum

I noticed that the most difficult sessions came after I had struggled to hit my routine the previous day. Yet, the easiest sessions often came on the fourth or fifth consecutive day in a row of being on the ball.

This isn’t a coincidence by any means. Momentum is a powerful tool. The simple act of marking anX’ on a large calendar for writing that day was extremely helpful to me. This hack is often attributed to comedian and actor, Jerry Seinfeld.

“After a few days you’ll have a chain. Just keep at it and the chain will grow longer every day. You’ll like seeing that chain, especially when you get a few weeks under your belt. Your only job next is to not break the chain.” — Jerry Seinfeld

Don’t break the chain. It’s that simple. To excel at something, you must take constant steps towards the end goal each day.

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Source: Pittand

Earn your ‘X’ and keep the ball rolling. You’ll thank yourself the next morning when you sit down, take a look at the blank page, and watch ideas flow onto the canvas out of nothing else but sheer habit.

More Input = More Output

This might seem intuitive, but it’s often overlooked. During my experience, I noticed an interesting pattern. There was a clear correlation between the amount of high-quality content I consumed and the ease of idea generation.

“Nothing of me is original. I am the combined effort of everyone I’ve ever known.” — Chuck Palahniuk

This mindset is incredibly freeing. Take solace in the fact that you don’t have to create from scratch. You can remix some of your other favorite things and create something new and exciting that way. The popular book by Austin Kleon, Steal Like an Artist, further explores this theme.

For me, this manifested itself in the form of podcasts, articles, and books. By actively reading or listening and taking notes, I collected different fragments and pieces of developed ideas. These pieces served as inspiration and eventually were molded and shaped into my own unique thoughts that served as the basis for posts later on.

Do What Resonates

Even when drawing inspiration from others, it’s not always easy to think of ideas to write about. I know I struggled with this while trying to ship every day for a month straight, of which I succeeded just 20 times. One thing that I found particularly helpful was to reset my mind and focus on what resonates with me.

Every once in awhile, I caught myself beginning to assess ideas for posts based on how I thought others would perceive it; rather than how I felt about it.

Trying to create for your audience isn’t necessarily a bad thing, but it can be dangerous when not contained.

Your best work will take place when you’re writing about something that excites you. There’s no avoiding that. If you aren’t interested in Blockchain for X or 10 Reasons Why Reading Will Change You, then don’t write those posts. They may do better from a views perspective, but they won’t be your best work unless the topic is interesting to you.

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Source: xkcd

By shifting your focus to doing what resonates with you, you guarantee that you’ll enjoy writing the piece more and in turn, it will come out better.

Furthermore, there are over 30 million monthly users on Medium. Trust that someone out there will takes interest in what interests you. Don’t play to the crowd, play to your interests and ideas. The crowd will come.

Let’s Recap

This experience began as a simple 30 day challenge. Initially, I wanted to become a better writer and reap some of the benefits that are widely reported by others. The experiment definitely didn’t fall short. Let’s go over the key insights and takeaways that we’ve touched on:

  • Writing Is a Black Box
  • Overcoming Hesitation
  • Building Momentum
  • More Input = More Output
  • Do What Resonates

All of these realizations have impacted me greatly. However, it’s important to note that the benefits don’t stop there. The responses and feedback I’ve gotten are truly priceless as well.

They mean that the time I spent over the last month wasn’t for my own personal growth alone. It didn’t only help me improve as a writer and thinker, but also had a positive impact on others, no matter how small.

Publishing is the act of giving your thoughts and ideas to the world. It’s nice to know that someone is on the receiving end.

While this challenge isn’t necessarily for everyone, I can’t recommend it enough. I’ve done a number of different experiments, but actively writing and shipping every day was the most beneficial by a long shot.

What’s next for me? I plan to continue writing every day and consistently shipping my work. Through this experience, I’ve seen the light and I don’t want to go back. I can only wish the same for you.

Thanks for reading! Feel free to check out some of my similar essays below and subscribe to my newsletter for interesting links and new content.

You can follow me on Medium for more posts like this and find me on Twitter as well. For more on me and what I’m up to, check out my website.

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Conor Dewey

Written by

Growth at Hugo. Previously data science at Squarespace. I write here now: www.conordewey.com

The Startup

Medium's largest active publication, followed by +681K people. Follow to join our community.

Conor Dewey

Written by

Growth at Hugo. Previously data science at Squarespace. I write here now: www.conordewey.com

The Startup

Medium's largest active publication, followed by +681K people. Follow to join our community.

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