9 Insights I Uncovered While Building a Writing Habit

Building a writing habit🔗

In the forever-trying year of 2020, I set my sights on earning the 16 week posting streak badge on Dev.to – and I did it! (Then I took a long break from posting.) Before I get started on more tech writing for 2021, I wanted to stop and reflect on this effort.

How did it go?🔗

Pretty well, to be honest. It has been one of the most challenging goals I’ve set for myself. After the 50% mark, I had exhausted the developed ideas in my backlog so it became harder to get in front of my schedule. I had to start the next post immediately after publishing.

I found a few insights while building my habit for writing, and you might find them helpful, too.

1. The hardest part is getting started🔗

It’s easy to say that some of this is due to the mood of 2020, but it was really easy to fall into self-doubt and self-rejection based on the worry that no one would read what I was going to write. Or that people would read it, but they’d hate it.

These are still feelings that I sometimes have today. But aside from SEO, marketing on social media, experimenting with the time I post, and other tasks that take effort – whether or not someone clicks and reads is out of my control.

Due to the mental effort required to overcome these feelings, the hardest part of writing is getting started. As such, it (almost) doesn’t matter what the resulting quality is. Primarily what matters is getting something on one topic on the page, to edit later.

2. Editing is easier than writing🔗

I have a much easier time editing than writing from scratch. Knowing this about myself meant that it was a lot more important to complete any kind of first draft, no matter how bad.

The editing phase takes at least twice as long as writing. This phase may involve complete rewrites of sections, but I still consider that to be less difficult than starting from a blank page. It’s also a lot easier to judge how much I have left to do when the edits are focused on formatting and pacing, and less on content or coherency.

3. Don’t be a perfectionist🔗

At least for the content that I’m creating, most people aren’t going to suddenly understand a complicated concept because I wrote a specific sentence in a particular way.

For the goal I was working toward, it was important to post on a predictable schedule. While it’s good to set your own standards for yourself high, keep in mind that it’s impossible to level up 10x with a single post. Writing well takes practice, and you get more practice if you are able to let go, call a story done, and move on to writing something else.

4. Writing consistently doesn’t always yield consistent quality🔗

I’ll be the first to admit that I think some of my posts are more useful or interesting to read than others. That’s just how it goes sometimes, where ambitions are better than the content produced.

Ira Glass spoke about storytelling and the taste gap (and how to close it). He encourages that the most important thing one can do when starting out is to produce quantity over quality. Over time you improve, if you can endure this creative, iterative phase. It is normal for quality to lag behind your ambitions.

With that in mind, it’s okay to write things that you never publish. I’ve learned that writing can be a method for understanding a topic, or just organizing my thoughts. Not all of that needs to be public.

What continued to give me encouragement was noticing that my first draft quality was (on average) getting better over time. That was a measurable improvement!

5. Be really specific about who you are talking to🔗

When I write, I always start the first draft always with a question: Who am I writing to?

It doesn’t always matter if the answer is a real person. This person I’m writing to might be based on my past experience, questions people have asked me, interactions I’ve observed, an organization, or just completely made up!

What is most important is that I focus my message so my intended target audience understands. I don’t want to unintentionally expand the audience or over-explain a concept if it doesn’t benefit the base group of people I am writing to. This technique has made it a lot easier to write in bursts, and edit for clarity. It helps each piece of writing have a consistent voice.

6. Writing titles is hard (because SEO is hard)🔗

I have to admit: I change the title of each post no less than 3 times, sometimes minutes before publishing the post!

Different publishing platforms have different audiences, so experiment with what works for your readers. If you plan on cross-posting across multiple platforms or you want to be discovered through search engines, you will need to learn a little bit about marketing and SEO.

I’m frequently torn between using technical jargon in my titles, or less specific concepts that can be generally applied.

Playing with this balance is a cheap and interesting game that, in my experience, avoids disappointment by taking a long-term perspective. It’s been validating to see what kind of content does well though organic search visits vs. people sharing links. I’m still caught off guard when an article from many months ago begins to trend. The lesson here is to be patient and see what strategies pay off.

7. Keep a backlog of ideas🔗

I have a spreadsheet that I use to keep track of ideas in various states. When I think of something that might be a good topic to explore in a post, I add it to the list. These can be title ideas, posts that are in progress, and links to drafts.

I try not to dismiss an idea too early. Just writing it down gets it out of my mind, with low pressure to fully explore the idea. Sometimes this collection of thoughts ends up presenting patterns or themes that, when combined, contain enough material to create a full post around. This strategy is really practical, and comes in handy when I am feeling like I’m in a creative rut. If I have a deadline to meet, I can always pull from the pile of ideas I already had.

8. Building structure and motivation for writing is moving target🔗

I am generally informed about trending topics within tech, but I’m trying to discover my niche and I don’t want to spend an eternity looking for ideas. I’ve also discovered that I’m most creative when I have constraints and have a structure to lean on.

I have a long-term goal to work for myself creating educational products / services / consulting. So a structure I lean into is that each post contributes to that long-term goal.

It’s also important to address shorter-term motivation. My approach has been to identify what motivates me to create, and then slowly build systems to support producing content. Aside from the obvious need to set aside time to write, creating that motivation for a post takes three things:

I really enjoy creating software developer advocacy and tech education content, and the topics I (mostly) write on reinforce these areas.

I aspire to have objectives that can be described as SMART. Admittedly, my short- and long-term goals are still pretty abstract. I think that’s okay right now, as long as I am making progress in the right direction.

9. Don’t be afraid to be seen trying🔗

Credit to a video by Evelyn From The Internets for helping me articulate my feelings about this point.

This relates to my previous point of starting being the hardest part. Some of my internal friction stems from the feeling of being afraid to be seen trying something I’m not good at.

With some rare exceptions, I’ve decided to keep my old content online. It likely won’t be an issue where stuff I created in the past while I was still learning has embarrassed me. Largely, this content is ignored and no one but myself cares about it.

To be concise, haters gonna hate. That’s what they do. So don’t pay any attention to the inconsiderate folks who “just want to help” but are not actually helpful. The tech community is full of strong personalities that aren’t always inviting or pleasant to engage with. (I’m not saying this is the majority. I see you...)

I see enough 💩 being talked in social media threads that it constantly occupies space in my mind when I’m about to publish a new piece of content. However, the truth is that most people are not focused on you for even a moment. So a way I like to view that is that most people will not even see you fail – that’s the blessing of no one knowing who you are yet. Therefore, there’s no reason to not try.


Building a writing habit has been very humbling. I learned that I actually know a lot less about certain topics than I thought. I had to research more than I expected. But as I gained experience, I leveled up my time management and my process.

Now that I’m not trying to post weekly, what I would do differently is to spend more time developing my production processes. And that’s what the focus of this next year will be about.

Aside from continuing to stream my product development on Twitch, this year I will be creating short videos, starting with some of my more popular blog posts as topics. I hope this will lead into more types of educational content, and more opportunities to work with other people in achieving their goals.

I started a consulting business (Figbee Labs) in the latter half of 2020. I will continue to travel out of my comfort zone into the deeper waters and hopefully meet new people or organizations that want to work together. It’s important to me to help people from all backgrounds succeed in sustainably building and running their own software products. I will document my experience over 2021 through posts and various social media.

If you’ve undertaken a similar challenge, what did you learn about your process? What do you want to achieve with writing this year?