What I Learned About Writing Online in 2020

Photo by Glenn Carstens-Peters on Unsplash

Through the past five years, I’ve written digital content for several industries. Each assignment followed a familiar formula: research the target audience, determine what that audience wants to learn and what they enjoy reading about, write, publish, review the work, and refine my focus for the next piece.

I never understood why this process was so hard to replicate for my personal writing until I stepped back to reflect and write this piece.

This year I’ve focused on introspection and observation, learning from others and considering my place in the conversations I want to join. Most of my longer writing has been in private. Twitter became a place to sound off some new ideas and learn from others’ perspectives. This is my fourth time hitting publish on a blog post on my Medium page, and I have a massive written piece coming down the pipeline that will shape much of what I produce in 2021.

If — like me — one of your New Year’s resolutions is to hit publish more frequently, join me in following these tips to make sure we’re publishing great content.

Write as a Function of People, Not Ideas

You might not think a math function can explain something as subjective as writing. In my mind, it’s this simple. It made perfect sense the second Steven Kneiser said it in our conversation this fall.

The statement “Y as a function of X” implies a causal relationship: as one variable increases or improves, so too does the other one by an amount which can be defined. Typically, Y is not aware of what X is, or even what X wants or needs. It’s a loose connection we’re making here, but bear with me.

What do I think of when assessing what “writing as a function of ideas” means? The clarity with which an idea is communicated, or the depth it’s expanded upon, that all depends on variables that impact the writing. How much the creator of the writing understands the ideas, how well the writer can communicate the ideas, how often the writer communicates the ideas, these all factor into this “equation” we’re toying with.

As children, we spend a lot of time writing about ideas — often others’ ideas. The dreaded “document-based question” from middle school history class is based in reviewing physical evidence and written works to assert or disprove an idea. Success in English classes is largely based on critiquing great works of literature and trying to comprehend the ideas authors communicate in their own styles. In fact, the vast amount of academic writing is a function of ideas: adding new context to old ideas, analyzing even older ideas, projecting what new ideas might come to form, and so on.

It’s a pretty radical shift if you think about it. Writing as a function of ideas is conceptual. By focusing on the people impacted by ideas more than the ideas themselves, we write things that are actionable and easily understood.

Where the disconnect comes for so many people — including myself — is that we spend our whole lives growing up writing as a function of ideas, yet the writing required to build an audience, to build a career, or to make money is all a function of people.

  • Media outlets tell the stories that have the greatest impact on their constituency of readers.
  • Content marketers begin a strategy for written content with an analysis of the target audience.
  • Anyone working in sales, copywriting, or public relations is writing with the express purpose of convincing another person to take action.

Want to Get Better? Write Garbage.

You miss 100 percent of the shots you don’t take. Still, it seems so easy to just not take the shot.

Maybe we convince ourselves we can’t shoot as well as the other people we see shooting their shots.

Maybe we’re afraid of the ramifications of missing: not making the impact we want, not feeling the thrill of scoring, feeling others’ judgment when we miss.

But you score on 0 percent of the shots you don’t take. Numbers never lie. And when it comes to creating content online, you never know what it takes to score if you don’t take some shots.

When discussing the easiest way to beat writer’s block, Seth Godin said, “The best way to deal with it is to write, and to realize your bad writing isn’t fatal. Like all skills, we improve with practice and feedback.”

The only way to get past your bad writing and discover what your best writing looks like is to keep going. Keep taking shots, even if they’re bad shots.

I wrote a thread back in June about the worst writer’s block I’ve struggled with. Writing the script for my school’s holiday video last winter, I had a huge list of things we needed to show in the video, and no idea where to start. I spent four hours of throwing lines at the wall and it wasn’t working, like trying to get spaghetti to stick when it’s not done cooking.

So I started by asking a question:

’Twas the night before winter break, and all through the halls,

/ What conversations could be heard off the art-covered walls?

By asking a question (and borrowing from a popular holiday story) I didn’t have to worry about writing some original master work. I just answered the question, and I could answer it authentically because I had my list of items the story should include. However, I never would have reconsidered my approach to the final product if I hadn’t taken all that time to write garbage.

That’s how I am approaching writing online. I wrote a lot of garbage in private. Now it’s time to start taking some shots.

Write Together

You know how many times I went to “start a new writing process” and build new writing habits this year? Too many. And I’m sure many others out there endured the same choppy progress.

Writing with others makes all that an easier lift. Seeing a bunch of awesome people write cool stuff and getting to work with them is a great experience. Writer’s Bloc has been my place to do just that.

Having a group to share tips, celebrate publishing, solicit candid feedback, and meet up with a bunch of really smart people has benefited my writing immensely this year. I know that if I ask for specific feedback from the Bloc, I’ll get people from different walks of life analyzing my work through a different lens. I know that over 100 others come to the group like I do to build something new and grow together.

The best part has honestly been finding my own “group within the group” that really gets to know my work and my goals. I know I have at least five people in the Bloc who have a great perspective, are super honest and can help me get any piece of writing to where I want it to be. Shout out to Blake Reichmann and Ben Greenman for early-morning chats, accountability and catching all the edits I wish I found.

Starting any new habit is always easier — and more fun — when you do it together.

Extra Points

  • I’m a big proponent of the Two-Day Rule, because I know if I take two consecutive days off from any good habit, it goes off the rails for weeks. (Case in point: I took three days where I started this blog, then I left it for two weeks before spending two more days to finish it.) Matt D’Avella has an awesome explainer on the Two-Day Rule and how it helps him stay committed to the gym. I know there will be days off even if I make a commitment to writing daily. In my eyes, that is healthy. Just don’t make it two days in a row.
  • One of the most impactful blogs I read this year explained the importance of dissociating your goals and expectations from one another. Setting lofty goals is one thing; you can create a process to reach them over time. High expectations are a product of perfectionism. They are ever-present, looming over everything you do, casting judgment. And at the end of the day, those high expectations may not even be tied to your goals! Take the time to read that great blog post from Joe Garrison and set high goals with modest expectations.
  • How do you figure out what to write about? I used David Perell’s Personal Monopoly model to find intersections between 25 different personal interests and assess how they impact my experiences and how other people see me. That distilled my list of 25 potential writing topics down to a list of four which are most important to me and have significant overlap for the people I want to write for. Personally, I’m reassessing my Personal Monopoly every six months since I am still starting out and building my niche.
  • In my time writing online this year, I’ve seen so much chatter about whether it’s best to write in a blog on your own website, in a weekly newsletter on a platform like Substack, Mailchimp, or ConvertKit, or in your own space on blogging powerhouse Medium. I’ve learned that in the beginning, the absolute best place to write is the one that provides the least friction towards producing consistently. Personally, I use Notion for a lot of notes, so that is my database for collecting ideas and writing drafts. Then I publish here to Medium. It’s all free and leads to a great product.

There you have it. If you want to start a blog, a newsletter, a podcast, a video series, anything that begins from a written frame or outline, those are the seven best tips I have for you.

Here’s to helping people with our writing in 2021.



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Joe Ray

Joe Ray

Marketing and communications professional based in Buffalo, NY. Blank canvas to discuss branding, social media, and career advice