Weathering the unavoidable discomfort of writing online

online writing failure modes and how to avoid them

Hey! So you're thinking about publishing an article online but have some reservations?

Maybe you’re wondering if it’s worth it, if you should, if it’ll backfire, or if it’ll be any good. Totally understandable. Happens all the time. Don't worry—these concerns are completely normal and common. Fortunately, there are proven strategies to overcome these obstacles. Let’s meet the villain of your journey: Resistance

Battling the Resistance

In his book 'The War of Art,' Steven Pressfield identified this phenomenon as 'the Resistance.' The Resistance is the antithesis of the Muse. Instead of inspiring you to create, Resistance tries to stop you.

Creativity requires doing something others won’t do, to an audience that might not materialize, without a guaranteed reward. It requires vulnerability. The feeling of resistance is normal and unavoidable.

Understanding that resistance is normal and expected should help prevent it from stopping you. Being creative is supposed to be uncomfortable. It’s like going to the gym — discomfort signals growth.

What’s the point of publishing online? Is it worth the time?

I can promise you it is.

You have value worth sharing. Helping even one person justifies the effort. If you frequently get the same questions, Publishing an answer saves you time and helps others more efficiently.

Writing also crystallizes your thinking. While our minds are fuzzy, unreliable webs of thought, writing is concrete and linear. The page stares back at us. It begs for examination. And knowing that other people will see it now encourages us to raise the bar on the effort and quality of our thinking.

Publishing can spark meaningful conversations. I’ve reconnected with old friends (Hi Cory and Jeremy!) through writing. I didn’t anticipate that, but I’m grateful for it. Sharing your ideas has a way of attracting like-minded people. You’ll also be a more engaging conversationalist since you’ve refined your thinking and opinions more than most.

Writing online can create opportunities. The right person reading one of your pieces at the right time can open doors. Based on my articles, I’ve received job offers, invitations to give talks, and opportunities to lead initiatives at work. The internet is an infinite leverage machine.

Finally, humans are built to create, not just consume. I want to see more people putting their ideas out into the world. I’ve read articles and essays that have permanently altered the way I think, and changed my career path for the better. What if you could make that happen for someone else?

Okay, I see the value in publishing. Do I have to go build a whole website now?

This is a common sticking point, especially for engineers. They want a personal website to pull double duty as a platform to share work, and a playground to mess around with shiny new technologies. Do not turn your personal blog into an engineering project at the start. Single responsibility principle applies here.

If you can’t spin up a new website in four hours or less, you’re doing it wrong. Making a website is easier than it’s ever been. Use SquareSpace or WordPress or Ghost. It doesn’t even have to be a website! You could use newsletter-based publishing tools like Substack or Beehiiv.

Okay, I have a site, but I don’t want to be a “blogger”

You don't need to build an audience, commit to a schedule, or maintain a content calendar. Forget about creating a "personal brand," crafting a "positioning statement," or developing a "content strategy." Resistance is trying to make the problem sound bigger than it is.

What I am advocating for is an entirely different game. Tom Critchlow calls this ‘Small-b blogging.’ You aren’t writing for a massive audience. You are writing for your network.

Don’t write just to hit some frequency some hustle blogger said you should, or to maximize pageviews. Instead, strive for writing that has specific appeal, at a comfortable pace, aiming for meaningful engagement over empty metrics.

Don’t borrow trouble from future articles no one is forcing you to write. Focus on what’s interesting now. Who can you help, and what can you publish today?

I don’t know enough

You have more expertise than you realize. Years of experience becomes so familiar we take it for granted — like water to a fish. Ideas that are obvious to you could be a revelation for someone else.

Here’s a secret: experts don’t write because they have expertise. They have expertise because they write.

Writing is a method for building expertise more than sharing it. The root of the word "essay" means "to attempt." You ask yourself a question and attempt to answer it, going on an intellectual journey and bringing others with you.

My writing is smarter than be because I can rewrite it.” Susan Sontag

There’s an episode of the Simpsons(Spelling as Fast as I can) where Marge is trying to figure out how they are going to pay to send Lisa to college. They have this exchange:

Lisa: Mom I'm having a crisis of conscience. Can you and Dad afford to send me to college?

Marge: Oh of course. I mean, not on your father's salary, but I could and give piano lessons.

Lisa: But you don't play the piano.

Marge: I just gotta stay one lesson ahead of the kid.

There’s real value in being one lesson ahead of the kid. Your recent time in the trenches gives you an accurate memory and shared context with the reader. The fresh perspective of someone who just learned something enables you to communicate in a more relatable, high-fidelity way.

To discover what you know, you have to get it out of your head. Jot down a rough outline of supporting points for your idea. Try doing a 10-minute free write on the topic. You can try to fill it in with other notes, ideas, and links. You might surprise yourself with how much you come up with.

From there, targeted research can fill any remaining gaps.

An idea I value is intellectual activism: The art of taking existing information and making it more accessible, understandable, useful, or enjoyable to others.

Finding information in books, papers or online videos, or threads and distilling and sharing it in a way that’s accessible to others is a public service. Curating and combining resources generates new value from existing material. You can draw from multi-disciplinary knowledge. Warren Buffet says he learned about how markets evolve by reading The Origin of the Species.

This is why I take notes compulsively and collect information and links like Pokemon: When I sit down to write I don’t face a blank page. Instead, I can draw from my bank of ideas and evidence.

I have nothing original or interesting to say

Isn’t that cheating though? How is building off of others' work not plagiarism?

The concept of “originality” in writing is a myth. Can you name a writer that is truly “original”? Everything is a remix — we all build on existing ideas. The image of an author pulling inspiration from the ether is fantasy. It's all old hats through new lenses.

No one is original, but everyone is unique. Your personal perspective matters and is worth sharing. Anyone can share facts or links. Combining them with your experiences, skills, context, and stories creates something worthwhile.

Uniqueness is combinatronic. For every experience, memory, skill, and story you have, there are intersections between them all. These give you even more unique places to draw inspiration.

Your network is also unique to you. If you share something with someone, they will see something that otherwise wouldn’t have. Don’t feel bad because it isn’t original “enough.”

Once you have an outline, you can add color to it by adding bits only you can: your stories, experiences, memories, observations, and perspectives. Consider how these elements intersect with each other and with your topic.

This piece was inspired by other books and articles I’ve linked to. They all have one thing in common: All these authors have had much more writing success than me. I had to get over Resistance telling me I didn’t “deserve” to write this. I’m betting there is some value in someone saying, “Look, I don’t have impressive subscriber numbers to show you. My readership is tiny. I still think it’s worth showing up and putting my ideas out there.” Maybe you will too.

You can also remix your own work. Every piece does not need to be 100% brand new. Previous notes, comments, conversations, or documents might have material that can be reused. I call this stuff “grist” material that is ready to be refined into something useful.

By using the existing grist, you can craft version 2s and version 10s of your ideas. These are bound to be better than the original. Venkatesh Rao calls this The Calculus of Grit. If I had written it first, I probably would have called it “The Calculus of Grist.”

The idea that you aren’t smart enough or original enough is also a myth. It can be safely ignored. Take the path of least resistance. There is an abundance of work out there from yourself and others, ready to be refined, referenced, and remixed.

The twin anxieties of readership

People can have opposite reactions to the same stimulus. Some people lose their appetite when they get stressed. Others reach straight for the fries and Girl Scout cookies.

As you approach hitting “publish,” Resistance gets stronger. His final move manifests in one of two opposing fears: Either you are afraid that no one will read what you write, or are you afraid they will.

I’m afraid no one will read what I write

Even if no one reads your piece, there is still inherent value in writing and publishing. You refined ideas and have more material for next time. You have an asset that may pay off later. You have one more rep hitting publish. Maybe you needed to write this piece so it could tell you what you should write next.

Everybody can benefit from the result. You get to benefit from the process.

If you want readers, be proactive. Put your link out on all your socials. Sure, that’s table stakes. But also, if you wrote a piece that you think could help someone you know, send it to them directly.

Here’s an offer: If you’re scared you can use me to practice. Send me your published piece or even a draft in Google Docs. I promise I’ll read it and share some feedback. You are guaranteed to have at least one reader.

I’m afraid someone will read what I write

What if the end result isn’t “good enough?” What if we’re misunderstood or misrepresented? This is a classic move of the resistance. It’ll never turn out exactly how you pictured it. Vision is ahead of execution, as it should be. Just remember that so long as you try, whatever you were able to put out was, in that moment, your best work. That’s all anyone can ask of you.

You can’t be perfect but you shouldn’t be sloppy. It takes practice to find the correct amount of effort to put into a piece before hitting publish. In my experience, the quality of a piece is a function of the number of revisions, not some spark of genius.

What about negative feedback? If you ever have an article that gets any traction, you will get some haters. This is a good thing. It means someone thinks your piece is worth engaging with. Some are trolls that can be ignored. Others will give you the precious gift of feedback.

This is a valuable part of the process. You can only refine your ideas and perspective so much internally. The real magic is in when you use them to interact with others. Feedback counts as grist.

Internet writing remains malleable—you can always edit or delete content. The internet has a goldfish memory, and it remembers successes more than failures.

Anything you publish is a UI for the reader who wants to be entertained or informed. They want the piece to be good. They are rooting for you. Everyone is on the same side; The relationship between reader and writer is ultimately positive.

Godspeed

Don’t be afraid. Countless others have published blog posts and lived to tell the tale. In a world overrun by vertical videos and AI slop, online writing is one of the best asymmetric bets opportunities for knowledge workers. You can create a lasting, high leverage asset in a few hours, for free. By writing and publishing, you refine your thinking, create a shareable asset you own, and expand your luck surface area. How many other activities offer this much upside with such minimal investment?

All you have to do is get over capital-R Resistance and do some small-b blogging. I’m excited to see what you come up with!