If you are like I was just two short years ago, with no idea how to establish the habit of writing online, where to start, or what to expect, then this post is for you.

I’ve learned so much over that span of time. I could literally write hundreds of lessons I’ve learned about online writing! But in the interest of time and space, I’ve narrowed my endless thoughts down to the most vital 16 lessons that maybe, just maybe, could spark you to start (or restart) an online writing habit of your own!

1. Summoning the courage to hit publish is harder than the writing itself.

I originally planned to unveil my blog to the world on Friday May 1st, 2020. On the morning of May 1st, I was full of so much anxiety, so much dread, so much fear, that I decided to hold off until the following Monday. On the morning of May 4th, I geared up to launch! Then… I just couldn’t bring myself to do it. On May 5th, I realized the game I was playing, and I had to cut it off then and there. I remembered what Jamie Foxx once said: “What’s on the other side of fear? Nothing.” Then I hit publish.

2. Crickets or pitchforks, but it can’t be both.

And Jamie Foxx was so right: Nothing. My first post, “Why I Quit a Six-Figure Existence” received exactly nine views, and zero feedback on the first day. I had been working myself up with fears of “what if everyone hates my writing?” and “what if no one reads my writing?” All the while, I hadn’t stopped to think about the irrationality of having both of these fears simultaneously! But by hitting publish, I was forcing myself to grapple with either one of those problems.

3. Get in too deep to back out.

This is my secret sauce for doing anything crazy or committing to something outside my comfort zone. Remember the plane ticket to Spain that changed the course of my life? Well, in this case, I had two plane tickets: writing the first 10 posts before I publish anything, and spending dozens of hours designing my own website. I couldn’t just throw all of that away. I had to publish. Sometimes you can use the power of the Sunk Cost Fallacy to your advantage.

4. Leaning into your insecurities breaks them.

There is a reservoir of insecurity within each and every one of us. Publishing it online can be an effective way to drain it. If you’ve read my updated Start Here page recently, you’ll notice a section where I allude to my parents. I had never mentioned anything openly about them until I put that on my front page. I’ve since received nothing but positive and supportive feedback—far from the ridicule I so feared. There are a lot of people out there who suffer from the same insecurities as you. Help them by breaking down your own.   

5. Nobody wants to read your shit” -Steven Pressfield

Initially, I thought I could just write about anything I wanted and in any form I wanted. While that is true to an extent, there are certain constraints if your goal is to grow your audience. When I read Steven Pressfield’s essay “The Most Important Writing Lesson I Ever Learned,” it hit me that I needed to simplify my prose and add emotion–a process that I am still trying to get used to.

Writing is a transaction, and you need to give the reader a worthwhile experience in exchange for their valuable time. Nobody wants to, nor has the time to, come to your blog to read a bloated lecture. 

6. You’ll begin to pick your words and phrases carefully.

Writing for an audience, no matter how large or small, forces you to think and rethink many times before publishing. Your word choice could mean the difference between offensiveness and compassion when it comes to discussing topics like mental health. Wording could also mean the difference between a witty joke and one that falls flat. You also learn to reduce the use of cliches and platitudes, as they are uninteresting and are a sign that you’ve run out of ways to make the point. In short, you become a sharper, clearer writer and thinker through consistent online publishing.

7. Stop hedging—get to the point.

Hedging is what investors use to reduce their risk, it’s what politicians use to save face, and it’s what writers do to avoid criticism. Hedging also makes your work boring and bloated. Readers want you to take a stand for something and stick to it. Remember, people don’t have much time to devote to your work. You’re lucky they even clicked on your link in the first place! Get to the point succinctly and unapologetically.

8. Ideas are like wildfire.

Ideas are like wildfire

Fire is unlike anything on earth. A single spark can lead to a flame, and a single flame can lead to an 800-acre wildfire. Fire begets more fire. Similarly, ideas beget more ideas. Most people think that it is unsustainable to come up with ideas on a consistent basis, and impossible if those ideas are going out to the public every week. But this cannot be further from the truth! Once you thoughtfully put together one essay, you instantly begin to compile thoughts and ideas for a possible next essay. The key is to harness this concept into an organized note-taking system. Combine it with a daily reading habit, and you’ll have interesting content to write about for the rest of your life. But it all starts with one simple idea.

9. You become more observant.

Writing consistently online changes your whole orientation to life. In your search for interesting ideas and thought-provoking concepts, your mundane drive to the supermarket suddenly becomes an idea to write about traffic patterns and how roads resemble veins and arteries in the body. Sitting in the waiting room in the dentist’s office becomes a thought experiment in observing people’s social interactions, body language, or why the receptionist does what she does. Writing online adds color to your thoughts. It forces your brain into a mode of questioning, thinking, combining ideas, and creating new ones, all from the most mundane of daily experiences.

10. Length doesn’t matter all that much after all.

If you’re just starting out, you’ll probably come across endless advice to keep your word-count within a certain range. But this is a non sequitur. If you read widely enough, you will see that online writers have success with 200-word posts, or 8,000-word posts. The point is, readers don’t care as much as you think about length. What matters is how interesting your writing is. Like Steven Pressfield says, people aren’t mean or cruel, they’re just busy. Your job is to make your writing more interesting than whatever the reader might do once they click away from your page.

Do not conflate length and time. Yes, readers have limited time. But if they deem your content more interesting than anything else they will do with their time, they will have no problem reading thousands of your words. And if you’re really good, they will be begging for more!

11. Writing online is like public speaking, except…

You’re on stage 24/7. As long as your writing habit is in plain view to the public, you’ll be on stage when you’re out to lunch, when you’re in the shower, and when you are sleeping. Your audience is much larger. Rather than a finite room of 30 people to speak to, your words have a potential to reach innumerable eyeballs. You need to pick your words carefully and give great attention to detail.

Writing online is like public speaking

The intangibility of the transaction lessens its intensity. You feel safer behind the computer screen. Your palms may not be sweating, your heart may not be racing, but by putting your work out there for everyone to see, you will be more exposed than ever. You just can’t see your audience. When we take away eye contact, facial recognition and view of the crowd, we have a tendency to let our guards down and we become less efficient. We see it in the job search, we see it with COVID-19, and we see it in online writing. Do not fall victim to this cognitive bias.

12. It helps to write for one person.

If everyone is your audience, no one is your audience. In the crowded online marketplace for ideas, pinpoint focus is of the essence. Picture one specific person in your mind and write as if you are speaking directly to them. Your message tends to become diluted if you try to please everyone.

As Kurt Vonnegut put it, “Write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia.”

13. You can construct your own forcing functions.

If I write publicly about sticking to a regular writing habit, I am more likely to follow through with it. If I write publicly about future blog post topics, you can bet you’ll be reading about them in the near future. If I write about a project I’m working on… you get the point.

I’m using the principle of consistency to my advantage, one of six in Robert Cialdini’s classic Influence. We all want to appear consistent with our prior actions and statements. When a virus protection program on your computer gives you the choice between “Yes, I’ll pay for premium” or “No, I’ll accept risk,” they are using consistency against you. Use this principle to your advantage, don’t let it use you.

14. Sorry, you are fully accountable.

Everything you type online, everything you post, even if you delete it, will be attributed to you (or your pseudonym). There is nowhere to hide, no one to blame, nowhere to shift or redirect responsibility. Even if you delete something, chances are that there is a copy of it somewhere out there on the internet. Writing online is a form of ownership. It is skin in the game. You can try to cut corners and be dishonest, but it will be at the expense of your reputation. And at the end of the day, reputation is all you have.

Reputation is the backbone of credibility. Use it wisely.

15. Cunningham’s Law.

“The best way to get the right answer on the internet is not to ask a question; it’s to post the wrong answer.” Openness to being wrong and correcting your thinking is more useful than thinking you are always right. The reality is people on the internet generally do not comment to help unless they know you or identify with you. They comment to be the smartest person in the “room.” Use this behavior to your advantage. Start conversation with the intent of having your ideas and body of knowledge challenged. You will either change your mind after considering convincing evidence, or you will further confirm and sharpen your original stance. Either way, you become a clearer thinker when you prioritize the right answer over being right.

16. Writing online gets easier, I promise!

To piggy-back on #8, after two years of writing I am convinced that writing gets easier. The muscle memory of finding new topics, pushing new boundaries, confronting the blank page, hitting publish, and handling feedback establishes a comfort level and a momentum that will carry you through if you stay consistent. Your reorientation to the world around you, your eagerness to find new ideas, and your enthusiasm for exploration will redefine your writing. As you get better, the act gets easier. And as it gets easier, you get better! You expose yourself to the serendipity of new opportunities and new people. And when you get enough steam, this train will be hard to stop. And by that point, why would you want to stop it?

*17. Writing online is the foundation of prosperity in the 21st century.

I love throwing in the occasional unexpected treat. And if you’ve read this far, you deserve the best one of all!

The internet is the future. And the future is already here. Those redirecting their energies to an online writing habit will be well positioned for an uncertain future. The power of the internet allows you to create digital products that have no marginal cost of reproduction. There are little startup costs to an online business. Your market is now 7 billion worldwide, not just 700 in your small town. You will have the ultimate job security as your own boss. You will be well insulated from the havoc wreaked by pandemics and other global catastrophes. You will have the freedom to work when you want, where you want, and on what you want. And what does it all start with? Your ability to write online.  

Building a consistent writing habit online can be intimidating, painstaking, and labor-intensive. Establishing a writing habit is not for the faint of heart. After two years of writing online, these are the best lessons I can offer you. I still struggle with each and every one of these lessons, and I’m sure they will change drastically in the next two years.

The key to success is to show up every single day. Improve on what you did yesterday, every day, and there’s no telling what you can accomplish. There is a lot about life and about yourself you can learn through revisiting the blank page every day.

I hope this post inspires you to start (or restart) your online writing habit.

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