The February Writing Challenge (Win $500 For Writing Your First Essay)

Have you ever wanted to become a full-time writer? This is your push from the universe.

Have you ever dreamed of becoming a full-time writer?

This is your push from the universe.

Substack has not only completely changed my life, but changed the world for thousands of writers.

But for every writer who has been able to overcome their fear of publishing, develop a consistent writing habit, and build a real following, there are thousands more who are stuck.

I am creating The February Writing Challenge to fix this.

The goal of The February Writing Challenge is to help as many writers as possible either:

• Publish their first article on Substack, or

• Publish their next article on Substack

So many writers struggle to simply get started, but once they do anything is possible.

I want this to be the small push that ends up changing your life forever.

What’s The Challenge?

The challenge is for everyone to write and publish an essay on February 13th, 2026.

But there’s a twist.

Not only is everyone going to publish their essay on the same day, but in order to complete the challenge they also have to publish a Substack note containing a video showing them writing their entire essay in one-sitting (details below).

You read that right — it’s a one-shot challenge.

No procrastinating.

No endless editing and self-doubt.

Just write and hit publish.

Your publication deadline is 11:59 PM EST on February 13th.

“Why Do I Need To Post A Video Of Me Writing?”

I came up with this entire idea because when I sat down to write my next Substack article on a random Sunday morning, I opened the rough draft I was working on and realized it was a disorganized nightmare.

I wondered to myself, “is this how everyone writes? is it always like this?”.

This led me to think about how interesting and potentially helpful it would be for some of my readers who are aspiring writers to see how I work behind the scenes. To see a video of what its actually like for me to write an article from start to finish, talking about the process as I go. I also thought that it would be just as interesting and helpful for me to see how the writers that I look up on Substack share their own process.

We can all benefit from being more transparent and vulnerable with each other.

My hope is that if everyone shows the imperfections of their writing process at the same time, it would make it easier for thousands of aspiring writers to simply get started and publish their work.

Challenge Requirements

Here are the rules — they are pretty simple:

• You must create Substack note where you nominate 5 other writers for The February Writing Challenge using the @ symbol to tag them( Nominate any writers that you want to encourage to publish, or whose writing process you are curious about. Please avoid spamming individuals, and only tag those who you think would genuinely enjoy this challenge).

• Here is a template for your note: “I am taking the leap and joining the The Micro-Philosopher February Writing Challenge with a chance to win $500. The challenge is to write and publish an essay in one-shot on February 13th, 2026. But there’s a twist. You also need to post a video showing yourself writing the essay so other’s can learn from how you write and to prove that you did it in one sitting. I nominate XYZ to do it with me and publish their writing on Substack”.

• You must publish a Substack essay on February 13th by 11:59PM EST.

• Your essay must be a minimum of 800 words (longer is fine)

• Your essay must abide by Substack’s content policies

• After you publish your essay, you must post a Substack note with a video showing you write the essay in one-sitting (record your screen, not yourself! I recommend using Loom or another similar screen recording software. If you can’t post the full video to substack, include a link to Youtube).

How Do You Win $500?

In order to be eligible to win $500, you must:

• Send me a direct message on Substack after you publish on February 13th letting me know.

• You must be able to verify your identity if chosen to win.

• I am going to personally judge the submissions and choose what I believe to be the best essay (I will not choose someone I know personally — they are not eligible).

• The winner will be announced by the end of the month.

That’s it!

Conclusion

This could be a total flop with only one entry and I am forced to pay someone $500 even if their essay isn’t that good.

And to be frank, I probably can’t even afford this financially.

The thing is I am not afraid to take risks anymore.

I am putting something on the line in order to send a message to all of the writers out there who are afraid to risk hitting publish.

Let’s put an end to that.

I can’t wait to see what you write.

If you have questions about the challenge, leave a comment below!

-Paul