Lessons Learned from Publishing 1,000 Articles on Medium in 2 Years

Becoming a self-taught writer and getting paid for work that brings immense meaning and fulfillment

I’ve been on the Medium platform for two years, and this week article number one thousand went live.

When I began my journey on Medium, no one showed me what to do and I never thought I’d publish more than a handful of stories before getting bored and giving up.

It turns out I was wrong.

The joy of publishing on Medium is being able to articulate stories in such a way that people find what you have to say helpful. At the same time, it’s a competition with yourself to get better. You learn to see the lies you tell yourself, your ego that is present in your writing, your perception of the world, your biases, and most of all, your flaws.

You are forced to take both your successes and your struggles and package them up into neat little bite-sized Snickers Bars in the form of articles, and deliver them to the world whether they are ready or not.

There are risks, trolls, and people who won’t like you. The opposite is also true: there are huge highs, great people all around you, and a platform full of content to inspire you and help you learn a thing or two.

Investing my time in Medium is one of the best things I have ever done and it would bring me immense joy to see you do the same.

This advice is coming from a skinny dude from Australia who once patted a Koala and has seen Kangaroos on the footpath outside my office. I was never taught to write, spent a decade not reading a single book, am easily distracted by the shiny red notifications of my web browser and didn’t drink a green smoothie today because, frankly, I didn’t feel like it.

After publishing story number one thousand this week on Medium, I would have to be an idiot if I didn’t learn a few things that you the reader might find valuable.

Let’s start with the contrast between Year One on Medium and Year Two.

Year One

This was the year that writing on Medium became a habit. One of the early changes was that I went from writing in Microsoft Word to writing directly into Medium. The handy advantage of this shift is that Medium has a minimalist user interface and it’s inspiring to write words on.

As you write on Medium, you can shape your art with formatting, photos, and useful diagrams.

Your first year on Medium is always the hardest because the chance of you giving up is extremely high. The reason for this is as follows:

• There will be hardly any claps
• Major publications probably won’t be interested in your work
• You won’t reach many people

When it’s just you and your writing, it’s easy to tell yourself the lie that you are not good enough or that it’s all a waste of time. Finding meaning in publishing your work on Medium in the first year is tough.

Building the habit

The first year for me was all about building the habit. It wasn’t what I wrote but the focus of publishing consistently that set me up to eventually write one thousand articles on the site.

The quality of your work on Medium is subjective to the reader, so all you can really rely on is showing up each week with something to say.

Start with writing 30 minutes at a time so you don’t overwhelm yourself, and hit publish no matter how good or bad you think the finished product is.

Your work is never finished

That’s right — even today, my work is never finished. There’s always more to add and another editor that wants you to pay them so they can sprinkle some fairy dust on your work and help you get a book deal.

Tell yourself, “It’s good enough for now and I can always write about the same topic again with a different approach or a version two.”

Just publish your work and the rest will work itself out.

No money

In case you were wondering, year one resulted in making no money.

Don’t be greedy and focus on money when it comes to Medium, because that’s not the point of it. Your income will keep coming from your job or business and that’s how it is for all of us.

Finding your style

I didn’t have a style of writing in the first year and I still don’t. I can write about a new phone, losing my job, my writing process, a parking inspector, an act of kindness, or a romantic relationship from the past.

You don’t need to be known for one topic; you just need to be known as a writer that publishes something useful. That’s the best way to look at it.

Your worldview will change

In the beginning, my worldview was that I was the best, everyone else was an idiot, and it’s good to be addicted to success. This perspective has radically changed and the focus of my work has changed along with it.

Start out with whoever you are and enjoy the process of changing through writing.

As you seek to find more helpful advice, stories and lessons you can share with your audience, you’ll be forced to dig deeper into the well inside of yourself and see what you can find.

Year Two

The first year flew by and before I knew it I was in my second year on Medium. The second year is where things start to radically shift if you have been patient enough to make it this far.

Earning money

The dollars began to roll in and that wasn’t just from Medium. Offers to ghostwrite, consult, speak, and publish articles for a fee began to find their way into my tiny little email inbox.

The first month brought in a hundred dollars and now the income from writing has far surpassed my expectations. It all came from having one goal: being helpful (not making money).

Enter credible publications

The second year also brought credible publications into the picture.

Large Medium publications allowed my work to reach a bigger audience and publications outside of Medium, such as CNBC and Business Insider, began to syndicate my work.

The best approach is always to let them seek you out rather than seeking them out and accidentally appearing desperate or like a needy dog that hasn’t had a sip of water during a long hot summer’s day on the beach where Baywatch was filmed in Los Angeles.

Publications will help you a lot, but you have to earn it and ensure you talk to them with respect, understanding, and truckloads of humility.

Friends with benefits

These sort of friends find your email address and offer to help you or hang out, which improves your writing.

To be a great writer, you have to hang around other great writers.

These writers will push you, hold your hand during the tough times, and become the sort of childhood mate you will make and one day look back on and smile for the very fact that they came from writing in your office, alone.

The best advice is advice you have experienced

There’s a lot of written content on the internet that has come from arm-chair commentators who have never actually done the thing they write about.

You can read loads of books, quote famous people — like Branson, Jobs, Hemingway, Elon and Zuckerberg — and never actually leave your home to experience life for yourself.

The writing of mine that has been helpful to readers has always had one common trait: it has come from an experience that I have lived.

There are talkers and there are doers. Be a doer as a writer and you’ll go further than you ever thought was possible.

Lessons Learned From Writing 1000 Articles

So that is the two year journey to publishing 1000 articles on Medium.

Let’s dig into the specific lessons and takeaways that you can apply to your life, whether you are a writer or not.

As you grow, your writing will grow

My writing got better over the two years because I practiced these mantras:

• Put yourself in uncomfortable situations
• Help others
• Commit courageous acts as a form of experimentation

Doing these three things on a regular basis helped me grow as a person and that changed the way I wrote. Your writing won’t get better or become more helpful unless you find ways to grow, such as these three things.

Through the journey of growth, you unlock a little piece of wisdom each day that when tallied up, transforms your ability to connect with a reader and get through to them.

Your errors and mistakes make you different

Over the last two years I have got many things wrong.

From simple spelling errors to major misquotes to ideas and thoughts that were ridiculous looking back. These are the things that define you and make people consume your work.

Imperfection is a magnet and when you allow these blemishes into your writing, you show people who you are without the fake-ass bullshit that Instagram portrays—and that opens up a whole new range of possibilities for readers who can now consume your work, without feeling like they are not enough or not ready for what you have today.

Imperfection gives your audience permission to walk through the front door of your experience and be open to the thought of change or another way of living their life. This is one of the most helpful gifts you have as a writer on a platform such as Medium.

There are no minimum requirements

No one is going to check your resume or ask you to pass a test.

Being a writer is about learning to give yourself permission rather than having society issue you a permission slip that you’ll be waiting for your entire life never to receive and feeling miserable in the process.

You realize after enough time has passed that if there are no minimum requirements to be a writer on Medium, perhaps this philosophy applies to other areas of your life.

This lesson has been the catalyst for me sticking my middle finger up at myself and my incredibly high standards and just getting on with the simple act of doing the work I already know I must do.

You already know what to do

The endless Indiana Jones Quest of looking for hacks is an easy trap to fall into that leads to such mirages like overnight success.

If I told you that all you had to do was write heaps on Medium and it would be beneficial, I’m sure you wouldn’t be surprised. Working hard is so cliche, yet that’s the main strategy.

When you begin the process of writing, you realize that it’s not solutions you need; it’s to get out of your own way and just do the thing that you said to your friends you were going to do.

The answers in life don’t lie in seeking more knowledge — the answers lie in the doing part of life we all try desperately to ignore and attach to excuses about why we can’t.

The last two years on Medium have been the two greatest years of my life. I have loved every moment of it and I hope that you may try it for yourself. Even if you decide that Tim is a dickhead and you ignore that advice, I hope that you learned something from my blood, sweat, and tears that have been poured into these 1000 articles that are my life’s work.

That is 1000 articles down for me and a lifetime to go. Wish me luck for the next few thousand.

You’ll never regret dedicating two years of your life to something — but to sit there wondering what it’s like without ever getting started won’t end well. If I can do it, you can too.

Grab your laptop and give it a go. You can do anything you put your mind to and build a habit around.