How to Build a Successful Writing Career Without Getting Discouraged

So you’d like a writing career, eh? It sounds fun. Right? Just post a few articles on Medium a couple of times a week, and you could be making up to 10K a month while fulfilling your dreams of being a writer. You see visions of yourself sipping espresso in a café, dressed head to toe in black with a copy of Viktor E. Frankl’s Man’s Search for Meaning next to you while you ponder the larger questions of life and put the answers into coherent sentences for your audience so they know them too.

The reality is, it is much harder than that.

Some stats and background: My last payout was close to 6K, but that took a ton of effort.

What it takes:

  • Patience.
  • Writing daily.
  • Being OK with rejection.
  • Being OK with sucking first and putting in the time to get better.
  • Sharing a part of yourself with the audience.
  • Being OK with vulnerability.
  • Being OK with ignoring trolls, and the mental strength to do so.
  • Creating a system through trial and error.
  • Putting most things on the back burner until you gain momentum.
  • Put your writing first.
  • Once you hit a plateau, the ability to look at your writing critically to take it to the next level.

Writing isn’t easy. If it were, everyone would do it. And we wouldn’t see so many writers quit this platform. If you want to make a full-time income from writing, you have to commit. And commit hard — like an obsessive teenager addicted to their first love.

When I started Medium, I got the best advice from one of Tim Denning’s posts (I share his advice often with my readership). He said, try writing for an entire year (most likely with little to no pay) and see if this writing thing is for you. If you can write for an entire year and still want to write for a living after that, you are built for this writing thing.

That is what I did. Wrote non-stop for a year with little to no pay and refined my process along the way.

Making money online isn’t for the faint of heart.

There are algorithm changes to cope with, a lot of competition, lots of great writers who know how to hustle, unstable income, and burnout.

You aren’t just a writer; you are an entrepreneur, a marketer, a salesperson, and a writer — all in one. You lose sleep thinking about the article you’re currently working on, even the darlings you’ve published already.

Knowing all of this, if you still want to proceed, here are some things to digest that will help you.

1. Taking a course is being in motion, not action.

You can take twenty courses. But if you are not writing, you won’t be successful.

You need to take action to see success. I’m guilty of this and know a lot of people who’ve spent thousands of dollars on courses, only to be in the exact same place a year from when they bought the course. You can fill your brain with all the information you need to know how to succeed, but if you are not doing it (taking action), you’ll be treading in the same place a year from now.

  • If I outline 20 ideas for articles I want to write, that’s motion. If I actually write and publish an article, that’s action.
  • If I sign up for a writing course or a “How to Succeed on Medium” course, that’s motion. If I actually write and publish an article, that’s action.

2. Perfectionism is the enemy of the good. Just start.

Some stay in motion because it is easier than leaping.

Putting yourself out in a public space and hitting publish is daunting the first time out. You’re at the same time afraid no one will read what you wrote and afraid they will read what you wrote.

You do this to put off showing who you really are.

Vulnerability is terrifying — what if they don’t like me? Because of this, many will stay in motion and tell themselves on a conscious level, and, sometimes on an unconscious level, I’ll hit publish when my writing is perfect or better. This keeps us from growing — stuck in one place.

We can’t start the thing until we’ve perfectly mapped out how we’ll do the thing correctly once we finally start.

Which prevents us from starting at all — killing any possibility for growth.

Steven Pressfield, says,

Nothing is as empowering as real-world validation, even if it’s a failure.

Growth happens through trying, practicing, failing, and trying again. Sometimes in public. When you aren’t perfect at the thing yet.

Perfectionism will keep you from doing what you are scared of doing. It is sometimes called perfectionism, but it’s really procrastination.

It shouldn’t be about getting something perfect; it should be about getting it out the door. If we only publish a perfect piece, our writing will never see the light of day.

This is what Voltaire, the French writer, meant when he said, “The best is the enemy of the good.”

To beat procrastination, writers devise a system.

3. Devise several systems.

Some people get stuck thinking about what to write about. Try not to be one of those people. And just write. It isn’t so much what you write about that counts in the beginning. It is more that you write.

In the morning, focus on the task of the highest priority. Only move on to the second goal when you’ve completed the first. Repeat.

Stop multitasking: Instead, give laser-focused attention to what matters to you. Stay focused on the essentials — writing — instead of busying yourself with the non-essentials: Facebook, text messages, emails, cat videos.

Caveat: Searching for inspiration. Reading something inspirational to spark ideas can sometimes be a good idea. Just give yourself a time limit. For example, give yourself 30 minutes, and then start writing. Sometimes, when I have nothing to write, I’ll read a few articles to get the creative juices flowing and then hit the keyboard running. It is a great way to jump-start the writing process.

If you want to master a habit, the key is to start with repetition, not perfection (remember, perfection is masking procrastination).

After a while of practicing the act of writing (it took three months of pushing through for me), it becomes ingrained. The act of sitting down to write will be more effortless on the 100th day compared to the first day.

The more you repeat an activity, the more the structure of your brain changes to become efficient at that activity. — James Clear, Atomic Habits

Neuroscientists call this long-term potentiation.

Habits form based on frequency, not time. The more you write — the quicker you form a habit.

The more you practice, the more ingrained these habits become, making them easier to do.

4. You need a system to generate ideas.

Become an idea generator. I’ve written about how to never run out of ideas many times, and I’ll link more complete articles at the bottom of this post.

When I started writing, I had the same thought many new bloggers have, what am I going to write about? I have maybe ten to twenty posts in me.

You need a system to reliably generate new ideas. This is much easier than you think. Ideas are everywhere. Be curious. Pick up any book in your house, turn to a random page in the middle, and I bet you’ll find something to write about.

I’ll do it now. I really do have Man’s Search for Meaning by Viktor E. Frankl sitting next to me.

On the very first try, I randomly went to page 65, and the first thing I read was the second paragraph,

Screenshot by author

OK. This is a great one. It’s genuinely the first page I turned to. There is so much here to spark creativity and ideas.

If I were desperate for something to write about and turned to this page, I would write about how one’s environment affects who they are and who they become.

Your environment can be many things; it can be your physical environment or your emotional environment. Your messy writing desk or your abusive caregivers, the list is endless. You could go deep and write about the psychological changes people go through determined by the environment in which they are raised or how your writing desk environment affects your writing output. “I may give the impression that the human being is completely and unavoidably influenced by his surroundings.” That is a sentence with a lot to unpack. You could write an entire piece around this sentence. You could use it in your post. You could write about how we are the average of the five people we spend time with, or you could research life in a concentration camp and what that does to a person.

On a side note, this book should be required reading for all high school students.

Ideas are everywhere. Once you look for them, you’ll start to naturally see ideas to write about when you aren’t looking. When you form a writing habit, a system to generate ideas will happen more naturally because you’ll be more aware of finding things to write about for your next article, the one after that, and so on.

5. Build a readership on one platform first and then conquer others.

Don’t waste your time trying to be everywhere. Concentrate on one platform at a time. Pick the one that you like the best is the crucial part. Don’t try to be on Quora, Medium, News Break all at once, at first.

Pick one and build your audience on one platform at a time. Really commit to consistency on that one platform. If you want to be a paid writer, reliability through a consistent content schedule is a large part of the equation.

Many writers are gung-ho when they start. After reading posts like How I Paid My Mortgage from Writing for a Year, they think they will pay off their mortgage by posting a few times a month or a week. Set realistic expectations, so you don’t get discouraged and quit.

Give everything you’ve got to one platform. Then, when you have 10K plus followers, branch out to other platforms. You have to win at one first.

When you focus on one platform and sharpen your writing skills, it will be easier to make it on one another. There is only so much time in the day. You want to put the limited energy you have towards the most important place to see the most growth in name recognition, audience growth, and views.

Once you do, use that platform as your marketing engine by leveraging that traffic and driving your audience to other platforms or products you offer like books, courses, subscriptions, and blogs with affiliate links.

You have to think long-term and diversify as a writer, so you’re not always a slave to the algorithm.

Keep these things in mind when developing a writing career.

Entrepreneur + Writer. I care about helping others learn to live a better, healthier life. Hit FOLLOW ⤵

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store