5 Biggest Lessons From Publishing Online for 5 Years

Michael Leonard


Five years ago, I hit publish for the first time.

At the time, I was stuck in a 9–5 career I hated. My job was in sales, but I studied finance on the side as I was determined to retire early.

I openly shared all I knew with friends and coworkers as I wanted to fill in the gaps that college didn’t teach us. After helping enough people, someone at work said I should start a blog.

I figured why not — even though I had no clue what a blog was. So to start 2016, I put the new year momentum to use and launched my first blog. A week later, I hit publish on arguably one of the worst pieces of content on the internet.

But I did it.

I started.

While it sounds cliché, this one decision created a butterfly effect in my life. 15 months later, I quit my 6-figure job to blog and pursue professional golf. Some called it a quarter-life crisis, while I thought it was the only route to find happiness in my work.

Since then, I’ve become a top freelance golf writer, built a 6-figure writing business, and now coach other writers. Not to mention, I never had to crawl back to a 9–5 that I hated so much.

Don’t get me wrong, there was plenty of stress, anxiety, fear, imposter syndrome, and more, but it was all worth it.

But none of it would’ve happened if I didn’t start. I want to help more writers than ever this year by sharing these five biggest lessons that have led to my version of success.

Quit Assuming The Worst

Writing is an extremely vulnerable activity, and our mind doesn’t help make it any easier to hit publish. When I first started writing, hitting the publish button terrified me. Every time I did, I kept thinking people would tell me how awful my writing was, how wrong my content was, and that I should quit entirely.

If I’m honest, that did happen once. When I published a blog in 2016, a guy I went to high school with messaged me on Facebook and told me I should quit because it was so poorly written. Looking back, he wasn’t wrong.

Right then and there, part of me wanted to quit, but part of me wanted to prove him wrong. I chose to use his hate to fuel my fire for writing and making a difference with my words.

But in all reality, he’s a one-off.

Sure, you get some hate and negative comments from time to time, but in general, most people will love your work and cheer you on. Even if it doesn’t feel like it all the time, people will appreciate your writing.

When you start to get emails or comments from people on how much they love it, it’s an incredible feeling. Seriously, there is no greater experience than helping someone with your expertise in a specific area. Anytime someone comments on a post, I am genuinely excited because I’ve been on the other side as a reader too.

Sadly, the naysayers and critics tend to be louder than the positive readers (especially in the beginning). When you’re just starting, you have to become your own biggest fan. The fact that you had the courage to write something and hit publish is something that most people will never do.

Quit expecting the worst and start assuming the best could happen. When you do, I promise it’ll make it easier for you to hit publish more often.

Remember, you’re only a Medium story or freelance article away from changing your life forever. Don’t let the fear of others’ opinions hold you back from your own greatness.

Quantity Produces Quality

I can barely read my old blog posts or the first book I published. The words, flow, and structure makes me cringe (the lack of editing didn’t help either).

But I’m proud to say that my writing has improved dramatically over the past few years. While I’m convinced you’re never writing at the level you want, repetition will make you better.

One thing that helped initially was a writing challenge that I did to start 2018. I joined Benjamin Hardy, Ph.D.’s mastermind group, and he encouraged us to set a big goal for Q1 — mine was to write 45 articles in 90 days.

I was relentless about it, and it paid off.

Not only did I hit my goal, but I also grew my email list and got featured on major sites like Goalcast, Fearless Motivation and more. Then, I used these free guest posts to land recurring work and write over 100 posts for Fearless Motivation alone.

None of this would’ve happened if I hadn’t focused on pumping out content. Don’t get me wrong, many articles were okay (at best), but each one got a little better. Each one taught me something I needed to learn about the process of creating epic content.

I also actively sought out feedback and worked on my own editing as well. The secret benefit to this writing challenge was that it helped me crank out content like never before.

Now, I can easily write 1,500 or more words in under an hour. This helps me create more content for Medium and not take as much time when working with my freelance clients.

Tim Denning had a similar piece of advice when I bought his book about writing on Medium. He said to focus on the first 100 articles and get them published as soon as possible.

Quantity will lead to quality!

Finally, it will help you overcome imposter syndrome and just hit publish. In the beginning, it’s easy to overthink things and spend all your time procrastinating instead of hitting publish. When what you need to do is get your stuff out there so you can learn, improve, and keep going.

But when you are committed to a goal, it’ll help you crank out content faster than normal. This will help you build momentum, speed up your writing, and improve your writing skills drastically.

Own Your Story

You have a unique story and experience unlike anyone else in this world. Even if you’re an identical twin, no one has experienced the same things in life as you.

Don’t run from it, own it!

I find that so many beginning writers think they aren’t enough or don’t have enough experience to become a good writer. When in reality, you have years or decades worth of events that have shaped who you are. It’s up to you to tap into those moments and share them with the world.

If you’re writing on Medium, share past stories and your own “weirdness”.

That’s what makes you unlike anyone else! While it’s awkward sharing so much of your past with total strangers at first, it’s worth it.

Not only will readers resonate with you, but I think you will find writing to be an outlet as well. Your writing will almost act as a way to relive those tough times but overcome them by sharing advice for others to learn from. Vulnerability truly is a superpower once you learn how to tap into it.

If you’re freelance writing, use your passion, past jobs, and skills to start writing.

For example, most people don’t have 20+ years of golf experience — let alone playing at an extremely high level in competitive events around the country. I tapped into my uniqueness and used my experience to make golf writing a top income stream.

I owned the fact that not many people are great at golf and a solid writer.

My writing website even says:

“Why hire a normal freelancer who doesn’t know a thing about the game when you can hire a golf writer who is a +1 handicap and an expert writer?”

Own your past and share your gifts with the world to build an audience, land clients, and find success sooner than later.

Never stop learning

In my five years of entrepreneurship, I’ve spent a lot of money investing in myself and my business. If I had to put a number to my total investment, I would guess it’s around $60,000 total. This is between 1/1 coaching, masterminds, group coaching, and an endless amount of online courses.

Some people might hear that number and say, “I don’t have that kind of money.” Well, neither did I, but I had credit cards and a will to succeed.

While I’m not saying you need to rack up credit card debt to become successful, make sure you are actively learning all the time. Whether it’s reading books, listening to podcasts, or joining paid programs. Just keep learning and evolving so you can become the writer and entrepreneur you need to become!

I figured it was an investment in my future self and wanted to get results as soon as possible. That meant paying writers and entrepreneurs who were a few steps (or a lot of steps) ahead of me.

While it was scary at times, I chose to always have the belief that I would succeed, one way or another. And it worked!

“The world is a University and everyone in it is a teacher. Make sure when you wake up in the morning, you go to school.” — T.D. Jakes

Schedule Everything

I think one of the worst pieces of writing advice is to write every day.

I get the reason behind it, but for me, writing is mentally exhausting.

When I tried to write every day, I found myself tired and reaching for endless amounts of caffeine to create anything worth reading. But when I started to only write a few days per week with a day off in between, I could write way more content a lot faster. Not to mention, it was 100X better to read and required a lot less editing.

None of this would’ve been possible had I not done three things; found my ideal writing time, batched tasks, and honored my schedule.

First, if you want to build a successful online writing business, you need to find your ideal writing time. For me, it’s after a workout, in the morning. I outline my content the night before, listen to my AirPods, sip on caffeine (when will Rockstar sponsor me?) and focus only on writing.

During my writing time, I have my phone away from me and don’t judge any of my work. Nor do I edit anything (yet).

Writing time is just for writing!

Second, I batch everything. I never write and edit at the same time. In my opinion, editing is death to creativity.

Instead, I batch everything I do — from collecting images for Medium stories, outlining content, editing my freelance work, and writing.

Lastly, my batching wouldn’t be possible without creating a schedule for my week every Sunday. I start by identifying writing days, then add in the rest around the rest of my business, clients, and life.

Final Thoughts

Little did I know that publishing one personal finance blog to help millennials with their money would forever change my life. I want you to take the leap this year because you never know what will happen.

If even one percent of you wants to start writing online, do it!

I sat on my idea for probably a year before I ever made it happen because I was too scared. Don’t let the fear hold you back.

You already have everything inside you to make it happen. As best-selling author Jack Canfield said,

“You were not given a dream without the capacity to fulfill it.”

Remember that quote for the rest of your life. If any part of you wants to start writing (or create any content online), you have the ability to do it.

While it likely won’t happen overnight, and you’ll have to fight your own brain a lot in the process, it’s 100% possible!

Photo by Xalanx on Deposit Photos

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My name is Michael Leonard and I am the creator of Inspire Your Success. I'm on a mission to help readers build online writing businesses and quit their jobs to live a life of freedom!

Scottsdale, AZ

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