50 Writing Tips After Publishing Online for 50 Months

Michael Leonard


I know it sounds cliché, but hitting publish on my first blog post 50 months ago changed my life.

No, the post didn’t go viral or make me any money, but it changed the course of my entire life. Since that day in January 2016, I’ve created content nonstop.

It led to quitting my six-figure sales job at 29, writing hundreds of blog posts for myself and clients, publishing Medium articles, three self-published books, a podcast, YouTube channel, and an infinite amount of words.

I love it.

While I’ve made over six-figures writing online, I’ve also made every mistake you can think of and almost had to go back to a cubicle. But I refused to give up and just keep adapting in the quest to never go back to a 9–5 job.

During this pandemic I’m writing more than ever — I mean, what else can I do? As I was looking back at the start of all this, I realized it’s been more than four years since that first blog post.

As hindsight is always 20/20, I wanted to share my biggest takeaways to help you succeed a lot faster. These writing tips work whether you’re freelance writing, blogging, self-publishing or writing on Medium.

50 Writing Tips

  1. Understand that vulnerability is a superpower. The more you share about your own life experiences, the more likely people will connect with you and keep reading your stuff.
  2. Write to one person. Use words like “you” and “your” to connect with readers. This will help you build a deeper connection with the reader.
  3. Believe that you can make money writing. Even if you haven’t made a dime writing yet, just know it’s possible. Spend time visualizing, thinking, and acting as if you’re already successful. Your subconscious mind doesn’t know the difference between what is real vs. imagined — trick your brain into success.
  4. Get quick wins. Most writers stop because they aren’t making money or no one is reading their stuff.
  5. Do a writing challenge. In January 2018 I did a 30-day writing challenge where I created 30 pieces of content in 30 days. It built so much momentum in my business. It led to getting featured in big publications, starting on Medium, and landing my first freelance writing clients.
  6. Set clear goals. Whether you’re freelancing, blogging or writing on Medium, know the end goal. Then, break it down into smaller goals to make progress on the big ones.
  7. Be careful with blogging. So many writers think starting a WordPress blog is the answer to sharing a message. But the sad truth is, most bloggers give up before it gets good and instead, spend all their time doing blogging tasks instead of writing.
  8. Write more often. Not only will you improve your writing, but you will speed up your typing skills as well.
  9. Eliminate distractions. Trying to watch a Netflix episode while your phone is buzzing will never yield high-quality articles.
  10. Invest in yourself. One of the reasons I’ve made over $100,000 writing in the past two years is because I invested in myself through masterminds, coaching, and online courses.
  11. Consume more content. The more I read, listen to podcasts, and go to events, the easier it is to pump out new content. Ideas in equal ideas out.
  12. Find a schedule that works for you. Everyone is different, don’t listen to just one method when it comes to writing consistently. Test everything and see what works for you. Check out my $2,250 writing day routine.
  13. Get a thick skin. I’ve been fired by clients, suggested that I should quit writing, and been told all kinds of other horrible things from people online. But I didn’t let it affect me, I learned my lessons and kept moving forward.
  14. Use an editing tool. Don’t rely just on yourself to edit the content that you publish for yourself and clients.
  15. Spend way more time on your headlines. I still need to get better about this myself but if your headlines suck, no one reads your epic content.
  16. Don’t confuse copywriting with content writing. Writing copy is all about using persuasion and influence to get people to take a specific action. Writing content is about telling stories and breaking complex ideas down into simple action steps.
  17. Write at a fourth to eighth-grade level (seriously).
  18. Take breaks to recharge and get away from your computer screen. Disconnect from your phone, exercise, and get outdoors to give your mind and eyes a rest.
  19. Listen to my podcast (Inspire Your Success). I’ll help you avoid common mistakes that most freelance writers make and interview top writers, experts, and entrepreneurs.
  20. Celebrate everything. From your first blog post, first $1 earned and everything else in between. Your brain loves when you celebrate and doesn’t know the difference between a small win or a big win. So celebrate everything to program your mind for success.
  21. If you’re in a 9–5, plan your writing strategically. Write early before work, at lunch, and edit afterward. You can easily make $1,000+ writing online even if you’re in a full-time job.
  22. Spell check after you are done writing. Never worry about spelling during your first draft.
  23. Never write and edit in the same session. Please, give yourself some space before giving it a full edit.
  24. Learn to love failure. While most people don’t like to fail, it’s a habit among the most successful people in the world. Reframe failures as learning opportunities and just keep writing.
  25. Create a consistent schedule. Whether you’re blogging, writing on Medium, or applying to freelance writing gigs, keep some sort of schedule to stay consistent.
  26. Share your content everywhere! Facebook, LinkedIn, Instagram, and more. If you believe it’s epic, you owe it to the world to have more people read it.
  27. Laugh at yourself — don’t take this too seriously. If you take writing online too seriously you’ll suffocate your greatness. Instead, keep it light, laugh off old bad posts, and focus on helping people.
  28. Create an email list. Start collecting your readers’ emails from day one. Use a free site like Mailchimp to keep costs low. Make it easy for your readers by sending them your blog posts after you publish them.
  29. Learn keyword research. It’s not always a fun subject but it’s crucial for long-term success and making money for years to come.
  30. Publish your own book. While I’ve never made a best-seller list, I’ve published three books on Amazon. I’ve used them to land writing gigs, use as samples for clients, and get on podcasts.
  31. Get a stand-up desk — it’s the best $100 you’ll ever spend.
  32. Test everything. Whether it’s publishing to a new publication on Medium or pitching a guest post on Forbes, test everything and see what works!
  33. Become an avid reader. The easiest way to be a great writer is to become a voracious reader.
  34. Network with other writers. Reach out to people you admire, blogs in your niche or your favorite Medium writer. Also, join Facebook groups, masterminds, local meetups and other ways to get social.
  35. Master the art of storytelling. Readers want more out of posts than basic, generic text. Weave lessons in between stories to have your lessons sink deep into the reader’s memory.
  36. Use project management software to stay organized. Trello is one of my favorite tools as a writer. It makes it so easy to stay organized and not miss any deadlines. Create a board for each freelance client or for your Medium writing.
  37. Live life more. Travel, talk to strangers, and create more experiences. This will give you more insight into life, and make you a better writer.
  38. Learn about SEO. Whether you’re blogging, freelancing or publishing on Medium, knowing the basics of SEO will help your content get read by more people.
  39. Don’t expect miracles overnight. I used to get so frustrated when my pitches were denied or I heard crickets from editors. Instead, put in the work and play the long game.
  40. Ignore haters. People tend to get confused with things they don’t understand. Blogging and becoming an online entrepreneur is no different. If a friend, family member or co-worker laughs at your writing goals, let them.
  41. Read your words out loud before hitting publish. This is one of the easiest editing hacks out there.
  42. Write on airplanes. I don’t know why, but some of my best ideas come when I’m 30,000 feet in the air. Take noise-canceling headphones and just start writing. A cocktail always helps me — just saying.
  43. Love boredom. Boredom gets a bad rap — people tend to think of boredom as a bad thing, but in reality, boredom is where amazing ideas are born. Remember, you can’t get a life-changing idea while you’re mindlessly scrolling through your phone.
  44. Format properly and always think of a user reading on their phone! A few sentences on a computer turn into the entire screen on mobile devices. Plan accordingly!
  45. Ask for feedback. It’s not always easy to hear but feedback will help you improve your writing faster than ever.
  46. Clean your office or writing space. It’s nearly impossible to get inspiration if you’re seeing a mess all around you. Declutter and protect your space.
  47. Write in the mood you’re in. Today, I’m feeling confident, so I’m writing like it. If you’re feeling a little sad or frustrated, write like it. Like I said, test everything.
  48. Create a writing playlist that is associated only with writing — nothing else. This will help you get into a flow state faster.
  49. Quit waiting — just start. There’s no right time to start publishing online. The sooner you start, the sooner you’ll find success.
  50. Embrace the suck. My first blog posts were so horrible and lacked any real substance that I deleted most of them from the Internet. But I saved them on my G-Drive because I wanted to remember how far I’ve come. Anytime you start something new, it’s always going to suck — embrace it, learn new skills, and master your craft.

Final Thoughts

Writing is an art, there’s no exact science behind it. Quit looking for the perfect formula and just start writing.

Sometimes you think you’ve created the perfect post and no one reads it. Other times, what you think is an okay post goes viral or racks up money inside Medium’s partner program.

The moral of the story?

Just keep going — don’t give up. Adapt and evolve.

Publishing online is a gift, take advantage of it, especially during these challenging times.

You’re only one article away from changing your life forever.

Photo by EpicStockMedia 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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