My 10 Biggest Lessons From Freelance Writing for 2+ Years

What I wish someone would’ve told me

Michael Leonard
Mar 25 · 11 min read
Photo provided by kosmos111 on Deposit Photos

I’ve made every mistake imaginable since I started my publishing content online in 2016.

I have:

  • Created several failed blogs.
  • Published books that almost no one read.
  • Been told to quit writing because my content was so bad.
  • Had my biggest client fire me for being horrible at editing.

And I’m not ashamed.

Each of these “failures” has helped me earn over six figures as a part-time freelance writer since 2018. Once I pivoted from blogging to freelancing, everything changed — but I still made plenty of mistakes freelancing as well.

I could have let any of those failures define me, but I chose to keep going. I knew that I’d figure it out if I just kept writing long enough.

So I created this post for someone who is just starting on their journey and wants success as bad as I did.

If I can do it, so can you — but learn from my many mistakes to get even faster results (and a lot less stress, anxiety, debt, and depression).


1. Blogging Is Only 10% Writing

When I first heard about blogging, my entire life changed.

The thought of making passive income from having people read your blog and take a few clicks seemed like magic. But in reality, blogging is much more difficult than most people know.

Sadly, blogging is so much more than just writing epic content. I’d argue that writing is only 10% of running a profitable blog.

Being a profitable blogger is about:

  • Finding a niche.
  • Driving traffic.
  • Building an audience.
  • Growing an email list.
  • Earning the trust of Google.
  • Creating consistent content with little return.
  • Monetizing your site via ads, affiliates, courses, and/or coaching.

This process can take years.

The sad truth is that most bloggers quit before they ever reap the rewards of their hard work.

Most bloggers want the results but don’t want to learn SEO, Pinterest, email marketing, affiliate marketing, social media advertising, growing a team, etc.

If you need money fast, freelance content writing is the quickest way to make money online. You can apply for a job posting today, write content tomorrow, and get paid this week or month.

While I’m not saying you should quit blogging, just know you won’t be writing very much.

Lesson 1: Know the end goal with writing online.


2. Pitch More Clients

When I first started freelance writing, I was terrified of reaching out to clients.

Sometimes, I could barely hit send and would read my proposal five to ten times as if something would change on the tenth read.

I think this is because when you are cold pitching strangers or applying to job boards, you get a lot of rejection. And rejection can sting at times, especially if you are a brand new writer with imposter syndrome.

But if you are committed to earning money as a writer, you need to pitch like crazy. One lesson I learned from my past sales career is that getting writing clients is just a numbers game.

The more you pitch, the more likely you are to land clients

If you pitch 15 potential clients, you might not hear anything. But if you pitch 50 clients, you are bound to get a few bites and open up a few conversations.

Remember, you don’t need tons of clients to make a full-time income from your writing business. Over the past six months, I’ve averaged $10,000+ each month with only three clients.

So get over the fear of rejection so that you can give yourself a chance to succeed. Get off the sidelines and get in the game by pitching more people.

Lesson 2: Pitching is just a numbers game. If you want more clients (and more money) get your offer in front of more people.


3. Outline Before Writing

If you’re a writer, nothing is scarier than a blank Google doc.

But when I first got started, I would open my laptop each morning and expect magic to appear on the screen. It never did.

Instead, I procrastinated, jumped around from task to task, and got frustrated for not getting my work done.

What I learned is that creating epic content from thin air almost never happens. Anytime I create great content for Medium or other clients, it all starts with a plan.

I’ll usually be at the gym or driving in my car and get an idea. Then, I’ll add a note to my phone, start a draft on Medium, or send myself a voice memo.

From there, I draft out the main points, turn off spell check, flesh out the body, and then go back to work on the intro and conclusion. Then edit separately.

To set yourself up for success, draft a clear outline about your topic before diving into the writing portion the next day.

Every night, before I go to bed, I make sure I have an outline and any articles pulled up on my computer, so I can get right to work after my morning routine.

Lesson 3: Set yourself for success by outlining in advance.


4. Separate Writing and Editing

Have you ever tried to edit your work right after putting your blood, sweat, and tears into an epic post?

For me, this never ends well. Early on in my writing career, I lost my biggest client at the time — a $3,000/month retainer, because I sucked at editing.

Getting fired really hurt… I lost 70% of my income overnight.

But it taught me a valuable lesson, and I chose to learn from that event. And honestly, they weren’t wrong. I did suck at editing and didn’t have the routines to give me enough time to edit.

Think about it, if you just crushed a 4,000-word long-form blog post, the worst thing you can do is edit it immediately after finishing it.

I’ve found that it’s nearly impossible to have an unbiased opinion of your work and edit properly after writing. Instead, I suggest giving yourself a break before diving into the joy that is editing.

Personally, I try to always edit the following day, when I’m in a different state and can look at my own work objectively.

But if you don’t have that amount of time, make sure to give yourself a few hours between editing and writing to ensure you submit quality work.

Lesson 4: Write on different days than editing.


5. Learn SEO (and Keep Learning)

SEO is one of the most valuable skills you can learn as a writer.

If you can get your posts (or clients' content) to rank high on Google, they will keep paying your invoices. That I promise.

But learning SEO isn’t a one-time event. SEO is an ongoing process as Google is constantly updating its algorithms to provide the best results for users.

As they keep updating, you should keep upgrading your skills.

You can’t read one blog post or watch a long video about SEO and think you know it all. You should constantly level up your skills so that you can get your client’s content to rank in Google.

Remember, the best place to bury a dead body is the second page of Google search results. By constantly educating yourself about SEO, you can stand out among other writers and impress your clients.

Some ways I’ve gotten better at SEO include online courses, 1:1 coaching, and listening to podcasts from SEO gurus. Keep adapting to ensure you can always help clients out and make more consistent money writing.

Lesson 5: Study SEO so you can make Google and readers happy.


6. Avoid Context Switching

One of the biggest mistakes I made in my entrepreneurial journey is jumping around from task to task.

But it’s not all my fault, I learned this awful habit in the 9–5 world and carried it with me to my home office.

A few years ago, I would jump from task to task and then wonder why I didn’t get much done that day. Or, why I was so exhausted at the end of the day.

Until I learned about the power of context switching.

These stats and graphic from Rescue Time explain context switching perfectly:

  • Focusing on one task at a time = 100% of your productive time available.
  • Juggling two tasks at a time = 40% of your productive time for each and 20% lost to context switching.
  • Juggling three tasks at a time = 20% of your productive time for each and 40% lost to context switching.
Photo provided by Rescue Time

Basically, it takes your brain time to adjust to a new task.

For example, if you’re in the midst of a 5,000-word post, then jump to checking your email, then to recording videos, you are using your time ineffectively. Context switching is not only exhausting for your brain, but it kills your productivity as well.

To minimize context switching and work more productively, schedule more of the same tasks each day.

I suggest changing how you structure your days and weeks, so you can stay in a flow state and work on the same tasks as much as possible.

For example, keep all of your writing in one day. Then edit your work the next day and apply for new gigs the next day.

Staying in the same tasks will help you stay in a flow state and not waste energy. I talk more about creating a productive writing routine below.

Lesson 6: Schedule your time to focus on doing more of the same tasks.


7. Know Your Success Is Inevitable

Mindset is everything.

If you don’t think you can make money writing, chances are you never will. Even when I was failing as a blogger, getting rejected by clients, and getting told by readers how awful my writing was, I never gave in.

I always knew I’d make it, one way or another, even though I had no proof of it. Believing in yourself is the first secret of success.

The more I invest in personal development and study the brain, the more this makes sense. Because here’s the thing…your mind will act as your best friend or your worst enemy when you’re starting a business. Your brain is designed to align your life to fit your beliefs.

Read that again…your brain creates your reality based on your beliefs.

Meaning, if you don’t believe you will become a successful freelance writer, chances are, you won’t. But if you start to believe you can make it happen, then you are setting yourself up for success.

This doesn’t mean you need to read affirmations in the mirror until you are blue in the face. Believing in yourself just means that deep down, you know you will find a way.

If others have done it, you can too.

Lesson 7: Believe in yourself. If you keep upgrading your mind and skills, success will find you.

“He who thinks he can and he who thinks he can’t are both usually right.” — Henry Ford


8. Take More Action

Get off the sidelines and get in the game.

If you’re just getting started as an entrepreneur, it’s easy to draw your message on a whiteboard and think big picture, especially if you identify as a visionary. It’s fun to visualize and think about your goals coming to life.

But for a lot of ambitious entrepreneurs, the hard part is actually getting into action mode. Because oftentimes, your mind will make it hard to get going and build momentum as it’s trying to keep you safe.

By procrastinating, your brain is trying to protect you. Because once you start taking action, you might fail. But don’t forget, procrastination is nothing more than a survival mechanism trying to keep you in your comfort zone.

This is why so many people fail.

They simply stay in planning mode without ever getting started.

You can’t win the game if you never get off the sidelines. So instead of brainstorming, just start doing and take more action.

Understand that failure is inevitable along the way and that’s okay. The people who fail the fastest are always the first to find success.

If you’re committed to the end result and reframe failure as learning lessons, you can achieve so much more.

Lesson 8: Quit waiting for the right time and get in the game. Give yourself a chance to win!


9. Always Set Goals

Whether you’re a brand new freelance writer or a seasoned grizzly veteran, I think setting goals is crucial to success. Like a good fitness goal, you can’t measure what you don’t manage.

If you’re brand new and don’t have any clients yet, set goals like:

  • Pitch 5 clients per day.
  • Apply to 10 job boards.
  • Create 5 portfolio pieces.
  • Earn my first $1,000 in 30 days.

If you’re a seasoned writer, set goals like:

  • Land a retainer client.
  • Get one new client at a new higher rate.
  • Pitch a big publication like Forbes, Business Insider, etc.

Also, don’t set goals once and get complacent. I did this once I started earning $4,000/month pretty regularly and it kept me at that income level for months.

Instead, don’t get complacent. Make sure to keep setting big goals, pitching new clients, and force yourself to level up.

Lesson 9: Keep setting goals to level up and play bigger.


10. Just Keep Going

Everything gets easier in your freelancing journey, as long as you don’t quit. When things get tough, the universe is testing you.

It’s up to you to learn from the challenge and grow stronger. The weak ones quit, the strong ones succeed.

Here’s the thing…

  • Your first blog posts are going to suck.
  • Your first client pitch will probably make you cringe six months later.
  • The first piece that you write for a client will probably need a lot of edits.

Trust me, I know from experience. I can’t even read my first book. I hate watching my old YouTube videos. And I’m embarrassed by my old blog posts.

This is all part of the learning curve. The people that win in business and life never give up. Even when things are tough, they find a way (or make one).

If you really want the freedom and lifestyle from writing online, you can’t give up.

Lesson 10: Trust the process.


Final Thoughts

I love writing content like this.

It’s fun to go back mentally to where you were a few years ago and see how far you’ve come.

Because as you can tell, I was never a natural talent, and making money as a writer didn’t come easy for me. But I never quit, and that’s why I’ve become a six-figure writer.

Finally, as you go on with your journey, make sure to look back and appreciate what you’ve accomplished as well.

Because here’s the thing, you’ll always be chasing a goal. The carrot that you dangle in front of yourself is always moving.

If you’re making $3,000/month, then you’ll want $5,000, then $10,000, etc.

So as you climb the ladder of success and get new clients, make more money, become a top writer, or get featured in big publications, never forget to look back. Always congratulate yourself for far you’ve come.

It’s amazing how much can change in six months or a year if you do the work and believe in yourself.

Get out there and make it happen.

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Thanks to Niklas Göke

Michael Leonard

Written by

Inspirational Writer, Coach, & Creator of Inspire Your Success Podcast. Earn your first $500 as a writer —> https://lynxinbio.com/michaelleonard

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