24 Epic Lessons From 24 Months of Freelance Writing

Tips and strategies after earning over $100,000 writing online

In May of 2017, I had a millennial life crisis.

I was tired of working for someone else and wanted more than a good job with a few weeks off per year. I wanted to wake up excited for life and no longer drag myself to a job that meant nothing to me.

With money saved, I left my six-figure career to grow my personal finance blog and pursue professional golf.

Despite the fact that my blog wasn’t profitable and Tiger Woods could have beaten me left-handed.

Everyone in my life thought I was crazy (part of me did too).

But I figured if other people found ways to make money online, I could too. I chose the path of digital entrepreneurship as it would allow me to create my own schedule so I could pursue golf as well.

At the time, I knew pretty much nothing about digital marketing. Despite my best intentions, after seven months of 50–80 hour weeks and buying endless online courses, I had pretty much nothing to show for it.

My blog was failing.

I was losing money like my bank account had a hole in it.

I knew if I didn’t learn how to make money online, my dreams of digital entrepreneurship and pro golf would soon be a thing of the past.

So I went all-in on freelance writing in January of 2018 and it changed my life forever.

Thanks to my commitment and perseverance it paid off, literally. In 12 months I 10X’d my monthly income, doubled my annual income in 2019 and even had my first $20,000 month.

Don’t let these numbers fool you, it hasn’t been all sunshine and rainbows though.

Entrepreneurship has been more like riding a Six Flags roller coaster, in the rain, with a New Year’s Day hangover. Part of you just wants the ride to be over, part of you is exhausted, and part of you is glad you made it happen.

If you’re the type of person who wants to make money writing online, here are 24 lessons to help you speed up success.

1. Freelancing is the Fastest Way Way to Make Consistent Money Writing

There are a lot of ways you can monetize your words online. Whether you’re blogging, self-publishing, ghostwriting, copywriting, freelance content writing and more.

And I’ve tried nearly every way out there. But if you need money fast, I think that freelance writing is the best option.

Blogging seems like the dream for most writers — passive income from affiliates and ads. But in reality, blogging is much more difficult than most people know. It can take years for your site to turn a profit, assuming you understand SEO, Pinterest, email marketing, affiliate marketing, and other tech skills.

Publishing a book also isn’t overnight riches. In fact, most books don’t even make money, it’s the speaking gigs and programs that come with it.

So if you need money fast, freelance content writing is the fastest way to make money quick. You can find a job today and get paid this week or month.

2. Writing Can Get Lonely

My personality type is an ENTJ — meaning I am an extrovert and enjoy spending time around people. This is ironic because I couldn’t stand some of the people I worked with at my corporate job.

One of the reasons that lured me into quitting my 9–5 was wanting to work from home and get my stuff done on my time. But working at home has its challenges as well.

So if you’re an extrovert like me, understand that writing itself is a pretty lonely gig. You have to make a concentrated effort to get out of the house and get around people. By knowing this in advance you can make sure to schedule activities that get you out regularly.

3. Invest in Yourself

“The best investment you can make is in yourself.” — Warren Buffet

The only reason that I’ve found a lot of monetary success from writing and digital entrepreneurship is my commitment to investing in myself. In less than three years, I’ve spent nearly $30,000 on courses, coaching, and masterminds.

A lot of people will read this and say, “That sounds good but I don’t have the money right now to invest in myself.”

Here’s the thing, I didn’t either for most of these investments. All I had was a credit card, 0% balance transfer offers, and an insane amount of belief in myself.

You will never feel ready to invest in yourself (and that’s the point).

I think that having faith to act and bet on yourself is the first step to achieving your dreams. When you begin to spend thousands of dollars in yourself, you force your mind to level up, think differently, and play big. Not to mention, surrounding yourself with smarter, more successful people will only help you succeed faster.

Plus, paid accountability goes a long way in making sure you get stuff done. Writing and entrepreneurship give you freedom with your time but don’t forget, no one is making sure you get work done. But if you know money is leaving your account and people are following up, you are much more likely to get stuff done.

Invest in yourself, you are worth it.

4. Don’t Edit and Write in the Same Session

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 so quickly 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 fresh 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.

5. Raise Your Rates Sooner

After joining Benjamin’s mastermind in 2018, I got a chance to speak with him on a hot seat call. I told him I wasn’t making enough money writing and didn’t know what else to do. I’ll never forget how simple his answer was, “Double your rates. Believe in yourself enough and get the offer in front of clients.”

Sure enough, it worked.

The following week, I landed a client at double my normal rate. The week after that I landed another and almost instantly earned another $2,000 more each month.

For some reason, a lot of writers don’t charge their worth.

As a freelancer, you are your own boss and it’s up to you to give yourself a raise as you get new clients. Don’t expect anyone to give you permission. No one is going to tell you that it’s time to raise your rates (like the 9–5 world).

If you have the right experience, skillset, and know you can deliver, raise your rates so you can earn more money writing.

6. Use Grammarly Pro to Edit Your Work

I hate editing, literally I hate it.

If an editor reads this article and wants to work with me, please reach out (seriously).

I’ve lost clients because I’m so bad at editing but Grammarly Pro has been my lifesaver that I wish I would’ve used sooner in my writing journey. While it’s not a perfect app, it’s one of the most effective tools out there to make sure your writing is error-free.

If you’re serious about making money as a writer, this small investment will pay off almost immediately. Like anything, the free version is good but the paid version is even better.

7. Learn SEO (and Keep Learning)

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

But just like golf or writing, it’s something you will never master, it’s always changing. Google is constantly changing its algorithms to provide the best results for users so it’s up to you to keep learning SEO as well.

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.

8. Always Hit Deadlines

Clients will forgive you for some spelling errors and grammar issues but they hate missed deadlines more than anything.

I’m proud to say that I’ve never missed a deadline and think that’s why I’ve retained nearly every client and only parted ways on my terms.

If you’re serious about your writing career, make it a point to retain clients and only stop working with them on your terms. Remember, clients have content calendars so missing a deadline screws everything up for them.

Never miss a deadline and if you want to be a rockstar writer, submit it a day or two early.

9. Pick a Writing Niche

Before I went all-in on freelance writing I did a few random gigs on Upwork as a generalist. I wrote about everything; from personal finance, golf, pet writing, insurance, self-improvement, millennials and more. While I enjoyed most of it, jumping from topic to topic was challenging.

This is one of the many reasons I think you should have a niche. When you pick a niche you have experience in (or want to learn about), you can become an expert in your space. This will allow you to charge more and also deliver higher quality work.

Don’t forget, clients want to work with experts, not some generalist. If you’re scared of niching down, don’t forget you can always change it in the future as well.

10. Pitch More Clients

At the beginning of my writing journey I was terrified of pitching clients and most new writers I coach have the same feelings.

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

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 conversation. Plus, it doesn’t take more than a handful of clients to make consistent money online.

Once you get to 3–5 clients, you can easily make $3,000 — $7,000 per month (or more) assuming that they need recurring content.

Get over the fear of rejection so that you can give yourself a chance to succeed.

11. Outline Before Writing

There is nothing more frightening for a writer than staring at a blank Google doc. In my experience, creating epic content from thin air almost never happens.

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

12. You Need a Writer’s Website

If you want to consistently earn more than $1,000 per month as a writer, I fully believe you need a freelance writing website or blog.

Your website is your home base online; it allows you to showcase your testimonials, samples, publications you’ve been featured in and more.

If you don’t have a website, it’s easy for potential clients to think you aren’t fully invested in yourself or their business. Spend the $200 dollars and get your own domain and a basic website. Trust me, the investment will pay off quickly.

13. Learn How to Write Headlines

“On the average, five times as many people read the headline as the body copy. When you have written your headline, you have spent eighty cents out of your dollar.” — David Ogilvy

If your headline sucks, no one is going to read your content.

To help you learn how to write headlines, make sure to use free tools like CoSchedule Headline Analyzer.

14. Writing Routines are Crucial

When I first started writing, my routines were awful. Now, I can write 3,000 words before 8 am pretty easily. The key is to create writing routines that allow you to maximize your time.

Find your optimal writing time, turn off your phone, put on your headphones, and get to work. Use the Pomodoro technique to work 25/5 or 50/10. Repeat this until your writing is done.22. Become an Epic Story Teller

Everyone loves a good story as it’s one of the oldest forms of communication among human beings.

“Marketing is no longer about the stuff that you make, but about the stories you tell.” — Seth Godin

15. There is No ‘One Way’ to Land Clients

I’ve found paying clients in almost every way possible:

• Upwork
• LinkedIn
• Referrals
• Job boards
• Social media
• Cold pitching
• Facebook groups
• In-person events

If one of these methods doesn’t work, try out different ones. While cold pitching will usually yield the highest paying clients, it’s also the one that most writers avoid as rejection is inevitable.

Remember, don’t fear rejection, it’s part of the process. Each “No” you hear will lead to a “Yes.”

16. Social Media is Your Friend

I see a lot of my writing students avoid using social media and I think this is a huge mistake. The world is constantly on social media, including your clients.

If you’re not on there showcasing your skills on popular platforms, you are missing out on landing clients.

While you don’t need to strive for verified status on Instagram or make a daily vlog on Youtube, neglecting them entirely is a mistake. In fact, I had one client find me through Instagram and in 2019 we collaborated on over $30,000 of work!

If you’re just starting out, get active on Twitter and Instagram to land your ideal clients.

17. Love Your Writing

After a few years of freelance writing, I think it’s vital to like what you’re writing about consistently.

I used to write just about personal finance topics as it was a profitable niche but I grew to hate the work. After writing endless articles about Roth IRA’s and insurance I was over it.

Eventually, I dropped all of my personal finance clients and started attracting new clients with topics I was passionate about. Over time, I kept raising my rates, learning new skills, and eventually fell in love with writing all over again.

I’ve found that if you hate your writing topics and are only doing it for the money, it’s kind of like working at a job you hate just for the paycheck — pretty miserable.

To avoid burnout, try to find a niche writing about something you care about! Focusing on topics you love will make writing more manageable, and I bet you will also make more money each month as well.

18. Quit Hustling

Over my four years of blogging and two years of freelance writing, I have gone in spurts where I hated writing. One of the main reasons I felt that way is because I was “hustling” way too much.

Too many times I would try to blog, write for clients, and it would leave me scattered. Now, I don’t hustle anymore — my personal health isn’t worth 80-hour weeks.

If you don’t love your writing anymore, I suggest taking a few days off or even a few weeks if you can. To help you stay fresh and focused, I think it’s vital to take breaks and recharge. When I’m feeling off, I like to meditate, exercise, read, get out in nature, travel, and have more fun.

When you come back, I bet you will have more energy and drive than ever before.

19. 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

Also, don’t set goals once, achieve them, and stop setting. 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.

20. Use Medium to Hone Your Writing

I love Medium for writers. This is a great platform for bloggers or anyone who wants to start writing online.

It’s great because you don’t have to write about the same topics all the time as you do with a blog.

Don’t forget, the more you write and test out different styles, the better you will become. The “10,000” hour rule is real.

“It takes ten thousand hours to truly master anything. Time spent leads to experience; experience leads to proficiency; and the more proficient you are, the more valuable you’ll be.” — Malcolm Gladwell

21. Keep Experiencing Life

I rarely have writer’s block and I think it’s because I am constantly creating new experiences in life. My mind is always thinking about new things to write about for my business and my clients.

One of the main reasons is that I am always trying to experience life by traveling, learning, and investing in myself.

Whether it’s joining a 12-month mastermind, playing in professional golf tournaments as an amateur, reading random books, or all of my endless personal development, I have never had a shortage of things to write about.

So if you want to get really good at writing, don’t sit around all day expecting for inspiration to hit you. Get out in the world and experience life. I am confident you will have all the writing ammo you need.

22. Calculate Your Hourly Rate

Instead of basing clients off of how much they pay you per word or per month, start thinking on an hourly basis. Once I started doing this it was a game-changer for my business.

For example, one of my golf clients is .10 cents per word which is an intro rate for most writers. But I can write the content so fast that I can easily make $150 to $200 per hour.

Another client is .25 cents per word but I have to do more research, SEO, and editing so the hourly rate is the same. So instead of just basing each client on rate, evaluate them on an hourly so you can make the most of your time.

23. Embrace the Suck

Anytime you start anything new, you are going to suck. My first pitches and articles were so horrible I still cringe thinking about them. But so was my golf game when I first started 20 plus years ago.

Remember that it takes time to get really good at anything — writing is no different!

To improve, stay consistent, read a lot, keep learning, and ask for feedback from clients so you don’t keep making the same mistakes. Over time, you will find your tone and style to attract the right audience and clients.

24. Have Fun

For a while during my first year, I fell out of love with writing. At the time, I was still blogging and writing about topics I wasn’t passionate about and it felt like a job more than fun.

So if you choose this path for yourself, don’t forget to have fun along the way.

If a client makes you miserable, fire them.

If you get bored in your niche, add a second niche or pick a new one and reinvent yourself. Or, you can always write stuff to get your creative juices flowing.

Remember, when it’s fun and you are passionate about writing, you can impact people worldwide at a deep level.

Final Thoughts

Hopefully, you can these lessons to launch and scale your own freelance writing journey.

Even after two years of freelance writing, I still get excited every time a client pays an invoice. I always remind myself that a few short years ago, I was going to a job I hated every day.

Not to mention, even when I did start entrepreneurship. I was a struggling, broke blogger so I am always grateful for my clients and the ability to make money from home with my laptop.

Freelance writing has allowed me to:

• Earn over $100,000 in 2 years
• Have the time to pursue professional golf
• Have my words get read by hundreds of thousands of people
• Receive nearly 2,000,000 views on Youtube from a video voiceover I did with one of my clients
• Grow a virtual team, launch a podcast, and impact people around the world

None of this would have happened if I played it safe and listened to what society told me to do.

While I won’t say freelance writing or entrepreneurship was easy, I will say it was worth it.

You only get one life, make sure to pursue your dreams with relentless intention.

Learn how to start freelance writing and earn your first $5,000 fast.