How I Made My First $1,000 Freelance Writing

Where I Started

I knew I wanted to work for myself when I graduated from college, but I did not know what I wanted to do…

So I took a job working for an IT consulting company and I was able to work online. What a blast! This was the first time I was able to work completely remote and be in charge of my own schedule. 

While working for this company I built my van, and then I lived in my van full time and traveled the Western states of the US. After a few months of this, I became bored with my job and knew that I had to move on soon. I had been reading some blog posts on freelance writing and it sounded interesting, but I did not know where to begin. 

Nor did I have any previous professional writing experience when I decided to start freelance writing. Sure I had written plenty of papers in college, but that is completely different than writing blog posts or landing pages. 

Why I Decided To Start Freelance Writing

I became bored with IT consulting after about 6 months and knew I was going to have to do something else for work soon enough. Location Rebel and some other blogs portrayed freelance writing as an amazing lifestyle and experience. It absolutely is! After you get your business off of the ground. 

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My goal is to become a serial entrepreneur with the availability to start whatever venture I find most interesting at the time. Not only will this be enjoyable and fulfilling, but it will also lead me towards financial freedom, location independence, and time independence. 

So here’s the thing, instead of diving headfirst with zero relevant experience into an affiliate-based blog business, I figured building skillsets and relationships on a smaller venture would be beneficial. This way I could have a skill that I provide to other businesses that pays me well. A bridge business to cross the gap between where I was, and starting an affiliate-based blog. 

This is why freelance writing seemed like a great turn in my career to take. My path to accomplish my goals looks like this: 

The problem that I saw with starting a product or service-based business at this time is that I did not have the skill sets and relationships to do so. After freelance copywriting, my goal is to build an affiliate blog, then an event business and/or a product-based business. I knew that if I dove into creating one of these larger scale businesses before I could consistently acquire and satisfy clients with a writing service, the road to success would be long and bumpy!

So the first step was for me to start freelance copywriting to get experience running my own solopreneur business. Not to mention, my emergency savings were soon to run out. I needed more money to be able to live. Freelance writing would not only generate me money to live on but set a nice foundation of skillsets and relationships needed to become an entrepreneur.

Now naturally with my current set of goals, freelance copywriting will lead me towards running an affiliate based blog. From here, I will move into a larger and more scalable business model, preferably around a series of events or selling physical products.

On the other side of things, I wanted to live a remote working lifestyle to be able to travel and control my own schedule. I am more of a morning person and prefer to start working around 6:30 am, instead of 9. Plus I have a very serious skiing problem hobby that pushes me to travel around the US.

How I Lost My IT Consulting Job

Even though I was bored and over my previous job, I still was afraid of moving on to the next step in my journey. I knew IT consulting wasn’t for me, but I still was scared to make the jump of going headfirst into freelance writing. 

After setting up a website and writing a few example articles, I knew I was going to have to quit my current job to be able to go full time with freelance writing. I am an all or nothing kind of guy. 

Basically, I was freelance writing part-time and was not getting very far. 

Then out of nowhere, the least expecting blessing in disguise came to my rescue.…..


Leaving my friend’s place in Seattle after a fun weekend, I heard the news of the government mandating closures to all in-person non-essential businesses. 

If we are being honest, 2 hours went by on the morning of 3/16/2020 before I fully understood what this actually meant. No gyms, no ski resorts, no restaurants, no nothing. Instead of my plans to go skiing that day, I finished up my current IT project and sent it in. Then I asked my boss about the next project.

To my disbelieve, he told me there wasn’t going to be any work for a while due to the pandemic, and that I should probably look for something else in the meantime.

At first this was terrible news to me. After some thought about what my next steps should be, I realized that I could:

The answer became obvious, I needed to go full time with freelance writing!

What Has Worked So Far For Me

When I started out, I knew nothing. 

Reading blog post after blog post on how to get started gave me some wonderful direction. I realized that I should write a few example articles around topics that I was passionate about. 

Writing posts around hiking and camping were the first steps I made. But I was lost on how to actually acquire new clients, and get paid for my work. 

I started applying to gigs off of ProBlogger and got nowhere. I knew I needed feedback and to surround myself with people who are on a similar journey. When listening to the ‘My First Million’ Podcast, Sam Parr recommended Nevilles Kopywriting Kourse, so I joined. 

Inside the course, I was given direction and feedback on what I should do. And soon enough I got my first freelance writing gig!

Even though it was only $10, it got the ball rolling. Soon after I had a $30 blog post-gig. Shortly after that, I had a few consistent weekly gigs coming in at $80-$120 each for a gardening site. 

These gigs were all from ProBlogger. After these successful gigs, I learned that it was time for me to start cold emailing local marketing agencies about overflow work. 

Cold emailing local agencies have been the most successful tactic to date for me! After I exhausted the local agencies, I started to reach out to agencies in all of the places that I love to ski. There are plenty of agencies throughout Oregon, Washington, and Utah. 

In the near future, I plan to narrow down what type of content and industries I write about. Then to go straight for the businesses themselves. Niching down is the common phrase for this action. But doing this too soon can close opportunities for me (and anyone). 

For now, I have been working with different agencies, writing about Tahoe beaches, custom home buildings, and a few other topics. 

I recently sent out my biggest invoice to date. $650 for rewriting the copy of a custom home builders website based out of Bend Oregon. Making my total revenue in my business over $1,000 =). A small but worthwhile milestone! 

This did take me about 4 months to accomplish and I completely exhausted my emergency savings. I was selling things on craigslist and doing way too much yard work in the meantime to get by. 

My Strategic Approach Vs My Make Some Money Approach

One of the biggest changes I experience in my business was during the 2nd month of Nevilles Kopywriting Kourse. In the 1st month, I started out with a strategy we called ‘TTGMISP’ (time to get money in Shaggy’s pocket). This basically meant “how do I make money as quickly as possible to avoid going broke”. It worked in the short run and forced me to do the things I didn’t want to do. Like outbound sales, making images, cold emails, and some other necessary things that I had never done before.

I shifted to a more strategic approach, one where I divided my time between “Work For Clients”, “Outreach To New Clients” and “Writing For Myself”. This allowed me to spend my time a lot more methodically. 

I also organized everything that I should be doing in a command center. These two actions gave me a clear direction on what I should be doing, and how much time I should spend doing what.

Once I started reviewing where my time went, and what was driving revenue, it all changed for me.  

Advice For Other Beginner Freelance Writers

  1. Pursue clients that will give you consistent work.

This is the biggest piece of advice I can give. Spending a lot of time acquiring clients, and less time actually completing work will dramatically affect your bottom line. (It sure did for me!)

Even if they are lower-paying at first, having a consistent flow of work coming into your schedule will generate you more revenue. Also, it will ease the pressure of getting your business off the ground. Not to mention you will gain more and more experience with the process of receiving work and completing it while communicating and negotiating with clients.

  1. Get feedback from people who have done it before.

Surround your self with people who have done it before, or are doing it currently. I cannot emphasize this enough! Immersing oneself in an environment where the norm is what your goals are is crucial (James Clear anyone!?). You’ll have people to support you, you’ll get answers to questions you didn’t even know to ask, and you can get feedback. 

  1. Never stop writing and reading!

This is where your skills become refined and how you can create new ideas. Listening to podcasts is another great use of your time. 

Advice For Any High Achiever Out There

And That’s It!

Glad you read this far! Are you considering freelance writing or currently freelance writing?

Either way, I’d love to hear from you in the comments below!

P.S. You’re goals are never too big, only your work ethic and imagination are too small. 

P.P.S. If it were easy, it would be boring. ;)