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7 Lessons I’ve Learned From Freelance Writing

“It’s all very well to know it intellectually, but how do you feel about it? What is your experience of this?” -Jamgon Kongtrul

I work from home (or coffee shops), I make my own schedule, and I decide when I want to take a vacation. It’s all…really cool.

But when I talk about freelance writing, this is far as I get. People want to hear about the luxury of working from cafes, waking up whenever you want, and never having to use the words PTO. Intellectually, they see the benefits.

And that’s surface-level cool stuff. The type of benefits that initially reel you in when you’re thinking about becoming a freelance writer.

But, below the surface, that’s where the good stuff lives. That’s where the lessons that improve you, change you and put you in a different direction are. That’s where your experience as living as a freelance writer sparks from a candle flame to a roaring fire that engulfs you and—seemingly—brings you back like the phoenix.

It’s here that I learned about improving my EQ, how essential systemization is, and why not having a long-term goal is a huge mistake. It’s in this fireball that I figured out how wasteful I was with my time, that I was blaming others for my lack of success, and that strategy would turn this into a lifetime career gig.

It was here that I learned 7 lessons that changed my life.

#1: Improve My EQ Or Go Home

My first year as a full-time freelance writer was rough. I chose to backpack the world while growing my client base and it ended up in disaster. I was broke, alone, and really confused as to how my dreams had burned me so badly.

While feeling at rock bottom, I had no choice but to figure out how I was going to rebuild. I put personal development book, podcast, Youtube video, poem, ANYTHING into my hands and I thought long and hard about what it was telling me.

At the time, I was just searching for something that would bring me out of the hole I’d found myself in. Now, I realize that I was setting the foundation for the rest of my life.

#2: My EQ & IQ Could Set Me Apart From The Competition

I don’t want to be “just another content writer” to my clients. I focus heavily on being a linchpin for each of them so that they see me as their go-to freelancer. This mentality has helped me secure the biggest projects of my career, both short-term and long-term.

Last year, I realized that if I had the emotional intelligence to be a rock to my clients, they would always come to me for help.

Then I realized, if I was their most knowledgable freelancer—I’d be giving them the best of both worlds. I spent 2019 learning everything I could about marketing (the industry one of my clients is in) so that I could be the absolute best writer for them. As I’ve brought on new clients, I’ve dove headfirst into their industry (SaaS and personal development) to be able to write as if I’m an industry leader. This is what makes my clients look good, which means that it makes me look good to them.

A consistent reading practice has become an absolute necessity in my life and in 2019 I read 15 books.

#3: Successful People Live By Systems

Last week I found out that all of my clients (multi-million dollar business owners) use Trello. This opened my eyes to just how important systems are when it comes to creating success.

I used to say, “I want to make $5,000 a month as a freelance writer.” and then wonder where my paycheck was. There is no system behind this goal. This goal is a dream that will probably never come true.

The dream that will come true is the one that says, “I want to make $5,000 a month as a freelance writer. I’m going to make $2,500 from a month from one client writing emails for them on a weekly basis. I’m going to make 2,000 from another client writing blog posts on a weekly basis. And I’m going to make $500 from my other client writing 1–2 articles per month.”

That’s a dream with a plan. And that’s what you call a goal. As a freelance writer working with successful businesses and having worked with unsuccessful businesses, you can see a huge difference between how the two are set up.

One has systems. The other doesn’t.

#4: I Have To Think Long-Term

At the start of my writing career, I was hungry to grow my resume. I accepted one-time projects that paid me $20 every single day. Once I had built up my resume, I saw how dangerous this would be for my future.

I couldn’t rely on $20 projects to fund my life. I needed to know I had incoming money which meant that I needed contracts. Now that I’m thinking long-term, my clients and I have contracts for consistent work.

These contracts let me think bigger. I can buy tickets to events and summits because I know that I have more money coming in. This gives me an even more in-depth long term plan as I network with others in my industry and start to grow my name as a content writer.

#5: There Is So Much Time In The Day

We each have about 16 hours to get things done every day. I don’t have kids which mean that I really have 16 hours to get things done. A few years ago, I used to think, “If only I had more time.”

That’s a poor mentality to have. Instead, I focus on how much time I do have and what I’m doing to be productive during those hours.

I’ve become a huge fan of the Pomodoro Technique, breaking my workday down into 25-minute intervals with 5-minute breaks. I’ll focus on one task for however many 25-minute intervals it takes to complete.

This has changed my productivity levels. There’s something about telling yourself how long you’ll be working on something and then obligating yourself to finish it that helps you get it done.

With this strategy, I’m always finishing my workday early and asking myself—what else can I do?

#6: My Success Is My Responsibility

While everyone is angry about how Kylie Jenner was named a self-made billionaire—I’m over here working on my own mini-empire.

We love to blame others for our trouble. Listen to ten interviews and you’ll hear 9 of those people talk about how they didn’t grow up with any money and their parents divorced when they were young.

It’s this interesting societal dynamic that motivates us to be the one who has suffered the most. Don’t fall into this trap.

I’ve completely thrown this mentality out the window and if asked about where I came from, I’ll tell you, “I have two extremely loving parents.” Because it’s the truth. Just because my parents divorced doesn’t mean that this is my life story now.

My success is my responsibility, regardless of whatever actions those related to me have taken. There’s no one else to blame for where I am in my life but me. So instead of being sad about where I am, I’d work hard and be in a place where I can be extremely proud.

#7: Career Isn’t Everything

My friends tell me that I’m one of the most focused people they’ve ever met. I know what I want and I’m going for it. I go above and beyond for my clients and I’m proud of what I have accomplished as a freelance writer.

I’m also looking to achieve much more.

With that said, I’m hyper-aware that my career is a playground. It’s a fun experience that I get to add to my life—but it’s not the only one. At the end of my life, it will be the relationships that I’ve had that will sit with me. I’ll think about the impact I had on the world and those around me, and I’ll either be proud or disappointed.

I’m not going to think about the money. I’m not going to think about the awards. I’m not going to think about the bragging rights.

So, while my career is a very important part of my life, I’m completely aware that I cannot let it become my entire life.

Because I will not live with that regret.

When I was fully engulfed in the flames of a first-year freelancer, I never thought that I’d actually make it to where I am now.

Now that the flames have died down and I’ve been able to rise out of from the ashes, I’ve realized how well that experience molded me for my life as a freelance writer.

It’s these lessons that can set you apart from the other writers and can make you the linchpin to your clients. They’re also the lessons that will create purpose in your life and ensure you don’t arrive at the finish line with regret.

Take them. Make them your own. And think of me whenever somebody says, “You’re a freelance writer? That’s so cool.”


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