The Journey Of This High Paid Writer

(Disclaimer: This is one of the few “journal” posts where I write aimlessly without a goal — as I write this, I’m climbing my way back up from rock bottom and will hit $100,000 per month as a freelance writer so, if you’re reading this, you’re watching the start of a new foundation.)

You hear it all the time…

…what would you do if you had to start completely from scratch?

No list of contacts, money in the bank dwindling fast, bills to pay, debt piling up, and you need to do something — anything — to get cash flowing again, as fast as possible?

You’ve also heard “expert” after “expert” say what they would do, while sitting high atop their golden throne in the castle that took them 20 years to earn…

But it’s incredibly rare you get to see it actually happen in front of your eyes.

I’m in that position — as shameful and embarrassing as it is to admit — I’ve been on top more than a few times, and I’ve been down in the depths just as many.


…this last time, it really hit hard and left me wondering “what the hell just happened?”.

Without getting too far down the rabbit hole that led me here, I do want to let you in on a few details about what I actually am “starting at the bottom”.

2018 was one of my best years ever and I thought the fun was never going to end — little did I realize that life had other plans for me, and my lack of foresight was going to leave me in a pretty precarious situation.

From clearing more than $38,000 in revenue during a single month, to being $28,000 in debt, less than $2,500 in the bank, car repossessed, living with family, and wrapping my head around the string of events that led me here…

All of the trauma, bullshit, and turmoil I’d dealt with in my personal life between 1984 and 2018 had finally come to a head, and I wasn’t quite ready for that level of success.

My bank account definitely wasn’t ready for what happened and, again, without getting too far into it, there were a ton of mental health issues that finally crept up and required immediate attention at a time when family and friends weren’t exactly helpful.

To say that my life got flipped completely upside down around me is a definite understatement — and far too depressing to ever talk about publicly.

Instead of revisiting the shit that led me to where I’m at as I write this post, I’m going to let you in on how to go about changing that situation. Since, I’m sure if you’re reading this, you either aren’t far away from it or you can see it on the horizon and want to make sure it doesn’t happen to you, too.

One lesson I’ve learned while working my way back out of the depths is that you don’t want to focus on the darkness.

I’ve gotta thank a dude I follow for this (if he sees it, he knows who he is), but look at it like this — if you’re put in the darkness and can’t see, eventually you will lose your mind. As hard as it seems to do when you’re surrounded by darkness, you need to focus on the light.

What’s going right for you instead of everything that’s going wrong.

I learned that lesson the hard way and it’s taken time so I can tell you that it definitely is possible. The worst thing you can do is give up hope that you’re going to make it out the other side.

Then, you can look into some of what I’ve done and accomplished and look at where I’m at while I’m writing this post to see what’s possible and that even the best of us can have our asses handed to us.

The High Paid Writer (Chapter 1)

Starting from 2007, I’ve not held a “normal” job. I left a mid-level management job to become a freelancer and then an SEO and never looked back.

Even today the prospects of getting a “normal” job aren’t possible because of my custody arrangements for my daughter. Another story for another time.

From 2007 to 2012, I was a freelance writer, an SEO, and an agency owner, building up a team of 22 other writers who were able to help my business partner and myself build and scale a network of 450+ websites using rank-and-bank strategies that worked up until, you guessed it, 2012.

That was my first lesson in disaster and lack of foresight. I spent the money as fast as it came, scaling the websites, putting back into the business, growing the team, keeping them fed, banking on the fact that our income streams would never dry up.

Needless to say, they did dry up — and fast. I went from $30,000 per month in revenue to $500 per month in revenue in a matter of 6 months. Coming from a family that never really knew what money was, let alone how to save for a rainy day, I was hit hard.

I eventually sold what was left of the business and was able to sustain myself and my ex-fiance on the money from the sale, until that started dwindling and I was forced into a sales role, pitching life insurance products to senior citizens.

While that role wasn’t necessarily what I’d consider “up my alley” it did teach me about sales. Combining my love of writing with my newly found sales experience gave me what I needed to become a direct response copywriter.

After 2 years of selling insurance, I’d had enough. I got screwed out of some major commissions, my team was seeing that the “opportunity” was nothing more than an MLM company masquerading as a life insurance company, and we all made the decision to bail.

That put me back out to pasture with a family to feed, little to no income, no prospects for income, and bills to pay every month — with little to nothing to show in my savings account.

On top of all that, my ex-fiance and I decided to call it quits, leaving me with pretty much nothing after the fact in order to make sure the split was as seamless as possible.

Instead of getting a job and giving up split custody of my daughter, I decided to do what any “retired” freelancer would do — get back in the game and learn from my past mistakes.

The first chapter of my life as a “High Paid Writer” consisted of generating $40,000 in my first 4 months, padding my savings account so I could leave a “semi-cushy” mid-level management position while working on building out an SEO empire.

That eventually evolved into a team of 22 other writers with clients reaching out to me for them to perform work in between me giving them work to build out the SEO empire my business partner and I originally set out to build.

Google’s numerous algorithm updates wiped the slate clean and forced me back to square one, letting go of all my writers, being too burned out to help clients, and scrambling to figure out how I was going to be able to feed my (then dwindling) family.

That’s one of those stories you won’t hear people talk about but, as you’ll learn, they’re part of what makes me who I am and you can’t have the good without the bad. I learned a lot of lessons from this first chapter in my newly-found life, and even more of what-not-to-do.

Which leads me to…

The High Paid Writer Chapter 2

Once I’d officially cut selling life insurance out, my ex and I had properly and formally split up, and the custody arrangements were up to the courts (and behind us), I knew I needed to do what it took to stop eating into my savings.

Which, on a side note, building a savings account was one of those tough lessons I’d learned from my first foray into becoming a freelancer — knowing that the hard times are always a little less rough when you have a bit of padding in the bank account. But, I digress.

It was back to the grindstone for me.

I immediately hopped into some marketing communities, a few forums, some Facebook groups, and began letting people know that I was a freelancer-for-hire.

Within a couple weeks, I’d landed a handful of clients that were able to take me from, essentially, $0 per day in income to anywhere from $500 to $1,000 a week. To say I was “back at it” was huge for me, and I’d finally felt like I was doing something for myself, by myself, and with an actual plan.

Coming from having significantly more revenue during my SEO days, though, meant that I wasn’t going to be content settling for $4,000 to $5,000 a month in income. I knew I needed more but I wasn’t able to scale what I was doing.

At the time, I was writing blog posts and website copy for a few entrepreneurs and marketing agencies and, while it paid the bills, my daily output was capped. There was no way I could reliably write more than 5,000 words per day, 5-6 days per week, while still maintaining my sanity.

Instead of sticking on that hamster-wheel-of-burnout, I started looking for my next move.

I wondered… “how am I going to be able to charge more for what I do? and who do I need to talk to in order to start charging more for what I do?”.

That led me to finding larger marketing communities where entrepreneurs gathered who were creating their own courses, informational programs, and people who were working with higher-end clients.

Those types of people needed “copywriting” not “content and blog posts”.

Specifically, they needed “direct response copywriter” — which was built around getting a specific conversion or getting the person reading it to take action in some sort of way.

Whether that be entering an email, clicking a link, or even purchasing a product, these entrepreneurs knew the value of copywriting to their bottom line and knew that hiring copywriters with actual sales experience was hard to do.

So I threw my hat into the ring, working for what most copywriters considered too little in order to make my name and start letting other people know what I was capable of.

To give you a bit of a timeline, I finally started calling myself a copywriter in 2014, and I’m sitting here writing this to you in July of 2019. After 5 years of busting my ass, climbing my way to “the top” and falling back down to rock bottom, I’ve managed to survive for that long.

Instead of writing content for offline business owners to fill out their web pages (like I’d been doing in my spare time and with my team from 2007 to 2012), I, instead, shifted focus to writing SEO-focused affiliate content, blog posts, emails, advertisements, landing pages, sales pages, and webinars.

The average price per word moved from 2 cents per word (from 2007-2012) to 5-10 cents per word (for blog posts) and anywhere from $1 to $4 per word for emails, landing pages, advertisements, sales pages, and webinars.

Now, even though my price per word was significantly higher, the amount of work was still the same — I was writing less words to make around 2x to 3x the “normal” monthly income, but I was doing significantly more research and “thought work” to figure out what to actually write.

Where SEO content is generally a lot easier to produce, conversion-focused copywriting was a lot harder and more mental calorie-intensive, requiring significantly more effort. The rewards were a lot greater, though — hearing clients win used to drive me to push even harder.

Until I pushed myself far enough to get completely burned out, with no way out except to keep digging myself further into the hole I’d created by neglecting everything else around me… namely, my mental health and relationships.

The High Paid Writer Chapter 3

Chapter 3 is where everything in my life fell apart — I lost relationships, my living arrangements, a good girl, even my truck bit the dust.

There was a lot going on during this time and being burned out from working too many hours and having too many highs and lows in life played a major role in it.

To say I had a mental breakdown is definitely an understatement.

I don’t plan on sharing much of the darkness from this time period but I’m including a little bit of it here to show you that life is full of up’s, down’s, surprises, twists, and turns, and if you don’t take time to look after yourself you could realize you have nothing left standing around you.

I went from having my largest month in revenue, ever, at $38,000+ in October of 2017, to having absolutely nothing to my name and my clothes being able to fit in a couple duffel bags.

If it wasn’t for family stepping in to help, I may have lost custody of my daughter while I was dealing with everything falling apart around me.

Your mental health is critical and if you’re trying to work, work, work all the time and neglect your physical well-being, your relationships, your clients, and your work, it is going to bite you in the ass sooner than later.

I don’t ever wish anyone to go through the low’s that I’ve gone through and I’ll include as many lessons as I can, without getting too, too personal, to help make sure you don’t have the same issues I’ve had to deal with — because you’ll be able to see them coming up the road and deal with them before they become major problems.

Something I do want you to think about is that we’re all human, we all have the same amount of time in the day, and we all need to stay compassionate and aware of what others around us are dealing with.

You never know when you’re going to be someone’s hero, so make sure you’re always trying to be a positive light in people’s lives and never turn your back on someone that you know is in need.

I’m more than grateful for the people who stepped up to keep me pushing forward, realizing that I was losing it all and there was nothing they could do about it — personal issues and my own upbringing played into my downfall but it doesn’t have to be the same for you.

Life isn’t about what happens to you, it’s how you react to what happens to you and if you stay focused, you will always pull through even the darkest days, I promise.

The High Paid Writer Chapter 4

From 2019 and beyond, I’m calling “Chapter 4”.

I’m also hoping it’s the successful chapter — finally.

Even though a lot of what’s happened in the past (the ups) has been what most consider “successful”, I consider the downward slides and spirals to be the unsuccessful, “rock bottom” parts of life. Those are the times I learned the hardest lessons. The lessons I usually saw coming and chose to ignore.

This time around, I hope life’s a little different. I plan to be a lot more calculated with my efforts and do things that I used to put off, in order to secure my future in a way that I wasn’t able to in the past.

In other words, I’m trying to learn from my mistakes and put safeguards in place to keep life from coming at me sideways — and having my business protect me in case it does.

With that being said, I firmly believe in synergy and only focusing on one thing at a time until you’re successful. Don’t try to do what I’m doing until you’ve built up enough momentum in the first thing you’re doing.

I’m laying it out for you here to show you what’s possible as a writer and let you know that life isn’t all about trading your time for money and being stuck to producing a certain number of words for a certain price tag, 5-6 days a week for the rest of your life.

Freelancing For The Win

As you can tell, I’m starting back from square one, freelancing to put money in the bank and pay the bills. I have a goal of saving to buy a house (to end the living-with-family situation I’m in right now) but that’s going to take a little while.

The goal for The High Paid Writer, at this point, is to write one blog post a week for at least the next 2-3 months, until I get a solid bank of content built up and have other projects checked off the list.

This blog is going to require a good bit of promotion to start gaining traction but it’s always helpful to have posts worthy of linking to before you actually start promoting your blog. I’m giving myself the leeway to just write without pressure while I get the two courses up that I want to launch — the Copywriting.University and the Blogging.University.

Once I have both courses live, I’ll work on promoting this blog to more freelance writers and blogs that teach people how to cut their own cloth so they can see what I’m doing and learn as I go along.

As it stands, right now, I have landed an SEO client that requests a few blog posts each month and have generated around $2,500 in revenue this year from him, while also picking up 2 solid direct response clients that are still getting the kinks worked out and working me into their business.

This blog is going to focus on teaching you both SEO/blog writing and direct response copywriting as a freelancer so you can generate consistent revenue and write your own way through life — no pun intended.

The Blogging.University

This is, as you guessed it, going to be a course surrounding blogging-as-a-business in a way that doesn’t teach people blogging by building a blog about blogging — those drive me nuts.

Instead, I’m going to be teaching affiliate marketing and how to generate traffic, income, and build an email list in niches and markets that people are actually interested in.

The goal for the case study is to build a 6-figure blog that can sustain itself and generate, at least, a semi-passive income stream for myself.

Now, I deem “semi-passive” as something that requires near-minimal upkeep and has consistent earnings from month, to month, without requiring 40 hours per week to manage. I don’t want to create another job for myself but, instead, show people how to build assets that generate revenue while also being able to be sold off down the road, if you choose to take that path.

I’ll post tutorials here on how to do it but once the course is live I highly recommend joining so you’ll be able to see the in’s and out’s of the case study blog, itself. I don’t plan on publicly revealing the blog on here because of copycats and lazy folks trying to “swipe” what they think works without doing any thinking for themselves.

Don’t fret, though, there will be plenty of content focused around helping you get started and putting your writing skills to use in order to build passive income streams — after all, that’s the goal for all of us, right? To get paid the most, for doing the least?

It is for me, that’s for sure.

The Copywriting.University

Direct response copywriting is, by far, the most lucrative way to make money as a freelance writer, provided you’re able to learn how to sell. That’s a big caveat — direct response marketing IS selling, no matter how you slice it.

It’s taken me around 6 years to become a proficient direct response copywriter but it’s something I’ve practiced since I was a kid, spamming emails across AOL in the mid-late 1990’s.

It wasn’t until 2014 that I actually started calling myself a copywriter, though, and really focusing on learning the art and science that is direct response marketing.

I can teach you the basics here, and I’ll have a free course on The Copywriting.University, but that program is going to be devoted to freelancers who are ready to take their business to the next level and entrepreneurs/marketers who are promoting their own products and services.

It won’t be cheap, but the payoff is massive when you learn how to do it the right way — or, at least, the way I teach you that’s always worked for me.

The Copywriting.University isn’t for beginners. The free course will show you the ropes and help you wrap your head around direct response copywriting but the course, itself, is going to be an intense program with 1-on-1 and group coaching formats to help people level in up major ways.

My Content Engineers

This website is a bit of a love/hate for me but I’m including it because a ton of other freelance writers could parlay into owning their own agency as a natural progression in their career.

Look at it this way — as a freelancer, there’s going to come a time when you have too much work to handle on your own and projects that you don’t necessarily want to work on, yourself.

You’re also going to have a network of other writers that you can outsource the work to in order to keep from having to do it yourself.

That is what creates the platform for you to own an agency and get paid while still overseeing the projects that come into you. You get to keep your list of clients growing while cherry-picking the projects that you want to work on and outsource the rest.

Owning a freelance writing and content marketing agency can easily carry you into the 7-figure per year range but is something you have to see yourself doing.

I’ve done it once in the past and don’t see myself doing it again but I’d be remiss if I didn’t teach other writers how to do it — whether I actually do it myself, again, or not.

Now, I am going to be building the site in order to get back into the feel of owning an agency and it may evolve into something on its own but I’m not going to go full-bore trying to build a content marketing agency — unless life demands it of me or makes it as effortless as possible.

I want to focus my own personal energy into other areas but it’s always a possibility that I end up building an agency and putting people in place to run it, taking minimal profits from it while it grows. You can never have enough assets in life — something else I’ve learned the hard way.

Investing In The Future

One of my favorite books ever is “Rich Dad, Poor Dad”, by Robert Kiyosaki.

If you’ve never read it, the title pretty much sums it up — he came from a divorced family and his mother remarried. One of his fathers was financially poor, the other was financially well-off, and they both taught him a ton of lessons that stuck with him long enough to write the book.

I consider myself both the Rich Dad and the Poor Dad — having come from a family with no fathers to speak of, and being raised by nothing but women, I’ve had to adapt and overcome nearly every step of the way, especially when it comes to showing up for my daughter.

Life has been a learning curve — that’s something you’ll see throughout everything I do.

One of the things I’ve neglected (majorly) in the past is not investing into the future — actual investing, as in, putting money into either a self-directed Roth IRA, a similar 401k, or just a basic eTrade account where I can learn how to make money with money.

Had I done that years ago, I wouldn’t be writing this to you today, so all things happen for a reason — I’m finally teaching other people what I know about freelancing and how to avoid making most of the mistakes I’ve made.

My Goals Going Forward

I’m going to be upfront and honest — I’m horrible at goal setting and keeping the goals that I do set for myself.

If you look at the list above and really think about the amount of work that goes into each, you can see that I’m more than burning the candle at both ends — I’m burning two candles at both ends, while still freelancing and taking care of stuff in my personal life.

After 12 years as a freelancer, off and on, there’s a lot that I can teach you, and a lot that I still have to learn. I hope that you’re able to stick around because I do have a ton of goals and one of them was just getting this blog started so I can document the process for other freelancers.

As it stands, right now, here’s a small list of my goals and what I’m hoping to achieve with what’s left of 2019. There’s a ton of work but I’m able to do this full-time, so I’m confident I can get it done!

  • Write 1 post per week on The High Paid Writer for at least the next 2-3 months until I get to a point that I can start promoting it, guest blogging, and getting myself “out there”.
  • Get The Copywriting.University and Blogging.University free courses launched so I can start running advertising to them and build the email lists.
  • Get my “niche blog” up and running, generating traffic and revenue so I can show you what it takes and build out the backend of The Blogging.University’s paid program.
  • Get My Content Engineers to a “stable” point where people can at least contact me to place orders and I can run advertising to it if I ever get in a position and need to.
  • Continue building my network of SEO agencies and marketers/entrepreneurs to bring in a steady amount of content and copywriting work for myself.

You can see, there’s a ton going on but it all works together, as long as I work the list that I have in front of me. 2019 may be a bit of a “slow” year as far as revenue goes, but it’s like a snowball and the more you push it the bigger it gets.

For now, thank you for taking the time to see what’s going on. Hopefully I’ve shown you what’s possible when you put your nose to the grindstone and just get stuff done and if you’re in a dark place right now, keep focusing on the light — as long as you do it always gets better!

Joshua, The High Paid Writer, signing off!

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