Why Most People FAIL to Make Money Writing

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Life Is Hard, Sweetheart.


Yep, it's pretty much a well known fact that for every successful writer out there, there are about a million others who gave up and failed somewhere along the way.


Encouraging, right?


Don't let this doom-and-gloom truth get you down, though - there are plenty of successful writers in the world, and more become successful every day. And having had some success myself - as well as having seen plenty of it through mentors and the work of other writers - I've noticed that a few roadblocks seem to come up more than others.


I'm going to share the reasons why most people fail to create a viable writing career - and how you can overcome these barriers to success and achieve the writing goals you've been dreaming of.


K-O, buddy. K-O.

Starting With The Wrong Paradigm (Do You REALLY Want To Be a Career Writer?)


Before I dive deep into the depths of crushing, soul-sucking failure, let me say a few words about the power of paradigms. Your paradigm is the model on which you base your idea of what a successful writing career consists of. In short: when you think about having a writing career, your paradigm is the image that sticks in your head.


A lot of us (myself included) start out with the wrong one. And by "wrong," I mostly mean "completely and hilariously inaccurate."


When I started out, I thought I was going to pump out books and blogs and articles like a fiend - I had a montage of typing, outlining, and publishing running through my mind like I was living in a 1987 blockbuster romance film, complete with Patrick Swayze in a tight black t-shirt and ripped jeans (he was sexily draped over the back of my office chair, amazed at my genius).


Boy, was I in for a reality check. "I'm going to embrace my starving artist phase, and then I'll just persist until I succeed," I proudly told my friends and family. "It's all about persistence." The funny thing is, if you're persisting on a nonexistent path, you're going to end up in the middle of nowhere.


If my montage had been accurate, it would have included a lot of really boring - and confusing - scenes of me on phone calls, me forgetting and resetting the passwords to about 2 million social media accounts, me trying to figure out how the hell to format a piece on 4 different platforms at a time, me making like, 58 Pinterest graphics a day, me staring at the ceiling at 4 am waiting for my overdraft account to kick in and prevent a penalty from my bank...

I'm still pretty fond of my montage, even though it was a big fat lie.

What I've come to realize is this: a little bit of idealism is necessary to get going on a writing career (would you watch a movie consisting of the aforementioned montage?), but too much will result in a lot of aimless wandering and an eventual breakdown of your motivation and resilience.


So, before you address the main failures I'm about to go over, make sure you aren't starting with the biggest one there is: a completely inaccurate idea of what it means to be a career writer. It's not sunshine and rainbows, nor is it a bloody battlefield. The reality is actually pretty...well, realistic.


Make sure you're okay with that before you dedicate yourself to the job. Anyway, here is that depressing list I promised you.



Failure 1: They Think It's All About Writing.


Ha! Writers, writing? What kind of nonsense is that?


There's so much more to a writing career than writing, it's like saying that an astronaut's career is based on that one month they spend in space. We aren't here for the as-seen-on-TV version of being a professional writer, my friends.


No one wanted to watch Neil Armstrong and Buzz Aldrin chugging protein shakes and testing out 200 poop-bag prototypes for their spacesuits - they just wanted to see the moon landing. That hour of television airtime wasn't even the tip of the tip of the iceberg when it came down to the mission as a whole, however.


Being a writer also involves a lot of metaphorical poop-bag testing. Out of the hundreds and hundreds of applicants for NASA's biggest missions, why do you think only one or two actually pass muster? Once they realize that actually writing is only a small part of what a writing career consists of, most people find themselves far less enthusiastic than they were at the start of the whole endeavor.


Before you go all-in as a career writer, the best thing to ask yourself is this: can you make the 20-30% of actual writing time worth all of the editing, marketing, engaging, revising, researching, planning, and administrating that the job requires?


So many well-meaning writers think that making money from their work looks like this:


Creating good content + "putting it out there" = SUCCESS!


The reality is more like:


Researching the market + creating content + revising the content + editing the content + developing a marketing strategy + online engagement + networking + investing in tools + failing + trying again + consulting the data + etc etc etc = SUCCESS!


Me after day 1 of my career. Not pretty, y'all. Not pretty.

This, my dears, is why there is a large difference between being a writer and being a Professional Writer. Neither is better or worse than the other, but the difference is there. The former is more about who you are, the latter is about what you're willing to do. It's being someone who can drive well to being a NASCAR champion.


When you focus only on the writing aspect of a writing career, you don't accurately calculate the amount of time, energy, or resources you're going to need in order to succeed at making a livable income. This mistake is probably THE most common reason people fall off the wagon and give up on becoming a professional writer.


Keep it real, my dude. Remember the big, many-layered picture.


Sometimes the picture is cold, wet, and requires a long hike to get.


Failure 2: They Won't Take The Leap (Or They Will, But They Forget A Parachute).


Newsflash - business is risky. Anytime you invest in something, you are by definition placing resources into a possibility. Investments are not guarantees. And most people? They want assurances.


People like certainty. They like to know that if they spend X, they're going to get Y. They want data, reviews, and testimonials to tell them that there will be a specific result if they make a certain choice. And, well, that's just not how business - or art - works. Sorry!


Just kidding, I'm not actually sorry. Look, you're not here for pity. If you are...wow, are you in for a disappointment. You want to be a professional writer? You're going to have to take some pretty serious risks.


The key is that you don't have to take them all at once. The "all-or-nothing" mentality is endemic to writers, and this mindset is a surefire way to fail either anticlimactically or spectacularly.


You will fail, at some time or another, it meeting your writing goals. That isn't the big question.


The question is - can you fail strategically? Building a writing career is exactly that: building. You don't have to lay all your bricks in one afternoon! Nor do you need to select every single material you're going to use all at once. The nice thing about today's world is that you can test the waters before you go for the cannonball.


A lot of people think that you start a writing career by giving up everything else. They're either willing to do that, or they're not. This simplification is their downfall. Writing may be all-or-nothing in our hearts, but as a career, it's a little more forgiving.


Take the leap and do the work, but don't do it all at the same time. My least favorite of all sayings is "eat your elephants one bite at a time," and now I'm making you suffer through it, too. It does have some relevance, here, however...


This brings me to my next delightful failure.


Looking before you leap is sage advice, but ultimately remembering a parachute is even more vital.


Failure 3: They Think They Know The Dance, But They've Got The Steps Out Of Order.


Starting a writing career is a delicate tango, a graceful waltz - it is the legendary Cha Cha Slide. This is all to say: it has steps. And those steps must be taken when the tempo is right. No sooner, no later. Otherwise you look like a complete MORON at that 12th birthday party and everyone just laughs and laughs -


Ahem, anyway, my point is that you not only need to know the right steps, you need to know when those steps should be taken. A lot of people get so excited or so anxious about pursuing their writing career, they just barrel on in. And by a "lot of people" I mean me. I barreled on in.


It was a bit of a rough start. If I had known what I know now, I would have started like this:


  1. I would have spent time reading (a guide like this one would have been nice to start with), taking courses, and just generally doing the research about what it takes to cultivate a writing career from the ground up. I would have started with a roadmap!

  2. I would have done an upfront cost estimate and comparison of all the tools I'd need to create a website, market my content, design strong graphics, manage my social media accounts, etc. Maybe the number would have seemed intimidating at the time, but after stumbling and wasting cash on things I DIDN'T need...I'd have saved money in the long run!

  3. I would have set my goals from the outset, with strategies in place and ideas in mind for building my brand.

  4. THEN, I would have done the things like building my site, revising my work, going about the business of publishing, etc.

The reason I didn't fail due to my many mix-ups is simple: I'm extremely, ridiculously stubborn. Not everyone has the energy to sustain such raw willpower, however, and so they end up quitting once they realize that they're in the middle of a chaotic mess due to getting the steps wrong.


The process to begin your writing career will be unique to you, but the main idea is to begin by learning, start by building a foundation, and then start putting out your content. Whether it's books, blogs, articles, or anything else, you'll have a far better chance at success when you do things in a systematic way.


And take it from me - if someone is telling you that there are "shortcuts" to writing success, they're trying to sell you something. This isn't a career that you can quick-fix into existence. You do the time, you put in the work, and if you think on your feet, you'll probably do fine.


Actual image of me performing the cha cha slide.

In Conclusion - Failure Isn't Why You Fail, You Fail Because You're Not Willing To Push Past It.


You're going to fail. Some way, somehow, you'll have to put out a few fires as you learn, grow, invest, and take risks to achieve your goals as a professional writer. You're going to have to build from the base and figure things out while you go, and that's hard.


Really, really hard.


HOWEVER, there are plenty of careers that are equally difficult and not half so rewarding. People fail to become professional writers for a lot of reasons, but the inability or unwillingness to learn from the bumps along the path to success is the number one dream-killer.


To earn a living from writing, you're going to have to grow thick skin and a sharp awareness of the reality that the job exists in. Sometimes you'll be disappointed - that's just the way life works, even when you have the most noble aspirations. If you let those disappointments bully you into quitting, you're not going to make it very far.


Instead, take the time to plan, to solidify the why and the how of your mission. Don't get caught up in the whats and the whens. They'll only hold you back, and you need to stay open-minded as you pursue this path. If you build your business brick by brick and word by word, you'll do just fine.


Oh, and I can't wait to see your montage, once you've got it in HD. Talk to you next time, you crazy kids!


Passion can lead you to a lot of places. Including abject failure. Don't rely on it too much, my friend.

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