Why Writers Fail … And What To Do Instead

I recently met Sarah, a freelance writer struggling to get her business off the ground.

“I’m just kind of stuck,” she admitted. “I’ve landed some clients, but I can’t figure out how to get the high-paying ones. And I really want to do this full time.”

She was on the verge of quitting.

I could hear it in her voice.

But here’s what I also learned about Sarah.

1. Sarah is an amazing writer. No joke. She is better than I am. And that brings me to my next point.

2. She is working an entry-level job that has nothing to do with writing. She isn’t using her talent … and she feels terrible about it.

3. And finally, lack of talent is not Sarah’s problem. The reason she is failing has nothing to do with her writing skills.

So, what is the problem?

Here are some of the biggest reasons why writers fail.

Reason #1: Looking for “love” in all the wrong places

I’m standing in front of a house. I’m considering buying it. The weather is 38 degrees, and I’m so cold, but my realtor begins telling this amazing story, and I almost forget my toes are half frozen.

Her daughter wants to buy a beach house, but all the homes on the market cost at least $650,000.

She can only afford $500,000.

Case closed, right?

Nope. You know what my realtor does? She does a little research and comes up with ten homeowners who tried, but failed, to sell their beach houses in the past year.

And then, she sends each of them a letter.

She only gets one response, but it’s all she needs because two months later, her daughter owns a beach house; she paid roughly $150,000 less than the price of everything else on the market.

So, what does this have to do with YOU?

If my realtor had done the same thing that everyone else did (only targeting houses currently on the market), would her daughter have landed that sweet deal?

Not a chance.

So, think about job boards. Like responding to a new house on the market, tons of writers apply once a new posting hits. It’s tough to land work this way. And you’re in a terrible position for negotiating higher rates.

Instead, market directly to prospects.

Think about it. A marketing manager who desperately needs writing help may be too overloaded to place an ad. And here you are, magically popping up in their inbox! Instead of competing against hundreds of writers, it’s you and ONLY you.

This strategy is actually how I’ve landed my best-paying and most awesome clients, who then refer me to more awesome clients. I’ve shared the exact email template I used to land thousands in new work if you need help getting started.

Reason #2: You have an 800-pound gorilla on your back

There’s an old story about two traveling monks. As they approach a stream, they see a woman having difficulty crossing. So …

Monk #1 offers to help and carries her across the stream. She thanks him and continues along her way.

Monk #2 is appalled. Apparently, carrying a woman breaks some kind of rule (gasp!). And he continues to scold Monk #1 for miles until finally …

Monk #1 says: “Hey, look, the only difference between you and me is that I set that woman down miles ago, but you’re still carrying her with you.”

What is the moral of the story? Let go of your stuff.

Maybe a prospect told you that your rates were too high. It doesn’t mean they are.

Maybe you accidentally screwed up a project. It doesn’t mean you suck.

Maybe you made another “mistake” that you’ve been beating yourself up about. It doesn’t mean that what you tell yourself is true.

When you spot the stories you’re telling yourself, you can change them. That’s because you’re in charge, and THAT means you get to make up new stories!

Let go of the 800-pound gorilla. It is very, very heavy.

“It’s not what you don’t know that holds you back. It’s what you DO know that isn’t true.” — Jack Canfield


Reason #3: You’re three feet from the “gold,” … and you don’t even know it

Napoleon Hill tells a great story about a miner during the gold rush. The miner wants to strike it rich, so he travels west and stakes a gold claim.

And believe it or not, he does strike gold, but shortly after, loses track of the vein. He tries very hard to find it again but comes up short and eventually sells the claim to a junk man.

The junk man takes a different approach and decides to hire an engineer. The engineer runs some calculations, which leads him straight to the gold.

And do you know the location?

It’s three feet from where the prior owner stopped digging. He was so close.

A top reason why writers fail is that they give up too soon.

Just imagine if Stephen King gave up after being rejected 79 times by publishers (he was published after the 80th!)

Or if J.K. Rowling gave up after Harry Potter was rejected 12 times.

Or if Walt Disney gave up when he was fired from his newspaper job for “lacking creativity.”

Rejection does not mean you’re terrible.

Sometimes it DOES mean you need to pivot and try something different, especially if you’re hitting a wall like Sarah was.

“Insanity is doing the same thing over and over and expecting different results.” — Albert Einstein


Reason #4: A four-letter word is CRUSHING You

I lived in Hawaii for a few years. My son, around ten at the time, loved to surf. So I sat on the beach and watched him for hours, and here’s what I noticed.

Sometimes a wave would come, and sometimes that wave was big.

He was a good surfer, and I knew he could handle it, but he didn’t always try to catch it.

He would paddle like he wanted to catch it, but then his arms would grow weak, he would hesitate and pull back.


Fear would set in.

Whether he caught that wave had nothing to do with his ability and everything to do with how confident he felt that day.

So, the four-letter word that is crushing you is fear.

And it looks like this:

You haven’t contacted Fortune 500 companies about freelancing writing gigs because you feel like you’re “bugging” the marketing manager.

You don’t pitch a retainer agreement to a client because you’re worried they’ll say no.

You don’t raise rates on new prospects because you’re afraid they’ll think you’re greedy.

Do you have other fears? I know I do. But don’t let them stop you.

Chris Guillebeau, the author of “The Art of Non-Conformity,” recently discussed why to never underestimate the strength of psychic resistance (aka spending a ton of time worrying about something so that you never do it!).

Do that thing you are afraid to do. And watch the fear wither away.

“I have lived a long life and had many troubles, most of which never happened.” — Mark Twain


You don’t need THIS to be successful

You don’t need more writing samples.

You don’t need more experience.

You don’t need more connections.

Or the right connections.

You are good enough now. And you deserve to be successful now, so don’t give up three feet from the gold.

Can you get better? Absolutely. But in the meantime, just keep moving forward — even when you’re afraid, frustrated, or having a bad day.

And by the way, remember Sarah, the awesome writer who was totally stuck? Do you know what her problem was?

Marketing. She wasn’t doing any. It was the ONLY thing standing between her and what she so desperately wanted — a high-paying freelance business. Talk about three feet from the gold, right?

“Don’t wait. The time will NEVER be just right.” — Napoleon Hill


Do you need help creating an ongoing marketing strategy?

Download the free template that I used to generate $24,500 in new work.

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