7 Problems That Every Single Writer Faces Before Becoming Successful


Starting out as a freelance writer can be scary, confusing, and leave you feeling more than a little overwhelmed.

There is so much information out there it’s hard to know where you fit into the bigger picture.

There is good news though: you’re not the first freelance writer to ever have to deal with these problems.

Every writer who came before you, and all of the ones who come after you, has to contend with the same problems in order to be successful.

1. Having no idea where to start.

Every new freelance writer finds themselves staring blankly at their computer screen with no idea what they need to do to get started.

Do you perfect your portfolio? Do you start a blog? Do you look for jobs on content mills? Do you look for jobs elsewhere because a guru said you shouldn’t use content mills? Do you create a LinkedIn profile? Do you start guest blogging? Do you try and do all of it?

It’s easy to see why the default response is closing your laptop, heading to the couch, and losing yourself in a new Netflix series. Trying to make sense of it all is a full time job in and of itself. No wonder Elon Musk likened starting a new business to chewing glass whilst staring into the abyss.

Dealing with this problem isn’t as hard as you might think, though.

All you have to do is choose one item from your Do I? List and commit to doing it until completion. It doesn’t matter if it’s the right action to take, it just matters that you do it. Why?

Because when you take action you’re not scared anymore. You’re lost in the moment, free from resistance, and able to tackle whatever might be thrown at you.

Once it’s completed you can take a step back and think, “Did that help me achieve what I set out this morning to do?” If the results are positive, do more of that. If they’re negative, choose a different option and try that one instead.

Wash, rinse, and repeat.

2. Feeling like you’re a sellout.

Writing purists will tell you that you’re not a real writer if you don’t make your money through publishing books or having a huge online following.

If you’re writing anything that they don’t consider to be true to the sacred art of writing, you’re a sellout. A hack. A word-based prostitute selling your soul.

…and it’s all bullshit.

As Jeff Goins points out in his book of the same title, “Real artists don’t starve.” Some of the greatest works of art have been made upon commission.

Neil Gaiman, Ernest Hemingway, Kurt Vonnegut, and Terry Pratchett all spent time writing for newspapers. It was a way to learn how to write, build a following, and get paid to learn to write. Were they sellouts too?

The modern day equivalent to taking a job at a newspaper is freelance writing. Finding niches that you love and writing about them because you’re interested, you want to learn, and you want to feed your family.

You’re not a sellout. You’ve just found a way to get paid to do what you love.

If there’s one thing I’ve noticed about these writing purists it’s that many of them don’t make any money writing. They preach their values at you from the comfort of their mother’s spare room, or after a hard day at a job they hate.

I’d rather use my skills to help people, master my craft, and pay my bills whilst I’m alive than hope my book sells when I’m dead.

3. Thinking your writing just isn’t good enough.

Each new freelance writer asks themselves the same question, “Is my writing good enough?”

It’s a sadistic question we all have to ask ourselves. And, in business, it makes sense. If you can’t string together a sentence you probably shouldn’t be a freelance writer.

But good writers being overcome by the fear that their writing isn’t quite good enough is what kills most careers before they ever began.

Every time I submit an article – even after four years of writing online – I’m worried is going to turn around to me and say, “Your writing is awful.”

I still toy with the fear that all of my clients are going to realize that I’m making this up as I go along and my writing is terrible and cancel their contracts and leave me to go back to my job in a shoe shop selling sneakers for seven bucks an hour.

But despite all of this, I’ve come to learn that this fear is a blessing. It’s what keeps you alive as a writer.

It makes you edit your writing. Try new techniques. Read books. Absorb feedback (even if it feels like a knife to the heart when an editor tears apart your piece). Then use it all to go on and become a better writer.

The writer who is comfortable, who has decided their writing is good enough, is the one whose writing will become truly awful.

If you ever feel like this problem will get the better of you, take the time to read this passage from Neil Gaiman and how he feels about his writing after publishing at least 37 books and having a net worth of around $18 million:

“The gulf between the thing I set out to make in my head and the sad, lumpy thing that emerges into reality is huge and distant and I just wish that I could get them closer.”

You have to have a level of confidence in your writing to sit down and have the audacity to write an article that someone will spend their time reading. But you also need to have a little self doubt to keep you from becoming stagnant.

4. Feeling like getting hired is impossible.

When you first start out it feels as though every client wants you to have published portfolio pieces to get hired. But in order to get those published portfolio pieces you need to get hired in the first place.

It feels like a never-ending cycle that you can’t see a way out of. And, it’s enough to turn your away from freelance writing altogether.

When I’d open my emails to find rejections letters saying that I didn’t have enough portfolio pieces I’d want to scream, “How the hell am I supposed to get them if you don’t bloody hire me!?” at the screen.

But when I took a step back I realized that there were lots of opportunities to get portfolio pieces that didn’t involve me getting paid. And when you realize this for yourself your entire business begins to change. Think:

Do you have any friends who need a website? Do you know someone with a blog? Can you contact a local business and offer to write for them for free? Can you contact someone on a job board and offer to write in exchange for a testimonial?

The cruel world of freelancing is that if you’re stuck it’s your job to get yourself unstuck. Nobody is going to come along and fix the problem for you. 

5. Dealing with rejection.

Every new freelancer has to face rejection and every time it feels like a dagger plunged straight to the heart of your self-worth. (It doesn’t get much better with experience, either).

In my early days I’d get rejected for articles, throw my arms in the air, walk away from my laptop, and proclaim that I was never going to make a success of this. You’ve probably felt like doing (or have done) something similar.

But there is a way to reframe rejection to make it work for, and help you actually feel good about getting rejected.

It all starts with a simple question you need to ask yourself before you start any interaction:

How can I help this person?

This question allows you to focus on the client and not the result (read: you getting paid).

When you look at it this way everything that happens is to help the client get the results they need.

You can help them by not working with them because it’s not what they need right now.

You can help them by giving them a few tips on how to improve their blog and then leaving them to do it on their own.

You can help them by recommending another freelancer because you’re not the right person for the job.

You’re also able to decide if you’re the person to help them. Perhaps the best way to help this person is to let them find another freelancer to do the work instead.

There is probably some self-help, spiritual term for this. I just call it putting the client’s needs first. And it helps rejection much more palatable by showing you it was the right decision at this time.

So, the next time you write a pitch, go into a meeting, or jump on the phone, ask yourself this question and watch the fear of rejection melt away.

6. Feeling like you can’t charge what you’re worth.

At the start of your career money is the most awkward topic of conversation.

You never know what to charge and it can be uncomfortable to name a price.

You’re met with this horrible fear that the potential client – who you’ve finally got on the hook – is going to turn you down and leave you with nothing if you charge what you really want.

How often has someone asked you for your price and you’ve written, deleted, re-written, and done some quick maths on your phone calculator before you finally replied to their email?

If you’re anything like I was, quite a lot. I remember once I wrote 5,000 words for $300 just to avoid mentioning the rate I wanted to charge.

This is completely normal and it’s not your fault that you feel that way.

But there comes a time when every freelance writer has to sit back and think, “I’m damn good at what I do. Why am I not charging what I’m worth?”

When you realize clients need you as much as you need them and that you’re equal in this relationship. You’re not inferior to your potential client. You’re not negotiating a contract so you get work for them.

You’re working on a contract so that you’re able to create something incredible together.

7. Your friends and family don’t understand what you do.

When I first started out I had a group of friends who could not wrap their head around what I did.

They told me it was a hobby, not a job. That I’d never get paid for writing. That I should go back and get a proper job with a pension plan and dental and stop trying to get paid for something I enjoyed doing.

My Mum thought it was a risky decision. There was no guaranteed income, so how would I pay bills? Surely there wasn’t money to be made until you were in the top flight of authors. You could see the worry on her face the minute I told her I’d quit my job to be a freelancer.

After four years of writing and a successful business later people still say to me, “I don’t get it, how do you make money?”

When I work from home people still come in and talk to me and ask me mundane questions and invite me to go to the shops. Despite the fact I’m clearly working. (They should be used to me still being in my pajamas at 2pm by now, right?).

The truth is that the majority of people you know won’t understand what you do. They’ll be confused – or scared – by it. They’ll try and talk you away from it because it doesn’t fit in with their view of the world and how it should work. They’ll distract you because the concept of making money whilst sitting in your slippers is alien to them. And it’s not their fault.

No matter what, you have to stay strong against their pull. Their arguments are convincing and their intentions are good.

But the reason you wanted to be a freelance writer is because you see the world, and your skills, in a different way. You want something else for yourself.

You have to learn how to say no, or that you don’t agree, or that you’re working right now and you’ll sadly have to decline. That the risks, once you realize someone will pay you for your work, are really worth it.