7 Reasons Why Most Freelance Writers Fail

Michael Leonard


I've failed a lot since I hit publish on my first blog post in January 2016.

But failing can teach you a ton of great lessons — as long as you are looking for them. As Bill Gates said, “Success is a lousy teacher. It seduces smart people into thinking they can’t lose.”

Learning from my failures is why I’ve found my version of success as a freelancer — being able to work at home, publish content online, and never go back to a 9–5.

But sadly, a lot of writers have the same goals but give up too quickly and never get to reap the rewards.

I’m confident that if you can avoid these seven mistakes, you can find more success than you thought possible.

Believing You Can’t Succeed

The biggest mistake I see with so many new writers is they don’t believe they can become a successful writer. They might “want” to succeed but deep down, they don’t believe it can happen.

But to become successful at anything, you need to first resolve in your mind that you can achieve it. Without your mind getting on board, it’s nearly impossible to hit your goals.

James Clear said it best,

“The biggest difference I’ve noticed between successful people and unsuccessful people isn’t intelligence or opportunity or resources. It’s the belief that they can make their goals happen.”

Once you believe it, everything else becomes possible.

Spend time getting clear on your outcome and using rituals like journaling, meditation, affirmations, or even hypnosis to train your mind for success.

The mind learns through repetition, so the more you speak and think your future into existence, the quicker your mind will believe it’s possible.

Scared to Pitch Clients

Freelance writing is made up of two things — freelancing and writing. None of this works if you aren’t a good freelancer and can’t land clients.

Landing more clients is simple. All you need to do is get your offer in front of more people and raise your conversion rates.

Pitching is just a numbers game — but you need to cold email and apply for job boards so you can get your offer in front of clients. Unfortunately, most writers don’t pitch nearly enough, and then get stuck wondering why they’re broke writers.

I’ve found that most writers don’t pitch enough because it’s “scary” — there is a lot of fear and rejection that comes with the territory. This holds so many people back from ever giving themselves a shot at success.

Rejection isn’t the end of the world either — sometimes it’s a blessing in disguise. Instead of fearing rejection, learn from it so you can evolve your writing and take advantage of the next opportunity.

“Every time I thought I was being rejected from something good, I was actually being re-directed to something better.” — Steve Maraboli

Terrified of Hitting Publish

Hitting publish is terrifying for a lot of writers.

Before the moment of truth, you start to doubt your abilities as a writer — I know I’ve been there. A lot of writers suffer from major imposter syndrome and worry so much about what others will think.

So many people are so scared of getting haters and trolls online that their work lives in a draft for weeks or months. Or, if they do get the courage, they never promote it and hope the internet just stumbles onto it.

Here’s what I tell them… “Just help one person.” When you hit publish, your story or blog post could help one person with some issues they are struggling with in their life and business.

I believe you have a moral obligation to teach what you know so others can speed up success. When you have this attitude, it’s much easier to hit publish and get your work in front of more eyes.

Remember, all it takes is one person to read it, reach out, and learn more about your writing services.

Don’t Have a Home Base Online

As a writer, you’re a personal brand whether you know it or not.

If you don’t have an online writing website or blog to show off your brand, it’s extremely difficult to get clients to hire you. I’m not saying it’s impossible because I know some writers use Upwork or Medium, but if you don’t have a writing website, you’re making it much harder on yourself. Here’s the thing, you don’t need an amazing writing website to attract high-paying gigs.

I designed my website in a few hours and it’s helped me earn six figures writing. I didn’t spend hundreds or thousands of dollars on designers or a crazy expensive theme either.

But having a writing website shows potential clients that you are committed to your business. It shows them you took the time to buy the domain, create the website, add writing samples, and then reach out. This makes them feel more confident in working with you and more likely to say yes.

For your first year of hosting and a domain name, it’s roughly $200, and I promise it’s one of the best investments you can make. Once I published mine, I instantly felt a shift in my identity. I started to really feel like a content writer and it gave me the confidence to pitch clients.

Struggle Retaining Clients

As I mentioned in the beginning, landing clients is the glue that holds this all together. Landing clients is step one but retaining clients is step two. The only reason I’ve earned over $100,000+ writing in two years is that I retained clients at an extremely high rate.

Think about it like this, when you’re searching for clients you’re scouring job boards, applying on Upwork, cold-emailing, or using social media to pitch, you’re working for free. You’re not getting paid anything and there’s no guarantee that you’ll even land a client.

In fact, according to the Consumer Affairs office in the White House, acquiring a new customer is at least 6 to 7 times more expensive than simply retaining existing customers.

If you write one piece of content for a client and then you have to do your search all over again, it’s nearly impossible to scale. The key is to retain clients so you have recurring gigs month after month.

Lack Writing Routines

Writing requires more discipline and structure than I care to admit. While it’s easy to think that you can kind of “wing it” when you work for yourself, the opposite is true.

Unlike a traditional 9–5, you have zero accountability. If you don’t want to do anything all day, you can just sit around and binge Netflix with no one scolding you like a normal job.

But if you want to make consistent income as a writer, you need to master your routines. I’m not saying you need to wake up at 5 am, write three hours at the same time each day, or meditate for 60 minutes each morning either.

Instead, find a routine that works for you and allows you to get more done in less time.

Once I did this — everything changed in my business. For the first eight months after quitting my job, I would just wake up and “try to figure it out” each day. This usually led to being scattered, flustered, and jumping around from task to task.

Now, I set quarterly goals, break them into monthly plans, then weekly plans, and review the following day each night.

Waking up and knowing exactly what you’re going to do that day is powerful! Create your own routines so you can get more done and hit your freelancing goals.

Quit Setting Goals

The final mistake that freelance writers make is that they quit setting goals when things are going well. Here’s the thing, it’s easy to set goals when you start a new project or a new business — you’re motivated, hungry for success, and ambitious.

But as things progress, the newness of anything wears off and it’s easy to get into a rut. I know because this happened to me once I started making $4,000 a month in my writing journey. Finally, I could pay my bills and not live off of credit cards, so I let my foot off the gas and I quit setting goals in my writing business.

This was a huge mistake and led to complacency, boredom, and a few months that were tough financially as I wasn’t pitching new clients. So if you want to succeed at a high level, you need to keep setting goals and striving for more.

Create momentum by constantly setting goals, hitting them, and celebrating your wins!

“Success is like a snowball. You gotta get it moving and the more you roll in the right direction, the greater it gets.” — Steve Ferrante

Final Thoughts

While all of these mistakes can hold writers back, they are all built on the first one — not believing in yourself.

Everything great starts with believing that you can achieve your goals.

If you’re new to this writing thing, understand that others have done it before you which means you can do it too. If you’ve been at it a while but haven’t found as much success as you want (yet)…remind yourself that your time is coming and eventually, it will happen.

Even during a global crisis, now is the best time ever to start an online writing business.

Get clear about what you want and make it happen.

“To be a great champion you must believe you are the best. If you’re not, pretend you are.” — Muhammad Ali
*Photo by londondeposit on Deposit Photos

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My name is Michael Leonard and I am the creator of Inspire Your Success. I'm on a mission to help readers build online writing businesses and quit their jobs to live a life of freedom!

Scottsdale, AZ

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