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How to Stop Being too Chickenshit to Start Freelance Writing

By Jorden Makelle

About 5 years ago, I was sitting in a Wal-mart parking lot in my Mazda hatchback.

I was working a door-to-door sales job under the hot ass Texas sun.

That day, I was tasked with handing out sales flyers to shoppers.

And I just… couldn’t do it anymore.

I was barely making ends meet, and I was commuting 2 hours to work then working 10 hours straight some days.

But as I thought of calling my boss and telling her that I was going to quit, a bunch of shitty thoughts started running through my head.

Stuff like:

“This job sucks, but at least I know where my next paycheck is coming from. If I quit, I’ll be jobless and completely on my own.”
“Where am I going to go if I quit? Where will I live?” (I had just split with my fiancee, and my family wasn’t going to support me long-term.)
“This is so stupid. I should just be a good worker and stop thinking that I can actually do something else. It’s not like I can do something better – the only useful job experience I have is working at call centers.”

And you know what?

All of those thoughts can be boiled down to one thing:

Fear.

Fear that I wasn’t going to have a place to go.
Fear that I wasn’t going to be able to pay my bills (my car DID actually almost get repossessed!).
Fear of the unknown – I mean, what the heck was a college dropout like me going to do?

All valid fears.

But none worth wasting my life doing something I hated.

I told my boss that I had to quit – immediately.

I took what little money I had and started driving to the next major city (because I knew I wasn’t going to find work or opportunities in the stupid small town I’d been stuck in for several months).

And you know what?

I didn’t become a freelance writer right after that. This isn’t THAT kind of story.

I had to go through some shitty stuff for a couple years, like working at another call center.

Enrolling in college again (only to drop out for the THIRD time).

Sleeping on people’s couches for a couple months while I got my shit together.

But eventually, I DID become a freelance writer.

I started my business on my own terms.

And I know that my willingness to do the thing that terrifies me is the main reason I’m a business owner today.

I 100% would not be where I am now if I had let fear control my life decisions at any point.

You might already know that I started freelance writing right after I got fired.

I could’ve just found another 9-to-5 gig.

I could’ve let my lack of experience and that little voice that says “you’re not good enough to do this!” control me.

But I didn’t.

I felt the fear, and took action anyway.

So I’m here, working from home. Not dealing with shitty office politics. Writing every damn day, and getting paid for it.

Don’t get me wrong – I’m still a huge fuck-up in a LOT of ways.

And I still deal with all kinds of fears. Every writer does. Every business owner does.

But the successful ones work to OVERCOME their fears.

So, I want you to ask yourself this question:

“Which fear is holding me back from freelance writing?”

Fear of rejection?

Fear of failure?

Fear of what other people will think?

Well today, my friend, is the day you call your fear out on its bullshit.

Because if you let it, fear WILL control all of your life choices.

And you’ll wake up one day (probably sitting in a cubicle that’s as grey as the hair on your head) thinking:

“Damn. Why didn’t I just fucking GO FOR IT when I had the chance?”

I don’t want that to happen to you.

It’s time to take action and stop letting fear hold you back.

Here’s how:

How to Deal When You’re Too Scared to Start Freelance Writing

1. Remind yourself that all freelance writers deal with some form of fear.

I’ve been freelance writing for a while now, so I feel like I know what I’m doing.

And you know what?

I still deal with fear sometimes.

Fear that my biggest client will drop me.

Fear that I’ll miss a client call or deadline simply because I’m that damn scatterbrained.

Fear that I’ll completely get tongue-tied on a client call and make it more awkward than having Thanksgiving dinner with uber-conservative family members when you’re liberal as hell (which is pretty damn awkward, FYI).

All kinds of fears.

But I don’t let fear hold me back. And you shouldn’t either.

Because the truth is this:

Every entrepreneur is scared of something.

The key is to remind yourself that you’re not alone and actively work to move past your fears.

So for example, if I’m afraid of forgetting about client meetings, it just means I need to prioritize project management more. Set alarms on my phone. Figure out ways to compensate for how scatterbrained I am so I don’t have to deal with that fear.

2. Know that no one is born an expert.

I’ve seen writers who have 5, 10, or even 15 years of experience and still don’t feel like they’re an “expert.”

Well, allow me to give you some good news:

You don’t need to be the world’s #1 writer to start freelancing (if you did, I’d be totally screwed… just sayin’). You don’t need years of experience.

No one is born an expert.

Decide what you want to get better at, and make it a priority to grow your expertise over time.

Now, I’m not saying to go out and pitch clients who are going to EXPECT a huuuuuuge amount of expertise.

You need to be able to deliver what a client needs if you’re going to work with them.

But here’s something that might surprise you…

Lots of clients don’t expect years and years of experience in their industry. They aren’t going to grill you about how much you know.

They just want to know that you can write well + produce results for their business.

So don’t hold yourself back.

You have to start somewhere, and if you wait until you feel like an “expert,” you’ll NEVER get started.

3. When it comes to being confident, fake it ‘til you make it.

Here’s a fun fact:

I get kind of anxious before client phone calls.

I don’t really know why, but it miiiiight have something to do with the fact that I worked in technical support at a call center for a couple years.

When I worked there, I got yelled at literally every day. Non-stop.

So, I learned to expect the worst when it came to handling business via phone calls.

But let me tell you – the LAST thing I’m going to do is let my phone call anxiety come across when I’m talking to a client.

When it comes to confidence, you HAVE to learn how to fake it ‘til you make it.

Here are some tips that will help:

Reflect on past successes. Ever received positive feedback from a client, teacher, or friend? Look back at that feedback, and remind yourself how awesome you are!
Move yo’ body. Strike a power pose and SMILE! All the physical movements that indicate you’re a confident person will make you feel more confident. It’s weird but true.
Do what you’re best at. For example, if you suck at writing whitepapers, don’t write whitepapers! I specialize in writing blog posts for clients, and that’s pretty much the only kind of project I accept because it’s what I’m best at. As a result, I’m only working on projects I feel confident about.

Of course, the steps you should take depend on what you’re feeling unconfident about.

In the case of client phone calls, you can ask yourself specifically what makes you feel unconfident about those calls.

If it’s something like “not knowing what to say” or “forgetting something important,” then you could combat those fears by creating a document with key information for you to reference on the call.

And just like that – you’d feel WAY more calm and confident!

The point is this:

Don’t just roll over and give up because you’re scared. Fight the fear.

[clickToTweet tweet=”Freelance writer? Don’t give up because of fear. Call your fear out on its bullshit, and FIGHT it.” quote=”Freelance writer? Don’t give up because of fear. Call your fear out on its bullshit, and FIGHT it.”]

4. Remember that everyone gets rejected sometimes.

Rejection is probably the number one fear I hear about from writers.

So, they don’t pitch their guest post ideas.

They don’t cold email.

And they don’t reach out to other writers for support.

…Not good.

Look – you have to be willing to put yourself out there.

You can’t be afraid to fail and get rejected.

Because it’s GOING to happen at some point. No matter what.

It happens to everyone.

Focus more on the good things that happen, and just accept the fact that rejection is inevitable.

Don’t let your fear of rejection stop you from growing your freelance writing business. Regret is a hell of a lot worse than rejection.

And here’s some encouragement:

When you get rejected as a freelance writer, it’s mostly going to be via email – a form of WRITTEN communication. And written communication is your thaaaaaang, boo.

Compare that to something like getting rejected over the phone while cold calling as a salesperson. Or getting rejected in person at an audition as an actor.

…Getting rejected via email doesn’t seem so bad anymore, does it?

5. Ask yourself: “What’s the worst thing that could happen?”

Scared to put yourself out there?

Ask yourself:

What’s the worst thing that could happen?

Maybe people from your hometown will talk shit about you (as if that’s not already the case anyway!).

Maybe your parents will think you’re crazy for trying to go freelance.

Maybe someone will leave a rude ass comment on something you wrote.

But…

Who fucking cares?

Seriously – the people from your hometown are probably just jealous that you’re trying to do something other than work at a soul-sucking 9-to-5.

Your parents won’t understand at first, but when you’re bringing in the bucks as a freelance writer, they can’t say shit to you.

People are going to leave rude comments on your stuff.

It’s just part of being a writer.

And even if people from your hometown hate you, your parents think you’re stupid, and people criticize your work every day…

…It doesn’t matter.

You have to learn to block that stuff out.

It’s YOUR life. Not your spouse’s life. Not your mom’s life. Not your high school friend’s life.

So if being a freelance writer is what you want to do, then DO that shit.

[clickToTweet tweet=”It’s YOUR life. If being a freelance writer is what you really want to do, then DO that shit.” quote=”It’s YOUR life. If being a freelance writer is what you really want to do, then DO that shit.”]

Deal with the fact that some people won’t like you or won’t understand where you’re coming from.

I’ll say it again:

Regret is a bitch.

Don’t wake up one day wishing you’d have busted your ass to become self-employed when you had the chance.

6. Use “exposure therapy.”

Hate client phone calls?

Schedule as many of them as you can.

Terrified to pitch your guest post idea to that website you’re obsessed with?

Set a day to write + send the pitch ASAP.

You get the point.

If you’re scared to do something, force yourself to do it.

I mean, you should still prepare.

But don’t over-prepare to the point where you never do anything about it.

You should still be strategic and all of that good stuff.

But it’s time to stop letting fear and perfectionism hold you back from getting shit done.

Just pull the fucking trigger.

Because most of the time, the anticipation of doing the thing is a LOT worse than actually doing it.

7. TAKE ACTION. NOW. (Because being scared to start freelance writing means you really need to get some momentum going!)

I shit you not – there’s no excuse for you to hold yourself back anymore.

I WANT you to win and achieve whatever level of success you’re after.

So, here are some super actionable, in-depth posts you can use to get your business up and running + start winning clients.

Look through these posts, and TAKE ACTION.

I’m serious – don’t bullshit yourself anymore.

(If you want a step-by-step walkthrough on how to become a freelance writer as a beginner, check this out.)

I’m a three-time college dropout who has been fired from full-time jobs three times. (#Goals, right?)

And I barely had any professional experience when I got started.

What I DID have was writing skills and the willingness to put myself out there (and FAIL) and learn how to market myself as a freelance writer.

If you’re a decent writer and refuse to let fear hold you back, you can build a profitable freelance writing business too.

What fears are holding you back from getting started as a freelance writer? Seriously – why are you scared to start freelance writing? Share in the comments section so I can give you some tough love. 😉