How I messed up before I even started.

Ilham Rahmansyah

You can’t go anywhere on the Interwebs these days without being smacked in the eyes with a listicle. Last Chance Writer will not be an exception.

There are a million ways to self-sabotage your chance for freelance writing success. From indecision to just wanting potential clients to think you’re a swell guy, there are a lot of ways to get this wrong.

I’ve tested out a lot of these tricks over my first several months, so you don’t have to.

Here are my top four picks for freelancing faux pas that are sure to keep you broke and unemployed. 

(Note: If you are missing a sarcasm gene, DO NOT do these. You’re goal is to succeed and never wearing a tie again, remember?)


Do you regularly read job posts on Problogger, BloggingPro, or other jobs boards? If you hope to stay broke and idle, make sure that’s as far as it goes.

You wouldn’t want to put yourself out there and be offered a freelancing gig.

Isn’t it better just to wait until the moment really feels right? Or until you find the perfect job posting?

No. You just have to get started.

You must put yourself out there. Sometimes you come off sounding like an idiot. Many times you send your pitch into the void never to be heard from again. On rare occasion, you will be offered money for work.

All of these are acceptable outcomes.

You are pitching your skills and working on your pitching skill at the same time.

You eventually develop a set email script you use to pitch yourself to potential clients. You change out the opening and closing, your list of most relevant skills, and your most relevant samples. But you’re following a formula that saves you from spending too much time on any one application.

And you send this pitch out to anything that 1) will pay you, 2) you have the knowledge and skills to complete, and 3) that could lead to more work (either from the same client or by growing your portfolio).

Here’s how this trick went for me: After I deciding freelance writing could be a viable option for me, I spent a couple hours looking for the best job boards. (Here’s a good list, plus this one.) Then I spent a couple hours reading through postings. Then I was out of time for the day. Then I did the same thing again the next day.

Eventually I think I applied to two super awesome-sounding perfect-for-me blogging positions.. Using the next easy trick.


I did not hear a word back from either of these posters. This was not the time to be charming or personable.

In a pitch, your job is to succinctly argue why you and you alone can solve their problem and best complete their job.

You have to inspire confidence in your abilities, get to the point, show that you’re business minded but easy to work with, and be convincing as hell so they will reply back to you.

Let’s not mince words. That’s a tall order.

I had to practice with about 30 pitches. A couple dozen were non-replies, a couple got initial replies that didn’t lead to a job, a couple more led to my first client projects.

It will feel weird at first, like you’re bragging or bluffing or sounding conceited. It’s probably more in your head.

Remember that text doesn’t carry the same inflection as speech, so the reader could read that into your words, or not.

Don’t worry about it and instead make it a numbers game.

Eventually enough people will read into your pitch that you know what you’re talking about and can solve their problem without any hassle.


Now look at you. All swole with a stack of writing assignments, typing away in a comfy Starbucks chair—it’s a nice Starbucks—one of the one’s with a fireplace.

While other coffee shoppers fritter away their time on a novel or some poem about wet leaves, you are making 4¢ per word, a drip coffee per minute, a utility bill per hour.

All is right in the world. Later this afternoon, you’ll take some time to relax from your business hustle. You’ll work on some more pieces tomorrow, then you might look for a couple more gigs once these are tapering off next week…

So what’s wrong with this picture? You’re working. You’re earning money. You’re focused on your work. It’s what you’re being paid to do.

Sadly, if you’re not hustling for new gigs while you are working the most, you are setting yourself up for an “income rollercoaster,” as Liam Veitch calls it. This is a ride you don’t want to be on.

I can tell you: This is the freelancing rule where even though I read about it and thought I knew better, I still let it happen.

I got busy with my work because I was focused on the tasks at hand. But I still needed to be on the outlook for good opportunities. I needed more discipline to set aside time daily or weekly to look for and pitch to the next set of gigs.

Tom Ewer emphasizes looking for gigs that can be long term or recurring. This part I did, but even as I chose to work with clients looking for long term work I hit snags.

One client ran into delays on their end with their process. If they aren’t ready to start publishing my work, there’s certainly no reason for me to keep churning it out.

Another had an open-ended pitch submission policy. When I was working I had less incentive to spend time coming up with original pitches which may or may not be greenlit and result in pay, when I could just continue filling my other standing orders.

Even in the beginning, it’s on you to set up some system where you can look for new projects and pitch to new clients on a rolling basis.


Thankfully, this is the one trick to staying broke and out of freelancing work that I haven’t fallen into. But many people do.

Do you put off replying to emails? Don’t. At least for this. People working at agencies and offices would rather hear back from you today than tomorrow. Even if it’s just to say you’ve gotten their message and will have an answer for them tomorrow morning.

While your world may be deliciously unstructured the person you’re freelancing for is probably sitting in an office staring at their gmail, wishing they were hiking on some snowcapped peak in that mountain backdrop stock image. Instead, they’re waiting for your slow ass to reply.

Did someone ask you for a re-write or additional tweaks to a project? The nerve! My work is fucking awesome, so’s yours. But that doesn’t mean we’re perfect.

The tone may be wrong for a particular client, polish it up and you can get paid. Or a client wants articles that are more how-to and less journalistic or inspirational. Maybe they should’ve been more clear on their needs, but there are ways to fix that going forward.

They’re not your boss, but you’re not their boss either. No one here is anyone else’s boss.

It’s much more like a college elective group project. No one probably wants to be friends. You may never talk to each other again after this. But for right now, you have to sit down together and get this shit done.

You want to get paid and they want a nice project.

And the best part of freelancing is that what happens afterwards is up to you. If you don’t feel like this is a good client for you, you have agency to decide whether you continue working with this client, redefine your relationship, wind it down, or sever all ties and move on.

Celebrate this freedom of choice. Because this is one of the best things about freelancing.

It’s worth it to put up with the vulnerability, the uncertainty, the rejection, the hustle, and the hassle when you have the freedom to decide what work you want to do and how. And to not wear a tie ever again.

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