Do you dream of lounging on the beach while making millions from your laptop? Would you like to do that by writing? Start today!

If you read an ad with those lines, click away immediately. Not because it isn’t possible, but because it’s not really what freelance writing is like at all.

That said, freelance writing can be an amazing career for the right person. And that’s what Laura Pennington, a writer and freelance writing coach, and I talk about in this episode of the Own Up Grown-Up podcast.

I think a lot of people hold back because there’s this belief that it’s [freelance writing] an esoteric job only a couple of people can do…the truth is if you have the drive and you have the base talent you don’t even have to be a great writer—you need to be a decent writer to make money and you can improve as you go—but if you have the drive and the willingness to produce something really good for the client all that other stuff, experience, degrees, certifications, are not that important.”—Laura Pennington, Six Figure Writing Secrets

I learn so much from these episodes. Like Laura, I was a bookworm when I was a kid. That didn’t translate into a full-time writing career until I was 30-years-old, but the seeds were planted early. And it shows that if you want to do something bad enough, you’ll figure out a way to do it, even if the path is totally different than the one you pictured taking.

If you love writing and you’re pretty good at it (or at least willing to learn how to get pretty good at it), freelance writing could be your thing. It certainly isn’t the easiest career, and it requires skills beyond writing to be successful, but it’s rewarding. There was a moment last week as I was finishing up a project for a client and I had to stop and take a moment to savour this overwhelming wave of gratitude that swept over me. I felt so content and thankful to be doing what I was doing. Who can say that about their work?

Freelance writing isn’t for everyone. As Laura explains, it’s kind of lonely. Like Laura, I’m a pretty happy lone wolf as long as I mix in social events every week.

You also have to be super organized, disciplined, willing to accept feedback, and good at problem-solving. You have to be good with people, assertive enough to avoid bad negotiations, and you have to have a realistic concept of time and the importance of deadlines. This stuff can be learned, but it’s a steep learning curve.

How to get started as a freelance writer

Both Laura and I started out doing a Google search. We found Elance and began ghostwriting (writing published under someone else’s name) for clients. After a while you begin to specialize in certain topics, some of which are more profitable than others, and you can start targeting certain industries by learning what they need.

That’s just one way to get started. I’ve met other writers who volunteered articles for blogs, or pitched local publications, or wrote website copy for their friend’s business. There’s an abundance of work out there if you’re willing to put the time into finding it and if you have the guts to go after it. And there are tons of resources out there to help you learn how to pitch media, write for the web, etc. A couple of my favourite sites are Copyblogger and Jeff Goins.

But wait, you should know this first

Let me repeat: there will be a learning curve. And there will be times when you have piles of work and times when you’re hunting for work. There will be clients who are impossible to please and clients who send you so many referrals you can’t keep up.

You need a thick skin for this job. You’ll meet people who harshly criticize you for missing a comma, who’ll express disappointment that you didn’t capture their essence well enough (sometimes they don’t understand themselves), and lots of people will try to undervalue your work. It helps to have a good sense of humour and a writer-friend you can shoot the shit with, because there will be shit from time to time. I think that’s true of any creative work.

You should also know that you’ll need to work hard, on your craft and on yourself, if you want to stand out above the pool of mediocre writers. Yes, I am actually writing this while sprawled out on my couch in sweatpants and a tank top while nursing a slight hangover. Yes, I take 2 hour-long breaks during the work day to do whatever I want or sit at a bar or a coffee shop with my laptop and work. But, you have to show up for your clients. You have to do your best work every time because your reputation is on the line. And sometimes, there will be 14-hour days and you’ll have to cancel your plans.

“Make the conditions conducive to coming up with good ideas”

Laura said this during the podcast and I love it because beyond working on your craft you also need to set yourself up for success. And that starts with discipline and routine.

What?! But I thought writing would be crazy and creative. Yeah, it can be, but chaos will probably burn you out fast.

Have a dedicated writing space. While I’m writing from my couch right now, I spend the other 30-40 hours a week at an ergonomically optimized desk. I have a cabinet where I keep my notebooks and I have a work-specific planner, project management software, favourite playlists, and headphones. Focusing can be the hardest thing about this job, so you have to learn how to hack yourself to develop discipline. It’s really easy to do nothing all day. Cal Newport’s “Deep Work” is a good read if you want to win the battle over distraction.

One thing Laura does is the Pomodoro Technique, where you work for 25 or 50 minutes and then take a 5-10 minute break. I do this in the afternoon when my energy and focus starts to decrease.

Writer’s block: myth or reality?

Writer’s block is really fear. You’re worried your client won’t like what you’re writing or that you don’t think you’ll do a good enough job. You’ll get stuck on trying to find the perfect word.

Or you could be exhausted, in which case you need a break. The best thing for writer’s block is to remove yourself completely from your work for a set amount of time. Go for a walk, run an errand, exercise, and then get back to it. Returning to a calm and energized headspace works wonders for writer’s block.

Laura recommends creating an Evidence List (or a list of why you’re awesome). List at least 20 pieces of evidence that show you’re good at what you do. It could be client testimonials or reasons why you think you’re good at what you do (with concrete examples). Refer to this when you experience self-doubt.

Freelance writing can be extremely rewarding if you’re willing to put the work in to make it a successful experience. If you want to learn more about Laura, check out Six Figure Writing Secrets, follow her on Twitter, and listen to her Better Biz Academy podcast.


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