Everything you need to know about the ups and downs of freelance writing.

Staff Writer

If you love writing or crave flexibility you’ve probably entertained the idea of becoming a freelance writer.

I don’t blame you–the thought of being able to work anywhere in the world wearing pajamas does sound pretty appealing. But freelance writing is probably very different than you imagine.

In the last decade, I’ve done thousands of writing projects for every kind of business under the sun. I’ve done copywriting for hot startups like Lyft and Gusto, but I’ve also ghost-written and done bios for Arab celebrities in the Middle East. I’ve worked with the C-suite of large Fortune 100 companies on large initiatives, and I’ve also helped mom and pop shops with little odd jobs.

While my passion for writing and creating persuasive copy makes me love my work, I’ve also had many days and weeks where I hated it and wished I did something completely different.

If you’re considering becoming a freelance writer, here’s what you need to know:

#1. Working at home can be distracting

Around half of the writers I’ve ever worked with tell me that they can’t be productive or stay focused working from home. Some of them are interrupted by noisy children or needy spouses, and others just prefer to keep their work and home separate.

I personally love working from home, and find it better for my creativity, but if you’re going to set up a home-office you need to have the right space, routine, and discipline, or else you’re setting yourself up for disaster.

#2. You have to hustle for the best gigs

I have never once done a paid writing gig from Elance, Upwork (formerly Odesk), or Scripted. Some people have a lot of luck finding work on free marketplaces, but I’ve always preferred being more selective with the type of projects and clients I take on.

Some of my clients have come from referrals, but the bulk of my freelance work has always come from cold outreach. In my experience, the chances of an amazing gig just falling in your lap are about as high as winning the lottery, but the best things in life usually require grit and hard work.

#3. Pick a niche or burn out

Writers often fall into the dangerous trap of being a jack of all trades. This is an easy path to burnout, though.

One of the best things I ever did as a writer was to pick a niche to focus on. Doing so allowed me to scale my freelance writing to be more productive, which eventually led me to scaling my work into a real business with employees and contractors.

Your niche could be a specific industry, like healthcare, tech or travel; or it could also be a type of writing, like white papers, web copy, or blog posts.

#4. You’re not really your own boss

As long as you’re working directly for your clients, you still have a boss to answer to. Having eight different bosses can be nice because you can “fire” one of them if they’re driving you nuts, but you still have to try to make them all happy, and sometimes that isn’t an easy task.

#5. Juggling projects is hard

The best freelance writers usually don’t have to worry too much about finding steady work after a few years, but staying on top of everything can be really hard.

You’ll be tempted to say yes to every project that comes your way because you never know for sure when clients might stop coming, but you need to pace yourself. Otherwise, you’ll piss off your clients and just burn-out. (I know, I’ve been there multiple times)

You need to stay really organized in order to manage your time effectively and not bite off more than you can chew.

#6. Some clients really suck

Some clients will be great, but for every great 20 clients you have, there will always be at least one nightmare. Some have given me impossible tasks that were set up for failure, others have contradicted themselves with every piece of feedback they’ve given, and a few have even called me at three in the morning, screaming insane, incoherent things at me.

Beware of nightmare clients and be ready to fire them. It’s never worth the money.

#7. Try it before you quit your day job

I’ve worked for myself for more than three years, and I will never go back to having a job again. But since I had already been doing freelance writing for years, I knew what I was getting into before I quit my day-job.

I’ve seen too many of my friends quit their jobs to try to do freelance writing or marketing contracting full-time, and most of them don’t last more than 3 months before they get a job again. So before you dive into the deep end, first spend a few months working on contract projects.

#8. You’ll pay more taxes

As an employee, your employer pays most of the employment taxes on your behalf, like social security, medicare, and payroll taxes. But if you’re a freelancer, you’re responsible for FICA in the form of a literal “self-employment tax,” which is currently more than 15% of your net income.

There are dozens of creative deductions that can help freelancers reduce their tax burden, such as deductions for home offices, but keeping track of all your accounting and books can be another job in itself. Especially because the IRS requires self-employed individuals to make estimated tax payments four times a year.

#9. Sometimes you don’t get paid on time, or at all

You can never count on the money you’ve billed your client until it’s actually in the bank.

I’ve actually only ever had a few clients ever not pay me, but that’s because I’m a shark when it comes to my contracts and chasing down delinquent payments. I can’t tell you how many times clients have paid me late, though. One time, it actually took me more than eight months to have a client pay me what I was owed, even though I had completed their project within only two weeks.

And even your good clients won’t pay you as soon as you finish your work; most of them have net 15 or net 30 billing, so you’ll be waiting a few weeks or a month (or more) to get paid.

You should always save some money so that you have some cushion, or else you’ll be desperate every time a client pays you later than you expected.

#10. You CAN make six figures as a freelance writer

If you can sort out all these other nine things, and you still think you want to be a freelance writer, then do it.

I am living proof that a good freelance writer can make a six-figure income by doing it full-time. Likewise, I’ve seen several of my own part-time freelance writers at Salesfolk finally pay off all their student loans in less than a year, after just doing a few projects a month for us on the side.

For more tips on freelance writing gigs and potential job opportunities, check out the Salesfolk blog.