Diana Kelly Levey

10 Challenges of Being a Freelance Writer

Woman feeling stressed

February 1, 2022

I was chatting with some freelance writer friends the other day about why I decided to start my freelance writing course and how people often ask us about our freelance writing careers: how to do it, tips for how they can get started, and how newbies can make money freelance writing.

We all agreed that from the outside looking in, it seems pretty cushy and like an ideal situation when compared to those who have to leave their homes and commute in order to earn a living. My freelance writer friends and I all love what we do, but there are plenty of things that are more challenging than they seem. Here’s the lowdown on the challenges freelancers face.

The Biggest Challenges of Working as a Freelancer

It’s freaking harder than it looks.

You think ‘working from home in your pajamas’ is ideal but you still need to set an alarm, be available during business hours, probably work weekends and nights, and be focused every day. Hungover? You can’t daydream at your desk all day watching YouTube videos if you want to get paid. (Learn freelance writer FAQs I always get asked.)

You have to write all the time.

Some days you’re not feeling creative, but you still have to write. You can’t mail it in and hope no one notices. If you turn in a half-ass article to a client, you could lose them for good—costing you thousands of dollars. (Read about morning routines of freelance writers and creatives.)

You don’t have paid days off.

In freelancing, there are no paid vacation days, holidays, personal days, sick days, disability time off (if you don’t have a disability plan) maternity leave, Family and Medical Leave Act (FMLA), or any “time off” that will be taken care of financially if you don’t work that into your rate. (So remember to ask for more money.)

It can be lonely.

I get it, your coworkers are loud, obnoxious, annoying and occasionally smelly. But if you’re a freelance writer who lives alone and don’t have any phone interviews that day, you might find yourself in the evening realizing you didn’t talk to a soul. If you don’t schedule social outings you might find yourself having long conversations with the postal worker—or dog—if it’s a particularly quiet day at your home office.

It can be draining.

My friend and I discussed how working as a freelancer for five to six hours is mentally challenging. You’re working. It’s not broken up by unproductive meetings where you chat with coworkers for the first 15 minutes about their weekend plans, or can daydream and click around on your work computer and still get paid for it. If you aren’t doing work that will lead to billable hours, you’re wasting your time as a freelancer. (Here’s how many hours freelancers work per week.)

Relationship building is crucial.

This is one people don’t seem to know about. My freelance writer friend who travels a lot for work says she hates it when people say to her “How do I get to travel the world for free like you and write?” Those inquisitors don’t understand how much time she puts in to meeting with PR reps, publicists, attending events, spending time with editors and other writers. Also, I know it looks fun—and it is—but anyone who’s been on a work trip/press trip knows they have to do a ton of work before they go for other clients, check in on assignments and edits throughout the day, and turn in deadlines in between outings—probably with spotty wi-fi. (Do freelance writers work weekends? Find out here.)

You’ll need to chase down payments.

Regular employees often get direct deposit from their employers weekly, biweekly, or monthly. A freelancer has to follow up on where their payments are and determine who to contact at their client’s company in order to get paid. Invoicing, accounting, contracts and paperwork takes about 10-15 percent of my non-billable time. (Here’s how to make more money freelance writing.)

No one is helping you save for your retirement.

When you’re in a corporate or government job, you might be getting a 401(k) match from your employer if you contribute or even a pension. As a freelancer, if you’re not thinking about your retirement, no one else is going to come knocking on your door telling you to put that money away for when you’re in middle age. It’s a good idea to put at least $5,500 into an IRA annually so you’ll benefit from compound interest and note that as a tax deduction. Ask yourself these money questions before going full-time freelance.

You’ll have to pay the government four times a year.

Yep, just as you’re looking forward to the change in seasons, it’s time to send the federal and state governments your estimated tax payments (since you’re being paid in gross).

You need to be marketing all the time.

Every freelancer has gone through the ‘feast or famine’ time and when you’re so crazy busy you can’t think  about taking on one more thing—you still need to spend time marketing as a freelancer. I try to send some pitches and letters of introduction to potential clients early in the week, schedule social media early in the week (like Sunday night) and then follow up on Fridays. It’s difficult to market and reach out when you’re busy but it pays off when your assignments are all turned in and you still have work for the next few weeks and months.

Appreciating your 9-to-5 more after reading this? Don’t get me wrong, I love what I do and working for myself. It’s just not all rainbows, roses, and the pajamas-while-watching-TV that everyone thinks it is.

What are the challenges you experience as a freelancer?

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