The Hard, Stressful, Tiring Side of Freelancing


Remember a few years ago when the Wait But Why article on “Gen Y Yuppies” went viral? Part of that post—the part about social media—really stuck with me. Here’s what Urban wrote:

Social media creates a world for Lucy where A) what everyone else is doing is very out in the open, B) most people present an inflated version of their own existence, and C) the people who chime in the most about their careers are usually those whose careers (or relationships) are going the best.

I’m very guilty of this. My social media presence is carefully curated to highlight only the best parts of my freelance career, and as such, people tend to think I lived this charmed existence where I work a few hours a week, make a boatload of money and have all the time in the world to travel, shop and go to brunch.

But freelancing is nothing like that, not really. Being a freelance writer is really hard, really tiring and really stressful. I’ve been having an especially rough time lately, and today, I want to talk about some of my struggles so you can understand the not-so-glamorous aspects of being self-employed.

Even in Good Times, Money Is a Concern

People often say it’s “feast or famine” for freelancers, and they’re not wrong.

I was lucky enough that the first several months of my freelance career went really well—honestly, much better than I expected. I was making steady income, slowly increasing my profits each month, and maintaining a group of quality clients who paid on time.

It didn’t last forever, though. There were cancellations from a few of my well-paying clients. Editors at my publications moved on, leaving me in the hands of newcomers who didn’t want or need my services. Clients scaled back on publication, leaving me with half the money I was making before. All of a sudden, I was losing work faster than I could find new gigs.

All of a sudden, I was losing work faster than I could find new gigs.

I had a few really, really tough months when I was falling way short of my financial goals and struggling to find consistent, well-paying jobs without compromising my integrity. I’m slowly recovering and getting back on track, but now, money will always a concern.

When you’re a freelancer, there’s no guaranteed check every month. Every week, I worry whether I’m doing enough, if work will come in before the end of the month, if there will be unexpected bumps in the road. The truth is that there’s no way to know. Financial insecurity is one of the hardest parts of being a freelancer, and unfortunately, it’s what I signed up for.

A Flex Schedule Isn’t Always a Blessing

“It must be so nice to make your own schedule.”

I can’t tell you how often I hear that. People who work 9–5 tend to lust after “flex hours,” but there are pros and cons to creating your own schedule, just like anything else.

I won’t lie: It’s nice that I can take an afternoon off to go to the doctors or have lunch with a friend. It’s nice that I can sleep in if I want to or plan a vacation without getting permission from a manager. But whenever I do any of those things, the work is still there waiting for me.

freelance-writing-problems-flexible-scheduleWhen I take time off, I have to put in extra hours to catch up. Starting work late usually means working late. Taking vacations means sacrificing a week’s worth of work and income.

Yes, I have a flexible schedule, but I work six days a week, every week, including both Saturdays and Sundays. Ask my friends how frustrating it is to make plans with me. They’ll tell you.

Sometimes Being the Boss Sucks

When I worked in marketing, I was never afraid to pass things off to my managers. Angry clients, unreasonable requests, and subjective editing all got handed off to someone with more seniority, and that was just fine by me.

I don’t have a manager anymore. I don’t have anybody but myself. I’m the the boss, the salesperson, the marketer, the editor and the writer, all rolled into one. It’s great not to have to take on jobs I don’t want and to always do things my way, but man, I would love to be able to hand projects off to a manager when shit gets complicated.

I miss having someone to handle “complicated” work situations.

Don’t Get Me Started on “Verified Income”

This is a particularly timely complaint, but I have a feeling it will be ongoing. I’m currently searching for an apartment, and I’ve come to dread the words “income verification.”

Look, I get it. If you’re going to rent an apartment to me, you want to know I’m making enough money to pay for it. I am, just not in a “traditional” way. I don’t have an employer who can say, “Oh yeah, Camryn makes $XX,000 per year,” and because I haven’t been freelancing for a full fiscal year, I don’t have tax returns that document my freelancing income. So yeah, the struggle is real.

My dad is also an entrepreneur, and he’s basically told me it won’t get easier anytime soon. Want to buy a house? Need a loan? Banks and other lenders don’t want to gamble on self-employed people. We’re risky because we don’t have guaranteed income. But c’mon, there are 15 million self-employed Americans, according to the Bureau of Labor Statistics—how are you going to count us all out?

Long story short, think long and hard about the tougher aspects of working for yourself. Freelance writing may seem like a “dream job,” but you have to take the good with the bad if you’re going to make it work.

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