It's Harder Than You Think: Four Challenges You'll Face As A Freelancer

You quit your job to focus on your freelance career, and now, you have all the time in the world. But now you're the only one with your best interests at heart, and you start forgetting that.

By Youmna Chagoury


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A little less than a year ago, I wrote a piece for Entrepreneur Middle East where I explained quite thoroughly how being a freelancer was so much better than being an employee. I haven't changed my mind, but I do believe it's just not so clear-cut any more- I'm stuck somewhere in that grey area. I haven't given up writing and doubt I ever will, but hindsight is 20/20 and I just wish I knew what I was getting myself into at the time. Here are the four top challenges you will most probably face at the beginning of your freelance career:

1. People will forget you: Technically, they will not forget you immediately. First, you will rest on your laurels, because everyone's always told you that you're a good writer, and people have asked you to write and/or edit for them, and so you thought the offers would keep coming without you lifting a finger (for anything other than doing the actual writing). But doing so will see your frequent writing jobs become less frequent, and you'll wake up one day and freak out, because you haven't written a piece in weeks.

What to do: Get off your high horse- there are literally hundreds of thousands of writers who are just as good as you, and even better. Get back in touch with the editors and editorial teams you used to work with, and let them know you're looking for writing jobs. You have to do the asking, not them.

2. You will have a hard time managing your time: You quit your job to focus on your freelance career, and now, you have all the time in the world. Somehow, you start procrastinating- you're your own boss, after all, and no one is there to push you to do your best and meet your deadlines. You're the only one with your best interests at heart, and you start forgetting that.

What to do: Make it a point to dedicate at least the same amount of working hours that you used to, at least at the very beginning. Once you reach the cruising speed of your new lifestyle, you can work more or less depending on your needs and goals, but every freelancer needs some kind of time-management structure.

Related: Why Investing Time (Not Just Money) Is Essential For Your Startup

3. People outside the industry will not take you seriously: "No, but I mean, what is your real job?" I've heard that one over and over (and over again) in the past year, alongside ugly onomatopoeias ("hmm…" or "aha…" or even "bleh"). That challenge is more of a social and psychological one. You might already be struggling with the thought of being "just a freelancer," as if you only were because no one wanted to hire you, but even if you aren't, some people just get to you. You feel the need to justify your career decisions ("No, but I got so many offers in Dubai/Doha/Beirut, but I want to be my own boss."), and explain to people that you do, in fact, make enough money to pay your own bills and buy your own things.

What to do: Each and every industry has their own system- you don't need to explain to people who aren't genuinely asking why you're doing it. Either embrace your freelancer status or go back to being a full-time employee with its perks and disadvantages- it's your choice.

4. You will have to learn your financial value: It's not your value as a person. It's the value of the hours you're putting in, your education, your experience, your stylization and creativity, your ability to follow through your train of thought, your accuracy, your fact-checking, your deadline-meeting skills, and so on. You think you can value the worth of your work the same way you did when you were a regular employee, but that's not how it works. You had a monthly salary that included writing both easy and more complex pieces and editing other writers' works (as well as a series of everyday tasks). Now, you just can't ask for the same writing fees, whether you're proofreading, editing a personal essay, or writing a beauty piece- it's not fair to them, it's not fair to you.

What to do: Write down the different types of works that you do. Ask yourself how much time and effort it takes you to do each one, and price them accordingly. You can (and I think you should) offer better rates for the editors or businesses that you've been working with for a long time, but you shouldn't be afraid to draw the line when they start asking for ridiculous "discounts."

Related: Six Tactics to Increase Productivity by Organizing Your Workspace

Youmna Chagoury
Youmna Chagoury is a freelance editor, writer, and translator based in the Middle East. She was formerly the Assistant Editor of a general interest magazine in Lebanon, and left it to pursue freelance projects in social media marketing, content consulting, and project-based content creation. Youmna welcomes business queries for projects local or remote, and as a senior level writer and digital native, can help you strategize reaching your target audiences via digital and content mediums.

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