How to Tell If You’re Making Freelancing Harder on Yourself Than It Needs to Be


When it comes to underestimated jobs, freelancing is a big-time winner. People have grand expectations about flexibility and a life of leisure: wake up when you want, work from wherever you want (from your local coffee shop, from your bed, or your sofa) and never have to deal with annoying bosses and stringent office politics again.

Yet – despite its multiple perks, there are also many drawbacks in freelancing …and most people fail to realize this until they’ve leaped. Maybe that’s a sign you’re not cut out for the freelance world, or you’re just doing it all wrong.

Although it seems like you’re living your dream, what happens is a Vida loca of insecurities and procrastination. Being able to call your shots and be your own boss is more than many people can ever hope for in a modern workplace, so if you’re already there, congratulations! It sounds like you’ve made it. Of course, that’s how it looks from the inside. While it seems to be the perfect fit for some people, what happens is that you are making that fit harder on yourself than it needs to be. To help future souls avoid the crippling freelance shock, we’ve put together a shortlist of warning signs that you should be aware of.

Self-Doubt: All-Time High

One of the worst things about freelancing is a haunting fear that you will never work again. And who can blame you? All it takes for your client to ditch you is a day late delivering that big draft. That, and you will never work again.

Freelancing is no easy job. You are pouring your tears (oh the tears), blood, and sweat into each sentence and wondering with every syllable if you’re good enough. To give you the delicious highlights, freelancer writers are constantly scraping for information, with one eye on the next client before the current draft has even landed in the editor’s inbox. And there’s aching self-doubt.

Sure, self-doubt is human, but when it starts to become a part of your everyday work personality, you’ve got a real dragon to slay. But how am I going to kill that beast? By applying tricks, tips, and valuable thoughts in your daily life.

  • If you weren’t any good, you wouldn’t be hired.
  • Learn to define yourself and be more confident in who you are and what you do.
  • Find your freelance allies and slay those dragons together. These allies should keep you sane by reminding you of all the things that fuel your self-doubt.

Organization and Productivity: Not Your Strong Suit

If self-directed productivity and organization don’t come naturally to you, freelancing will start to feel like a swarm of procrastination and deferred looming work. The more stuck you become, the more you start doubting and looking pensively to the full-time office world’s structures. But with enough dedication and a little bit of adjustment, you can quickly bring some of that office-life structure to your mere freelancing environment- and if you’re patient enough and get some perspective, you might see that your productivity is better than you think.

An essential way to bring organization and focus to your freelance life is to establish a regular, daily schedule. Indeed, you must get organized to get paid.

When you work in a big office department with an HR department, a finance department, and an IT department, you don’t have much to do other than fill out a bunch of forms at the beginning of the year to get paid. But that’s a whole different story when you work for yourself. If you’re the one in charge of your paychecks, track and manage your time, send invoices, tackle tax forms, expenses, and more. This can only mean that you need to be more organized.

A sure-fire way to improve your productivity is to invest in the right tools. And, as a freelancer, you will definitely need a full suite of devices on your personal computer.

While Google Docs is an all-time web-based alternative, most people like storing their documents on their external memory device or hard drive, however, instead of paying the cost of tools like Microsoft Office, most writers prefer the full suite of OpenOffice or other online tools that allow for better and faster conversion and edit of the PDF files like this one here, or tools that enable them to keep track of how they spend time on their computers.

At first, you won’t realize how much time or steps actually go into completing your work and getting paid. But with a plethora of editing and organizational tools, it would be a shame not to get yourself more organized and productive.

Too Afraid to Ask for Help

In the corporate world, all-hands meetings full of professional development activities, onboarding programs, and training libraries ready to use whenever you need them. Not to mention the number of people you can ask for help with anything from using the paper cutter to using the right template for a project to understanding your health insurance.

As a freelancer, these guides and resources either don’t exist or are just insufficient. That will make you feel clueless. Completely clueless. The best way to learn how to navigate those waters successfully and maybe slay some of your dragons is by asking other freelancers. Listening to their stories, tips, and advice will help you tremendously. If in doubt about something, ask someone. We guarantee you that experienced freelancers have been through it and would be more than pleased to save you the time and stress of figuring it out on your own.

For instance, if you don’t feel comfortable with your selling skills, you can always ask others to keep an eye on your project and pro bono between unpaid projects gigs. That plus, doing one job a year for a special project or a non-profit organization will help you hone your skills without the pressure of selling them.

Although freelancing doesn’t seem like your dream job, it can be. Once you slay all your dragons, you will learn your life has become considerably more comfortable.

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