5 mental challenges to overcome when starting out as a freelancer

A Library In My Luggage
The Post-Grad Survival Guide
7 min readJul 30, 2018
“Close-up of a person's hands on the keyboard of a MacBook” by Glenn Carstens-Peters on Unsplash

When leaving your “real job” to become a freelancer you have probably accepted that there are going to be challenges beyond finding a well paying freelancers jobs. Probably you know that you will need to sort out the marketing, keep books and decide what to outsource. You may even have an idea to to focus on a self-discipline and keep healthy work life balance. Amazing, all that is so important and can save you lot of trouble.

There are five other mental challenges that I found myself struggling with when I got started in freelancing and I think, maybe I am not along.

1. What do I really want to do with my life?

Before going to the university I didn’t know what I wanted. Things I actually loved doing were not considered a solid career choice. So studied STEM and got a few degrees. Not because I was terribly fond of what I was doing, but after all, it was a sensible thing to do. I got a job at the university and a career seemed to lining up ahead of me.

After years of learning, hard work and effort, I finally had my degrees. It was a safe and prestigious career choice. Only trouble, even the thought of years to come made me feel dead inside. I was done hoping for the eureka moment. I didn’t know what I wanted to do with my life, but I had the next best thing, I knew what I didn’t want to do! Call me a slow learner if you will, but it took me years learn to act on that lesson and I still keep reminding myself

Just because you can do something, doesn’t mean you should!

2. Shut up, pay me!

When you start looking into freelance jobs there are many freelance sites filled with job offers. You apply over the internet, work from anywhere in the world and choose your own hours. Sounds good, right? In theory, yes. However, even before you get to the “paid on publishing” that many freelance writers dread, you are faced with the notorious “do it for the exposure”.

We all love free stuff, that’s a human nature and doing complimentary portfolio pieces to a good friend or offering pro bono service to the charity you believe in is the most natural thing. If it would stay to that there would be no problem. Unfortunately society is conditioned with an image of the noble starving artist. Musicians, designers, writers are expected to work for the exposure.

However, at one point (as early as possible) you need to start asking a real money for your services to support bad habits like eating and paying rent. In this your own mind can become your worst enemy. There is a guilt-in understanding that if you enjoy what you do, then it’s not a job.

We are supposed to hate Mondays and wait for Fridays. Coming back from a holiday is difficult to everybody, right? Stability, security and dislike for a job seems to be the norm. If I don’t go sit in the office from nine to five, but instead spend days doing things that I like is it greedy to want money for it? This shouldn’t even be a question, allegedly an art and a creativity is valued in our society. Yet, I have to keep reminding myself:

Just because you enjoy what you do, doesn’t mean you should feel guilty about asking money for it!

3. Learn to window shop instead of rushing in

When starting out as a freelancer the amount of new things to learn can be daunting. Seemingly small details add up and before you know it, you are swamped and running between dozens of different tasks. Everything takes longer when you get started. For example, the share amount of energy that goes into creating and maintain social media presence can be scary.

I am a big believer in “works smart not hard” but the smart part can be tricky. There are so many different resources, people who “know the answer” and are happy to share their experience by selling you an online course, an e-book or a full access to the web community that will tell you the things you need to know to solve all your troubles.

There are plenty of scams and air-selling, but many are hard-working, honest freelancers just like you. They do their best to offer solid info, useful resources and earn living with their skill.

Despite the good intentions (or because of them) it has been a real challenge for me to train my monkey mind not to signing up for all the cool options. It become like a shopping addiction for a freelancer, should I sign up for this? It only costs ££ for an annual subscription. All this adds up pretty fast and before you know it you have spent £££ or ££££ and have a massive amount of resources that either take up your time and divide your attention or remain forgotten and unused.

It’s good to know about the latest trends in your field, but there is a real danger of overdoing it. From the hard-earned wisdom I now make maximum use of any test-versions before I decide to upgrade.

Just because it’s not a scam (and it costs “so little”) doesn’t mean you need or will use it!

4. Are we there yet?

Theory is simple enough, create value and get paid for it. That’s how it (should) work in corporate jobs. You are hired, somebody in the company set aims or gives you directions, you do the job and you get paid at regular intervals.

As a freelancer you set your own goals and make your own plans. When struggling to find paying jobs, it’s easy to start questioning everything. Do I actually create a value? Do I need to improve my skill or simply find a right way to sell it? Or is the market full and there will be no use of anything that I do?

You can put in an incredible number of hours, feel like stomping you feet and shouting to the world that it’s not fair. That you have worked longer and harder than ever before, none of it will make the difference, the world will not hand you a participation trophy. Life is not fair, and throwing a tantrum will not do a thing about it.

When that happens I take some time and remind myself that I am doing my best, but there are always room for an improvement. Keeping your head clear when out of your comfort-zone takes determination and flexibility. It’s worth remembering that the freedom comes with a responsibility for the choices you make.

I consider and reconsider things along the way, try to get perspective, change the angle and of course, improve my skills. There is a fine balance between jumping about like a monkey on a sugar-high or incorporating sensible new ideas into your business plan. Finding it is the tricky part.

Just because you work hard, doesn’t mean you get handed what you want!

5. When in doubt, travel?

When I started as a freelancer, I only had a vaguest idea what I would like to do and next to no idea how to make living with it. So I decided to leave a place where my life had become a habit. Changes can be made in less drastic ways, but for me it was easiest to explain for myself as well as others leaving a “perfectly good job”.

Travelling didn’t solve my problems, it’s far from being a magical fix. Learning how to becoming a freelancer is a challenge and trying to do that on the road is probably harder than it would be in home. However, making a decision forced me to sort out the life I left behind and look forward. Also it helped me to avoid the old routines that I had fallen into. It’s easier to make a change when you are not on the rails of habit.

Am I on the right track? I don’t know. There are plenty of days when nothing goes right, most brilliant story pitches are ignored, your timely invoices get the “will be paid on publishing” reply and it looks like the whole world is applying for the same freelance writing jobs. Then, I go left and try something different to keep moving and remind myself:

Just because you don’t know what you want, doesn’t mean you have to settle!

Above all the other questions is the big one, do you like what you do? Not every moment but at least sensible part of it, some of the things that needs to be done, not dreaming about the success but the non-glamorous stuff that makes up the everyday life of a freelancer? As long as the answer is yes the direction is right. From a steady job to a chaos of self-doubt, insecurity and juggling tasks, that’s what you may be facing when choosing to become a freelances. However, even in the search it’s possible to be happier than in the wrong destination.

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