5 Pitfalls of the Freelance DREAM and how to overcome them

Of course, there are always TIPS, on how to begin with a freelancing career. Like how you have to chose the thing you love doing, how you have to save up some cash for the upcoming 3/6 months of struggle, how you have to start working on your freelancer career before you go full out.

You get excited, as all of these articles, they touch the most sensitive things inside you — the things that you feel every day, the things that are considered most important in life. Being fulfilled, being with your family, being self-sufficient and free.

Then… In comes the reality, with all the problems, pitfalls and troubles.

Well at least that is what happened to me and I would love to share my experience, opinions and how I managed ( or didn’t ) to push through and make it better.

First of all, I want to state that I have been side-hustle freelancing for almost 10 years now and full-time freelancing for 2 years in the field of Digital Illustration, creating art for various board- and video games.

When you work a full-time job, 40 hours, and have the struggle of commute ( which RARELY is less than an hour a day ) with a very strict schedule and in a corporate hierarchy, then this point usually is one of the first things that catch your eye and fill your heart with hope.

For me, this really was one of the points, when I started my full-time freelance career. Me and my wife were struggling to juggle our time, between our work, our family, our little kid ( 1.5 years of age at the time ), sicknesses and all other little things that come into your life with being an adult and parent. My field of expertise allowed for freelance, while my wife didn’t have such an option, so we had a talk about it and decided that I should try it out.

Now, 2 years later, what I can say is — it is a very wiggly idea. Yes, I do work on my own terms, although most of the time those terms are, that I need to work during the night, weekends, holidays and while being sick. Yes, I do get the flexibility — when my son is sick, I am able to sit with him or get him to the doctor, but usually, that automatically means extra hours for me in the extra shifts ( working when everyone goes to sleep ).

Being your own boss for me now means, that I have multiple bosses. All of my clients are my bosses, although not like dictators, but your clients are and will always be your bosses. The benefit is that I get to chose, most of the time, who I wish to work with. If our relationship with the client for some reason doesn’t work out, I am free to choose not to work with that client anymore. At the expense of losing the income, that that client was providing.

What I found working best is a business mindset and loving the craft itself, without too many specifics. A client is a client, and if the only problems that come with the client are the problems of your feelings, I consider that client a great client, everyone else is not my client. And you have to come to terms with loving the craft, without any specifics. To make it less vague, I will provide a simple example — if you are a writer, you have to enjoy writing about any theme, be it “how growing carrots can be the most fun experience of your life” or “the true story of that one thing you always loved, since you were a kid”.

I never thought that this was a thing, and going into this I knew that I would work more hours than I did beforehand.

But what I somehow didn’t realize is that now I worked multiple jobs and all of them had to be done. I am my very own lead generator, marketer, sales rep, accountant, tax manager, art director and also I am the one producer my work. If I had the office job, doing my work, for 8 hours, I would be doing my work 8 hours. Now, if there is only a possibility to cram in 8 hours into a workday, I have to manage my time, to fit most of the tasks of other jobs too.

This makes you plan your time a lot better and helps you be a lot more organized so that you do not forget to, for example, find new clients, while in the middle of a gig. Or to market yourself out there, so that clients, someday, will come to you and you should not be in an active search all the time.

And of course, if you do not know these things from the start, you will learn them the hard way. As I did. I somehow managed to bump on ALL the rakes of freelancing, like Sideshow Bob here.

Best practice is to plan ahead for this — set up your day right now. What I did was making an analysis of my past experience. I did have that benefit, having had already a year of freelance behind my back. I sat down and counted — what is the percentage of gigs that I am getting from my initial search. First I say down and counted how many hours it would take per month, to make a stable flow of gigs. Then I also sat down with a timer and counted all the other hours that were involved in my work — paying the bills and balancing my finances, how much time I usually spend on marketing and of course what is the average time needed for my work to be completed. Of course, the time was over the 40 hour work week, but now I could plan my days and schedule these things and make my life a lot less stressful.

Also this type of analysis is great for finding way to improve your business — is the percentage of leads you are getting way too little ( writing this now, I understand that this IS about me ), then you can try and find the problem in your lead generation — for example maybe your search way is not good, or your emailing text is too generic, etc.

This is 100 % true. My commute boils down to me going from my bedroom to my kitchen, making coffee and then moving myself and my trusty coffee mug to the work table. And I have zero problems with my co-workers, as I do not have any.

But this may come at a price of feeling like a hermit. Sometimes you just end up feeling, like you have lost your connection with the outside world and that people outside are living lives full of wonder when you are here sitting and doing the same thing you have been doing last week/month/year.

You probably think that it is so great, that you do not have to compete with your co-workers for the attention of your boss to get a promotion. But guess what — now you have to compete with the WORLD for the attention of everyone around you, who might be a potential client. You can’t just be chilling at home and getting gigs from “insert-a-freelance-gig-generator-web-page”.

The loneliness of working at home can be dealt with by spending QUALITY time with people that are close to you, be it family or friends. If you are a busy freelancer ( which you should be ), then you have to set aside the time to spend with your close ones and try to make it count. Do the things that you enjoy, don’t just sit down by the TV screen with your family, go have a small Saturday trip for example.

And that promotion, now it is not something you can just simply work-hard-to-get, you have to understand where you are going, learn all the skills required and push for it yourself. Think about growth now, before you are too deep into your daily hustles, as it can get tough to stick your head out of the trenches. Sit down and make a plan for your freelance business, mark everything down — what is the path you want to take, where do you see yourself and your income in 5/10/20 years, how can you achieve those things.

Although, this probably does vary from field to field. From my experience — work itself is scarce, amazing clients are rare, the combination of two is a red zebra in a boreal forest.

I understand that this problem is greatly based on your chosen field, but I do hear, that it is almost the same in all the fields. Yes, as a programmer, you will have loads of work, to pick and choose, most of which will be sub-par. Or as a freelance ghostwriter, you probably can find a ton of work, writing about things, you do not particularly care about. And this is exactly the thing about freelance — you will do the things you like ( e.g. writing, coding, drawing, designing ) but with a caveat of doing it for a cause that you do not particularly enjoy.

If you want to make your career as a freelancer a profitable one, the thing you have to understand is — there are times, when you have to take work, that is almost the exact opposite of what you would call “your perfect client/gig”.

If you never wanted to take them and are a workaholic, then, yes that is also true.

Most of the time, with an average outcome of a freelance career, for the first year at least, you will be trying to make your income stream consistent enough, to make you have money all throughout the year, and not in patches.

Also trying to go on a vacation and taking your work with you, is just a change of scenery, that does rarely benefit you in any way. It CAN be a huge hindrance, with jet lag and bad internet, with a workplace that is uncomfortable, etc.

To make this work you have to upgrade your thinking from a freelance “worker” to a “freelance” business. You are not an employee anymore, you are a business and you now have expenses, taxes, and profits that you have to manage. You need to understand, that to have breaks, you have to make it possible financially and commission wise possible.

Ways to make this a possibility is to finally take things into your own hands. Take some budget app ( Mint: Money Manager or something like that ), or, like I do, an Excel spreadsheet. Sit down and write down all of your monthly expenses ( mortgage, home bills, food, internet, etc. ). Write down all of your planned income for a month. My spreadsheet automatically takes away the percentage of taxes on the income that I write down, then it takes away another 10%, which I consider to be a reasonable amount of profit for a small business like mine. Then you have to think about your short term and long term financial goals and write them down, let’s say that saving 10% and 10% on both of those per month, is a good starting practice if you do not have a habit of doing so, like me. And only then do you compare your income with your expenses and see if you are covering everything you need.

I came to this solution pretty late into my freelance career ( almost 2 years in ) and am struggling with the discipline that is needed to make it work this way. But it is the only way, that I found, to get the stability that my family is in need of.

Being a freelancer is hard and it does not get easier the further in you are, it is still the best choice that I think I could have made. My situation family wise and in my career path wouldn’t allow me to have a stable well paying job in an office and still have a happy home. It does come at an expense of me being more stressed, always learning new things and trying to juggle a bit too many things. Hopefully, I will be able to learn and share my knowledge and people that read my experience, find it easier to deal with this behemoth of a task.

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