How to quit your job and become a freelancer: 3 rules on the way to your independence

Illustration of a person with flying goggles and a scarf leaping into the air from the hatch of an aircraft, with an aerial view of clouds and land below. Illustration of a person with flying goggles and a scarf leaping into the air from the hatch of an aircraft, with an aerial view of clouds and land below.

My first thought when I turned off my alarm clock was “Oh God, I’m just wasting my life.” It was 7:30 a.m., April 10, 2012. “I can’t live this way anymore,” I thought. Thus, I decided I would quit my job and on the same day gave my employer notice. Friday was my last day as a payroll employee and I entered the void then.

This is what the decision to quit a job looks like for most of us. Even if it is a conscious choice, it’s incredibly hard to make a first step for many. I ,actually, was beating around the bush for several years.

The path to the void.

It took me ten years in total to realize what I actually wanted to do. I first started thinking it over when I was at school. Well, it wasn’t like I was contemplating who I wanted to be when I grew up, nope. But even at that age I knew for sure that regular mundane tasks (as the ones I saw my parents or relatives doing) at work weren’t for me at all. I wanted to do some creative stuff! I wasn’t exactly sure what kind of ‘creative stuff’ I wanted to do, though. That wish was more of a childish belief in the fact that I was unique and highly significant than a conscious aim.

As the years went by, this belief was almost completely destroyed by a harsh reality and a ruthless education system. I hadn’t even noticed the transformation. The first money I earned by myself even sugarcoated the situation and my wish to ‘create’ kind of disappeared.

But moving up the career ladder I every now and then came across the thought that I was job-hopping for a reason, that I always lacked something, some sort of freedom. I always had that feeling that I was doing something wrong, even when I was a department head or creating some new projects in the company. Something was always amiss. I usually spend from 8 to 13 hours at work, depending on my position. During that time I even developed a rule to leave work-related issues at work, which made my coworkers envious. But the idea that I was living someone else’s life in these 8-13 hours was driving me mad. I was spending my time making the life of some stranger unique and significant and it was incredibly annoying. Those strangers were, in fact, my employers, who hired all of us to make their wishes come true.

Those thoughts were highly destructive and I knew that I had to change something. My wish was to break free from all of that. I used to day-dream that one day I would pull myself together and start my own business. But it didn’t happen. I needed some turning point to finally make up my mind.

Well, actually, three of them. Three turning points that would make me quit my job at last and become a freelancer.

It wasn’t long before the first one. I got expelled from college, but not for poor progress (my progress was surprisingly good), but for absenteeism. I was bunking off as the studies weren’t really exciting for me, weren’t my cup of tea. I was made to enter college, by my parents in the first place, but also by the system itself.

I always wanted to be an architect, I had a knack for that. But what I had wasn’t enough to get myself a state-funded place and my family couldn’t afford to pay for my studies. So I entered the faculty for which my state exam results were okay. But it took me very little time to realize that I didn’t want to spend time on something I didn’t enjoy. This is how it is since then.

The second turning point was when I had already been working for several years. I was at the client’s testing the equipment and I had to work along with the employees at the car assembly plant. The client met me at the entrance and before we started showed me the workshop. There I saw a picture that got stuck in my memory forever.

It was some workshop with a bunch of different wires and cables. There were some workbenches standing in a row and several employees in front of them. They had two baskets from both sides of them. They would take a batch of wires from one basket, connect them in the correct way and put them into the other basket.

That was it. Taking the wires from one basket, connecting them and putting them into the other basket. Eight hours. Five days a week. They also had a one-hour lunch break and a one-month vacation.

If I ever had my personal hell, this workshop would be it. That was the worst job ever. Every time I got bored at my current job, I was thinking about that workshop and I felt better for a moment. But at the same time I was aware that any job as a payroll employee was basically the same workshop but under different conditions. The wires were different, trickier, I’d say, but that was it. I realized it more and more as the time went by.

The third one was my best work ever at Integrator, Eugene’s Volk startup. This was the place that made me realize how it might feel when you’re doing your thing. I found myself unique and significant again, just like in my childhood. Besides that, I learned to do a lot of new stuff and got an ability to set and reach goals. Oh, those were the days.

The work at Integrator made me realize that I would never come back to a proper employment. And I never did. One day the investor stopped funding the startup and my family underwent a budget shortfall. I tried to find a typical office job and I got it. A respectable position, decent by Moscow standards salary and terrible boredom.

I left after two months. All my previous experience, the ideas of what the job should be to enjoy it were in constant conflict with that office work. I recovered the feeling that this wasn’t my life. One fateful Thursday I came to realize that the only feeling I had after waking up was self-pity. “Nevermore,” I decided.


The step into the void.

The decision to quit a well-paid office job was spontaneous, my bank account had slightly above zero in money terms and I was eager to be my own boss. It might seem as a bonehead action and that such serious changes need serious planning. But it’s not like that.

It’s easier than it may look. No, it doesn’t mean that the whole path is easy. It’s incredibly difficult and do not believe anyone who says otherwise. However, it’s fairly easy to get on this path without getting scared of falling into the abyss. You just need to follow three simple rules I established going my own way.

It could have been easier for me to start if I’d read the article like that from the people who had already done it. They might have shared similar rules as well. By the way, the idea of people using the experience of others rather than fumbling around in the dark later became one of the main aims of

One way or another, I came a long way, suffered my own bumps and bruises and came to some conclusions. Remember, no matter what others say, no matter which warnings they give you, the main rule is...

Rule 1: dive without thinking twice.

The most common mistake of those who are thinking about quitting their jobs and start doing their own projects is that they try to plan and pave the way for everything. When you step into the void, you obviously don’t want to land on firm ground, you want to soften the blow. You need a plan B, just in case. In case something goes wrong, you’ll always have a chance to come back so you won’t starve to death while you’re up and coming. Some sort of financial cushion you can live on for a month, two, three or even six. It sounds right and legit. But it’s wrong.

The more you work on someone else, the more mental load you get. You get consumption habits, such as a car loan, mortgage and family needs, and you cannot get rid of them later. The load becomes bigger and bigger and you need a bigger financial cushion for such a load.

But no matter the size of this cushion, it’ll never be enough. Never. If you step into the void knowing that the blow is softened and there’s a cushion below, you will land exactly on it. If there’s only firm ground below, you’ll learn to fly, I guarantee it.

It’s going to be really god damn hard. It’s hard to break old habits. The process itself is very painful and at first it will cause lots of inconveniences. So if you don’t want to clean the ground of your brain, you need to follow two rules below.

Rule 2: do only the things you enjoy doing...

... and find someone who’ll pay you for it.

That is my personal motto now. The key point here is ‘things you enjoy doing’, as the whole process of your establishment as an individual specialist is going to be painful. Let me tell you why.

The need for self-fulfillment is in human nature, which is a result (or rather, a byproduct) of us having consciousness. We cover such needs in different ways. Some do that with career, money, sexual conquests, politics, buying expensive things, constantly customizing the car, bringing up the children, creating new stuff. We often do not even realize that our striving for something and satisfaction when we get it is just our need for self-fulfillment.

That’s why when you’re doing something you enjoy, something you want to get better at, you feel good because of the process itself as well as the result. So you’d better take advantage of it.

If you do even the tiniest simplest job, but you love it from the bottom of your heart, you will feel self-content. This fact will solve the difficulties of the initial stage, when you’re just learning to ‘flap the wings.’

Even if your work will not bring home the bacon at first, you’re not going to feel dissatisfied anyway, as you are always going to develop your skills and feel self-fulfilled. The thing is that you’re not going to feel as if you’re working. You’re just doing something you enjoy doing.

In my case it was drawing. Here you might say “It has nothing to do with me! I cannot draw, I like programming!” But the thing is that most fields are similar concerning the structure of work, searching for clients and whatnot. Which means that my experience in drawing might be helpful for you in programming.

When I quit my job, I decided to mull over what I actually liked to do. What did I really want to do? I had several options in my mind. The first thing was to become an astronaut. I wanted to lead scientific expeditions, conduct biological experiments in orbit and grow apples on Mars. I’m still chasing rainbows concerning this one, but it wouldn’t work out at that point. The second was to make computer games. I couldn’t. The third was to design houses and their interiors. But you should remember that I couldn’t choose my higher education and without proper education all my projects would be just a horrible mess. The fourth thing was drawing. Oh, I could do that! I’ve been drawing all my life: at school in notebooks, at college during lectures, at office meetings, in cafes on napkins, on iPad with my finger... The quality wasn’t the best at that time, but I could fix that.

Keep in mind that I wasn’t choosing from the things I could do. I could do a lot of stuff. I had a bunch of experience in sales, team management, Internet-store running and some commercial projects by this time. But I was choosing from something I loved and wanted to do. Only having decided on that I started thinking about what of the above I was actually able to do.

But you need to understand that at that moment I already had some drawing skills. It would be irrational to quit the job and then spend six months on improving the skills. That’s why you always need to develop the skills in the fields you like. Like, right now! Even though I’d never taken money for my drawings before that, I was always maintaining my skills so that I could do even the cheapest work without feeling ashamed.

This is how I started drawing for money. Since I was doing what I loved, I never felt dissatisfied. Even when I was short of money, when I worked 18 hours a day, when the abyss was really close, I always enjoyed the process. The money and feedback from my clients used to give my life meaning. I was falling asleep feeling that I’d done something incredibly important that day. I was waking up expecting new challenges and accomplishments. Self-fulfillment, damn it!

This is why it is crucial to do something you love. Thus, you’re going to conquer new peaks no matter what, develop, master your skills and become a professional in the end.

Rule 3: always set subgoals.

One of the biggest problems of payroll employment is that it forms some pattern of life and dependency. We become dependent not only on the daily routine, but also on monthly or weekly incoming payments. Our routine and the date of our paycheck become the point from which we plan our lives, shopping and leisure time. We start to enjoy living on a schedule. We then try to fit our needs and wishes into the salary we have. If we want something big, something we cannot afford yet, we do a mental tally and postpone the idea until we have more money. But that is wrong.

You need to set subgoals to break this vicious circle. And if you want to reach your goal quickly, you need to look for ways to do that instead of counting the time it needs to be done by itself.

How does it work? Well, first of all you follow both rules number one and number two. Then you set a goal. For instance, if some video game you really want to play is going to be released on a certain day, you need to upgrade your computer before it’s released. To do that you need some certain amount of money. This leads you to setting a goal to earn this certain amount of money by this certain day.

If you’re a freelancer or run your own business, it’s easier for you. The amount of money you can earn depends directly on what you do and how hard you work. Thus, when you set yourself a subgoal, you start thinking about what you might do to get more money. Find a better-paid freelance job? Work for 10 hours instead of 8? Make some particular deal? There are lots of options, it depends on what exactly you’re doing (rule number two).

You can plan the process of achieving your goal more thoroughly by breaking it into several subgoals. But the main point is still the same. You count how much you can earn during a certain time to reach your goal. In this case your money is a variable. But when you’re a hired employee, your money is a constant while your dreams are variables. It’s not fair, is it?

Moreover, having a clear objective and an idea on how to achieve it, you’re going to develop for sure. If today you want, let’s say, a $1,000 computer, next day you might want a $8,000 Bora Bora holiday. So you’ll have to improve your skills to reach a set goal.

That’s why you need to set specific, clear and attainable goals. You’re going to become better and better in what you do by reaching such goals (rule number two). It might seem as if you complete quests in a computer game. Every game has a set of quests, and you get experience by completing them. You get better and better and receive awesome rewards. But at your office work you just complete the same quest over and over again, get the same amount of experience and the same reward.

Of course, periodic payments will never disappear. You’ll always need to have some means to cover your living expenses, such as rent, bills, Spotify, Netflix, PS+ etc. I cannot earn less than the total amount of everyday expenses, as I will fall on firm ground again (rule number one.) So when I set the goals, I always keep those expenses in mind.

Over time it gets easier to earn the amount of money needed to cover the living expenses since you constantly improve your skills. You’ll soon spread out your wings, fly and beat against the wind. The rule number one will become irrelevant, as you’ll start to live according to the third rule by default. And rule number two will acquire more and more things you like and are excited to try. This is how I found some time to study astrophysics and biology and got closer to my dreams of space. Now I also have some friends in gamedev. Even though I still cannot make games, I know how to manage those who can. Or maybe even manage architects and create some projects together? Why not?

At some point you stop thinking about what you can do and what you cannot. You start thinking about different things such as ‘how to make money out of the things I love doing.’ So what if I never tried? I will, I have no other choice.

This is obviously not the last bunch of tips from me. You are now puzzled about where to find first clients and how to prove that you’re a professional? How to set long-term objectives and subgoals? All of that is just empty talk, what exactly should one do? Where are the specifics?

There will be some, I promise, but later. Let’s think of this article as an introduction for a new series of articles! :)