I'm writing this article from picturesque Montenegro. Outside my window, there’s the sea and mountains, and the great weather brings inspiration. When the time is right, I’ll drop everything and go for a swim. Yeah, that’s cool. This is exactly the kind of image people paint when talking about freelancing. But it doesn’t mean it will always be like that for everyone. You need to know about the hidden challenges of freelancing—the flip side of the coin.
Goodbye, schedule
The 8-hour workday gets old fast. The “5/2” format makes your eye twitch. Want to say goodbye to that? Great. Now you wake up when it’s comfortable, decide how long your lunch break is and when your weekend starts. But it’s not always so rosy. Freelancers often work far more than the typical 8 hours a day, especially at the start. You’ll need to get into the rhythm and build a client base. You won’t want to turn down projects. And you’ll be tempted by the chance to earn more. So now you’re juggling tons of work, trying to meet deadlines, working late nights and weekends.
If things go well, you’ll eventually be able to work less and still make enough money for a comfortable life. But you have to earn that. This kind of balance isn’t for beginners. And there’s no guarantee of stability. Many projects are seasonal—there will be busy times and quiet periods. Stable income comes with experience and reputation, and that takes time to build.
Multitasking
Every freelancer is not just a specialist in their field but also a planner, accountant, and manager. You manage your workflow, communicate with clients, know how to write commercial proposals, and understand payment systems and tools. Some freelancers eventually delegate tasks if they work in a team or can hire help. But most of the time, it’s all on you.
On top of that, you need to juggle multiple projects at once—and they’re not always the same type. You have to keep track of all the details, plan time wisely, and prepare for unexpected issues.
You can’t stop learning
You can’t just do what you already know. If you want good money and real freedom, you’ll have to grow constantly. In freelancing, that’s essential. The market evolves—new trends and tools appear—and every year more skilled competitors show up.
Competition grows quickly. Ten years ago, you had to explain what freelancing was. Now people ask why you’re not freelancing yet. And 2020 gave everyone a crash course in remote work survival. Since then, lots of professionals have joined the freelance world.
Top freelancers do pretty well. They get to pick projects, set their rates, and define terms. But you’ll have to work hard to get there. It’s especially tough for beginners—you’ll be fighting for your spot under the sun, so be ready.
To stay afloat, you need to track trends, master new tools, and invest time and money in your education.
Freelancing is not for the lazy
If you’re used to sipping tea, playing solitaire, and taking smoke breaks at work while still getting paid—forget freelancing. Here, you earn exactly what you work for. Honestly, it’s really motivating—you feel the true value of your work, and when you work hard, you see results.
No limits on income
Few companies offer the kind of potential that freelancing does. You grow faster, and you control your rates and workload. You don’t face the usual office unfairness—working harder for the same paycheck.
But there are no limits in the downward direction either. If things go wrong, you might not make anything. Don’t rely on a single project, ask for an advance or partial payment up front. And you need to know how to choose the right freelance platforms. Watch the online premiere “I want to be a freelancer: why Freelance.ru and not Upwork”.
No benefits
If you work officially as a sole proprietor, you pay taxes and qualify for a state pension. But let’s be honest—freelancers usually know their future is in their own hands.
You don’t get sick leave, paid vacations, holiday gifts, or office parties. Sure, you can rest when you’re sick. But your client usually doesn’t care. You’ll pay for treatment yourself—unless you get your own insurance, which is a smart move.
Vacation is a mixed bag. On the one hand, you can take time off whenever you want. On the other, every day off means no earnings. So you need to plan your time and budget, and realize that rest is just as important as work.
How to avoid burnout
This isn’t a discouraging article. We genuinely recommend freelancing. The pros far outweigh the cons. But you can’t romanticize any job—you need to put in the work. Plenty of people dreamed of a no-boss lifestyle but couldn’t handle it because they weren’t ready. Some people just do better going with the flow.
How you start matters. If you have a mentor, everything becomes easier. Doing it alone is tough. And early failures can kill your motivation. That’s why we offer practical freelance tips in all our courses. We know students need more than just technical skills. We cover this deeply in our coaching program “Freelancer: The Big Game”. Sign up for the next session!
