What No One Tells You About Your First Year of Freelancing

Lucie Viktorin
July 10, 2025
10 Minute Read

When entering social media, we see many dreamy lifestyle versions, worthy to get jealous off. One that always spoke to me, was the version that apparently comes with self-employment. You know, the one where you are chilling with your laptop on a beach. Cocktails at noon. Working two hours at best and the caption reads: “Quit my 9 to 5 and never looked back.”

But here’s the thing: I did quit.
And in the first two weeks of me being a full-time freelancer, I cried more than you can imagine.

Not because I had failed, but because I was terrified. Of failing just as much as not being able to sustain myself financially. I felt like I had no idea what I was doing, that I was completely clueless and naive. Of course I had a plan, but executing the plan showed to be scarier and harder then anticipated. I had no idea how much fear would come with the freedom I wanted.

As I’m celebrating my one year anniversary since I took the leap into full-time freelancing, I wanted to talk openly about the negative aspects that come with quitting your 9 to 5. Not because I want to scare you off from doing it. But because I want to make space for the whole story. Not just the glamorized parts. Because yes, freelancing, being a business owner and self-employed is fulfilling, meaningful and empowering. But that doesn’t mean it’s easy. Especially in your first year. Here are a few things I’ve learned along the way and wish someone would have told me about and prepared me for before I took the leap.

The Over-Romanticization of Freelancing

Work from anywhere, anytime. Never having to answer to anyone. Work only a couple hours per day. Freedom. Flexibility. Being your own boss.

Yes. But also, not exactly:

Freedom means you can create your own schedule. Therefore, you can take Monday off. But only if you work Sunday or longer hours on other days to keep up with your workload.
Flexibility means you can work from anywhere. But when your Wi-Fi cuts out mid-call, sand gets all over your keyboard or your laptop goes dark because there’s no outlets in sight, it’s not quite the relaxing dream many imagine.
Being your own boss means you can absolutely make your own rules. But it also means, enforcing them, answering your own questions and sometimes working 10 hours to meet the the deadlines, you set.

Without a doubt, self-employment means freedom, but not always in the way we are being sold. The main part of said freedom I’ve come to appreciate is that I have a choice. I can choose what to do, why I do it and how to handle the situation when things don’t go according to plan.

The Fears No One Warns You About

When I started, I was prepared for some fears to give me a slight slap on the wrist from time to time. To remind me of the risks I was taking. What I wasn’t expecting was, that the fears crept their way into my head through a backdoor and then punched me straight in the guts to the point I felt like I couldn’t breathe. The first fear that occured stronger than I anticipated, was not getting any clients.

When I closed my first client two weeks later, I thought the fear would disappear. After all, I had the client. I had made it. I proved the fear wrong. Of course, that was naivety speaking. Because instead of disappearing, it simply changed shape.

It changed from the fear ‘I won’t get work’ to ‘I will mess up the work’ to ‘I’m afraid of not being able to take time off and will overwork’.

So, how to deal with that dilemma? Unfortunately, ignoring the fearful passenger in my head and pretend like he wasn’t there didn’t take effect. Instead, I decided to give the fear a stable seat and take it along for the ride. Because the trick isn’t to get rid of it, it’s to learn how to sit next to it, without letting it drive the car.

For me, that meant grounding myself, for example in routines. Which for me was challenging in itself and sometimes still is. Never in my life, was I a big fan of routines, living my life the same everyday. So I struggled to really find what worked for me. Because if I made the routine too stiff and unflexible, I felt imprisoned immediately. If I created a routine that was too flexible, I didn’t follow through on my tasks. I needed to find the balance and it is still a work-in-progress.

Navigating Loneliness

One thing, that really caught me off-guard, was feeling lonely. Before I started my business, I loved working alone. Home office was my haven. So I didn’t expect to feel lonely at all. Especially in moments of high stress, I missed chatting with my favorite co-workers and complaining about that manager or that project. I missed the quick feedback from my work-friend before sending a project out and most of all the external validation that came with a successfuly finished presentation.

Because when these moments occur during self-employment, I have really only myself to lean on. And while that’s powerful, it also gets heavy.

Eventually, I found ways to cope. I started reaching out to friends who work remotely. We planned co-working sessions and while those weren’t daily, the few hours side-by-side helped immensely. When no one was free, I took myself to cafés for a matcha in a pretty outfit and worked from there. Because from time to time, even the loudness of a coffee shop can feel soothing in the presence of others and combat the feeling of loneliness.

Mental Health: Your Inner World Becomes the Workplace

In this first year freelancing, I experienced many ups and downs. With every turn came a lesson. But the biggest one? Mental health is non-negotiable. Without a stable mind, the body suffers. It can start small, with headaches, stomach aches, watery eyes, anything really. If left unchecked and the stress turns chronic, your body stops functioning the way it should. And when you’re self-employed and rely on yourself to do everything, this is the absolute last thing you need.

While getting stressed, upset or frustrated is human, regulating those emotions becomes a necessity. Otherwise, you risk spiraling into patterns that harm your body and ultimately, your business.

In our corporate world, we’ve unlearned how to truly prioritize our health. Even when our bodies beg for rest, we tend to ignore them. As a freelancer or business owner, that’s no longer an option. Your livelihood depends on your wellbeing from then on.

And while this sounds scary, it’s not meant to scare you. It’s meant to build awareness. To remind you that self-employment requires proactive care. Not by taking pills everyday to combat the occuring symptoms, but rather to prevent them alltogether. The tools I found that helped me stay (somewhat) sane in this first year of self-employment are the following:

Journaling – Calms an overactive mind and prevents emotional breakdowns.
Actual rest – At least one full day off, no work messages, no emails, no guilt.
Nature time – Sun and fresh air bring back clarity and decompress.
Boundaries – With myself (e.g. no late starts or all-nighters) and with others.
Trusting my intuition – When something feels off, I listen. If it’s fear, I explore it. If it’s misalignment, I walk away.

Understandably, many of these might sound like the typical self-help quick advices we also get a ton off on social media. The key here is, to find your own tools that help you! The way I journal, might be different from the way you should. Your rest, might look different than mine. Trust in yourself and think about what makes you feel good and relaxed, not what others say should make you feel that way.

“There’s No Right Time” - But There Is a Wrong One

“There’s no right time to start” is also very common advice in the hustle world. And in part, it’s true. Perfection never comes. Therefore, it makes no sense to wait for it. But if we are being honest, there is such a thing as the wrong time.

Naturally, starting a business always comes with risks. But depending on your mental, emotional and financial state, the weight of that risk can vary. For example, maybe you’re tired of your 9 to 5 and have a great business idea. You feel emotionally supported and mentally steady. But do you have the financial backing to keep you afloat in case your first few months don’t go as hoped? Rent, food, bills – all of these require money.

Without savings to cover you for a bit, quitting out of the blue could backfire and put you in a worse spot than you were before. Keep in mind, financial stress affects mental health just as much as any other. And even with supportive people around you, they may not be able to help out financially. And shouldn’t be made to. You carry the risk of your endeavors.

In no way am I saying that any of these factors should discourage you from taking a leap of faith, but do it wisely, not blindly.

The System Isn’t Built for You

One realization that hit me early on was that the system isn’t made for freelancers and the self-employed. Especially not for first-year business owners. Growing up in Germany, the path I was meant to take was clear: school, university or apprenticeship, then full-time work until retirement. Most things are handled for you. Health insurance, structure, social payments, certain taxes even.

But leave that path? You’re on your own. Information on how to become self-employed is buried in legal jargon. Advisors are expensive and mostly don’t try to understand your individual situation. Safety nets? Please, they don’t exist. I’ve found that this failure to support entrepreneurs, was not only true for my home country but for many others as well.

So, if you are struggling, keep in mind, you are doing your best in a system that wasn’t built to support you in building your own path. And you are doing it anyway!

Would I choose self-employment again?

If all that I’ve mentioned sounds difficult and stressful, it’s because it is. I was never one for sugar-coating things. Becoming a freelancer and business owner with only yourself to support you isn’t an easy cookie to swallow. Therefore you might be wondering, is it even worth going for it? In my opinion: Absolutely. I don’t regret my decision at all. More so, becoming a freelance copywriter and web designer was one of my best decisions I’ve ever made.

The freedom to live on my own terms, even just the thought of it, had always outweighed the struggles for me. Yes, there’s fear. There’s loneliness. There’s stress. But those feelings aren’t exclusive to freelancers and the self-employed. They exist in every work environment.

The difference is: I now face them doing something aligned with who I am. I’m building something that’s mine. And that feels worth it.

As you can see,

self-employment isn’t as glamorous as it looks online. It’s messy and sometimes exhausting. But it can also be one of the most fulfilling paths if you’re clear on your “why”.

If you’re still figuring it out, that’s okay. The idea first popped into my mind at 17. Although I didn’t truly consider it until I was 19. And yet, I didn’t take the leap until 25. Looking back, earlier wouldn’t have been the right time. I was a kid, not knowing what to do with my life, no skills, no knowledge. Not saying that last July was the right time either, but it wasn’t the wrong time anymore and that’s what mattered.

If you’re on the verge of starting your business, I get it! It is a freeing, yet terrifying thought. To help people with this decision, I created a free 5-question reflective guide to give you a better idea of where you stand right now. Questions, I wish people would have asked me before I started, instead of throwing their own worries in my face. Because the goal shouldn’t be to discourage someone from following their dreams, but to support them to do it with open eyes!

And if you’re already in your first year of freelancing – congratulations! I’m launching a journal on August 8th to support new freelancers, business owners and self-employed through this messy, beautiful chapter. Sign up for a personal discount code and receive it directly into your mailbox when the journal launches!

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