The Harsh Truth About Being a Freelancer – Nobody Told You This
Spoilers: It’s Not All Coffee Shops and Freedom
Hello fellow freelancers, it’s your man Dan, and today we’ll talk about the ugly truth about being a freelancer.
Everyone saw that everybody posts photos of “laptop life” — the beach, the coffee, the freedom, that BS is just for instagram likes, reality is a bit more than just these appearences. Sure you will have these too, but be prepared because these are only the top of the iceberg, you need to put in a lot of work to really live that life, ifykyk.
That’s because nobody shows you the 3 a.m. panic before a deadline, the ghost clients who disappear mid-project, or the weeks, maybe months (January & February) without any contract.
Freelancing is freedom — but it’s also pressure, chaos, and self-management on hard mode.
After 10 years on Upwork, and also other places, including freelancing on my own, I can tell you: this career can change your life…
But only if you survive the first few months and a few truths nobody warns you about.
Truth #1: You’re Not Your Own Boss — Every Client Is
The first thing everyone tells you: “You’ll be your own boss.”
Let’s be real — you’re just replacing one boss with ten smaller ones.
Each client has their own rules, their own deadlines, their own version of “urgent.”
The trick isn’t escaping bosses — it’s learning to manage expectations like a pro.
👉 Set boundaries early. Say no when you need to. For example when you know you can’t finish a project in time, is better to refuse the client, rather than get it, and do a messy job that will destroy your reputation. Because this is true, your reputation is everything.
I’m old enough to remember the first dialogue in GTA1 – That say: “Remember, RESPECT is everything” – This is tru in freelancing too, just replace Respect with Reputation, it’s basically the same: respect, but online.
Failing to say NO, will get you in trouble – your “freedom” will feel like ten 9–5s running in parallel. I don’t know how to explain in better freelancing terms, but that’s how it feels like working on bad projects, and with deadlines, bonus if one of the clients is a Karen.
🧩 Truth #2: You’ll Work More Than Ever
Think this is a game? Think again:) I’m not here to scare you, but hey, it’s kinda scarry, and if you’re not build for the online streets, its better to work for McDonalds, fr fr! If you can’t handle stress, don’t even think about it. In your first months, freelancing feels like a 24/7 job.
You’re the marketer, the accountant, the negotiator, the customer support… and sometimes, the therapist for your clients. Say thank you that you’re noth their baby sitter.
You’ll chase invoices, tweak proposals, fix last-minute bugs — all before breakfast or the 1st coffee. And remember if you don;t drink coffee, or any other related energy elixirs, well… you better start testing this, or other things to keep you awake and working.
But here’s the reward:
Every extra hour you invest builds your future, not someone else’s.
It’s exhausting — but it’s ownership. Also did I forgot to tell you about money, dineros, lárgent ? :)) You’ll put your own price, on your own work, and getting the money as fast as you can finish the job, well kinda +5 days escrow waiting in some cases, at least that’s how it is on Upwork.
💸 Truth #3: Feast or Famine Is Real
You’ll have months when money flows — and others when it’s just silence.
The “freelance feast-or-famine cycle” is real, and it can mess with your head. So be prepared to live like our ancestors, when you had 4 seasons in which 1 of them is complete rest, 2 are good for work and 1 is kinda ok.
Here is your Freelancing Calendar based of how good it is to get clients in 90% of niches.
January: 10-30% changes to get a new client – everyone is broke after New Years Eve and Christmass.. It’s cold af, and its depresing, aka – Blue Monday its a thing.. so yeahgood luck getting clients in January. I mean its not impossible, but I suggest you’ll take off at least the firrst 2-3 weeks of the year. Go on a trip in a warm place or something.
February: Same hsit but kinda better, let’s say 10% better maybe? Who knows, depends of your luck here.
March is when things start to get a bit of traction, you’ll see somewhere between 30-50% chances to get new contracts for your freelance career.
April, May and the first half of June are good for business like over 50-70% chances to land clients.
July, August and the last part of June are kinda good but not so, you will think you’ll make a lot of sales asa a freelancer in the summer, well maybe if you are a roof contractor 🙂
That’s because most of your clients enjoy their lifes, people go to vacation, yeah, you can’t imagine that because your a freelancer, and our days are basically the same, every day you can work, you will work 24/7 if possible, no vacation until you’re getting that goal.
That’s we choose the freelance life, for work and life balance, so don’t blame others that want to enjoy their summer! You’ll have your chance to get their money soon. And by that I mean:
September, October and November: These are the best 3 months to make money asa a freelancer. I don’t even have to tell you why, I don’t know either.. maybe people stay in houses and want to be productive because winter is comming?
Maybe the winter arc is real? And everyone is on their ground, so you need to lock up too in fyou wanna make it in the freelance game. No mater if you freelance on the streets or online, these 3 are your months of glory! Notice that I said in the streets? Yes, because you can be a freelancer offline too, like uber driver or glovo or other corner street activities that can make you money working as close to a freelancer as possible 🙂
And of course you’re wondering, but what about December?
Well that’s because … as Linkin Park will say: This is My December
December is a special month for people in general and for freelancers in particular. December can make or brake your year! why? Because it’s Christmas, that’s why… Believe it or not, my first sale ever as a freelancer was made on 25 December 2013!
It was a miracle, for sure because I was freelancing in the hard way, on Linkedin, cold messaging, not on a freelancing platform, where the clients are already looking to hire a freelancer for their project.
So here’s the deal – the first week of december is kinda ok to get clients, then 2 weeks before Christmass, nothing special will happen, maybe you won’t get anything at all, then Boom!
On 25 and 26 December, maybe even 27 all sales go trough the roof! Why? Well because its Christmass of course! People just tay inside after they eat dinner at familly and friends, and browse the internet, or TV.. So because you saw something you like, or want, not even something that you need, you’ll buy it! Don’t try to deny, don’t lie to yourself, you bought something that you didn’t need on Christmas Day, just because you were bored, and you wantet to treat yourself with a lill something, because its Christmass, and everybody wants to be happy one more time because the year is over, so fuck money!
Think about this day as a 2nd birthday, but for almost 2-3 billion people, and the others that will be free too, because everything is closed lol… so they are trappedin in house too, and yeah, they are online looking for stuff.
Anyway you got the point, then comes a few days until New Years Eve, you can make sales or not, nobody cares because everybody already spend their money for the last party of the year, so yeah..that’s a wrap of my Freelancing Calendar.
Hope it helps and brings you a bit of clarity when you can’t get a client..because maybe its not the good time for sales:)
The trick?
Diversify your income streams:
- mix long-term clients with short gigs
- create passive assets (templates, ebooks, mini-courses)
- and save during feast months to survive the famine ones.
➡️ (This links perfectly to a future post: [How to Build a Freelance Income That Doesn’t Die When You’re Offline])
🧠 Truth #4: Motivation Isn’t Always There
There will be days you don’t want to open your laptop, like the most days in your working life, freelancing is the same, if not worse. Why? Because you work from home and freelancers identifies as cats or dogs, which means laying in bed or around the house and do nothing plus maybe eat and drink 2-3 coffees. So how do you snap back on track?
If you have days when proposals get ignored, projects get cancelled, and you question everything… there is just one way to solve this- Discipline. I know I hate that too, and for some people discipline doesn’t work either. For rebel souls, only motivation works.
But, how to stay motivated, if you don’t have motivation in the first place? I’m glad you’ve asked, you see I’m that type of guy who doesn’t do hsit if he doesn’t like or want too, and I need to motivate myself the hard way. This means wishpering these warm words:
“You like to eat a ton of fast food, go to the gy, buy fire clothes and get on as many dates from tinder as possible, right? Well guess what MF! You need money to be that guy, so get your ahh to work!” Easy, you see? No all you need to do is find something you like, and apply the same concept, voila!
However, if you can build discipline > motivation, you’ll outlast 90% of freelancers.
Because most people quit right before things start working.
🚀 Truth #5: You’ll Grow Faster Than You Ever Did in a 9–5
Freelancing is a pressure cooker for personal growth, you will not see results fast, but if will happen all at once. You can have a month without nothing, no clients, then you can make 3-5 sales in 1 week, and don’t have time to finish all projects, and you will ask yourself: “why did I accepted so many clients?” Well, because you don’t refuse money! I will explain in other article how to get out of this situation.
You’ll learn negotiation, marketing, design, sales, finance, and time management – all at once.
And eventually, you’ll look back and realize:
“I’ve become a one-person business.”
That’s the magic part of being a freelancer and nobody tells you this.
The chaos is the classroom, the teacher, and the school!
🎯 Final Thoughts: Freedom Comes With Friction
Being a freelancer is both the hardest and most rewarding decision you’ll ever make.
Yes, you’ll fail sometimes.
Yes, you’ll lose clients.
But you live, to fight another day!
You’ll also gain something priceless — control over your time, your income, and your future.
Freelancing is not easy. It’s earned.
🎁 Want to Learn How to Survive (and Win) the Freelance Game?
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👉 100 Tips to Become a Top Freelancer
It’s everything I wish someone told me when I started.
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