I am a successful freelancer for more than 8 years now, here are 5 reasons why I hate it.

“You are your own boss” — Ughh… While the life of a freelancer is deemed as full of freedom from many aspects, here’s why I hate being a freelancer, and the common myths associated with the term. I’m Al, I’ve been a freelance business consultant for more than 8 years now.

1. You are your own boss

It’s almost the same as saying — you are your own father as a child. You get to set the rules and eat as much candy as your heart desires. Yet, at the end of the day, you’re not qualified to be the best father.

Being your own boss gives you more responsibility and pressure than the alternative. You’d think that that annoying boss of yours is making your life a living hell. That may be true, but at the end of the day, you’re responsible for a piece of the puzzle. Your boss is responsible for another piece.

It’s important to note that I’m addressing here, freelancers who aim to be successful with ambition. If you’re intending to make a small amount of cash per month, it’ll be an adequate challenge. However, it gets more challenging the more successful you get.

You generally don’t see that in a freelancer, the pressures falling on her/his shoulders are caused by her/his work. A “9–5” usually ends at 5. A freelancer’s mind is usually occupied 24–7 whether she/he likes it or not. That adds to a freelancer a burden that one could despise and hate over time.

2. You learn more

You get more responsibilities, so you learn more. That’s correct. However, you are not learning very important professional lessons that you would almost never learn as a freelancer. The more you are a lone freelancer, the more you grow your confidence and ego, the less you’re capable of depending on others. That’s the problem. Teamwork is a skill that is vital for any worker’s psychological health. 

“If I need to get it done right, I’ll have to do it myself.” — is the most poisonous phrase you could hear. I said it before, and I’ll say it again. Chances are there are people out there in this world, who are doing whatever you think you’re good at better than you. 

3. Cashflow

No matter what you do as a freelancer, your pocket is most certainly uncertain. Yes, you can be making more money than what you have been making in a 9–5. However, your flow could be very inconsistent. My earnings chart looks like this. Others might not have this, particularly the same. 

Yet at the end of the day, the truth of the situation is that you might lose your clients next month, and take a hit.

The steady flow is healthy for projecting monthly expenses. Don’t go buying a car on your good month, when the future might hold a bad month.

Hate Freelancer's Life

4. Specialization

If you’re a freelancer, then you’re a sales, marketing, financial, HR, and operations person. You’ll learn a great deal from the range. Yet, chances are you won’t be a master of any. 

“Jack of all trades, master of none”

Although I’ll give freelancers credit, the aspect of range qualifies them to become successful CEOs in the long run.

5. Working hours

You don’t have to wake up in the early morning and see your boss at 9 AM. That’s true, but if you aim to be a successful freelancer, then it’s quite a challenge to succeed without working a tremendous amount of hours, far more than the average 8 hours per day. 

Additionally, your working hours are determined by your clients. You could be self-disciplined and inform all your clients that you work from X to Y and that’s it. The problem is when a client sends you an email, and you see it during your working hours. Your mind will still process it during the whole day. Your freelancer mind has different working hours, and that’s all the time.


I’ve been having a vision for the past several years. A vision of me going to work in the morning with a pack of donuts to give my teammates, and to learn from my boss’s work experience during a working day. Shut down my work and brain at 5 PM, and go enjoy the other aspects of life.

Not quite a bad vision if you ask me.

In the end, it’s how you look at it. Some freelancers are having the greatest time, others are having the worse times; Similarly for non-freelancers. In a nutshell, there are people out there who are want freelancing as a lifestyle, and others who want a “9–5”.

I’d advise you to not get hooked up on a system. They’re like apples and oranges. They’re different, but they both provide value and always will.

My Website: https://www.alanany.com
My Journal: https://www.alanany.com/journal

A few interesting related reads:

Freelance platforms that are actually worth it.
I’ve been freelancing for as long as I can remember. The easiest thing in freelancing is getting demotivated, and some…alanany.medium.com

$0 to $100,000 via Upwork, how you can do it in exact steps — Guide
Freelancing is very much like dating on Tinder. Clients are looking for someone, and they’ll probably swipe you away…alanany.medium.com

I made $100,000 on Upwork, and so can you.
The world’s system puts you subconsciously in a constant feeling that when you’re not specialized in something, you…alanany.medium.com

I did 3 everyday things — my income quadrupled, and my life upgraded.
I’m a risk-taker, always was, and always will be. I’m not your usual 9–5 employee. I usually perform well with my own…alanany.medium.com

If you’re interested in starting your own business, here’s an interesting read: https://albusi.com/business-reads/coffee-shop-business-plan-your-guide-for-2023/

One response

  1. I’ve done it for 30 years. I am also successful and yes I now loathe it. I actually signed up to be an Uber driver as there is nothing left of my personal life. I don’t even have a decent website but found it growing on it’s own faster than I was.

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