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The Reality of Freelancing: Why Many People Quit

Freelance is not a freedom paradise. Freelance is hard. Freelance is for everyone. Here are the caveats of being a freelancer that will try to push you out of the boat.
The Reality of Freelancing: Why Many People Quit
Photo by Jan Tinneberg / Unsplash

I just keep saying that freelancing is not for everyone.

I've got a mate who has been working in a web development agency. The agency was running on an Upwork and landing clients there. Employees were also using Upwork for billing purposes.

When my mate left he arranged with the agency to keep his established Upwork account and he also managed to keep the client to himself.

At that point, he had a carte blanche to skyrocket his freelance business.

However, when the project has come to an end, he quit freelancing and switched to 9 to 5 job in a local, not-so-remarkable development company.

His main concern was a lack of stability and a permanent feeling of uncertainty. If he had a chance to work as a freelancer for a longer period, he would have even more reasons to quit.

Here are the most common ones.

Juggling Freelance With Full-Time Job

Many people start freelancing by combining it with a full-time job.

May seem unobvious, but doing that is a terrible idea.
The most reliable way to perform badly on both sights and burn out.


Even if it's a remote one, a full-time job typically implies permanent high availability. That's exactly why it's called full-time.

Freelance is usually associated with a flexible, constantly changing workload. Running several freelance projects is doable by juggling and leveraging floating availability.

Being involved in freelance together with a full-time job is a failure in the majority of cases. Typically because there is not enough room for juggling the availability.

It's just one of the most reliable ways to try and then quit freelance, I swear.


Speaking about freelancing as a software developer... well it's badly exposed to burnout.

Lack of stability, high level of stress, and responsibility pressure, in the long run, it's unbearable to the majority of people.

Another trap is the uncontrolled working schedule with an unlimited amount of work.

As a freelancer, you can always increase your workload by finding more projects.
It's very attractive and I would even say, addictive, because the compensation linearly depends on the workload. Who would refuse from getting more money?

As a result - overwhelmed capacity and inevitable burnout.

Project and Time Management Failure

Freelance brings freedom that comes at a cost. It requires extra project and time management skills.

It's a part of a freelancer's work even if the primary service is not related to project management. As a freelancer it's you who make estimations, plan things, and take responsibility for it. It's you who should take extreme ownership of the project.

If not done right, it may lead to the failure of the whole project. That's the scope of responsibility that many people are not ready for.

Abusive Clients and Scammers

One of the most painful problems is non-paying clients. Careful clients cherry-picking and billing through escrow on freelance platforms partly solves the problem, but shit still happens and no one is 100% secured.

Another problem is abusive clients. Unbelievable, but there are people out there who are impossible to work with! Furthermore, they are hardly possible to spot until they abuse you.

Paperwork, Billing, Taxes

Nobody likes dealing with that. If you are providing services to international clients, while carrying out a nomadic lifestyle, multiply the headache by 3.

Freelance Strategy Failure

Last but not least.

The most straightforward way to quit freelance is by doing fundamentally wrong things.

Freelance strategy is almost like a career, but a bit more complicated because it includes other domains like pricing, marketing, sales, and client acquisition.

It also requires a lot more financial and tax planning as well as a time and money investment vision in the long term.

It's easy to do things wrong.

Is It Still Worth It?

Reading all this would make you think that I'm talking you out of freelancing.

I would say that freelance is not a holiday resort and spa way of doing a job.

Freelance is like coffee. Coffee is not sweet. It's bitter, sometimes a bit sour, but it makes you feel good. Freelance gives benefits that are sometimes worth the hassle.