Why Freelancers Fail: 11 Reasons Why Freelancers Quit

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Over nearly 20 years of freelancing and five years of coaching other freelancers, I’ve met surprisingly few people who’ve switched to self employment and then decided to switch back to being an employee.

(I’m met plenty of “aspiring” freelancers who’ve never dared to “make the jump” at all, but that’s another story!)

When freelancers do quit, there are some common themes in what seems to go wrong. In this article on why freelancers fail, we look at what those themes are.

The main objective of this article is to learn what not to do. Many of the reasons why freelancers fail are actually pretty easy to avoid. Read this, and you won’t have to make those mistakes yourself.

Why Do Freelancers Fail?

1. Not Giving it Long Enough

Building a freelance business is hard work. You don’t become a successful freelancer overnight.

It’s particularly difficult at the start. You’re likely to spend the vast majority of your time hustling, pitching, paying your dues and proving yourself. Moments of panic, self-doubt and imposter syndrome are inevitable.

It does get easier, but it takes time – and we’re talking years, not weeks and months. If anybody could – on a whim – quit their job, get a full roster of well-paying clients, and experience total professional freedom – everybody would do it.

Those things can and do happen for many of us. But they only happen to people who are willing to put in the grind. Freelancing doesn’t deliver a consistent monthly paycheck just for turning up.

One big reason why freelancers fail is unrealistic expectations around this.

2. Being Flaky

There are some things that all successful freelancers do:

  • They answer the phone.
  • They avoid making excuses.
  • They maintain the quality of their work.
  • They notify their clients when they’re going to be away.
  • They set an out-of-office response when they are away.
  • They agree to sensible deadlines – so that they always meets them, even when life gets in the way.
  • They check their work properly before submitting it.

All pretty obvious stuff, right?

You would think.

Many, MANY freelancers get these things wrong (believe me, I’ve hired enough of them).

With around 1.57 billion freelancers in the world, clients don’t have to go back to flaky freelancers – and they don’t. They probably won’t tell you what you did wrong – you just won’t hear from them again.

There’s nothing charmingly quirky about being one of those people who doesn’t answer the phone, or somebody who has 1000 unread emails in their inbox. As a freelancer, it’s simply unprofessional.

3. Missing Deadlines or Providing Poor Service

Once you’ve built a relationship with your clients, they’ll likely be perfectly reasonable if you’re unwell or delayed, or if you request a little more time to do something to the best possible standard.

(Small caveat to the above: When you’re first working with a new client, it’s important to do everything you can not to do any of the above things – including being ill! No, it may not seem fair, but until you’ve proved yourself, they have zero evidence to know whether you really are ill or whether you’re being flaky – as above. Sorry, but that’s just the way it is…)

Providing poor service is very different. It means persistently not doing things on time, or handing in work with obvious mistakes.

Freelance clients just want the work doing well, for a price they’re happy with. If you deliver that, they’ll often come back for more.

Whether you’re writing articles, teaching maths to university students, or coding the next killer app, clients just want it done, and want it done well. As we’ve established, if you’re not going to achieve that, plenty more people are queuing up to do it.

4. Thinking Like an Employee

This leads on from the point above.

As a freelancer, clients owe you nothing beyond the money they’ve agreed to pay you for the agreed service.

This can be a pretty stark adjustment for people who’ve come from years of paid employment. You don’t get paid on the productive days and the lazy days.

As relationships with clients build, you can move beyond something transactional and towards something that feels like a partnership – but that takes time. While it happens, consider the next point…

5. NOT Thinking Like an Employee

I know what you’re thinking. How can two opposite things both be mistakes, and reasons why freelancers fail?

The key is balance. While it’s important to remember that clients hire freelancers because they want certain work done, they’re also impressed by freelancers who go above and beyond.

Clients are impressed by freelancers who learn about their broader business – freelancers who come up with ideas of their own, and suggest other ways they can help.

Some freelancers really fail at this. Techies and IT support people are particular culprits. I’ve dealt with so many IT support freelancers who know nothing about the businesses they support. They view them as nothing more than their routers, their servers and their email accounts.

What’s better than that? Learning what days and times of the year the business comes under particular pressure. Learning which employees have particular system requirements. Learning what the company’s long-term aspirations are, and suggesting technical solutions to help them move forward.

Yes, clients just want the work done – and that should always be the main priority. But it’s still important not to work in silos. Learn more about the bigger picture, and you can make yourself more useful and win more work. That’s how partnerships are built.

6. Not Keeping Taxes in Order

Another huge culture shock for new freelancers is suddenly being responsible for accounts and taxes.

It’s scary and overwhelming, and also fraught with risk.

Some freelancers quit because of the stress of taxes. A real beginner’s mistake is treating every penny that comes in as direct income.

The reality is that it’s not all yours.

Unless you already have considerable experience of running a small business, professional advice is essential. After nearly 20 years of freelancing, I now have a much better idea of how much money I have to leave untouched to pay my regular tax bills – but I still get a nasty shock from time to time!

The worst case scenario is getting to the end of the year, receiving a big tax bill and not having the money to pay it. “I’m new to this” isn’t an excuse the authorities will accept.

7. Contracting Instead of Freelancing

A freelancer with only one client is NOT a freelancer. They’re a contractor.

However well paid you are, freelancing for just one client basically means having a job without the job security. It can also land you with legal issues around being identified as a “disguised employee.” (If you really want to frighten yourself about this, read about the UK’s IR35 laws.)

The reality is that successful freelancers often find themselves in situations where the bulk of their income is coming from one client. But diversification and a selection of different streams of income should always be the aim.

Always try to have multiple irons in the fire.

8. Not Learning New Skills

As a freelancer, you’re responsible for your own personal development.

If you’re not regularly taking courses and learning new things, you can be sure that plenty of your competitors are.

Check out these articles:

9. Failing to Nurture Small Clients

Today’s “little” client who gives you a $50 job on Upwork could be tomorrow’s major income stream.

Some freelancers quit before they realise this. Or they behave in a shabby way towards those smaller clients because they think of nothing other than the price tag on the work.

Many years of freelancing have taught me that work tends to come in fits and starts regardless of the client. What builds a more consistent income over the long term is having some clients “get busy” when others are quietening down.

Stellar freelancers treat every client like their only client, and deliver the same high levels of service whether it’s a $50 job or a $5,000 job.

The alternative – taking a disdainful attitude to the smaller players – means that when they have money to spend, they’ll spend it with the freelancer who showed them greater respect.

Apple started with Jobs and Wozniak working in a garage. Many of tomorrow’s big names are hiring their first freelancers right now – handing out their first $50 jobs on online platforms.

Not every small client turns big. But the surefire way to not be part of the success stories is to treat them like they’re small.

10. Snobbery Around Online Platforms

It baffles me how dismissive some people still are around freelance platforms like Upwork and Freelancer.

It doesn’t help that there are certain freelancing “influencers” who perpetuate the theory that these platforms are a complete waste of time.

Yes, they can be something of a viper’s nest of scams and low paying clients. Yes, you really have to have your wits about you to choose the right clients. And, yes, Upwork fees are high, and lots of people moan about them.

But right now, at the time of writing this, there are over 178,000 clients searching for freelancers on Upwork alone. More jobs arrive on the platform almost as fast as you can hit “refresh.”

I’ve worked for startups on Upwork that have gone to become eight figure companies. I’ve ended up managing entire teams of people as a result of meeting clients on Upwork. I’ve written for household-name websites that I’ve found recruiting on Upwork. I’ve travelled internationally for clients I’ve met on Upwork.

I’ve also had some stressful experiences, and worked with clients that I still have nightmares about! But I’ve come across just as many of those in the “real” freelance world.

A recent article we posted backed up the kind of success you can have on Upwork. I urge you not to turn your nose up at a freelance platform used by 20% of Fortune 500 companies.

11. Poor Invoicing and Credit Control

It’s well documented that late payment is a huge problem for small businesses. I don’t deny it’s a problem.

But I’ve also seen a LOT of the following:

  • Freelancers invoicing seemingly at random, rather than sticking to a regular monthly schedule.
  • Freelancers sending invoices that lack detail – increasing the potential for queries and for invoices going unpaid.
  • Freelancers not chasing late payments and being suitably strict on credit control.

Freelancers fail if they don’t get paid. And it’s reasonable to point out that sometimes they make it hard for themselves by not getting their invoicing properly in order.

These articles can help:


Some of the reasons why freelancers fail can be easily mitigated. Freelancing isn’t for everybody. If you read this list and recognise areas where you fall short, I strongly recommend working hard to rectify them. Alternatively, you could look at buying in some help with certain areas of your freelance business.

My Freelance Kickstarter course can help you build the firm foundations that you need for a thriving freelance business.

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