The Honest Advantages and Disadvantages of Freelancing

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Freelancing can transform your working life, and give you more freedom and balance than you could ever hope for in a “traditional” job.

But it’s not all picking and choosing the best projects and working from somewhere with a beach view. There are plenty of downsides too. It’s actually surprisingly difficult to find people willing to share the honest advantages and disadvantages of freelancing.

There are a couple of reasons for that: First off, many people who promote freelancing online have ulterior motives. Those keen to push courses and membership schemes at any cost often give in to the temptation of sugar-coating the realities. There are also plenty of freelancers who, for reasons of pride and “saving face,” prefer not admit that – at times – freelancing can be a stressful struggle.

In this article, I reveal the REAL truth, and share all of the pros and cons of freelancing.

Why Listen To Me?

I’ve been working as a professional freelancer since 2004, doing everything from IT consultancy to freelance writing, editing and project management. My wife is also a freelancer, making us a 100% self-employed household.

I’ve been running HomeWorkingClub since 2017, a site I launched to provide people with an honest and down-to-earth take on freelancing and remote working. And I didn’t swap freelancing for talking about it (as many bloggers do). I remain an active freelancer, with various different gigs on the go.

As well as coaching aspiring freelancers, I also regularly survey the freelance community. As such, the advantages and disadvantages of freelancing listed here are based both on my experiences, and on feedback from lots of global freelance workers.

It’s incredibly rare to encounter freelancers with any desire to go back to working as an employee. Before sitting down to write this article, I asked myself if there was a salary I’d accept to abandon my freelance freedom and return to working for a single “boss.” While I can’t pretend that a seven-figure offer wouldn’t turn my head, there’s no realistic figure that would tempt me – even if it were double what I earn now. The freelance lifestyle is a lot to give up.

But this article on the pros and cons of freelancing is about balance. There ARE plenty of downsides, and depending on your personality, your priorities, your aspirations and your commitments, freelancing might NOT be a good fit for you.

Once you’ve read this, you will know either way.

The Disadvantages of Freelancing

I’ve decided to begin by listing the cons of freelancing. Why? Because I believe in hearing the bad news before the good. Let’s get the nasty stuff out of the way first.

1. Inconsistent Income

If you enjoy the stability and security of a dependable monthly pay-check, freelancing will be a BIG culture shock. If you need that stability and security to stay sane, freelancing is not you.

Imagine things like this:

  • Hearing from a client that they would like an extra couple of days of regular work from you, to the tune of $1000 per month. That’s equivalent to an instant $12,000 per year “pay rise.”
  • Landing another new gig doing work that truly enthuses you. An extra $1,600 this month for work you’re genuinely excited about!
  • Receiving an email from a client you worked with years ago: They’ve moved to a new company and have some ongoing requirements they’d like to use you for. Should add up to $500-1000 each month. Boom! Another “pay rise.”
  • Noticing one particular client has gone a little quiet, and wondering if you’ll struggle to get the $2,000 they owe you.
  • Getting a call from another client to say that they’re awfully sorry, but they’ve decided not to outsource any more. From next month, the work you’ve been doing for them for years (paying about $800/month) will be taken “in house.”

Every one of those is a REAL LIFE example of things that have happened to either me or my wife.

Not only that, every one of those things happened LAST WEEK. In ONE WEEK. And all while we continued with our ongoing work and a whole host of other client and personal projects.

On one hand this is incredibly exciting. If that was your overriding feeling when you read it, you may be a freelancing natural. But the flip-side is that it can make your life an emotional and financial rollercoaster – and you either have the stomach for it or you don’t.

A while back, I surveyed freelancers who visit this site, and inconsistent income was the number one disadvantage of freelancing that they highlighted.

Disadvantages of Freelancing screenshot

2. Dealing With Being Unwell

Being ill SUCKS when you work freelance, and makes you highly envious of those who can just call their manager and say “sorry, I can’t come in today.”

It makes you even more jealous of people who get sick pay.

When you’re unwell as a freelancer, you don’t only have the stress and discomfort of the illness itself. The moment you accept that you’re ill enough to need to slow down, a clock starts ticking on potential missed deadlines and dissatisfied customers.

Clients are usually reasonable, but it’s not as simple as saying “well, I’m ill, they’ll be OK to wait.” They probably have deadlines too. And if you’re working for any brand new clients, they have zero evidence that you’re usually fast and reliable. Having to extend your first deadline is a bad look, even if you literally can’t move – and clients have a limitless selection of millions of other freelancers to turn to instead of you.

There’s no way to put a positive shine on this. When you freelance and you’re unwell, you end up with a combination of deadline renegotiations, days when you force yourself to work when you really should be resting (which tends to drag out your illness), and days of catching up on everything when you’re feeling better.

It sucks.

3. The “Feast and Famine” Nature of The Work

Despite decades of combined freelancing experience, and plenty of regular clients, my wife and I still experience periods of what we call “feast and famine.”

Months when you have exactly the right amount of work are rare. Freelancers tend to have too much work (which is lucrative but tiring), or not enough, which in theory means you have time to relax, IF you can learn to stop panicking about when things will pick up again.

It’s a similar problem to the inconsistent income. The solution – such as it is – is similar too: Over time these things do level out, and you just have to trust in fate. Despite both “feast and famine” and inconsistent monthly income, our yearly financial results are steady and consistent (with our turnover and profit usually rising year on year.)

The feast and famine thing does require you to roll with the punches. Nobody wants to turn away well-paid work, so you tend to take it when it’s there, even if it does mean some late nights. And, over time, you start to spot seasonal trends and learn to make the most of the quieter periods – relaxing rather than fretting.

Once again, you either have the stomach for the rollercoaster, or you don’t.

4. Having No Insurance or Benefits

One of the disadvantages of freelancing is the fact that everything is on you: saving for retirement, ensuring you have medical cover and other insurance, and even paying for your own training and self development.

We’re very fortunate to be based in the UK where – for now – we have the wonderful National Health Service. Freelancers in the US and other countries have much more to think about (and to spend) to ensure they have medical coverage.

A trade-off for being master of your own destiny is that you don’t have the security of an employer providing all kinds of safety nets and funds for the future. When you set your freelance rates, you need to ensure you’re charging enough to allow for such things.

5. Doing Your Own Marketing

I don’t really mind marketing. If I need more work, I can generally head to Upwork and find something interesting, or reach out to my professional network. I actually quite enjoy the buzz of seeing what’s out there and getting started on a new project.

But many freelancers HATE marketing, and don’t realise at the start that it’s as integral a part of freelance life as doing the actual work. Marketing was the second most mentioned con of freelancing when I last surveyed my readers.

6. Doing Your Own Admin and Accounts

Just as marketing is something freelancers have to do alongside the work they actually get paid for, so is admin and accounting.

Once again, everything is on you: making sure your technology works, and that your data (and your clients’ data) is safe, submitting annual accounts and tax returns, and dealing with compliance and legal issues.

These are all things I readily accept after so long, but they come as a surprise to some new freelancers. There are plenty of great designers who shudder at the thought of dealing with tax and VAT, and plenty of writers who struggle with providing their own IT support.

There are only really two choices: do these things yourself, or pay people to do them for you. Even if you choose the latter, you don’t get a completely free pass. It’s YOU who signs off on your accounts and is responsible for what you declare to the government. And it’s YOU who has to confess to a client if you lose their data and haven’t backed it up.

Admin tasks were the third most mentioned con of freelancing when I surveyed readers.

7. Lack of Understanding from Others

This is a tricky one, and it manifests itself in various ways.

We’ve just talked about doing taxes and accounts. People who only work as employees never have to worry about these things: The taxes are deducted at source, and they don’t have to understand capital allowances, dividends, profit and loss and distributable reserves.

People who work as employees don’t understand that you might not be able to finish at five because you’ve just won a job for a new client, and impressing them could mean a huge boost to your income. And they don’t understand that you may be rolling in cash one month and tightening your belt the next.

People who work as employees don’t always understand that your home is your workplace, and that you still have deadlines to hit, even if you’re hitting them wearing sweatpants.

I could go on, but I imagine you get the picture. A downside of freelancing is a lack of empathy from others around some of the challenges you face every single day. And that CAN be draining. There will always be certain friends and family members who just don’t get it.

The Advantages of Freelancing

The upside of starting with the bad is that it’s all uphill from here. Next we have the PROs of freelancing:

1. Freedom To Do The Work You Want For WHO Your Want

Only last month, I was keen to get a couple of new clients on board – for a few reasons:

First off, we plan to move house in the coming months, so want to maximise our income. I also like to “keep my hand in” with freelancing, rather than relying on income from my websites and existing clients – it’s important to me that I “practice what I preach.” Finally, if you don’t keep doing work for new clients, your freelance portfolio gets stale and outdated.

The time that elapsed between me deciding to get some new clients and having them “signed and sealed” was less than a week – and they were both gigs that I was genuinely excited about.

The first came from a trawl of the Upwork job board. It was a ghost writing gig on a subject I’m hugely fired up about and inspired by right now. The second came from a previous client who’d moved to a new tech firm, and it’s work involving technology that’s fresh to me. It’s already proving fascinating.

Screenshot of searching for jobs on Upwork

I’m not going to pretend it’s always as easy as that, and it certainly isn’t when you’re just starting out. But one of the huge advantages of freelancing is being able to pick and choose work that genuinely inspires you. Freelancing provides you with enormous variety.

In my years of freelancing I’ve worked with dozens, if not hundreds, of different companies. I can’t imagine a working career that only involves working with a handful or (shudder) just one.

(It’s also worth mentioning here that you also have the freedom NOT to work with people you don’t like, or clients you get a bad feeling about. That is a whole separate benefit, and one not to underestimate the value of!)

2. The Ability to Branch Out

Lots of freelancers start blogs, have one or more side gigs on the go, create courses, or freelance in more than one area.

They do it because they CAN.

There’s something both inspiring and liberating about being free to branch out in any way you like. The blend we personally aim for in this household is a mix of client work (for guaranteed income to pay the bills) and more long-term, slow-burn projects – the kind that build assets and create passive income.

It’s worth remembering that you can’t do this – at least not to anywhere near the same level – if you have a 9-5 office job. Try telling your boss that you’re blocking out Fridays to work on your new blog and see how that works out for you!

This freedom also allows you to move into different areas of work. At any time, you can take a course, learn some new skills, and begin to offer a different service to clients. It’s exciting.

3. Diversifying Your Risk

Saying that working freelance is inherently more “risky” or “less secure” than being on the payroll is – to me – a huge myth.

During the pandemic, plenty of people lost their jobs overnight. People in some affected sectors lost six figure incomes overnight, and ended up swapping lavish lifestyles for visits to food-banks.

My wife and I were affected too. We immediately lost some clients when the first lockdown started, and had others that gave us less work. But we didn’t lose all of them.

Anyone can lose a job. It’s perhaps a controversial opinion, but one of the advantages of freelancing is that you don’t tend to lose ALL of your clients at once. And you can immediately begin markAnd you can immediately begin marketing and trawling the job boards to find more.

I’ve repeatedly seen people in high-paid jobs being laid off, and then waiting months to find something else, during which time their financial position crumbles.

I’m not denying that freelancing can feel financially precarious, especially in the early days of getting established. However, I think the idea that employment is “safer” is beginning to look rather outdated.

4. Not Having a Boss

While there’s a (valid) argument that the “clients become your bosses,” it’s not the same. One big pro of freelancing is the fact that YOU are the boss. You work in partnership with clients, on activities that work for both parties. If things stop working for you, you can even say “enough’s enough” and fire a client. You can’t do that with a boss!

I agree things with clients. I negotiate with clients. Yes, it’s my job to please them, but that’s a matter of professional pride, and not just about keeping them happy.

Being your own boss is a whole different paradigm to working for somebody. As a freelancer, the only “toxic line manager” you ever have to worry about is you. (That can be an issue, but it’s one for another article!)

5. Working How, When, and Where You Like

Freelancing means no fixed working hours, no dress code, and no set location. Not even the most laid-back remote first company will offer you the kind of flexibility you have when you’re freelance.

Ironically, my wife and I – and many other freelancers – still stick broadly to a 9-5 Monday to Friday working pattern. It makes sense for a whole bunch of reasons, not least fitting around the school day and when other clients are around. But we do take advantage of the freedom in various other ways:

  • First warm, sunny day of the year? No WAY I’m working. I’m going for a bike ride and a coffee, and then reading my book on the beach.
  • Sick of the same four walls? There’s nothing (other than pandemics!) stopping me from doing my work from an Airbnb or a hotel anywhere in the world.
  • Children unexpectedly off school? No problem, we can shuffle things around and work in the evening.

Different freelancers make use of their freedoms in different ways. Before we had a family, we took much more advantage, with less regimented hours, loads of travel, and even five years doing the whole “digital nomad” thing and living in Portugal. We don’t do so much now, but that freedom is still there, and it offers a permanent sense of potential and possibility.

Laptop on a hotel bed
Working freelance from a hotel bed!

It’s certainly one of the advantages of freelancing that makes it very hard to contemplate going back to an “old school” job.

6. Not Needing to Ask For Time Off

When I’m asked my number one pro of freelancing, I always give the same answer: “I never have to miss a parent’s evening, a nativity play or a school performance.”

I also never have to utter the phrase, “I’ll see if I can get time off work.”

If I need it and want it, I can have it.

This is a HUGE deal, and it’s not only about school plays and doctor’s appointments. My wife and I have had a long break for Christmas – at least 7-10 days – every year since we’ve both been freelancing. We don’t have to wait until it’s our turn, or have a “but you took the time off last year” argument with a colleague.

Like not having a boss, this is profoundly different to being employed.

It’s important to emphasise that this doesn’t just mean you can take time off at the drop of a hat. The planning that goes into our holidays is immense: We have to notify clients of when we won’t be around, make financial plans (because we don’t get holiday pay), and usually have crazily busy weeks before and after. But there’s never any question of us being told “no” by a boss – which is pretty sweet.

7. Unlimited Earning Potential

Earlier, we talked about how employees have the stability of a regular monthly pay check. The trouble is, for most of them, the figure on that pay check will only ever go so high. Employees can work towards a promotion, but the salary of the next level up is almost always predictable and capped.

It’s different for freelancers. They can learn more skills, increase their rates, branch out into passive income side gigs, and gradually move from being an individual freelancer to being a fully-fledged business. Something a lot of creative freelancers do is graduate to an “agency model” once they hit the ceiling of work they can do personally. My wife and I both do this, outsourcing “overflow” work to other freelancers, when we have it, managing them and taking a cut.

Many people treat freelancing as the first step to entrepreneurship, eventually spending more of their time “on the business” than “in the business.” The sky really is the limit when you get to that stage.

The advantages and disadvantages of freelancing are pretty evenly balanced, and one person’s “exciting” can be another person’s “terrifying.” But if, after reading this, the pros excite you more than the cons frighten you, that could well mean that freelancing is the lifestyle for you.

If you’d like to share your own views on the pros and cons of freelancing, feel free to add your contribution in the comments.

The Inevitable Plug

If you enjoy my down-to-earth approach and would like to start a freelance career of your own, take a look at my Freelance Kickstarter course. It takes you right from deciding what you’d like to do to winning your first paid gigs. It takes very much the same approach as this article, and unlike many such courses doesn’t shy away from the hard work and realism required to become a successful freelancer.

Here’s one of the testimonials:

“This is a course created by a man who is clearly passionate about what he does, who anticipates questions and provides links to further very lucid reading matter that addresses those questions, and who is not in the business of taking your money and giving you dross in return. Indeed, in my opinion, the price of the course is absurdly low.

I can honestly say that this is, without doubt, the most thorough and beneficial course that I have ever bought, and I congratulate Ben on his superb achievement.”

Peter O

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