5 Not So Enjoyable Things About Being A Freelancer

Earlier this month, I wrote a blog post called ‘The Highs of Being a Freelancer‘. As promised, I’m back with another blog post, and this time, I’m aiming to balance out the highs with the things that are slightly less enjoyable about freelance life. 

I mulled over the title of this post for ages. Should it be the ‘The Lows of Becoming a Freelancer’, should it be ‘The Negatives of Becoming a Freelancer’?

Neither of these felt right because, in all honesty, even the negatives aren’t really negatives, and the lows certainly aren’t lows, especially when you’ve come from the industry I have. 

On reflection, the ‘negatives are those things that are slightly less enjoyable. The positives have so far outweighed the negatives, but as I said at the beginning, it’s not all roses. 

I think it’s important to understand some of the trickier things we have to navigate as freelancers, which is why I decided to call this post ‘5 Not So Enjoyable Things About Being A Freelancer’.

1. Learning how to manage annual leave and sickness

I’ve always lived for my annual leave, which is possibly why this has appeared first on my list of not so enjoyable things. I was used to taking a week off every three months and needed that time to recover from a busy and stressful job. 

Having started my business in January this year, when mid-March came around, I was exhausted. I couldn’t even think about taking time off as I was still building my client base and was busy getting my business off the ground. 

Thankfully, a few bank holidays were coming up in April and May. Ok, so I knew I couldn’t afford to take a week off, but with the bank holidays looming, perhaps adding a day or two of leave at the beginning or end of the bank holiday would be manageable? All of the bank holidays in the UK fall on either side of a weekend, so adding a days leave at the beginning or the end of the bank holiday would mean that I would be able to get a nice 4-day break. 

Taking these mini-breaks has worked out well for me. Taking a 4-day weekend is just the right amount of time I need to give me some R&R and get the energy boost I need. 

I’ve also taken the occasional day off in the week to go away. So long as I plan these days in advance, I can often work around my days off, either by putting in a few extra hours before my day off arrives or by managing my diary more effectively. 

I’m yet to feel comfortable taking a whole week off work, although I have a family holiday looming next month, which will be the first real test. I will still have to do some work whilst I’m away, but if I can limit this to checking for urgent emails and some social media engagement, fingers crossed, I should be able to go away and switch off for the most part.

Interestingly, since March, I haven’t had so much need for time off. My batteries stay charged for much longer, and I have so much more energy. Take from that what you will!

Sickness is another thing us freelancers have to try to navigate. Thankfully, so far, the only sick days I’ve had to work around were after my covid vaccinations (you can guarantee if anyone’s going to get side effects, it will be me!) and a bout of sickness, which I suffered from during a love spa break with my boyfriend! Timing!

It’s important to consider all of this before heading into freelance life. Being unable to work for any time means no income, which means no money to pay the rent!

2. Learning to do what your clients want you to do

This ‘less enjoyable thing’ isn’t really about learning to do what your client wants you to do. It’s more to do with learning when to do as they say rather than doing what you think would be best (or at least knowing the difference between when to challenge and when not to challenge them on something!).

I have to admit I have found this challenging, especially when a client has brought me in to do something which requires a skill set that I have, and they admit to knowing little about that particular world.  

The first time it happened, I had published a post on social media which I thought looked great. I had no pre-designed templates to work from, and I thought I had been given pretty loose reins. My client didn’t like it and asked me to take it down, despite the fact it had already had a load of likes. I pushed back that I thought it should stay on there as it had already had plenty of engagement, but my pushing back didn’t go down too well. 

I kept my role but had to learn quickly. Despite having a reasonable level of expertise at something, sometimes you have to grit your teeth and do whatever your clients want you to do. 

The biggest challenge isn’t just knowing when to push back but knowing how to push back. You want to find a way of pushing back or suggesting a different approach in a way where you maintain your professionalism whilst keeping the client satisfied.

My solution to this problem is to really get to know your clients. Understand your client’s expectations and set some boundaries. And most importantly, find out how loose those reins actually are. 

Thankfully, I now know most of my clients well enough to know when it’s ‘safe’ to suggest a different approach and when it’s best to keep my head down and do what they have asked of me.

The thing to remember is that you are there to help them with their business. You’ve been brought in as a freelancer to make their lives easier, not more complicated. 

It may even be worth agreeing with them upfront whether they are happy for you to make suggestions or recommendations and ask them when it’s best to run these ideas by them.

3. Unpredictable Income

The joys of getting paid as a freelancer! The chances are, as a freelancer, your income will fluctuate frequently. 

With unpredictable income comes unpredictable workloads.

And that’s without mentioning clients who take forever to pay. From experience, it’s often the larger companies who are the slowest to pay!

If truth be told, a lot of things to do with being a freelancer can be unpredictable, particularly when you’re still learning the ropes and getting your head around things. 

I knew the first year of being freelance would be unpredictable. I had no existing client base, and I was starting from scratch. 

I’ve been lucky enough to have regular clients who always pay me on time. I also have regular clients who consistently pay late and who I have to chase every month.  

I had a client who decided during the summer that he had very little work for me. He gave me a days notice to let me know he didn’t need my services the following month. A month later, he let me know that he wanted me to start working for him again. Once again, giving me very little notice. 

I’ve had months where I’ve earned enough money to pay my rent and bills. I’ve had some months where I’ve had to dip into my redundancy pot.

I don’t think I’ve had two consecutive months whereby I’ve earned the same income. 

Financially, it’s helpful to have savings you can dip into if you need to, but not essential, as long as you’re ready for what could be a bumpy financial ride ahead.

Tip: I find it helpful to leave some flexibility in my diary for picking up new clients, meetings, changes in client requirements, and other random things that come out of the blue. It’s exciting picking up new clients, and it can be hard to say no. If they want you to start working on something immediately and your diary for the next few days or weeks is looking chocker block, you may be unable to meet their expectations, which will cause you a further headache down the road. You’ll either need to learn to say no to things or leave some space in your diary for those sorts of circumstances. 

4. Remote working isn’t always easy

Ah, the dream of remote working. As a freelancer, I dream of travelling the country, or perhaps, even the world, working from cool surf shacks by the sea, cosy cottages in the hills, or skyscraper hotels in the city. Oh, the dreamy, flexibility of freelance life.

These are all incredibly romantic images, but are they realistic?

Well, certainly not so far! 

With the world in and out of lockdown for the best part of 18 months, the first few months of being freelance were spent sitting in my living room with nowhere else to go. 

Even when the world started opening up again, unpredictable income meant I couldn’t afford to go and splash out in cafes every day. 

I’ve been for afternoon walks where I’ve thought about sitting in a nice lush green space to do some social media engagement, only to find I can’t get a good enough phone signal. Likewise, on the odd occasion that I’ve ventured into a coffee shop, I’ve often been unable to connect to their networks, and my hot spot has been against me too. 

I would also love to know what the coffee shop etiquette is. How long is it ok to be in there? And how many drinks or food items are you expected to eat and drink whilst you’re there? What do you do with your laptop when you need to go for a toilet break?

I can’t wait to test out ‘real’ remote working. I’d be lying if that hadn’t been one of the reasons freelance life had lured me in. 

Oh, to be sitting in a beautiful beachside shack in Goa, watching the monsoon rains fall, as I write my future best-selling novel.

5. You never really know if you’re doing the right thing

Every freelancer I’ve come across since starting my business has confessed that they are simply winging it. Nobody really has a clue what they are doing. 

We are all different beings, offering differing services to clients with very different needs. 

There is no manual to being a freelancer. Yes, there are books, but I’ve found the best way to learn is by networking with other freelancers. Joining Facebook groups, following people who do similar freelancing roles on Instagram and growing my LinkedIn network have all been great ways of learning and improving how I perform as a freelancer. 

I’ve also taught myself a lot. I had to become an expert in Marketing & Finance. I was also working in an industry I hadn’t worked in before, although I wouldn’t go as far as saying I had to learn my trade from scratch. I was already writing a lot and was always on social media, two things critical for my new role. 

Thankfully I love to learn. Whilst I may never be an expert in Marketing or Finance, I taught myself everything I needed to know to do my job. It’s saved me some money in the long run as I haven’t had to go out and hire other people to help. Although, I haven’t ruled it out for the future once my business has grown. 

So much of what I do daily is a case of ‘let’s give it a go and see if it works’, which seems to be working so far. Life is all about trial and error. Why should work be exempt from that?

Some people wouldn’t dream of turning freelance until they felt like they were an expert in everything. But there is no need to wait. I’ve learnt so much over the last eight months. Not once has my lack of expertise in a specific area stopped a client from wanting to work with me. 


If you’re still reading this, then congratulations 🙂 You haven’t been scared off by my ‘5 Not So Enjoyable Things About Being A Freelancer’, which probably means that it’s time to take a leap of faith and give it a damn good go 🙂 

As I said at the beginning, these aren’t real negatives to the job. They are just some of the hurdles you will need to leap over to do the job you’ve always wanted to do. 

If you haven’t checked out my blog post ‘The Highs of Being a Freelancer‘, go check it out if you need any more convincing whether freelancing is the right career move for you. 

I wish I could sit here and say that being a freelancer is a dream come true. If the truth be told, I never dreamt big enough to imagine I could become one. But I can honestly say that taking that leap of faith was the best career decision I’ve ever made. 


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5 Comments Add yours

  1. capost2k says:

    Newsflash, Becky! We’re ALL just winging it! 😁 Nobody gets a guaranteed “Tomorrow.”
    That’s why we need to keep short accounts with our Creator. ❤️&🙏, c.a.

    Liked by 1 person

    1. Haha brilliant! I’m glad I’m not the only person winging it 🙂

      Liked by 1 person

  2. A fascinating insight!! Thank you!

    Liked by 1 person

    1. I’m pleased you found this interesting 🙂

      Liked by 1 person

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