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The 5 Hardest Things About Being A Freelancer

Being a freelancer is awesome, on the whole – but it comes with its challenges.

Here are the five biggest hurdles I've encountered since going solo.

1. Less human interaction

As someone who's extroverted and thrives off the energy of others, I've found this aspect of being freelance the toughest.

I can go days without speaking to anyone in a working capacity sometimes. It's great in some ways, as I can get my head down and work. But in other ways, I miss talking to people as frequently as I used to. And my mental health has definitely been affected by this lack of communication at points.

It can also be easier to lose focus when you don’t have that direct, face-to-face accountability as you would in an office or on a video call.

I’ve found that attending more networking events and getting out of the house every day without fail has helped me overcome my isolation-based malaise and improve my overall productivity.

2. Repeated rejection

Now, I'm happy with the clients I currently have, and I'm grateful that I've even been able to run my own business for the last year because many people don't get this far.

However, the fact is – if you're a service-based business and want more clients, you're going to have to put yourself out there. And the more you put yourself out there, the greater the likelihood is that you’ll face rejection (or, worse, be ghosted). From my experience, this happens around 95% of the time.

Whether you apply for a project or put out a LinkedIn post, you’re going to get people turning their back to you – on a daily basis.

It's not like when you're a full-time employee at a company belonging to someone else, and once you've got the job, you're tied in and don't have to think about applying for another one (hopefully) for a long time.

I know that's the risk that comes with the territory, but rejection is still hard to take sometimes – particularly when you think you're a perfect fit for a project and are told you're not.

3. Fear of losing clients

This is an obvious one.

Sometimes, you can make that much money from just one client that the thought of how much your income would shrink if they stopped working with you makes you anxious as anything.

You can also lose one or two lower-paying but consistent clients, and in this scenario your income could drop by 10-15% (and possibly more in some cases). Imagine if that happened to someone in a ‘regular job’?

This is why I always use the phrase ‘risk-reward’ when summarising what being a freelancer is like. If you get a stream of regular clients (and secure them for the long term), you make more money than you would in a similar position at someone else’s company. It’s just a fact.

But with that increased income comes a hell of a lot of risk – and to get the reward of more income, you have to take the risk of knowing you could lose everything in a given moment. With no severance pay, let’s not forget.

Speaking of risks, here’s another big risk you take when going freelance…

4. Way less overall financial security

When you go freelance, you forfeit your right to paid days off, a company pension scheme, company-sponsored healthcare, unemployment benefits, and probably some other perks I’ve forgotten about (fresh fruit every Monday doesn’t fucking count).

But when I went to America last summer, I had to work over and above my usual hours for four weeks (which I had to kindly ask my clients to honour) just so I had enough money to get through the two weeks that I was off. That period brought it home to me how tough it was to take time off as a freelancer and the importance of planning ahead.

5. Having to manage (almost) everything yourself

Here’s the thing. I know a few things about content marketing (which is a relief), and how to do my job to a certain standard. But I still haven’t got to grips with:

  • How to create and maintain a consistent daily working schedule (i.e., I start at X time and finish at Y time).

  • How to promote my business effectively.

  • How to be a good ‘salesperson’ (I’m getting there, but it’s tough to know which tactic is definitively the best).

  • How to do a tax return.

  • How to keep track of my income and outgoings (thank fuck for the Starling app, though, am I right?).

  • How to optimise my payment terms on my invoices for the rare occasion that someone pays late or doesn’t pay at all (thankfully, I’m yet to experience the latter).

You get the idea. I’m a creative person, but I don’t think of myself as a businessperson. I know I am – on paper – but I’m not like some suit who sits at a desk working his way through balance sheets with unwavering confidence. Sometimes, I haven’t got the slightest clue what I’m doing.

That’s why I’ve hired an accountancy firm, hence why I included (almost) in the heading. They’ve taken that weight off my shoulders, for now at least. If I didn’t have them sorting out my payslips (I still don’t understand what PAYE is) and advising me on various bits and bobs, I’d well and truly be up Shit Creek without a paddle.

Thanks for reading! Like I said at the start, there are more good things than bad about being a freelancer. Otherwise, I wouldn’t do it. One of the best things about it is meeting different people with unique stories, motivations, and goals.

If you'd like to talk with me about your marketing goals or just anything relating to your business, shoot me an email and let's talk :)


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