ready to freelance

To freelance or not to freelance?

Posted on 10th October 2017 by

Working in your pyjamas with nobody else to answer to? The freelance life can seem like a dream! And with self-employment on the rise, you may be tempted to make the leap too.

Since setting up my own business four years ago, I’m certainly not considering going back into employment any time soon, and I love the freedom and flexibility that I get from being freelance.

Having said this, it’s not necessarily a lifestyle that will suit everybody. So how do you know if freelancing is right for you? Whilst there’s a lot to love, here are some of the more challenging areas of self-employment that are worth considering.

Being the boss

You’re the boss. You’re also in charge of admin, sales, marketing, social media and finance. When you’re freelance you need to be ready to take on all of these roles, or be willing to outsource them (and this second option costs money so may not be feasible initially). Are you ready for this, at least at the start?

It can help to know your strengths and weaknesses; some people enjoy the variety and learning or developing the skills. For example, I’m a bit of a nerd so I enjoy reading the HMRC tax guidelines and understanding what I can and can’t claim for. If this doesn’t sound like you, it might be something that you want to outsource to an accountant.

If you’re coming from an agency background and your love is design and coding, then you’re probably used to doing what you love all day. Do you want to get distracted by managing clients and dealing with other areas of responsibility? If you want someone else taking care of this for you, then being freelance isn’t necessarily the best fit.

Avoiding isolation

Being freelance can be a bit lonely; if you’re used to working in an office and being surrounded by a team all day then it can be a shock to the system when you’re working from home and don’t have anyone around to bounce ideas off, share successes and challenges, or generally just have that human interaction.

If you’re thinking of going freelance and you know you’re an extrovert, it could be useful to look into options for co-working spaces and meetups like Freelance Folk, and look for communities where you can find like-minded people and create a support network. Facebook groups can also be good for this!

Staying motivated

There will be times when it gets tough, so it can help if you know why you’re doing it. If you’re passionate about a particular area (or just about having your own business) that can be more motivating compared to just leaving a job you hate – as this could be answered by employment or self-employment. So, is the motivation just not being in your current job? Or is it something bigger than this?

Because you’re the boss, nobody else is going to tell you what to do (other than perhaps your customers or clients, and trust me, they’re biased). You will therefore need the skills to manage and prioritise your time. This can be hard, especially if you’re feeling unmotivated or the deadline is quite far into the future. Do you have the discipline to do the work when it matters?

Managing your time

There is a saying that entrepreneurs are the only people who will work 80 hours a week to avoid working 40 for someone else. The difference is that even if you do end up working more hours, you can generally have more control over when those hours are. It’s also satisfying to know that the income from extra hours worked is going directly into your pocket rather than increasing the wealth of your employers.

If you’re the kind of person who likes to leave work behind at the end of the day then I would go so far as to say that freelancing probably isn’t for you. Yes, you can define boundaries and generally have some control about when you work – but unless you’re exceptionally good at compartmentalising you may struggle to switch off completely, as it’s your business.

You will also need to think about where to draw the line in terms of how you balance your “work” and “personal” time. If you go on holiday, will you need to take calls in the day? How about responding to emails? I personally have an out of office telling clients to call or message me if it’s urgent, and I can only think of one instance where I had to find a computer at my hotel to quickly fix an issue.

I check my emails when I’m away, but don’t reply, as I just like to be mentally prepared for what’s awaiting me at home, and it doesn’t interfere with my holiday enjoyment. If you know you’re the type of person that might dwell on something you’ve read in an email, maybe don’t check them if you can avoid it.

Not only can it be a challenge to protect your time from your customers or clients, you may have to set boundaries with friends and family too. Many of us who have partners who aren’t freelance voluntarily take on tasks that are harder for someone in a 9 to 5 office job to do, but there can be a perception that your time is “up for grabs” sometimes. If you need to work in the evenings and your family want to spend time with you but you have work to do, can you handle that?


Especially when you’re just starting out and you don’t have clients or customers, it can be tricky to manage your cashflow. Are you financially in a position where you could go for a few months if you don’t have work coming in? Do you have savings? Do you have a partner or family who can support you? Perhaps you’ve had a redundancy pay-out?

Or perhaps, you actually see this as a way to motivate you.

Some people prefer to work part time and start their freelance business on the side; others want to jump straight in and are driven by the fear and need to bring money in! Which category seems more like you? That can help you to think about your route into freelancing.

Getting a mortgage is easier than it used to be and there are specialists who offer mortgages for freelancers, but it can still be more difficult than if you’re employed. If this is relevant to you, it’s probably worth getting advice from a professional beforehand.

So what’s the answer?

I love being freelance and think it can be a challenging but ultimately it’s a much more rewarding way to earn a living. If you’re drawn to it for the right reasons and haven’t been scared off by any of the potential downsides, then chances are it could be a good fit for you too.

I also think that it’s ok to try and it not work out – after my first 6 months of freelancing I had gained more skills than in 6 years of employment, so I knew that if it came to it, I would be more employable having tried freelancing.


Katy Carlisle helps people to create lovely Squarespace websites. She started her business The Wheel Exists in 2013 and also runs the popup coworking community Freelance Folk.


Related Articles:

Top 10 Challenges Every Freelancer Faces – Part One

Top 10 challenges every freelancer faces – Part Two

Freelance Freedom or Full-time Framework?