Should I go freelance? The benefits (and challenges) of being self-employed

Going Freelance: Building Work Around Your Life, Going Freelance, freelance, freelancer, self-employed, solopreneur

Going freelance can seem like an attractive prospect for anyone who’s looking for a new career challenge. Working for yourself, ditching your highly annoying boss and creating a more flexible way to earn a living all sound like definite plus points.

But is the reality of being a full-time freelancer as positive as it looks from the outside? As a freelancer of nearly six years, I can tell you that it’s not always plain-sailing – but it’s a career path that can help you build a better life around your work.

To help you decide if freelancing is for you, I’ve summarised some of the key benefits and challenges, so you’re ready to make this life-changing decision.

The benefits of going freelance

Let’s start with the really good news first. We’ll look at the core advantages of going freelance, how they will benefit you and why you’re right in thinking that now is the ideal moment to give up the security of a salaried day job:

As a freelancer:

  • You’re the boss and in charge of your destiny – as a self-employed person, you’re the CEE – the Chief Executive of Everything – and the boss of your company. There’s no manager, no supervisor and no-one micromanaging what you do. If you thrive well working on your own initiative, freelancing is the perfect occupation.
  • You have more flexibility and freedom – as a successful freelancer, you have the freedom to choose who you work with, what projects you take on, and how you balance your work life with your social life, family life or any personal interests and hobbies. You need no-one’s permission to take a duvet day, or to approach a new customer – the buck stops with you, and you make all the big decisions about your work life and business.
  • You can work when you want – there’s no ‘9 to 5’ as a freelancer. You can work a structured 5-day week doing office hours (if you want to), but you can also choose to work earlier, later, or for less hours. The flexibility of this working arrangement makes the solopreneur life extremely attractive to people with multiple responsibilities, limited time to work, or a desire to improve their overall work/life balance.
  • You have a mobile office wherever there’s Wi-Fi or 4G/5G – the advances in mobile and cloud technologies means you can easily run your business from a laptop or mobile device. If you want to work from home, you can. If you decide to work from a local coffee shop, you can. If you prefer the community feel of a coworking space, you can join one and get yourself a hotdesk to work from.
  • You profit from the hard work you put in – when you work harder on a project, you’re directly rewarded for this work. There’s no waiting around for a performance-related company bonus. As a freelancer, if you put in the hours and negotiate the right contract and fees with your clients then you will earn more money – it’s that simple. So there’s a direct link between the effort you expend and the health of your bank balance. And, for many, that’s a really big reason to jump ship and go it alone.
  • You work with a more varied selection of people – when you work in a corporate environment, the chances are that you work with a limited number of people – usually those in your direct team and any customer contacts you spend time with. Freelancers get to work with a whole range of different customers, bringing you into contact with a wide network of different client contacts (not just those in your office).

All sounds great so far, doesn’t it! But let’s not forget that there are a few challenges associated with the self-employed route that you’ll need to take into account.

Man using laptop, Going Freelance: Building Work Around Your Life, Going Freelance, freelance, freelancer, self-employed, solopreneur

The challenges of a freelance approach

The corporate life does have a strong allure for many, and that usually comes down to the security and career potential of the salaried route. So, before you tell your current boss where to stick their job, make sure you’ve thought through these vital considerations of the freelance life.

As a freelancer:

  • You have less overall job security – freelancers tend to be taken on for short or medium-term projects – clients are unlikely to be offering you a ‘job for life’ when they contract you to work for them. The way to overcome this is to have a broad portfolio of different clients on the books, while also making sure there’s a regular pipeline of new projects, new leads and new prospects and customers coming your way.
  • Your income is less stable – when you’re self-employed there’s no safety net of a guaranteed monthly salary payment. Income can go up and down over time, depending on the amount of work carried out, what the seasonal demand is for your services and (crucially) how good your clients are at paying your invoices on time. Again, the answer is to have a regular pipeline of work, agreed payment terms and a highly persuasive way when it comes to getting accounts payable departments to settle your bill.
  • You have no corporate benefits – the employee benefits you take for granted in a salaried role don’t exist for freelancers.  There’s no sick pay, no holiday pay and no pension payments from an employer. But by taking out income protection insurance, managing your cashflow and setting up your own personal pension plan with a provider, there’s no reason why you can’t give yourself more security – it just means being organised enough to set these things up.
  • You must file your own tax return – as an employee, your tax is deducted at source from your wages by your employer, and then paid directly to the tax body in your particular jurisdiction (HMRC in the UK, the IRS in the US etc.). But when you’re a freelancer, you must file your own tax return, and that’s not only tedious to complete, but also a truly time-intensive process. Getting help with your tax return filing makes a lot of sense. The extremely helpful team at have a very useful post that gives you the lowdown on all the latest tax preparation software, and how it helps to make preparing and filing your freelance tax a much less painfull process. Take a look at their tax preparation post here.
  • The buck stops with you – being the Chief Executive of Everything can have some downsides. There’s no-one to delegate work to, no-one else to make the big business decisions and no-one to push you if you’re feeling demotivated or disengaged – so the freelance life can be stressful. The answer is to carefully manage your workload, ask for support from friends, family and your peers and to achieve a work/life balance that achieves your core goal of freedom from work.

Do you want stability, or freedom?

You’ve probably noticed that the ‘cons’ list is shorter than the ‘pros’ list – and that’s no accident. I believe that being self-employed is the best fit for many people.

If you ask most freelancers, they’ll say that the advantages of the self-employed life FAR outweigh the possible risks. For many of us, if you can escape the corporate life and build work around your choice of lifestyle, that’s a bonus that can’t have a tangible price put on it.

Your decision, ultimately, comes down to what you value most in your life.

Do you want:

  1. Stability, a predictable salary – but little control over your destiny
  2. Freedom, flexibility and personal control over your life – but a less predictable future

Going Freelance: Building Work Around Your Life, Going Freelance, freelance, freelancer, self-employed, solopreneur

Going Freelance: Building Work Around Your Life

So, does this freelance lifestyle sound inviting? If you’d like to start achieving the benefits of a more flexible career, where YOU are in control of your destiny, then now’s the time to start.

‘Going Freelance: Building Work Around Your Life’ is a comprehensive 101 guide for anyone setting out on the freelance journey. Each chapter gives you the simple, easy-to-follow tips you need, with clear advice on setting up your own freelance business.

The book explains how to:

  1. Understand the Benefits (And Challenges) Of Going Freelance
  2. Ensure You Have The Right Experience And Skills
  3. Make The Jump And Get Started
  4. Know Why You’re In Business
  5. Find Your First Customer
  6. Market Your Brand And Services
  7. Choose Where To Work
  8. Join The Freelance Community
  9. Build On Your Client Relationships
  10. Manage Your Workload
  11. Manage Your Numbers
  12. Get Paid On Time
  13. Pursue A Good Work/life Balance
  14. Get Started As A Freelancer

Going Freelance is available in Kindle and Print editions on Amazon.





It has never been easier to find a job!

AppJobs, jobs, job sites, work, employment, job search, gig economyAppJobs lets you pick and compare app-based jobs in your city. You can browse hundreds of jobs, find your best fit and start working immediately!

Apply for your next job here

One thought on “Should I go freelance? The benefits (and challenges) of being self-employed

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s