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Becoming a self-employed contractor can be lucrative and fulfilling – but you’ll need plenty of hard work and discipline

For the disillusioned professional fed up with the 9-6 grind, navigating office politics or managing thankless workloads, ditching the commute and striking out alone as a self-employed contractor, whatever the field, is an exciting prospect.

While not a new phenomenon, this trend is becoming particularly apparent across industries such as banking and finance, construction, technology and life sciences.

Working for yourself can be lucrative and fulfilling, but don’t be fooled: going solo means taking on long hours, hard work, and leaving your comfort zone behind without colleagues and line managers to help you out.

Therefore whether you’re a software developer, engineer, project manager or brand expert, you’ll need to consider some key questions before you can confidently call yourself ‘boss’ and start taking on work.

1. Am I good at being my own boss?

While it’s true that freelancers determine their own hours – and managed carefully, that can lead to professional and personal fulfilment, and a highly rewarding work-life balance – those who aren’t willing to set themselves goals and limits won’t last long.

Once you start working for yourself, you’ll quickly find that there’s a whole lot to organise, from marketing to paying yourself, functions that were likely performed by entire departments at your last job.

The freedom of freelancing can be difficult to adapt to, and that’s why it’s important to ask yourself whether you have the determination, focus and perseverance required to succeed.

2. How organised am I?

Being a freelancer means being a business of one. You’ll have regular, tedious administrative tasks to do, like preparing and dispatching invoices and paying your own tax. You might even decide to form your own limited company, in which case you or your accountant will be responsible for managing all such paperwork.

Alternatively, you may consider joining a third party umbrella company who will take responsibility for completing these labour intensive tasks. Either way, both options entail substantial paperwork and deadlines – and that’s all before you’ve done any real work.

It’s important to be diligent, too. Towards the end of each contract, it’s a good idea to update your CV and LinkedIn profile when the skills and experience gained are still fresh in your mind, and file all your receipts and expenses.

3. How adaptable am I?

As a freelancer, each and every project will challenge you and push you further out of your comfort zone. You won’t have colleagues to help you out or bounce ideas off. For some, this is rewarding, but for others the constant pace of work can be daunting. You must be adaptable to change.

You’ll also be working with different kinds of people, different processes and protocols, and different cultures and attitudes. Some clients will be domineering and push you to your limits, while others will hand you the reins and expect results with little to no guidance. A thick skin and patience are prerequisites.

4. Can I work alone?

As a freelancer, you’ll spend most of your time working alone at your own pace. You’ll be able to pick and choose your own clients.

The trade-off is that you’ll have no one to help you develop your ideas or check your work. If you’re coming from an office environment, you may even find working alone lonely. Make sure you’re comfortable with long periods with just your laptop for company.

5. Am I proactive and disciplined?

Without a constant flow of work, your life as a freelancer will be a short one. To keep your bank account in the black, you’ll need to call in favours, reach out to old colleagues, network with potential clients, engage with recruitment agencies and pitch your services constantly.

In between each job, you’ll need to hone your pitching and interviewing skills to secure your next project. One of the benefits of freelancing is that over time, you’ll start to build a rich and varied CV. However, it is still important that you have the skills and ability to succeed in a pitch or interview.
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