A young man sitting at a desk working on his laptop. He is an IT contractor.
Image: © Jeff Bergen/peopleimages.com/Stock.adobe.com

Six things to consider before becoming an IT contractor

7 Jun 2023

Hays’ James Milligan looks at the questions a worker must ask themselves before making the leap from a permanent role to IT contracting.

Are you thinking about leaving your permanent role and starting a career in IT contracting? If so, this can be an incredibly exciting prospect, which will no doubt benefit your long-term career. You won’t be stuck doing the same thing day in, day out and you’ll have variety in your job roles, where you work and the people you meet.

But, how do you know if you’ve really got what it takes to forge a successful career in IT contracting? Will you be able to cope with the uncertainty, take on the challenge and thrive in this new career path? Asking yourself the following six questions will help you decide whether life as an IT contractor is for you.

Am I good at being my own boss?

Being your own boss sounds great, doesn’t it? Especially if you’re currently in a job you don’t like or you’re working for someone who is a poor manager. It’s easy to get lost in fantasising about being able to take days off whenever you like and do what you want, when you want, while money auto-magically pops into your bank account.

But when you actually take the plunge and reality sets in, you’ll find that there’s a whole lot to organise, from marketing yourself to paying yourself. The freedom and autonomy that IT contracting brings can also be difficult for some to adapt to. So, ask yourself honestly, do you have the determination, focus and perseverance required to succeed as an IT contractor?

I do want to reiterate that there are massive advantages to IT contracting. One of these is that you will have the flexibility you need to ensure you have a fulfilling work-life balance. By choosing IT contracting as a career path, you will find that control over your own time is very much placed back into your own hands, which can be hugely fulfilling, both personally and professionally.

How organised and disciplined am I?

It’s important to understand that contracting can be very much like running your own business. You’ll have regular (and monotonous) admin tasks to do that you probably won’t have ever had to deal with in your permanent job, from preparing your accounts to paying your own tax. You might want to form your own limited company, or register as self-employed – either way, there’ll be paperwork that you have to manage and deadlines for tax returns.

As an IT contractor, it will also be your responsibility to ensure you have a consistent pipeline of work and are always thinking one step ahead. It’s important to be diligent here – towards the end of each contract it’s a good idea to update your CV and LinkedIn profile when the skills and experienced gained are still fresh in your mind and file all your receipts and expenses to keep your accounts up to date.

So, before you dive into a life of IT contracting, be confident that you have the organisational skills and discipline needed to ensure all of your affairs are in order.

How adaptable am I?

As an IT contractor, each and every project, sometimes each and every day, will be different and you will constantly get pushed outside your comfort zone. This can be hugely motivating, not to mention great for your CV. However, you must be confident in your ability to adapt to change well.

You will also need to be able to handle different operating systems and tools as you move from project to project, from company to company. While you’ll probably be great at picking up new software and IT systems, you’ll also need to be adaptable enough to deal with the different admin systems and processes of each company you work at.

How do I feel about not being a consistent member of a team?

While this can be a hard concept for some, especially if you’ve come from a long-term permanent role with a tight-knit team, the benefit of contracting is that you will avoid office politics and gossip. In addition, if you find you don’t get on with someone, or you find the contract manager difficult to deal with, you just have to remember that this is temporary and soon enough you’ll never have to deal with them again (if you don’t want to).

On the other hand, along the way, you will also meet and forge great relationships with other IT contractors. These contacts may well turn out to be useful sources in the future, particularly in terms of recommendations for new projects and securing work.

Will I be committed to being proactive in finding new projects?

Part and parcel of successful IT contracting is maintaining your network, building relationships and keeping in touch. You’ll need to be proactive in searching for your next project, marketing yourself and your brand, networking, following up and managing all of that while working at your current role.

It’s also important that you maintain regular and open communication with your recruitment consultant, if you have one, as well as being great at building rapport with past and current clients, in case opportunities arise in the future.

How good am I at selling myself?

In between each IT contract, you will need to attend interviews to secure your next project. One of the benefits of IT contracting is that over time, you will start to build a rich and varied CV.

However, it’s still important that you have the skills and ability to succeed in an interview and feel comfortable and confident in an interview situation. After all, you will need to ensure you can sell yourself and highlight why you are better than the other IT contractors out there.

By James Milligan

James Milligan is the global head of technology at Hays. A version of this article originally appeared on the Hays’ blog.

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