6 questions to ask before IT contracting

James Milligan, Global Head of Technology at Hays

Thinking about leaving your permanent role to start a career in IT contracting? If so, this can be an incredibly exciting prospect, which can benefit your long-term career. Breaking free from a fixed routine and accessing a diverse number of job roles is attractive to many.

But, how do you know if you’ve really got what it takes to be successful in IT contracting? Will you be able to manage the uncertainty, take on the challenge and thrive in this new career path? Asking yourself the below six questions will help you understand your suitability to this type of career path. 

1. Am I good at being my own boss?

The notion of becoming your own boss sounds great, doesn’t it? Especially if you’re current employment situation is less than ideal. 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 automatically 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 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?

It’s important to underscore 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. 

2. How organised and disciplined am I?

Contracting can be 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 and managing your super contributions. 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 experience gained are still fresh in your mind, and file all your receipts and expenses to keep your accounts up to date.

You’ll need to be confident that you have the organisational skills and discipline, outside of the actual work that needs to be done, to ensure your affairs are in order. 

3. How adaptable am I?

IT contracting presents a dynamic landscape where each project and often each day, unfolds uniquely, continually pushing you beyond 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 navigate different operating systems and tools as you move from project to project and 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. 

4. 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 respite from typical office politics that come with a permanent role. In addition – if you find you don’t get on with someone, or you find the contract manager difficult to deal with, remember that these engagements are temporary and you have the freedom to choose your next venture. 

On the other hand, along your 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. 

5. 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’re partnering with one, as well as being great at building rapport with past and current clients, in case opportunities arise in the future. 

6. 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 the interview situation. After all, you will need to ensure you can sell yourself and highlight your unique value proposition.

As well as reading through this list, we also recommend talking candidly to any of your IT contracting friends about their experiences – this will allow you to build a full and realistic picture of exactly what it’s like to do this as a career. Ask them to be honest and tell you if they would recommend you explore this career path.

There are also some excellent and extremely active IT contracting online forums which can be a great source of information and advice and whose members will no doubt be more than happy to answer any of your questions. 

About this author

James Milligan is the Global Head of Technology at Hays, having joined in 2000. In his role, he is responsible for the strategic development of Hays ‘ technology businesses globally.

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