Have you got what it take to be a contractor?

Last week we wrote about the benefits of being an independent professional, or contractor. Flexibility, freedom from office politics, earning potential, independence and variety of work were some good reasons to consider the contracting lifestyle. We touched on the personalities most suited to contracting…if you need high levels of security it may not be the best career choice for you.

This week we look in more detail at some of the personality traits or attributes that characterise the successful contractor. Many of these can be acquired, even if they are not your natural inclination. But if the thought of developing these qualities leaves you cold, it’s probably advisable to keep your day job!


Above all, you need discipline. When a contract comes to an end, and long lie-ins beckon, this is precisely the time to focus on finding the next assignment. It is not a time for an extra holiday. If you are fortunate enough to have a steady stream of contracts, you must still make time for admin, financials, networking and personal growth. No training department will conduct a needs analysis and provide you with a training plan each year. You must do this for yourself. You must log your expenses and ensure you have adequate insurance cover and investment for the future. Finally, you must be able to resist taking all your profits, and instead prioritise reinvestment in your business, to ensure growth and sustainability.

Thick skin

While it may be refreshing to be spared the annual performance review, at the same time no one is particularly interested in your morale, or your career growth. Your employer wants results, and as a contractor you are paid to deliver them. The soft benefits that permanent employees enjoy do not apply to you. If you make a mistake, prepare to feel the full extent of your employer’s dissatisfaction. This may not happen; you may have an employer who treats all staff alike, permanent or temporary. But very often more is expected of contractors, with less margin for error. If you don’t handle criticism well, or need constant praise and affirmation, contracting may not be for you.


This may well be what drove you to consider contracting in the first place. Successful contractors are not satisfied with the status quo and always seek ways to do things more efficiently and/or effectively. The desire to enhance processes and tasks, when unfulfilled, often provides the motivation to leave a permanent post and take up contracting. The quest for continuous improvement is why contractors are in demand by employers, particularly for projects like system upgrades and migrations.


The complement to dissatisfaction is curiosity. If you are dissatisfied with a way of working, you are probably also curious about how you could make it better, which leads to continuous improvement. You are also curious about the world around you. You are interested in meeting new people (otherwise you’d find it very tedious going from one organisation to another); you have an enquiring mind and enjoy figuring things out, like the intricacies of a new situation that may appear baffling at first.

Tolerance for risk

Inevitably, risk is a factor of contracting. Risk accompanies lack of security. There is always the risk that you might not win another contract, or that you might experience a very long gap between contracts. There is a risk you might not perform to the standard the new employer expects, and you may be let go. You have no job security. If you find risk difficult to stomach, stay in your permanent job. But if you have an appetite for risk and find new challenges exciting, and don’t crave guarantees in life, contracting may suit you.


Allied to risk tolerance is resilience. You must be able to bounce back when things go wrong, or when the risks become actual events. You need to be able to rely on yourself and not depend on others to help you out when the going gets tough.


Your employers must know they can count on you to come through, no matter what. Even more importantly, they must trust you to be discreet and protect confidential information. You are perfectly placed to disclose industrial secrets to the next employer; as a contractor certain key corporate data has to be shared with you. It is your integrity that creates trust in your employers and will lead to you being hired over and over again.


Whether you are an extrovert or an introvert, you need to be able to communicate effectively to be a successful contractor. As a systems analyst or coder you might have got away with hiding out in your office when you were permanently employed, but as a contractor you have to build relationships and keep your employer informed about progress, setbacks, scope changes, etc. And you have to communicate to win contracts; no one is going to market your services except you.

And that’s not all

There are other traits that successful contractors demonstrate, such as the ability to innovate, focus, and adapt. We’d like to hear from you…what qualities do you have that make you an excellent contractor? If you are an employer, what do you look for in contractors? What attributes characterise the best contractors you have employed? Leave your feedback in the comments box at the bottom of this post.

Contact us

If you’re new to contracting or thinking about a career change, Highveld can help you structure your business and maximise your earning potential as an independent professional. If you are an employer, let Highveld show you how to get the most you’re your continegent workforce.

Contact Highveld on 012 367 5600 or info@highveld.co.za. You’re worth it.

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