What makes a successful IT contractor?

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It’s a very interesting question to ask – what makes a successful IT contractor? But before I can get to actually answering it, first we should consider what we mean by ‘success,’ writes Alan Watts, a service management consultant (retired), with more than 40 years’ experience as an IT contractor.

In business terms, ‘success’ is a measurable thing; was the project delivered on time, to budget and does the end result actually work? These are things that can be quantified fairly easily. The success/failure division is pretty clear cut.

Success; work out and keep in mind what being successful means to YOU

In personal terms however, you can’t really define a success factor. More accurately, you can define it, but everyone will have their own criteria for ‘success’!

That said, in my professional experience, there are perhaps three key things we tend to apply to the question of success

  • Financial

  • Personal, and, for want of a better word;

  • Satisfaction.

Let’s take the first; financial success.

Following the money

Well, most (not all) people are attracted to contracting in IT for the money. They look at the hefty day rates on offer and think – ‘This is the fastest way to pay off the mortgage and the Bentley!’

Obviously, those sorts of goals can be achieved. But right off the bat with IT contracting, you must remember that a lot of that juicy day rate -- probably 40% but as much as 60% in some cases -- will disappear in taxes and overheads before it reaches your personal bank account.

A good grasp of days, demand, and deliverables (-- or other types of contract)

Also, keep at the forefront of your mind if you want to succeed at freelancing in the UK technology sector, you won’t be being paid 260 or so days a year like salaried employees; more like 180 days -- on average. More billable days would be a good thing, if you can achieve it, but it will depend on the nature of your contract and the assignment.

Financial success as an IT contractor also hinges quite a bit on what you actually do. For example, it’s easier to be in fairly continuous work (and therefore fairly continuous invoicing) if your skills are in demand, either because your IT skills are fairly generic and can be applied anywhere or are sufficiently niche that they are always sought-after. For many an IT contractor, that latter is the Holy Grail!

Further consider, there are roles centred on ‘business improvement,’ where short-term contracts are the norm. After all, you can only fix things once! There are other contractor roles where you are being paid for a ‘deliverable’ of some kind. With these deliverable-based contracts, if you get paid for the end result, then that’s ‘success’ in and of itself!

The ability to get yourself renewed

The other big measure of success as an IT contractor is how often you get renewed.

In other words, are you doing the job that the client wants to the quality they expect, so much so that they want you back to keep doing it, and so keep extending your contract? Projects and programmes invariably come to an end but for some IT contractors, a series of lucrative renewals is unquestionably ‘success.’  

If you put all the above together -- i.e. having a series of contracts including contract extensions, getting properly paid for your skills, and generally being well enough remunerated that you don’t have to worry about paying your household bills, then for most IT contractors I know, that absolutely is success.

I’d go so far as to say that the above three are really the whole point of being an IT contractor. After all, any business is there to make a regular profit for its shareholders, so if you’re doing that as a limited company IT contractor then yes, you are successful. At least in the financial stakes!

Succeeding, personally speaking

Personal success is harder to define. And it’s very much down to what you are looking for, as an individual.

In permanent employment, success is usually measured by moving up the corporate ladder -- as far as you can; the higher the better.

Accepting that ‘career progression’ isn’t really going to be a thing for you

For IT contractors though, it’s rather more difficult. For one thing, promotion and career progression are not really ‘a thing.’ Most of the time, if ‘progression’ is something you’d like to have in your work as a freelance techie, all you can really do is take on harder or more complex contracts.

Therefore, coming to terms with the fact that the default position as an IT freelancer is that there isn’t ‘career progression’ (in the conventional sense of the term that everyone else in the office will talk about it), is helpful to do early on.

That said, you can define personal success as a contractor in various ways.

Working in different areas, different industries, or simply obtaining recognition

For many it’s the independence and the ability to work in different areas and industries. For some, it’s recognition by their peers of their expertise, which is always a valuable source of references anyway, ideal if another freelance contract or a full-time opportunity suddenly turn your head.

For other IT contractors I know, ‘success’ is quietly working diligently away with their same skill; enjoying the comparatively relaxed environment of no HR-type demands for one-to-one reviews, not having to chase promotions and being able to generally avoid office politics!

Being able to start, build and run your own tech empire (or not)

For you though, personal success as an IT contractor might be starting, building and then running a freelance technology business from scratch. Similarly, if you’re ambitious, personally ‘making it’ as an IT contractor could be you finding work and then hiring people for your company to deliver it while gaining a reputation as the ‘go-to’ person for a specific skill, type of project/programme or competency.

Personal success as an IT contractor can be more straightforward and less entrepreneurial. Indeed, there’s absolutely nothing wrong with simply acquiring enough money through a series of similar contracts over a period of years, purely so you can stop working altogether and go off to do something you really enjoy. After all, that horse farm, pottery workshop or Yoga retreat in the mountains isn’t going to build itself!

Feeling satisfied

Finally, satisfaction, is rather more nebulous.

Simply put, satisfaction as an IT contractor is generally either being happy with the job you are doing or looking back at your work and thinking ‘That was a job well done.’ And if you can say that about the majority of the contracts you have completed, then you have very probably been successful.

All of which begs the question, ‘How do I achieve success?’ Well, as I’ve tried to demonstrate above, first you have to decide what your version of success actually is, be it just one or several of the options. Then you can decide how you aim to achieve that ‘success’ or ‘successes,’ and do your utmost to stick to your plan!

Penultimately then, in terms of what makes a successful IT contractor is, you need to consider:


Deciding how you’ll achieve success as an IT contractor starts with properly understanding what it is you are selling to the end-client.

If you are going to be better than the many rivals which exist for almost all IT positions you have to be good at your trade; up-to-date on the technology and/or methodologies you use, and ideally have some real success stories in your recent past. So yes, success to achieve success, so-to-speak!

A professional working mode, with a network to match

Once you are in work, you obviously have to deliver timely and accurate results and generally make yourself known as a good and reliable worker; a true professional.

Also regarding the workplace, nobody really does traditional references anymore, but professional recommendations on LinkedIn and the like will make the road to success smoother, and provide a measure of how well you are doing.

Build a network of contacts because (more than recruiters) ‘who you know’ is more and more the route to landing future engagements as an IT contractor. In fact, I know IT freelancers who have never been through an agency but have been in work for many years, mostly thanks to word-of-mouth.  

Not panicking, but instead knowing exactly what you’ll do if things sour

Be happy in your work. If you aren’t -- and it happens from time-to-time to the best of us -- then exercise the other main benefit of being an IT contractor; move on to something else.

Eventually, one day, you will be in a position not to have to work again, either because you no longer need to or you’ve got better things to do with your time. That’s when you can look back and see just how much of a success you have been. Good luck!

Written by

Alan Watts

Independent Service Management Consultant

Alan Watts has been in IT for most of the last 45 years, apart from a short spell in accountancy, eventually turning to Operations Management before going freelance in 1996. Since then he has worked with clients ranging from FTSE100s to major Government departments, with roles varying between Project Management, Interim Management and pure Consultancy.

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