Contracting – The Perks and Pitfalls

For a large part of my time in Digital I have been a contractor, dipping in and out of projects. I want to share here what I have learned about working as a temporary contributor.

Taking the leap

For somebody initially taking the leap into contracting, the sense of freedom and autonomy is like a breath of fresh air. There is a wonderful sense of freedom in ‘being your own boss’, dealing with your own monetary affairs and setting your own objectives.

Just be prepared that you might find yourself working more intensely some of the time and at other times you may find yourself out of work for a few weeks or months. It will become a part of your job to market yourself, develop your skillset to fit market requirements, and possibly carve out a niche so that you can offer unique value.

Is more expected of you as a contractor?

In my experience, yes – some if not most companies take on contractors because there is an expectation of long term experience and professionalism and often the project will have tighter deadlines with broader or less well defined scope. You will likely be expected to make decisions in your area of expertise and carry the ball forward into the unknown.

Don’t be put off by this. If you are passionate about what you do then you likely understand that working hard with enthusiasm will see you through.

A note on Passion

Often you will see a Guru in some industry, espousing that to be successful you need to ‘Find your Passion’. Whilst this is not untrue, in my opinion it is misleading.

You will notice that I have emphasised the words working hard and enthusiasm above. This is because for me, passion is not something that exists to be discovered, rather it is derivative of working hard to nurture enthusiasm.

Or to put it another way, through your struggle you will grow and be grateful of it – People see this, and they call it Passion.

Are you given more allowances as a contractor?

Again, in my experience yes – in most cases I have been granted more autonomy and authority as a subject matter expert and I appreciate this greatly.

Contractors are also paid more money than permanent employees because there are no company benefits. This has to be balanced with the amount of unpaid work involved in being a freelancer, searching for work, managing clients and arranging your taxes.

A note working in teams

It’s important to build relationships quickly when joining a team as a contractor and I do this by showing an example of what it will be like to work with me right at interview stage. I’ll look at a real challenge in the project and talk practically about how I will investigate and attempt to solve it.

Building relationships of course, goes beyond the interview. In your time on a project as a contractor it’s important to listen well, show respect for the work done in your absence, give credit to individuals and make it clear that you are there to support the team.

Leaving projects

When you are due to leave a project, there are a few things that I always try to do.


Practically, this is the most important thing for the project and the team. Be prepared to hand over any access or permissions to software, documents and codebases as well as any knowledge that may not have been recorded – make time to do this.

Some companies will not like to contact you outside of your contract for various reasons, so make sure you leave them in good stead.

Manager feedback

You aren’t going to get an exit interview as a contractor, so try to make time with your direct report to get an overview of what really worked or didn’t. There is always feedback and it’s all important, good and bad. I like to ask the question: “What about my time here could be improved for the future?”.

Not only does it get you that vital information, but it shows humility and lets your manager know that the new and improved version of you will be here for them when they need you next!

A note on giving feedback

You should be able to approach anybody with feedback, we are all just people after all – really good people will value this greatly.

Speak your truth, but be clear and positive in your tone. Most of all, say something constructive or don’t say anything at all.

Speak with individuals

Something I always bring up when leaving a role (permanent or contract) is that, I am leaving this project, but not the industry.

The individual relationships that you build are the most permanent thing about work. You never know who you will work with again in the future, or what kinds of opportunities could emerge from your network.

Take time to speak with members of the team individually if you can, and leave them knowing what it is that you appreciate about your time with them. Everybody will teach you something if you’re listening – be authentic and kind, it is your responsibility.