I guarantee this question constantly goes through your mind, especially at year end when your salary adjustment or performance appraisal does not meet your expectations.

After the extended break though, you always make the decision to stay another year, work harder if that is even possible and hope it gets better this year.

But is that the right decision for you and your family?

Do you feel anxious that you have even made the right decision?

I have been a contractor for a number of years and an employee for even longer and am going to outline what I have experienced to help you evaluate whether you are making the right decision.

Do you want to remain technical or do you have aspirations for management?

If your career aspirations are for management, then you should stay employed. It is rare that a contractor is put into a managerial position. If you are unsure, check out my post Technical track or management.

If management is for you, then outline your career goals, find a mentor, work with your manager, seek out training and succeed with this company or another.

If you are passionate about staying technical then contracting could be a good route for you. You can change your mind at a later date as I did when I lost the passion for coding, I was offered a role as a team lead at the company I was contracting it and took it with open arms.

Can you handle uncertainty?

Contracting comes with a lot of risk, especially when the economy is in a bust cycle. You could go weeks or months without finding a new contract or you rate can be reduced.

Throughout my contracting career I was lucky enough to always start a contract straight after finishing another, but I have seen others not be so lucky.

If you go this route, then be prepared for uncertainty and ensure you save for a rainy day.

Does your salary give you the life you would like?

Lets face it, contracting can be more lucrative than being employed, especially after the tax advantages when running a limited company.

Check out the contractor rates on internet job sites for your skill set and work out how that compares to your salary, make sure to include any benefits your company make give you in the calculation i.e. pension, private healthcare, gym membership, etc.

Here is a good calculator to use if you are based in the – UK Contracting To Permanent Calculator.

A friend of mine worked out that if he continued with his current salary then his pension would not be what he needed when he retired in 15 years time. He negotiated with his boss, but could not get what he needed, so he went contracting to ensure his future was more secure.

Remember though if you navigate a successful career as an employee and reach senior levels, your compensation can well exceed that of a contractor. This is a long term play and risk, but many of my colleagues have achieved this.

Travel & Relocation

This is one of my biggest regrets of not working for a large global organisation when I was younger and contracting. I have spent a lot of my time in my employed role travelling to Singapore and NY and wished that I had relocated to these regions for a couple of years to experience the culture and the lifestyle they have. I even tried to get my wife to move to Singapore in 2008, but to no avail. If I had asked before we had children and were both working then it would of been different story.

Global organisations can offer you a vast amount of opportunities that contracting cannot, you need to weigh this up in your current and future goals.

Do you like long commutes or being away from home?

Some contracts require you to work long distances from your home that will require either a long commute or staying away from home in a hotel during the week.

Can you sell yourself?

Contracting requires you to establish a good network with recruitment agents to ensure you are always in the front of their mind when a new contract comes up as well as being able to sell yourself well during interviews. Interviews will always be highly competitive so it is key you are good at selling your skills and keeping those skills up to date with the latest changes in technologies.

The most uncomfortable contractor interview I saw was when I was contracting for a small company and they were interviewing another contractor. As I had done before, the contractor was required to take a verbal skills test as well as write a small program in C++. The technical lead used a special Microsoft RSI keyboard at the time and exchanged it for a standard one to make the candidate comfortable. He forgot however to plug the new one in.

The poor candidate sat there for 30 minutes going red and sweating as the test should only take 10 minutes. When he was asked how he was getting on, he said the keyboard was not working. He was thanked for his time and told he did not get the role due to not speaking up and wasting time. He should of really figured out the keyboard was not plugged in.

One thing that got to me in the later stages of my contract career was being interviewed by people younger and less experienced than me asking me questions that had no relevance to the role. I was good a biting my lip, you will have to be to.

Are you quick to learn and be adaptable?

Aa contracting is for a limited amount of time. you will be required to get up to speed as soon as you walk through the door and you could be using company toolsets and standards you may not like, but have to adhere to.

Training is a must in your own time

As a contractor, you have to train on your own time at your own expense as you will be expected to be right up to speed at this and your next role.

However the experience you get as a contractor as you move from company to company can be invaluable, both from a technical side and a soft skills side as you have to interact with lots of new people with varying personalities.


I have heard people say that contractors can take lots of holidays, but in my experience taking holidays when you are brought in for only a short time with for a specific requirement can be difficult to arrange. You will need to work around any deadlines a client may have.

When I first starting contracting I felt though I was out of pocket twice, once for paying for the holiday and then for the loss of money I was not earning while I was away. One year, I did not take any holiday and even though I was young, I became very burned out and was in a huge amount of trouble with my wife. You really have to be able to put his out of your mind.

Funnily enough you never take days off sick as a contractor.

Red tape hassle

Self employment comes with form filling, accounts, invoicing, etc. This can be hassle on top of everything else you are doing.

Opening doors

Contracting can open doors that you will not normally be able to open. The company that I landed my first employed team lead role at would not of employed me if I had not contracted with them before hand. The company screens out all candidates without a degree, but because I was already on the inside, i got past this screening process and passed the interview.

Wrap Up

Overall for me, contracting was great for me when I was young and passionate about software development. It gave me a lot of the soft skills I have used to be successful in my leadership roles and a great network of colleagues and friends that I still interact with. When my passion changed and I looked at other challenges, then a employed role gave me everything I was looking for.

You have to make the decision that is right for you today as you can always change it at a later date as I did.  I hope the following has helped you make an informed decision, if not and you need some more help, then please ask me ask a question below in the comments or ping me an email at nicholas.foster@develite.com

Your virtual mentor & coach
Nick & nicholas-foster.com

Categories: Resources